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Chemistry of Heterocyclic Compounds, Volume52 D. J. Brown Copyright 0 1994 by John Wiley & Sons, Ltd.

REFERENCES In each case, information was collected from the original publication except where an additional reference to Chemical Abstracts, Chemisches Zentralblatt, or some other secondary source is included below. Each citation of a Russian journal or to Angewandte Chemie refers to the original Russian or German version, not to the respective English translation. The abbreviations for journal titles are those recommended initially in the Bibliographic Guide for Editors and Authors (American Chemical Society, Washington, DC, 1974) and subsequently, with occasional modifications, in the Chemical Abstracts Service Source Index (American Chemical Society, Washington, DC, 1989) and its quarterly supplements. The abbreviation Frdl. stands for Friedlanders Fortschritte der Teerfarbenfabrikation (Springer, Berlin), a multivolume compilation of German chemical patents, especially useful for access to those issued before World War 11. 1. M. S. Shingare and D. B. Ingle, J . Indian Chem. Soc., 53, 1036 (1976). 2. 1. A. Clark and W. B. Cowden, in Oxidative Stress, (H. Sies Ed.), Academic Press, London, 1985, p.131. 3. M. E. Perlman, P. S. Conti, B. Schmall, and K. A. Watanabe, Int. J . Nucl. Med. Biol., 11,215 (1 984). 4. T. L. Su and K. A. Watanabe, J . Heterocycl. Chem., 21, 1543 (1984). 5. T. J. Delia, J . Org. Chem., 49, 2065 (1984). 6. H. Yamato, T. Nagamatsu, and F. Yoneda, J . Heterocycl. Chem., 28, 1209 (1991). 7. J. A. LaMattina and C. J. Mularski, Tetrahedron Lett., 25, 2957 (1984). 8. C. Venturello and R. d’Aloisio, Synthesis, 1983, 937. 9. H. Meinert, V. Gross, and S. Rudiger, J . Flourine Chem., 24, 355 (1984). 10. M. Botta, R. Salidino, A. Gambacorta, and R. Nicoletti, Heterocycles, 32, 1537 (1991). 11. Z. Fang, R. Li, and Y. Xu, Yiyao Gongye, 19, 346 (1988); Chem. Abstr., 110, 75441 (1989). 12. A. F. Hadfield and C. Sartorelli, Ado. Pharm. Chemother., 20, 21 (1984). 13. T. Harhyama, R. Yanada, K. Kotoji, F. Yoneda, T. Taga, K. Osaki, and T. Nagamatsu, Nucleic Acids R e x , 15, 1 (1984). 14. M. S. Akhtar, M. Seth, and A. P. Bhaduri, Indian J . Chem., Sect. B, 26, 556 (1987). 15. T. Nagamatsu, Y. Hashiguchi, Y. Sakuma, and F. Yoneda, Chem. Lett., 1309 (1982). 16. F. C. Georgescu, E. I. Georgescu, E. G. Georgescu, and I. ZugrPvescu, Rev. Roum. Chim., 28, 653 (1983). 17. Y. Sakuma, T. Nagamatsu, Y. Hashiguchi, and F. Yoneda, Chem. Pharm. Bull., 32,851 (1984). 18. K. A. Watanabe, T. L. Su, K. W. Pankiewicz, and K. Harada, Heterocycles, 21, 289 (1984). 19. K. Burger, V. Wassmuth, F. Hein, and S. Rottegger, Liebigs Ann: Chem., 1984, 991. 20. T. Nagamatsu, M. Koga, and F. Yoneda, Chem. Pharm. Bull., 32, 1699 (1984). 21. S. B. Gashev, V. P. Lezina, and L. D. Smirnov, Khim. Geterotsikl. Soedin., 1983, 1252. 22. V. P. Krivopalov, E. B. Nikolaenkova, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1983, 1401.

1183

1184

References

23. S. B. Gashev, V. P. Sedova, L. D. Smirnov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1983, 1257. 24. 1. I. Naumenko and G. V. Shishkin, Khim. Geterotsikl, Soedin., 1983, 1406. 25. G. Ya. Remennikov, A. A. Kiselenko, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1983, 1393. 26. W. Wendelin and R. Riedl, Monatsh. Chem., 115, 445 (1984). 27. W. L. F. Armarego and P. Waring, Aust. J . Chem., 34, 1921 (1981). 28. M. Sako, Y. Kojima, K. Hirota, and Y. Maki, Heterocycles, 22, 2509 (1984). 29. S. R. Landor, P. D. Landor, and V. E. Williams, J . Chem. Soc., Perkin Trans. I , 1984, 2677. 30. W. Wendelin and H. Kerbl, Monatsh. Chem., 115, 309 (1984). 31. F. J. Cuadrado, M. A. Perez, and J. L. Soto, J . Chem. Soc., Perkin Trans. I , 1984, 2447. 32. J. J. Hlavka, P. Bitha, I. Y. Lin, and T. Strohmeyer, J . Weterocycl. Chem., 21, 1537 (1984). 33. T. Veda, J. Sakakibara, and J. Nakagami, Chem. Phurm. Bull., 31,4263 (1983). 34. J. Barluenga, L. Muniz, J. M. Iglesias, and V. Gotor, J . Chem. Soc., Perkin Trans. I , 1984,611. 35. V. V. Lapachev, A. Zagulyaiva, P. 0. Petrenko, S. F. Bychkov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1984, 827. 36. 37. 38. 39.

M. V. Jovanovic, Can. J . Chem., 62, 1176 (1984). M. M. Litvak, Khim.-Farm. Zh., 25, 64 (1991); Chem. Ahstr., 116, 41413 (1992). A. Kreutzberger and J. Gillessen, J . Heterocycl. Chem., 22, 101 (1985). A. Dlugosz, Pharrnazie, 42, 381 (1987).

40. T. Higashino. Y. Matsushita, M. Takemoto, and E. Hayashi, Chem. Phurm. Bull., 31, 3951 ( 1 983). 41. 42. 43. 44. 45. 46. 47. 48. 49. 50. 51. 52. 53. 54. 55. 56. 57. 58. 59. 60.

M. A. Perez, J. L. Soto, F. Guzmin, and H. Alcala, J . Chem. Soc., Perkin Trans. I , 1985, 87. A. H. Pedersen and K. Undheim, Acta Chem. Scand., Ser. B , 37,947 (1983). F. Rise, L. Ongstad, M. Gacek, and K. Undheim, Acta Chem. Scand., Ser. B, 37, 613 (1983). T. Bennechc and K. Undheim, Acta. Chem. Scand., Ser. B, 37, 345 (1983). K. Weinhardt, M. B. Wallach, and M. Marx, J . Med. Chem., 28, 694 (1985). R. A. Grigsby, K. J. Irgolic, and F. F. Knapp., J . Organornet. Chem., 259, 171 (1983). E. C. Taylor, M. J. Thompson, K. Perlman, R. Mengel, and W. Pfleiderer, J . Ory. Chem., 36, 4012 (1971). A. Lorente, J . L. Garcia-Navio, J. J. Vaquero, and J. L. Soto, J . Heterocycf. Chem., 22, 49 (1985). K. T. Potts, M. J. Cipullo, R. Ralli, and G. Theodoridis, J . Org. Chem., 48, 4841 (1983). H. Gotthardt and K. H. Schenk, Tetrahedron Lett., 24, 4669 (1983). K. A. Cruishank, J. Jiricny, and C. B. Reese, Tetrahedron Lett., 25, 681 (1984). K. V. Sadek. S. M. Fahmy, R. M. Mohareb, and M. H. Elnagi, J . Chem. Soc. Perkin Trans. I , 1982, 2667. J. Arukwe and K. Undheim, Acta Chem. Scand., 45, 914 (1991). K. Tanaka, T. Okada, and F. Yoneda, Tetrahedron Lett., 25, 1741 (1984). C. J. Shishoo, M. B. Devani, V. S. Bhadti, S. Ananthan, and G. V. Ullas, Tetrahedron Lett., 25, 1291 (1984). E. Picquenard, J. Riand, and J . P. Brun, Can. J . Chem., 62, 655 (1984). D. J. Brown, S-B. Lan, and K. Mori, Aust. J . Chem., 37, 2093 (1984). 0. S. Sizova and R. G. Glushkov, Khim.-Farm. Zh., 18, 717 (1984). M. H. Holshouser, A. M. Shipp, and P. W. Ferguson, J . M e d . Chem., 28, 242 (1985). A. H. Pedersen and K. Undheim, J . Eleterocycl. Chem., 21, 1149 (1984).

References 61. 62. 63. 64. 65. 66. 67. 68. 69. 70. 71. 72. 73. 74. 75. 76. 77. 78. 79. 80. 81. 82. 83. 84. 85. 86. 87. 88. 89. 90. 91. 92. 93. 94. 95. 96. 97.

98. 99. 100.

1185

A. Katoh, Y. Omote, and C. Kashima, J . Heterocycl. Chem., 21, 53 (1984). M. Sakarnoto, T. Akimoto, K. Fiikutomi, and K. Ishii, Chem. Pharm. Bull., 32, 2515 (1984). T. Yamamoto and M. Muraoka, J . Heterocycl. Chem., 25, 835 (1988). T. Sakamoto, H. Yoshizawa, and H. Yamanaka, Chem. Pharm, Bull., 32, 2005 (1984). T. Nagamatsu, Y. Hashiguch, and F. Yoneda, J . Chem. Soc., Perkin Truns. I, 1984, 561. P. I. Svirskaya, V. Yedidia, C. C. Leznoff, and J. M. Miller, J . Heterocycl. Chem., 22, 149 (1985). Y. Takikawa, S . Hikagi, Y. Matsvda, K. Higashiyama, Y. Takeishi, and K. Shimada, Chem. Lett., 1991, 2043. J. Hung and L. Werbel, J . Heterocycl. Chem., 21, 741 (1984). J. Knabe and W. Schmitt, Arch. Pharm. (Weinheim,Ger.), 317, 789 (1984). A. Kreutzberger and J. Gillessen, Arch. Pharm. (Weinheim, Ger.), 317, 749 (1984). G. Mueller, J. Riede, R. Beyerle-Pfnuer, and B. Lippert, J . Am. Chem. Soc., 106, 7999 (1984). K. Hirota, Y. Kitade, and S. Senna, J . Chem. Soc., Perkin Trans. I , 1984, 1859. J. Barluenga, M. Tomas, and V. Gotor, J . Chem. R e x , Synop. 154, Minipr. 1567 (1984). B. Stanovnik, 0.Bajt, B. Beltif, B. Koren, M. Prhavc, A. Stimag, and M. Tiiler. Heterocycles, 22, 1545 (1984). W. Wendelin and K. Schermanz, J . Heterocycl. Chem., 21, 65 (1984). N. S . Habib and T. Kappe, J . Ileterocycl. Chem., 21, 385 (1984). R. Troschutz, Arch. Pharm. (Weinheim,Ger.), 317, 709 (1984). A. H. Pedersen and K. Undheim, A c t a Chem. Scund., Ser. B, 38, 341 (1984). A. Millcr, .1. Org. Chem., 49, 4072 (1984).

H. Singh, S. Kumar, and P. Singh, J . Chem. Res., Synop. 137, Minipr. 1641 (1984). E. Peichl and T. Kappe, Arch. Pharm. (Weinheim, Ger.), 317, 946 (1984). C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, Synthesis, 1983, 151. T. Nagamatsu, Y. Sakuma, and F'. Yoneda, Synthesis, 1983, 923. A. M. Ebd-Elfattah, S. M. Hussain, A. M. El-Reedy, and N. M. Yousif, Tetrahedron, 39, 3197 (1 983). A. Kreutzberger and J. Gillessen, Arch. Pharm. (Weinheim,Ger.), 318, 370 (1985). E. Rougeot, H. Moskowitz, and M. Miocque, J . Heterocycl. Chem., 20, 1407 (1983). Y. H. Kim and N. J. Lee, Heterocycles, 20, 1769 (1983). D. R. Hicks and 3. J. Hangeland, J . Label. Compd. Radiopharm., 24, 747 (1987). M. Mirutani, Y. Sanemitsu, Y. Tamaru, and Z. Yoshida, J . Org. Chem., 50, 764 (1985). J. W. Chern, D. S. Wise, and L. B. Townsend, J . Heterocycl. Chem., 21, 1245 (1984). J. 1. Turchi and T. G. Cullen, Heterocycles, 22, 2463 (1984). A. S. Prasad, J. S. Sandhu, and J. N. Baruah, J . Heterocycl. Chem., 21, 1657 (1984). G. Menichi and M. Hubert-Habart, J . Heterocycl. Chem., 21, 209 (1984). H. Cho, M. Ueda, Y. Ohnaka, and M. Hayashimatsu, Heterocycles, 22, 1959 (1984). P. Matyus, P. Sohar, and H. Wamhoff, Heterocycles, 22, 513 (1984). K. M. Ghoneirn, F. A. El-Telbany, M. El-Enany, and K. Youssef, E g y p t . J . Pharm. Sci., 28, 127 ( 1 987). M. F. Braiia, J. ILI. Castellano, and M. J. Yunta, Heterocycles, 22, 113 (1984). T. Chiba, H. Sato, and T. Kato, Heterocycles, 22, 493 (1984). S. Konno, Y. Sato, T. Sakamoto, N. Katagiri, and H. Yamanaka, Heterocycles, 22, 1331 ( 1984). B. Singh and G. Y. Lesher, Heterocycles, 22, 1133 (1984).

1186

References

101. M. Sako, Y. Kojima, K. Hirota, and Y. Maki, Heterocycles, 22, 1021 (1984). 102. A. Weis, F. Frolow, D. Zamir, and M. Bernstein, Heterocycles, 22, 657 (1984). 103. E. S. Kandeel, K. M. Hassan, N. A. Ismail, and M. H. Elnagdi, J . Prakt. Chem., 326,248 (1984). 104. M. Berridge, D. Comar, and C. Crouzel, Int. J . Appl. Radiat. Isot., 34, 1657 (1983). 105. D. N. Abrams, Y. W. Lee, E. E. Knaus, and L. I. Wiebe, Int. J . Appl. Radiat. Isot., 35, 531 (1984). 106. J. F. Menez, M. Bourin, M. G. Colombel, C. Benamou, C. Larousse, and L. Bardou, Eur. J . Med. Chem.-Chim. Ther., 18, 521 (1983). 107. V. Skarii: and D. Skarik, Croat. Chem. Acta, 57, 183 (1984). 108. W. Wendelin, K. Schermanz, K. Schweiger, and A. Fuchsgruber, Monatsh. Chem., 114, 1371 (1983). 109. M. Takahashi, T. Nogami, and K. Nidaira, Heterocycles, 22, 581 (1984). 110. I. Z . Lulle, R. A. Patgle, M. Y. Lidak, and V. Krisane, Khim. Geterotsikl. Soedin., 1983, 1545. 11 1. I. 2. Lulle, T. I. Kagan, R. A. Paegle, and M. Y. Likak, Khim. Geterotsikl. Soedin., 1983, 1540. 112. G . Jones, D. J. Tonkinson, and P. C. Hayes, J . Chem. Soc., Perkin Trans. 1, 1983, 2645. 113. S. Ozaki, Y. Watanabe, T. Hoshiko, H. Mizuno, K. Ishikawa, and H. Mori, Chem. Pharm. Bull., 32, 733 (1984). 114. T. Nishio and Y. Omote, J . Chem. Soc., Perkin Trans. I , 1984, 239. 115. M. Yokoyama, K. Tsuji, and T. Imamato, Bull. Chem. Soc. Jpn., 57, 2954 (1984). 116. R. G. Glushlov, L. A. Nikolaeva, 0. V. Kozlova, L. N. Dronova, V. A. Chernov, and S. M. Mihakova, Khim.-Farm. Zh., 18, 674 (1984). 117. T. Benneche and K. Undheim, Acta Chem. Scand., Ser. B, 38, 505 (1984). 118. T. Sakamoto, H. Yoshizawa, S. Kaneda, and H. Yamanaka, Chem. Pharm. Bull., 32, 728 (1984). 119. T. A. Dashevskaya, Yu. A. Fialkov, V. A. Khranovskii, and V. M. Cherkasov, Khim. Geterotsikl. Soedrn., 1984, 402. 120. Y. L. Yagupol'skii, M. T. Kolycheva, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1986, 710. 121. T. Sakamoto, H. Yoshizawa, S. Kaneda, Y. Hama, and H. Yamanaka, Chem. Pharm. Bull., 31, 4533 (1983). 122. T. Sakamoto, T. Sakasai, H. Yoshizawa, K. Tanji, S. Nishimura, and H. Yamanaka, Chem. Pharm. Bull., 31,4554 (1983). 123. D. Korbonitis, K. Simon, P. Kolonitis, Tetrahedron Lett., 24, 5763 (1983). 124. A. Katoh, Y. Omote, and C. Kashima, J . Heterocycl. Chem., 21, 915 (1984). 125. R. R. Covington, J. S. New, J. P. Yevich, and D. L. Temple., J . Label. Compd. Radiopharm., 20, 1207 (1983). 126. J. Hung and L. M. Werbel, Synthesis, 1985, 80. 127. S. Kambe, K. Saito, M. Hirose. A. Sakurai, and H. Midorikawa, Synthesis, 1984, 860. 128. M. Diksic, S. Farrokhzad, Y. L. Yamamoto, and W. Feindel, Int. J . Nucl. Med. B i d , 11, 141 (1984). 129. K. B. Sloan and K. G. Siver, Tetrahedron, 40, 3997 (1984). 130. M. Botta, M. Cavalieri, D. Ceci, F. de Angelis, G. Finizia, and R. Nicoletti, Tetrahedron, 40, 3313 (1984). 131. H. Yoshida, S. Sogamt, Y. Takishita, and T. Ogata, Bull. Chem. Soc. Jpn., 56, 2438 (1983). 132. K.A. Thakak and C. H. Gill, J . Indian Chem. Soc., 61, 550 (1984). 133. S. C. Nigam, G. S. Saharia, and H. R. Sharma, J . Indian Chem. Soc., 60, 583 (1983). 134. G. Jaenecke, H. Voigt, F. Hofmann, and B. Feuerstein, Z. Chem., 24, 437 (1984).

References

1187

135. V. A. Golubcv and A. N. Rosenberg, Izv. Akad. Nauk. SSSR, Ser. Khim., 1984, 1823. 136. G . Tarzia, G . Panzone, L. Zerilli, M. Lanfranchi, and G . Pelizzi, Gazz. Chim. Ital., 114, 431 ( 1 984). 137. A. L. Weis and R. Vishkautsan, Chem. Lett., 1984, 1773. 138. T. Fuchikami, A. Yamanouchi, and Y. Suzuki, Chem. Lett., 1984, 1573. 139. T. Fuchikami and A. Yamanouchi, Chem. Lett., 1984, 1595. 140. T. Sakamoto, Y. Kondo, and H. Yamanaka, Synthesis, 1984, 252. 141. L. W. Singh, A. K. Gupta, H. Illa, and H. Junjappa, Synthesis, 1984, 516. 142. H. Yamanaka, S. Nishimura, S. Kaneda, and T. Sakamoto, Synthesis, 1984, 681. 143. G. Maas and B. Feith, Angew. Chem., 97, 518 (1985). 144. T. Takajo, S. Kambe, and W. Ando, Synthesis, 1984, 259. 145. A. L. Weis and R. Vishkautsan, Heterocycles, 23, 1077 (1985). 146. V. G. Granik, S. I. Grizik, S. S. Kiselev, V. V. Chistyakov, 0. S. Anisimova, and N. P. Solov’eva, Khim. GeterotsikL Soedin., 1984, 532. 147. L. V. Ershov, S. S. Kiselev, and V. G . Granik, Khim. Geterotsikl. Soedin., 1984, 538. 148. K. Hirota, T. Sugiyama, Y. Kitade, S. Senda, and Y. Maki, J . Chem. Soc., Perkin Trans. I , 1984, 583. 149. E. A. Zvezdina, M. P. Zhdanova, and I. 1. Giryavenko, Khim. Geterotsikl. Soedin., 1983, 893. 150. V. P. Krivopalov, E. B. Nikolacnkova, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1983, 1222. 151. V. G . Granik and S. I. Kaimanakova, Khim. Geterotsikl. Soedin., 1983, 816. 152. K. Burger, U. Wassmuth, H. Partscht, A. Gierin, T. Hubner, and C. P. Kaerlein, Chem.-Ztg, 108, 205 (1984). 153. K. Burger, H. Partscht, E. Huber, A. Gieren, T. Hubner, and C. P. Kaerlein, Chern.-Ztg, 108, 209 (1984). 154. K. Burger, H. Partscht, U. W muth, A. Gieren, H. Betz, G. Wcber, and T. Hubner, Chem.Ztg., 108, 213 (1984). 155. T. Nishio, T. Tokunaga, and Y. Omote, Synth. Commun., 14, 363 (1984). 156. Y. T. Wei and H. C. Chiang, Chung-huu Yao Hsueh Tsa Chih, 41, 19, (1989); Chem Ahstr., 111, 134079 (1 989). 157. H. Takahata, T. Nakajima, K. Matoba, and T. Yamazaki, Synth. Commun., 14, 1257 (1984). 158. M. Botta, F. dc Angelis, G . Finizia, A. Gambacorta, and R. Nicoletti. Synth. Commun., 15, 27 (1985). 159. A. S. Mikhalov, N. G. Pashkurov, V. Reznik, and G. I. Podzigun. Izc. Akad. Nauk SSSR,Ser. Khim., 1984, 1396. 160. S. A. Grachev, E. V. Kropachev, and G. I. Lituyakova, Izv. Akad. Nauk S S S R , Ser. Khim., 1984, 1270. 161. A. Kreutzberger, and M. Sellheim, Arch. Pharm. (Weinheim, Ger.), 318, 385 (1985). 162. J. P. Spengler and W. Schunack, Arch. Pharm. (Weinheim, Ger.), 317, 425 (1984). 163. G. Blaschke and H. Markgraf, Arch. Pharm. (Weinheim, Ger.), 317, 465 (1984). 164. I. Kompis and R. Then, Eur. J . Med. Chem.-Chim. Ther., 1984, 529. 165. R. Alonso, G . Shaw, and D. Wright, J . Chem. Soc., Perkin Trans. I , 1984, 2795. 166. Z. Machon and J. Cieplik, Eur. J . Med. Chem.-Chim. Ther., 1984, 359. 167. C. Stropnik, M. TiSler, and B. Stanovnik, Vestn. Slou. Kem. Drus., 31, 229 (1984). 168. P. Dostert, T. Imbert, M. Langlois, B. Bucher, and G . Mocquet, Eur. J . Med. Chem.-Chim. Ther., 19, 105 (1984). 169. R. Mosquera and A. Orjales, An. Quim., Ser. C., 79, 388 (1983).

1188

References

170. T. J. Kress, J . Org. Chem., 50, 3073 (1985). 171. M. Otsuka, S. Kobayashi, M. Ohno, Y. Umezawa, H. Morishima, and H. Umezawa, Chem. Pharm. Bull., 33, 515 (1985). 172. A. Moskvin, N. A. Smorygo, and B. A. Ivin, Zh. Org. Khim., 20, 156 (1984). 173. A. S. Prasad, J. S. Sandhu, and J. N. Baruah, J . Heterocyl. Chem., 21, 267 (1984). 174. A. Kreutzberger and J. Gillessen, J . Heterocyl. Chem., 21, 1639 (1984). 175. M. Yokoyama, H. Hatanaka, and K. Sakamoto, J . Chem. Soc., Chem. Commun., 1985, 279. 176. Y. Inouye and Y. Higuchi, J . Fluorine Chem., 27, 231 (1985). 177. D. Prajapati and J. S. Sandhu, Indian J . Chem., Ser. B, 23, 758 (1984). 178. P. C. Parthasarathy, S. Iyer, M. Hendi. D. K. Ray, and V. B. Srivastava, Indian J . Chem., Ser. B, 22, 1233 (1983). 179. P. Kumar, C. Nath, J. C. Agarwal, K. P. Bhargava, and K. Shanker, Indian J . Chem., Ser. B, 22, 955 (1983). 180. D. H. Kim, J . Heterocycl. Chem., 22, 173 (1985). 181. R. 0. Kochkanyan, S . S. Lukanyuk, and L. M. Zueva, Zh. Ory. Khim., 24, 2012 (1988). 182. S. M. Hussain, A. A. El-Barbary, and S. A. Mansour, J . Heterocycl. Chem., 22, 169 (1985). 183. K. Kimura, S. Fujii, M. Ogawa, G. P. Bodley, and P. Alberto, Fluoropyrimidines in Cancer Therapy, Proc. lnt. Symp., Nagoya, 1983 (Excerpta Medica, Amsterdam, 1984),xxiii + 563 pp. 184. A. M. Gero, W. J. O’Sullivan, and D. J. Brown, Biochem. Med., 34, 60 (1985). 185. S. Gregson and G. Shaw, J . Chem. Soc., Perkin Trans. 1, 1985, 187. 186. G . Y. Reminnikov and V. M. Cherkasov, Ukr. Khim. Zh., 51, 313 (1985); Chem. Abstr., 103, 104916 (1985). 187. W. Zielinski, Pol. J . Chem., 56, 93 (1982). 188. A. L. Weis, Adu. Heterocycl. Chem., 38, 1 (1985). 189. J. T. Bojarski, J . L. Mokrosz, H. J. Barton, and M. H. Palvchowska, Ado. Heterocycl. Chem., 38, 229 (1985). 190. F. Savelli, G. Pirisino, F. C. Alamanni, P. Manca, and M. Satta, Farmaco, Ed. Sci., 38, 869 ( 1 983). 191. P. Strande, T. Benneche, and K. Undheim, J . Heterocycl. Chem., 22, 1077 (1985). 192. Y .Ye, Z. Zhou, D. Shen, and Y. Wang, Hesishu, 59, 69 (1984). 193. L. V. Sokolyanaskaya, A. N. Volkov, E. 0. Tsetlina, and G. I. Stukalova, Zh. Ory. Khim., 12, 2063 (1976). 194. V. N. Boiko, T. A. Dashevskaya, G. M. Shchupak, and L. M. Yagupol’skii, Zh. Org. Khim., 15, 396 (1979). 195. I. A. Pomytkin and E. S. Balenkova, Zh. Org. Khim., 19, 1982 (1983). 196. R. Jeyaraman and C. B. Jawaharsingh, Synth. Commun., 15, 417 (1985). 197. A. Lorente, J. L. Garcia-Navio, L. Fuentes, and J. L. Soto, Synthesis, 1985, 86. 198. A. Lorente, J. L. Garcia-Navio, and J. C . Lopez-Perez, Synthesis, 1985, 89. 199. I. Yamamoto, K. Fukui, S. Yamamoto, K. Ohta, and K. Matsukaki, Synthesis, 1985, 686. 200. M. Hori, K. Tanaka, T. Kataoka, H. Shimizu, E. Imai, K. Kimura, and Y. Hashimoto, Tetrahedron Lett., 26, 1321 (1985). 201. K. A. M. El-Bayouki, E. F. Nielsen, and E. B. Pedersen, Synthesis, 1985, 104. 202. K. Hirota, K. Banno, Y. Yamada, and S. Senda, J . Chem. Soc., Perkin Trans. I , 1985, 1137. 203. M. Legraverend and E. Bisagni, Tetrahedron Lett., 26, 2001 (1985). 204. A. Kreutzberger and M. Sellheim, J . Fluorine Chem., 27, 203 (1985). 205. H. Cho, K. Shima, M. Hayashimatsu, Y .Ohnaka, A. Mizuno, and Y. Takeuchi, J . Org. Chem., 50, 4227 (1985).

References

1189

206. H. M. Bell, D. R. Carver, J. S. Huhbard, Y. P. Sachdiva, J. F. Wolfe, and T. D. Greenwood, .1. Org. Chem., 50, 3442 (1985). 207. H. Gotthardt and K. H. Schenk, Angew Chem., 97, 604 (1985). 208. Y. L. Singh and L. F. Lee, J . Org. Chem., 50, 4642 (1985). 209. V. B. Ivanov, V. S. Resnik, and Y. Y. Efremov, Izv. Akud. Nuuk S S S R ,Ser. Khim., 1983, 2364. 210. V. P. Savin, N. F. Popova, G. E. Semenova, A. B. Galeeva, and V. B. Tyupkin, Zh. Prikl. Khim. (Leningrad), 58, 1185 (1985); Chem. Abstr., 103, 215249 (1985). 21 1. C. G. Freeman, J. V. Turner, and D. A. Ward, Aust. J . Chem., 31, 179 (1978). 212. Y. Yamamoto, Y. Azuma, Y. Watanahe, and S. Kamaishi, Annu. Rep. Tohoku Cull. Pharm., 79 (1984); Chem. Ahstr., 104, 5838 (1986). 213. A. D. Shestakov, Y. L. Kaminskii, 1. M. Nurova, V. N. Nikitina, V. L. Zaionta, 0. V. Maksimova, and G. A. Mikhailov, K h i w k ' a r m . Zh., 19. 400 (1985); Chem. Abstr., 104, 5834 ( I 986). 214. B. Hingerty, E. Kulikowska, W. Saenger, and D. Shugar, Z. Naturforsch., Teil C, 31, 518 (1976). 215. E. Kulikowska, B. Hingerty, W. Saenger, and D. Shugar, Z. Naturforsch., Teil C, 31, 514 (1976). 216. A. Kreutzberger and M. Sellheim, Chem.-Ztg., 103, 253 (1984). 217. S . S. Sahri, A. Q. Hussein, and F. H. Al-Hajjar, .I. Chem. Eng. Data, 30, 512 (1985). 218. F. Rise and K. Undheim, Acta Chem. Scand., Ser. B, 39. 195 (1985). 219. F. Rise, C, Ramming, and K. Undheim, Acta Chem. Scand., Ser. B, 39, 459 (1985). 220. J. Solberg and K. Undheim, Actu Chem. Scand., Ser. B, 40, 381 (1986). 221. F. Rise and K. Undheim, J . Organumet. Chem., 291, 139 (1985). 222. F. Rise and K. Undheim, J . Chem. Soc., Perkin Trans. I , 1985, 1997. 223. S. S. Al-Hassan, R. J. Cameron. A. W. C. Curran, W. J. S. Lyall, S. H. Nicholson, D. R. Robinson, A. Stuart, C. J. Suckling, and H. C. S. Wood, J . Chem. Soc., Perkin Trans. I , 1985, 1645. 224. R. J. Cameron, S. H. Nicholson. D. H. Robinson, C. J. Suckling, and H. C. S. Wood, J . Chem. Soc., Perkin Trans. 1, 1985, 2133. 225. S. S. Al-Hassan, R. J. Cameron, S. H. Nicholson, D. H. Robinson, C. J. Suckling, and H. C. S. Wood, J . Chem. Soc., Perkin Trans. I , 1985, 2145. 226. H. I. Skulnick, S. D. Weed, E. E. Eidson, H. E. Renis, W. Wierenga, and D. A. Stringfellow, J . Med. Chem., 28, 1864 (1985). 227. F. A. Kuliev, K. A. Galsytan, and R. A. Bahakhanov, Dokl, Akad. Nauk Az. SSR,41,27 (1985); Chem. Abstr., 104, 19555 (1986). 228. J. D. McChesney and M. Gonzalez-Sierra, Phurm. Kes., 1985, 146. 229. E. Kulikowska, Z, Zawadzki, and D. Shugar, Zesz. Prohl. Postepow Nauk Roln., 1984, 271. 230. E. Kulikowska, I. Miura, K. Nakanishi, Z. Zawadzki, and D. Shugar, Photochem. Photohiol., 39, l(1984). 231. A. T. M. Mareelis and H. C. van der Plas, J . Org. Chem., 51, 67 (1986). 232. H. P. Wang and L. M. Werbel, T a i w a n Yao Hsueh Tsa Chih, 36, 204 (1984). 233. H. Gotthardt and J. Blum, Chem. Ber., 118, 4578 (1985). 234. G . B. Barlin, D. J. Brown, B. J. Cronin, and M. Ngu, Aust. J . Chem., 39, 69 (1986). 235. G . B. Barlin, D. J. Brown, and M. D. Fenn, Aust. J . Chem., 37, 2391 (1984). 236. D. J. Brown and K. Mori, Aust. J . Chem., 38, 467 (1985). 237. M. Kawase, K. Samejima, M. Okada, K. Ochi, and I . Matsunaga, Chem. Phurm. Bull., 33,2395 (1985).

1190

References

T. Nishio, T. Tokunaga, and Y. Omote, J . Heterocycl. Chem., 22, 405 (1985). E. de la Cuesta and C. Avendano, J . Weterocycl. Chem., 22, 337 (1985). J.-P. Montheard and J.-C. Dubios, J . Heterocycl. Chem., 22, 719 (1985). A. Kreutzberger and M. Sellheim, J . Heterocycl. Chem., 22, 721 (1985). H. Gotthardt and J. Blum, Chem. Ber., 119, 1445 (1986). M. P. Nemeryuk, A. L. Sedov, T. S. Safonova, A. Cerny, and J. Kiepelka, Collect. Czech. Chem. Commun., 51, 215 (1986). 244. F. V. Bright, R. A. Bunce, and L. B. McGown, Org. Prep. Proced. Int., 18, 209 (1986). 245. D. Sen, S. Bhowmik, and P. Sengupta, J . Indian Chem. SOC.,63, 420 (1986). 246. S. Hu, S. Xu, H. Chen, Y. Ye, and Y. Ling, Yiyao Gongye, 16, 210 (1985); Chem. Abstr., 104, 109565 (1986). 247. J. Rocek, V. Svata, and L. Leseticky, Collect. Czech. Chem. Commun., 50, 1244 (1985). 248. T. C. Thurber and L. B. Townsend, J . Org. Chem., 41, 1041 (1976). 249. A. Radzicka and M. Konieczny, Pol. J . Chem., 58, 737 (1984). 250. Y.-T. Wei, Hua Hsueh, 43, 62 (1985); Chem. Abstr., 104, 186369 (1986). 251. T. J. Delia and J. D. Crandall, Nucleic Acid Chem., 3, 1 (1986). 252. A. S. Jones, G. P. Stephenson, and R. T. Walker, Nucleic Acid Chem., 3, 3 (1986). 253. L. Kiriasis, S. Farkas, and W. Pfleiderer, Nucleosides Nucleotides, 5, 517 (1986). 254. W. B. Cowden, Aust. J . Chem., 38, 1499 (1985). 255. M M. Al-Arab, Collect. Czech. Chem. Commun., 50, 2910. (1985). 256. J. Kiepelka, A. &my, R. Kotva, J. Vachek, and M. Mtlka, Collect. Czech. Chem. Commun., 51, 1140 (1986). 257. A. Wada, T. Yamamoto, T. Hase, N. Nagai, and S. Kanatomo, Synthesis, 1986, 555. 258. I. Winckelmann and E. H. Larsen, Synthesis, 1986, 1041. 259. S. Kim and S. S. Kim, Synthesis, 1986, 1017. 260. T. Kinoshita, M. Kondo, H. Tanaka, and S. Furukawa, Synthesis, 1986, 857. 261. V. Kvita, Synthesis, 1986, 786. 262. N. Fukada, Y. Takahashi, and M. Hayashi, Synthesis, 1986, 484. 263. Y. Inoue, M. Taguchi, and H, Hashimoto, Synthesis, 1986, 332. 264. Z. Machon and J. Cieplik, Synthesis, 1986, 142. 265. J. Barluenga, L. Muniz, M. J. Inglesias, and V. Gotor, Synthesis, 1985, 1146. 266. G. Bram, G. Decodts, Y. Bensaid, C. C. Farnoux, H. Galons, and M. Miocque, Synthesis, 1985, 543. 267. A. L. Weis, Synthesis, 1985, 528. 268. H. Wamhoff and W. Schupp, J . Org. Chem., 51, 2787 (1986). 269. L. Celewicz and H. Koroniak, Synth. Commun., 15, 1001 (1985). 270. M. Gacek and K. Undheim, Acta Chem. Scand., Ser. B, 39, 691 (1985). 271. A. Kreutzberger and J. Gillessen, J . Fluorine Chem., 29, 385 (1985). 272. A. Takaoka, M. K. Ibrahim, S. R . F. Kagaruki, and N. Ishikawa, Nippon Kagaku Kaishi, 1985, 2169 273. A. Y . Aizikovich and F. F. Zaripova, Zh. Org. Khim., 22, 1564 (1986). 274. R. N. Goyal, R. Bhushan, and A. Agarwal, J . Indian Chem. Soc., 62, 229 (1985). 275. P. Vainilavicius, V. Rocka, V. Sederviciute, A. Dieniene, A. Berganskiene, M. Kreneviciene, and G. L. Abramova, Khim.-Farm. Zh., 25, 55 (1991); Chem. Abstr., 116, 21020 (1992). 276. M. Mizutani, Y. Sanemitsu, Y. Tamaru, and Z.-I. Yoshida, Tetrahedron, 42, 305 (1986). 277. S. Gronowitz, A.-B. Hornfeldt, V. Kristjansson, and T. M u d , Chem. Scr., 26, 305 (1986). 238. 239. 240. 241. 242. 243.

References

1191

278. M . Botta, F. de Angelis, G. Finizia, N. Rosaria, and M. Delfini, Tetrahedron Lett., 1985, 26, 3345. 279. T. Takahashi, S.-I. Hirokami, M. Nagata, and T. Yamazaki, Tetrahedron Lett., 26, 3247 (1985). 280. 0. Rousseaux, D. Blondeau, and H. Sliwa, Tetrahedron Lett., 27, 3127. 281. A. Atmani and M. Kajima, Tetrahedron Lett., 27, 2611 (1986). 282. K. Hirota, Y. Kitadi, H. Sajiki, and Y. Maki, Tetrahedron Lett., 27, 3263 (1986). 283. H. Cho, Y. Ohnaka, M. Hayashimatsu, M. Ueda, and K. Shima, Tetrahedron Lett., 27, 6377 (1986). 284. S. N. Mazumdar, I. Ibnusaud, and M. P. Mahajan, Tetrahedron Lett., 27, 5875 (1986). 285. H. Gotthardt, J. Blum, and K.-H. Schenk, Chem. Ber., 119, 1315 (1986). 286. H. Gotthardt and J . Blum, Chem. Ber., 119, 3247 (1986). 287. H. Gotthardt and J. Blum, Chem. Ber., 120, 109 (1987). 288. H. Gotthardt and J. Blum, Chem. Ber., 120, 115 (1987). 289. R. J. Griffin, C. H. Schwalbe, M. F. G. Stevens, and K. P. Wong, J . Chem. Soc., Perkin Trans. I, 1985, 2267. 290. A. L. Weis and F. Frolow, J . Chem. Soc., Perkin Trans. I , 1986, 83. 291. N. Vivona, S. Buscemi, V. Frenna, and M. Ruccia, J . Chem. Soc., Perkin Trans. I , 1986, 17. 292. M . Smal, H. T. A. Cheung, and P. E. Davies, J . Chem. Soc., Perkin Trans. I , 1986, 747. 293. G. M. Brooke and J. A. K. J. Ferguson, J . Chem. Soc., Perkin Trans. I , 1986, 515. 294. T. Herseggen, F. Rise, and K. Undheim, J . Chem. Soc., Perkin Truns. I , 1986, 849. 295. T. Nishio, S. Kameyama, and Y. Omote, J . Chem. Soc., Perkin Trans. 1, 1986, 1147. 296. M. Yokoyama, H. Hatanaka, A. Sasaki, T. Shiraishi, K. Kumata, K. Sakamoto, and K . Ogata, J . Chem. Soc., Perkin Trans. 1, 1986, 1187. 297. G. Stijer, A. E. Szabo, G. Bernath, and P. Sohir, J . Chem. Soc., Perkin Trans. I , 1987, 237. 298. T. Nogimori, C. H. Emerson, L. E. Braverman, C.-F. Wu, J. Gambino, and G. E. Wright, J . Med. Chem., 28, 1692 (1985). 299. 0. W. Lever, L. N. Bell, H. M. McGuire, and R. Ferone, J . Med. Chem., 28, 1870 (1985). 300. T. S . Lin, L. Wang, 1. Antonini, L. A. Cosby, D. A. Shiba, D. L. Kirkpatrick, and A. C. Sartorelli, J . Med. Chem., 29, 84 (1986). 301. H. I. Skulnick, J. H. Ludens, M. G. Wendling, E. M. Glen, N. A. Rohloff, R. L. Smith, and W. Wierenga, J . Med. Chem., 29, 1499 (1986). 302. C. Gutremy, F. Audiau, C. Renault, J. Benevides, A. Uzan, and G. Le Fur, J . Med. Chem., 29, 1394 (1986). 303. H. Schickaneder, H. Engler, and I. Szelenyi, J . Med. Chem., 30, 547 (1987). 304. H. M. Taylor, C. D. Jones, J. D. Davenport, K. S. Hirsch, T. J. Kress, and D. Weaver, J . Med. Chem., 30, 1359 (1987). 305. G. L. Anderson and S. G. Richardson, J . Heteocycl. Chem., 22, 1735 (1985). 306. C . A. Lipinski, R. H. Craig, and R. B. Wright, J . Heterocycl. Chem., 22, 1723 (1985). 307. D. Simon, 0. Lafont, C. C. Farnoux, and M. Miocque, J . Heterocycl. Chem., 22, 1551 (1985). 308. A. Gangjee, K. A. Ohemeng, J. J. Talachka, F.-T. Lin, and A. A. Katoh, J . Heterocycl. Chem., 22, 1149 (1985). 309. E. A. A. Hafez, M. R. H. Elmoghayar, and M. M. M. Ramiz, Liebigs Ann. Chem., 1987, 65. 310. T. Harayama, H. Jinno, Y. Tezuka, and F. Yoneda, J . Heterocycl. Chem., 23, 1507 (1986). 31 1. J. J. Wade, J . Heterocycl. Chem., 23, 981 (1986). 312. A. Haas and M. Lieb, J . Heterocycl. Cheni., 23, 1079 (1986). 313. S. Buscemi, G. Macaluso, V. Frenna, and N. Vivona, J . Heterocycl. Chem., 23, 1175 (1986).

1I92 314. 315. 316. 317. 318. 319. 320. 321. 322. 323. 324. 325. 326. 327. 328.

References

R. S. Sodum, P. S. Klein, and B. A. Otter, J . Heterocycl. Chem., 23, 1239 (1986). M . Kimura and 1. Okabayashi, J . Heterocycl. Chem., 23, 965 (1986). S. Pegiadou-Koerntjopoulou and G. Tsatsaronis, J . Heterocycl. Chem., 23, 335 (1986). P. de Meester, M. V. Jovanovic, S. S. C. Chu, and E. R. Biehl, J . Heterocycl. Chem., 23, 337 (1986). R. Beyerle-Pfnur, B. Lippert, H. Schollhorn, P. Matischok, and U. Thewalt, J . Heterocycl. Chem., 23, SO5 (1986). M. Takahashi, T. Mamiya, and M. Wdkao, J . Heterocycl. Chem., 23, 77 (1986). C. Kashirna, M. Shimizu, A. Tagaya, A. Katoh, and Y. Ornote, J . Chern. R e x , Synop. 88, Minipr. 901 (1986). B. Abarcd, M. Jiminez, G. Jones, and C. Soriano, J . Chem. Res., Synop. 395, Minipr. 3358 (1986). M. M. Cashyap, M. B. Mitchell, D. C. Osborne, and D. Saunders, J . Label. Compd. Radiopharm,, 22, 1239 (1985). T. Itahara, R. Ebihara, Y. Fujii, and M. Tada, Chem. Lett., 1986, 1319. K. Seki, Y. Bando, and K. Ohkura, Chem. Lelt., 1986, 195. M. S. Shingare, Indian J . Chem., Sect. B, 22, 714 (1983). S. Fukushirna, K. Noro, T. Noro, and A. Ueno, Chem. Pharm, Buil., 33, 5053 (1985). T. Hoshiko, S. Ozaki, Y. Watanbe, T. Ogasawara, S. Yarnauchi, K. Fujiwara, A. Hoshi, and M. Iigo, Chem. Pharm. Bull., 33, 2832 (1985). S. Kamata, N. Haga, T. Matsui, and W. Nagata, Chem. Pharm. Bull., 33, 3160 (1985).

329. M. Sako, Y. Kojima, K. Hirota, and Y. Maki, Chem. Pharm. Bull., 33, 2525 (1985). 330. V. P. Mamaev, V. F. Sedova, G. G. Moskalenko, V. N. Odinokov, V. R. Akhmetova, and G. A. Tolstikov, Izc. Akad. Nauk SSSR, Ser. Khim., 1986, 954. 331. V. P. Mamaev, T. A. Andreeva, V. P. Krivopalov, and V. I. Eroshkin, Iza. Akad. Nauk S S S R , Ser. Khim., 1986, 955. 332. I. S. Salikhov, V. S. Reznik, Y. S. Shvetsov, V. V. Petrova, and R. R. Shagidullin, Izu. Akad. Nauk SSSR, Ser. Khim., 1986, 1173. 333. I. S. Salikov, V. S. Reznik, Y. S. Shvetsov, and R. R. Shagidullin, Izu. Akad. Nauk S S S R , Ser. Khim., 1986, 2283. 334. A. L. Weis and D. Zarnir, J . Org. Chem., 52, 3421 (1987). 335. S. Hirokami, T. Takahashi, M. Nagata, and T. Yamazaki, J . Org. Chem., 52, 2455 (1987). 336. Y. Okamoto, T. Osawa, Y. Kurasawa, T. Kinoshita, and K. Takagi, J . Heterocycl. Chem., 23, 1383 (1986). 337. T. Nishino, M. Kiyokawa, and K. Tokuyama, Tetrahedron Lett., 1969, 3553. 338. N. S. Kozlov, R. D. Sauts, and V. A. Serzhanina, Dokl. Akad. Nuuk SSSR, 282, 331 (1985). 339. R. Kiritani, T. Asano, S. Fujita, T. Dohmaru, and T. Kawanishi, J . Label. Compd. Radiopharm., 23, 207 (1986). 340. L. Strekowski, S. Chandrasekaran, Y.-H. Wang, W. D. Edwards, and W. D. Wilson, J . M e d . Chem., 29, 1311 (1986). 341. W. Pfleiderer, M. Schwarz, and H. Schirmeister, Chem. Scr., 26, 147 (1986). 342. L. Strekowski, A. Strekowska, R. A. Watson, F. A. Tanious, L. T. Nguyen, and W. D. Wilson, J . M e d . Chem., 30, 1415 (1987). 343. D. J. Brown, Chem. Aust., 1987. 116. 344. 345. 346. 347.

W. B. Cowden, I. A. Ramshaw, and P. Badenoch-Jones, M e d . Sci. Res., 15, 997 (1987). F. Yoneda, M. Koga, T. Ibuka, and Y. Yano, Chem. Pharm. Bull., 34, 2653 (1986). C. Seoane, J. L. Soto, and M. Quinteiro, J . Prakt. Chem., 328, 35 (1986). G. Eichberger, W. Hayden, W. Schwarz, and H. Griengl, Monatsh. Chem., 117, 385 (1986).

References 348. 349. 350. 351. 352. 353. 354. 355. 356. 357. 358. 359. 360. 361. 362.

1193

W. Wendelin, H. W. Schrarnrn, and A. Blasi-Rabassa, Monatsh. Chem., 116, 385 (1985). W. Wendelin and R. Riedl, Monatsh. Chem., 116, 237 (1985). A. M. Treston and W. D. Hooper, Arzneium.-Forsch., 35, 1627 (1985). U. Urleb, B. Stanovnik, and M. TiSler, Croat. Chem. Acta, 59, 79 (1986). J. Elguero, A. de la Hoz, and C. Pardo, Crout. Chem. Acta, 59, 153 (1986). G. N. Lipunova, N. A. Klyuev, Y. I. Aleksandrov, L. I. Sharova, V. G. Erernina, N. P. Bednyagina, L. I. Rusinova, and G. 1. Sigeikin, Zh. Obshch. Khim., 55, 1414 (1985). T. V. Stupnikova, T. V. Nuzhnaya, and N. A. Klyuev, Khim. Geterotsikl. Soedin., 1984, 1693. V. Gefenas and P. I. Vainilavichyus, Khim. Geterosikl. Soedin., 1984, 1429. 0. A. Zagulyaeva, 0. A. Grigorkina, V. I. Marnatyuk, and V. P. Marnaev, Khim. Geterotsikl. Soedin., 1984, 1537. V. G. Granik, L. V. Ershov, S. I. Grizik, and V. V. Chistyakov, Khim. Geterotsikl. Soedin., 1984, 1252. I. Z. Lulle, R. A. Paegle, and M. Y. Lidak, Khim. Geterotsikl. Soedin., 1984, 1260. K. V. Fedotov, N. N. Rornanov, and A. I. Tolrnachev, Khim. Geterotsikl. Soedin., 1984, 969. Y. Zhang, X. Hou, and C. Huang, Zhonyyuo Yaoke Daxue Xuebao, 20,35 (1989); Chem. Abstr., 111, 134074 (1989). N. KujundiiC, K. KovateviC, M. Jakovina, and B. GlunCiC, Croat. Chem. Actu, 61, 121 (1988). B. M. Khutova, S. V. Klyuchko, L. P. Prikazchikova, and V. M. Cherkasov, Khim.Geterotsikl. Soedin., 1985, 559. M. A. Mikhaleva, M. N. Repkova, and V. P. Marnaev, Khim. Geterotsikl. Soedin., 1985, 378.

363. 364. M. P. Nerneryuk, N. 1. Traven’, N. A. Nerscsyan, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1985, 131. 365. R. G. Melik-Ogandzhanyan, A. S. Gapoyan, V. E. Khachatryan, and V. S. Mirzoyan, Khim. Geterotsikl. Soedin., 1985, 678. 366. L. V. Ershov and V. G. Granik, Khim. Geterotsikl. Soedin., 1985, 646. 367. 0. A. Zagulyaeva, I. V. Sernushkina, and V. P. Marnaev, Khim. Geterotsikl. Soedin., 1985, 1695. 368. V. P. Khilya, M. Y. Kornilov, N. V. Gorhulenko, G. M. Goluhushina, E. N. Kovtun, N. V. Kolotusha, and G. V. Panasenko, Khim. Geterotsikl. Soedin., 1985, 1542. 369. R. G. Melik-Orandzhanyan, T. A. Khachaturyan, V. S. Mirzoyan, A. G. Manukyan, and G. M. Stepanyan, Khim. Geterotsikl. Soedin., 1985, 974.

370. E. L. Khanina, D. K. Mutsenietse, V. P. Kadysh, and G. Y. Dubur, Khim. Geterotsikl. Soedin., 1986, 1223. 371. E. I. Ivanov, A. A. Yavolovskii, V. V. Danilin, A. E. Tkach, and R. Y. Ivanova, Khim. Geterotsikl. Soedin., 1986, 1138. 372. 0.A. Zagulaeva, I. V. Sernushkina, and V, P. Marnaev, Khim. Geterotsikl. Soedin., 1986, 963. 373. P. Waring and W. L. F. Armarego, Eur. 1.Med. Chem., 22, 83 (1987). 374. S. P. Tumkyavichyus and P. I. Vainilavichyus, Khim.Geterotsikl. Soedin., 1986, 81 8. 375. N. B. Chernyshova and V. N. Shibaev, Khim. Geterotsikl. Soedin., 1986, 649. 376. I. I. Kuz’rnenko, Khim.Geterotsikl. Soedin., 1986, 710. 377. M. P. Nerneryuk, M. M. Likhovidova, I. D. Mitsev, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1986, 566. 378. Z. V. Stepanova, G . G. Skvortsova, V. K. Voronov, and A. V. Afonin, Khim. Geterotsikl. Soedin., 1986, 567. 379. M. A. Mikhaleva, G. A. Kolesnichenko, K. I. Rubina, Y . S. Gol’dberg, V. A. Savel’ev, L. Y. Leitis, M. V. Shimanskaya, and V. P. Marnaev, Khim. Geterotsikl. Soedin., 1986, 380. 380. M. P. Nemeryuk, A. L. Sedov, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1986, 416.

1194 381. 382. 383. 384. 385. 386. 387. 388. 389. 390. 391. 392. 393. 394. 395. 396. 397. 398. 399. 400. 401. 402. 403. 404. 405. 406. 407. 408. 409. 410. 411. 412. 413.

References J. Arukwe and K. Undheirn, Acta Chem. Scand., Ser. B, 40, 764 (1986). W. Zielinski, Heterocycles, 23, 1639 (1985). P. Matyus, L. Lowinger, and H. Warnhoff, Heterocycles, 23, 2057 (1985). J.-W. Chern, D. S. Wise, and L. B. Townsend, Heterocycles, 23, 2197 (1985). H. I. Skulnick and W. Wierenga, Heterocycles, 23, 1685 (1985). B. Stanovnik, U. Urleb, and M. Tiller, Heterocycles, 23, 2819 (1985). A. Knoll and J. Liebscher, J . Prakt. Chem., 327, 455 (1985). A. Kreutzberger and M. Sellheirn, Arch. Pharm. (Weinheim, Ger.), 318, 801 (1985). A. Kreutzberger and E. Kreutzberger, Arch. Pharm. (Weinheim,Ger.), 318, 821 (1985). F. Eiden and G. Patzelt, Arch. Pharm. (Weinheim,Ger.), 319, 242 (1986). W. L. F. Armarego, H. Taguchi, R. G. H. Cotton, S. Battiston, and L. Leong, Eur. J . M e d . Chem., 22, 283 (1987). A. Kreutzberger, A. Tantawy, and J. Stratmann, Arch. Pharm. (Weinheim,Ger.), 318, 1043 (198 5). E. L. Khanina, D. K. Mutsenietse, and G . Y . Dubur, Khim. Geterotsikl. Soedin., 1984, 529. R. Zirnon and A. Zejc, Acta Pol. Pharm., 42, 231 (1985); Chem. Abstr., 107, 7146 (1986). J. Kulig, B. Lcnarcik, and M. Rzepka, Pol. J . Chem., 60, 715 (1986). A. A. Avetisyan, A. V. Galstyan, and S. G . Melikyan, Arm. Khim. Zh., 38, 718 (1985); Chem. Abstr., 105, 78905 (1986). J. Riand, M.-T. Chenon, and N. Lurnbroso-Bader, J . Chem. Soc., Perkin Trans. 2,1987, 1551. L. Giamrnanco and F. P. Invidiata, Farmaco, Ed. Sci., 41, 225 (1986); Chem. Abstr., 105, 208826 (1986). H. Takahata, T. Nakajirna, and T. Yarnazaki, Synth. Comrnun., 14, 675 (1984). G. Uray and I. Kriessmann, Synthesis, 1984, 679. P. Vainilavicius, S. Tumkevicius, A. Deniene, V. Rocka, and N. Lauciuvene, Khim.-Farm. Zh., 18, 1335 (1984); Chem. Abstr., 102, 131987 (1985). H. Koroniak and K. Golankiewicz, Zesz. Probl. Postepow Nauk Roln., 271,201 (1984); Chem. Ahstr., 102, 220822 (1985). P. H. Boyle and R. J. Lockhart, Tetrahedron, 40, 879 (1984). Z. Machon and R. Jasztold-Howorko, Farmaco, Ed. Sci., 40, 695 (1985); Chem. Abstr., 105, 78894 (1986). V. N. Stepanova, A. E. Tsil'ko, I. A. Maretina, and S. A. Grigor'eva, Zh. Prikl. Khim. (Leningrad),57, 1801 (1984); Chem. Abstr., 102, 6388 (1985). B. V. Golomolzin, E. A. Tarakhtii, 1. P. Tregubenko, and N. M. Perova, Khim-Farm. Zh., 18, 1032 (1984); Chem. Abstr., 102, 62184 (1985). M. V. Korsakov, A. G. Ushrnorov, V. D. Yakovleva, E. P. Studentsov, and B. A. Ivin, Khim.Farm. Zh., 18, 1041 (1984); Chem. Abstr., 102, 78823 (1985). E. V. Vladzimirskaya, I. I. Soronovich, R. V. Rudyi, and L. G. Khveshchuk, Farm. Zh. (Kiev), 43 (1984); Chem. Abstr., 101, 23424 (1984). T. L. Antonova, N. A. Andrianova, L. N. Ivanovskaya, I. A. Avrutskaya, and M. Y. Fioshin, Elektrokhimiya, 20, 416 (1984); Chem. Abstr., 101, 7116 (1984). G. N. Krutovskikh, G. F. Gornaeva, L. P. Vartanyan, M. B. Kolesova, and N. V. Srnirnova, Khim.-Farm. Zh., 18, 325 (1984); Chem. Abstr., 101, 38420 (1984). R. Pelova, N. Spassovska, L. Maneva, and E. Golovinskii, Pharmazie, 39, 270 (1984); Chem. Abstr., 101, 171200 (1984). C. A. Maggiali, M. R. Mingiardi, G. Morini, and F. Ronchini, A c t a Nut. Ateneo Parmense, 19, 105 (1983); Chem. Abstr., 100, 103288 (1984). S. Robev, Dokl. Bolg. Akad. Nauk, 36, 1315 (1983); Chem. Abstr., 100, 191827 (1984).

References

1195

414. A. Kodzhikov and I. Pozharliev, Dokl. Bolg. Akad. N a u k , 36, 1191 (1983); Chem. Ahstr., 100, 191820 (1984). 415. A. S. Mikhailov, N. G. Pashkurov, V. S. Reznik, T. Y. Makhan’ko, V. V. Zobov, and S. M. Gorbunov, Khim.-Farm. Zh., 18, 64 (1984); Chem. Abstr., 100, 191823 (1984). 416. L. A. Grigoryan, M. E. Akopyan, and M. A. Kaldrikyan, Arm. Khim. Zh., 36,722 (1983);Chem. Ahstr., 100, 209739 (1984). 417. T. L. Antonova, L. N. Ivanovskaya, 1. A. Avrutskaya, M. A. Fioshin, and L. I. Gorbacheva, Elektrokhirnya, 20, 1126 (1984); Chem. Ahstr., 102, 6381 (1985). 418. G. A. Reynolds, G. H. Hawks, and K. H. Drexhage, J . Ory. Chem., 41, 2783 (1976). 419. X. Zhang, K. Wu, W. Zhou, Z . Xin, and K. Shu, Yiyao Gongye, 17, 485 (1986); Chem. Abstr., 106, 156405 (1987). 420. Y. Lin, J. Wu, H. Guo, G. Xu, J. Yao, J. Qian, S. Huang, and H. Fan, Guodeng Xuexiuo Huaxue Xuehas, 7, 600 (1986); Chem. Abstr., 106, 102222 (1987). 421. G. Stajer, A. E. Szabo, G. Bernath, and P. Sohar, Mayy. Kern. Foly., 92, 234 (1986); Chem. Ahstr., 106, 84543 (1987). 422. J. Filip and L. Bohacek, Radioisotopy, 25, 483 (1984); Chem. Abstr., 106, 84535 (1987). 423. V. A. Chuiguk and K. G. Nazarenko, Ukr. Khrm. Zh. (Russ. Ed.), 52, 82 (1986); Chem. Ahstr., 106, 32969 (1987). 424. G. Stijer, A. E. Szabo, J. Pintye, G. Bernith, and P. Sohir, J. Chem. Soc., Perkin Trans. I , 1985, 2483. 425. G. Stajer, A. E. Szabo, J. Pintye, and G. Bernith, Mugy. Kem. Foly., 92, 18 (1986); Chem. Ahstr., 106, 4967 (1987). 426. G. F. Shey, C. T. Chen, J. M. Horng, and C. H. Wang, Shih Ta Msueh Pao (Taipei), 29, 631 (1984); Chem. Abstr., 101, 230476 (1984). 427. P. K. Srivastava and U. K. Tiwari, J . Chem. Eng. Data, 30,133 (1985); Chem. Ahstr., 102,45872 (1 985). 428. J. Liu, B. Zhang, J. Sun, and Y. Chen, Yiyuo Gonyye, 20 (1984);Chem. Ahstr., 102,6403 (1985). 429. C. Fan, C. Mai, H. Yu, J. Xiang, Q. Ding, and R. Zhuo, Wuhan Daxue Xuebao Ziran Kexueban, 1984, 115; Chem. Abstr., 102, 6404 (1985). 430. Y. Gu, Y. Liu, and W. Jiang, Yiyao Gonyye, 1983, 5; Chem. Ahstr., 100, 174771 (1984). 431. B. Zhao and H. Chen, Shandong Yixueyuan Xuebao, 1983, 44; Chem. Ahstr., 100, 156562 (1984). 432. S. Wang and P. Zhang, Youji Huaxue, 1984, 111 ; Chem. Abstr., 101, 55042 (1984). 433. V. T. Kolesnikov, L. P. Slesarchuk, L. V. Vid, and A. P. Kartoflitskaya, Deposited Doc., SPSTL 1237 Khp-D82 (1982); Chem. Abstr., 101, 130655 (1984). 434. 435. 436. 437. 438. 439. 440. 441. 442.

D. Randles and W. L. F. Armarego, Eur. J . Biochem., 146,467 (1985). L. B. Clark and I. Tinoco, J . Am. Chem. Soc., 87, 11 (1965). E. Doody, E. R. Tucci, R. Scruggs, and N. C. Li, J . Inory. Nucl. Chem., 28, 833 (1966). S. F. Mason, J . Chem. Soc., 1957, 4874. E. S. Golovchinskaya, I. M. Ovcharova, and A. A. Cherkasova, Zh. Obshch. Khim., 30, 3332 (1960). W. D. Jones, E. W. Huber, J. M. Grisar, and R. A. Schnettler, J . Heterocycl. Chem., 24, 1221 (1987). K. Hirota, Y. Kitade, Y. Isobe, and Y. Maki, Heterocycles, 26, 355 (1987); Chem. Abstr., 107, 96673 (1987). Y. H. Kim and H. R. Kim, Heterocycles, 24, 3023 (1986); Chem. Abstr., 107, 77734 (1987). A. Alberola, L. F. Antolin, A. M. Gonzalez, M. A. Laguna, and F. J. Pulido, Heterocycles, 25, 393 (1987).

1196

References

443. E. C. Taylor, W. A. Ehrhart, C. 0.S. Tomlin, and J. B. Rampal, Heterocycles, 25, 343 (1987); Chem. Abstr., 107, 77746 (1987). 444. T. Fuchikami and I. Ojima, Tetrahedron Lett., 23, 4099 (1982). 445. A. de la Hoz, J. L. G. de Paz, E. Dietz-Barra, J. Elguero, and C. Pardo, Heterocycles, 24, 3473 (1986); Chem. Abstr., 107, 77740 (1987). 446. J. Csaszar, J. Morvay, and 0. Herczeg, Acta Phys. Chem., 31, 717 (1985); Chem. Abstr., 107, 7153 (1987). 447. U. Urleb, B. Stanovnik, V. Stibilj, and M. TiSler, Heterocycles, 24, 1899 (1986); Chem. Abstr., 106, 176311 (1987): 448. S. Caronna, 0. Migliara, and S. Petruso, Heterocycles, 24, 1377 (1986); Chem. Ahstr., 106 156392 (1987). 449. K. Hirota, J. Huang, H. Sajiki, and Y. Maki, Heterocycles, 24, 2293 (1986); Chem. Abstr., 106, 138382 (1987). 450. G . J. Koomen, H. Wolschrijn, J. B. M. van Rhijn, M. J. Wanner, and U. K. Pandit, Heterocycles, 24, 939 (1986); Chem. Abstr., 106, 67239 (1987). 451. P. K. Tripathy and A. K. Mukerjee, Indian J . Chem., Sect. B, 25, 1059 (1986); Chem. Ahstr., 107, 77743 (1987). 452. J. N. Vishwakarma, S. Apparao, H. Ila, and H. Junjappa, Indian J . Chem., Sect. B, 24, 466 (1985); Chem. Ahstr., 105, 6471 (1986). 453. P. B. Talukdar, S. K. Sengupta, and A. K. Datta, Indian J . Chem.,Sect. B, 25,275 (1986); Chem. Abstr., 106, 196371 (1987). 454. A. K. M. Gohar, F. F. Abdel-Latif, and H. A. A. Regaila, Indian J . Chem., Sect. B, 25, 767 (1986); Chem. Abstr., 106, 138385 (1987). 455. P. J. Bhuyan, R. C. Boruah, and J. S. Sandhu, Indian J . Chem., Sect. B, 24, 1166 (1985); Chem. Abstr., 106, 18476 (1987). 456. P. Neelakantan, R . Rani, M. F. Rahman, and U. T. Bhalerao, Indian J . Chem., Sect. B, 24, 1180 (1985); Chem. Abstr., 105, 226477 (1986). 457. S. Singh, G . P. Gupta, and K. Shanker, Indian J . Chem., Sect. B,24, 1094 (1985); Chem. Abstr., 105, 208820 (1986). 458. A. K. Sen and D. K. Sengupta, Indian J . Chem., Sect. B, 24, 535 (1985); Chem. Abstr., 104, 168430 (1986). 459. P. K. Das, G. B. Behera, A. K. Sahay, and B. K. Mishra, Indian J . Chem., Sect. B, 24, 437 (1985); Chem. Abstr., 104, 109568 (1986). 460. T. Fuchikami, A. Yamanouchi, and I. Ojima, Synthesis, 1984, 766. 461. Y. Wataya, Y. Sonobe, M. Maeda, Z. Yamaizumi, M. Aida, and D. V. Santi, J . Chem. Soc., Perkin Trunx. I , 1987, 2141. 462. E. A. Bliss, R. J. Griffin, and M. F. G. Stevens, J . Chem. Soc., Perkin Trans. 1, 1987, 2217. 463. M. D. Threadgill, R. J. Griffin, M. F. G. Stevens, and S. K. Wong, J . Chrm. Soc., Perkin Trans. I , 1987, 2229. 464. K. Senga, Yuki Gosei Kayaku Kyoknishi, 45, 318 (1987); Chem. Abstr., 107, 134230 (1987). 465. A. E. Frissen, A. T. M. Marcelis, G. Geurtsen, D. A. de Bie, and H. C. van der Plas, Recl. Trau. Chim. Pays-Bas, 106, 547 (1987). 466. T. Harayama, Y. Tezuka, T. Taga, and F. Yoneda, J . Chem. Soc., Perkin Trans. I , 1987, 75. 467. K. Tanaka, T. Kimura, T. Okada, X. Chen, and F. Yoneda, Chem. Pharm. Bull., 35, 1397 (1987). 468. K. Tanaka, X. Chen, T. Kimura, and F. Yoneda, Tetrahedron Lett., 28, 4173 (1987). 469. P. F. C. van der Meij, T. B. R. A. Chen, E. Hilhorst, E. R. de Waard, and U. K. Pandit, Tetrahedron, 43, 4015 (1987).

References

1197

470. H. R. Kim, N. J. Lee, and Y. H. Kim, Bull. Korean Chem. Soc., 8, 53 (1987). 471. M. A. Abhady, S. R. El-Ezhawy, Sh. M. Radwan, B. E. Bayoumy, and A. A. Khalaf, Egypt. J . Pharm. Sci.,27, 43 (1986). 472. H. Singh, N. Malhotra, and S. Aggarwal, Indian J. Chem., Sect. B, 26, 66 (1987). 473. C. Sun and R. Wang, Yiyao Gongye, 17, 538 (1986); Chem. Abstr., 107, 175975 (1987). 474. A. Wada, J. Yamamoto, and S. Kanatomo, Heterocycles, 26, 585 (1987). 475. A. Gangjee and K. Ohemeng, J . Heterocycl. Chem., 24, 123 (1987). 476. H. Singh and S. Kumar, J . Chem. Soc., Perkin Trans. 1, 1987, 261. 477. H. Gershon, A. T. Grcfig, and D. D. Clarke, J. Heterocycl. Chem., 24, 1243 (1987). 478. H.-W. Schmidt, G. Koitz, and H. Junek, J . Heterocycl. Chem., 24, 1305 (1987). 479. D. J. Buurman and H. C. van dcr Plas, J . Heterocycl. Chem., 24, 1377 (1987). 480. F. Lcngfeld and J. Stieglitz, Am. Chem. J., 15, 504 (1893);J. Chem. Soc., Abstr. (i), 64,631 (1893). 481. T. J. Delia and J. Niedzinski, J . Heterocycl. Chem., 24, 1421 (1987). 482. S. G. Rosenficld, H. P. Bcrcnds, L. Gelmini, and D. W. Stcphan, Inorg. Chem., 26,2792 (1987). 483. M. A. Romcro-Molina, M. D. Gutierrcz-Valero, R. Lopez-Garzon, J. M. Salas-Pcregrin, M. I. Arriortua, and F. J. Zuncga, Inorg. Chim. Acta, 136, 87 (1987). 484. T. C. W. Mak, C. H. L. Kcnnard, G. Smith, E. J. O’Reilly, D. S. Sagatys, and J. C. Fulwood, Polyhedron, 6, 855 (1987). 485. A. Kreutzberger, E. Kreutzberger, and D. Wiedcmann, Chem.-Zgt., 109, 153 (1985). 486. G . Singh, B. Deb, H. Ila, and H. Junjappa, Synthesis, 1987, 286. 487. G. Stajcr, A. E. Szabo, G . Bcrnith, and P. Sohar, Synthesis, 1987, 290. 488. M. A. Andriyankov, A. V. Afonin, N. N. Chipanina, G. A. Gavrilova, A. M. Shulunova, and G. G . Skvortsova, Izv. Sib. Ord. Akad. Nauk S S R , Ser. Khim. Nauk, 1986, 99; Chem. Ahstr., 107, 198220 (1987). 489. A. M. Karpeiskii, S. P. Stepanova, T. M. Filippova, and V. I. Gunar, Bioorg. Khim.,12, 1274 (1986); Chem. Abstr., 107, 198221 (1987). 490. V. M. Cherkasov, N. A. Kapran, I. A. Grafova, and E. A. Romanenko, Ukr. Khim.Zh. (Russ. Ed.), 52, 984 (1986); Chem. Abstr., 107, 198224 (1987). 491. W. Zhang, R. Li, and Q. Wang, Yaoxue Xuebao, 22, 136 (1987); Chem. Abstr., 107, 198241 (1 987). 492. I. A. Latham, G . J. Leigh, C. J. Pickctt, G. Huttner, I. Jibrill, and J. Zubieta, J . Chem. Soc., Dalton Trans., 1986, 1181. 493. A. D. Brewer, G. Ferguson, and M. Parvez, Acta Cryst. Sect. C, 43, 144 (1987). 494. S. Gupta and J. K. Dattagupta, Acta Cryst. Sect. C, 42, 1563 (1986). 495. C. Nofrc, A. Cicr, R. Chapurlat, and J.-P. Mareschi, Bull. Soc. Chim. Fr., 1965, 332. 496. B. Stanovnik, U. Urlcb, and M. TiSlcr, Monatsh. Chem., 118, 601 (1987). 497. B. Koren, B. Stanovnik, and M. TiSler, Heterocycles, 26, 689 (1987). 498. V. J. Ram, D. A. Vandcn Bcrghe, and A. J. Vlietinck, Liebiys Ann. Chem., 1987, 797. 499. T. Sakamoto, Y. Kondo, R. Watanabe, and H. Yamanaka, Chem. Pharm. Bull., 34, 2719 (1986). 500. A. L. Weis and R. Vishkautsan, Isr. J . Chem., 27, 105 (1986). 501. M. M . Bagga, B. Everatt, and I. G. Hinton, 1.Chem. Soc., Chem. Commun., 1987, 259. 502. J. Arukwc and K. Undhcim, Acta Chem. Scand., Ser. B, 40, 588 (1986). 503. V. A. Dyatlov, Y. G. Gololobov, P. V. Petrovskii, A. A. Espcnbctov, Y. T. Struchkov, 0. A. Zagulyaeva, and V. P. Mamaev, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 2491. 504. M. V. Korsakov, M. 0. Bystrova, T. A. Mironyuk, V. K. Kapustin, V. V. Leonov, A. Y. Likhachev, E. N. Sinotova, V. D. Ncfedov, and B. A. Ivin, Zh. Org. Khim., 23, 422 (1987).

1198

References

505. A. Joshi, J. Tonannavar, N. H. Ayachit, M. A. Shashidhar, and K. S. Rao, Spectrochim. Acta, Part A , 43, 1017 (1987). 506. S. C. Shim and E. Shin, Chem. Lett., 1987, 45. 507. M . Yokoyama, K. Sato, H. Tateno, and H. Hatanaka, J . Chem. Sac., Perkin Trans. I , 1987, 623. 508. L. I. Akhmetov, A. V. Ivanov, V. P. Savin, and V. P. Talzi, Zh. Org. Khim., 22, 1959 (1986). 509. T. Nagamatsu, C. Kawano, Y. Orita, and T. Kunieda, Tetrahedron Left.,28, 3263 (1987). 510. J. Krepelka, R. Kotva, J. Vachek, J. Holubek, and M. Melka, Cesk. Farm., 36,54 (1987); Chem. Ahsfr., 107, 236653 (1987). 511. G. G. Moskalenko, V. F. Sedova, and V. P. Mamaev, Izu. Akad. Nauk S S S R ,Ser. Khim., 1987, 701. 512. G. G. Moskalenko, V. F. Sedova, and V. P. Mamaev, Izu. Akad. Nauk S S S R ,Ser. Khim., 1987, 702. 513. N. Ogawa, T. Yoshida, E. Makino, E. Koshinaka, H. Kato, and Y. Ito, Yakugaku Zasshi, 107, 11 1 (1987). 514. G . G. Moskalenko, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1986, 1523. 51 5. V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1986, 1528 516. M. G. Voronkov, Z. V. Stepanova, A. V. Afonin, and V. K. Voronov, Izu. Akad. Nauk SSSR, Ser. Khim., 1987, 672. 517. K. Munesada and T. Suga, J . Org. Chem., 52, 5655 (1987). 5 18. A. Garcia-Martinez, A. Herrera-Fernandez, R. Martinez-Alvarez, E. Teso-Vilar, A. GarciaFraile, J. Osio-Barcina, and L. Pargada-Iglesias, Tetrahedron Lett., 28, 1929 (1 987). 519. H. G. Beaton, G. R. Willey, and M. G. B. Drew, J . Chem. Soc., Perkin Trans. 2, 1987, 469. 520. H. Gershon, A. Grefig, and D. D. Clarke, J . Heterocycl. Chem., 24, 205 (1987). 521. A. Lapucha, Synthesis, 1987, 256. 522. Y. Zhao, S. Liu, and H. Wang, Shandong YikeDaxue Xuehao, 24,32 (1986); Chem. Ahstr., 105, 172396 (1986); 108, 21831 (1988). 523. P. J. Garratt, C. J. Hobbs, C. S. J. Walpole, and R. Wrigglesworth, J . Chem. Soc., Chem. Commun., 1987,568; P. J. Garratt, C . J. Hobbs, and R. Wrigglesworth, J . Ory. Chem., 54, 1062 (1989). 524. Y. Inouye, K. Tezuka, W. Takeda, and S. Sugai, J . Fluorine Chem., 35, 275 (1987). 525. B. Abarca, C. Soriano, and G. Jones, J . Chem. Res., Synop. 158, Minipr. 1286 (1987). 526. J. Barluenga, M. Tomas, A. Ballesteros, and V. Gotor, Synthesis, 1987, 489. 527. Q. Wang, Y. Zhai, W. Zhang, P. Liu, J. Yao, and Y. Meng, Gaodeng Xuexiao Huaxue Xuebau 8, 438 (1987); Chem. Abstr., 108, 37777 (1988). 528. Y. Tominaga, Y. Matsuoka, S . Kohra, and A. Hosomi, Heterocycles, 26, 613 (1987). 529. M. H. Mohamed, N. S. Ibrahim, and M. H. Elnagdi, Heterocycles, 26, 899 (1987). 530. B. C. OReilly and K. S. Atwal, Heterocycles, 26, 1185 (1987). 531. K. S. Atwal, B. C. O’Reilly, J. Z. Gougoutas, and M . F. Mally, Heterocycles, 26, 1189 (1987). 532. P. B. Sulay and I. C. Ivanov, Liehigs Ann. Chem., 1987, 1101. 533. K. M. Ghoneim, F. El-Telbany, and K. Youssef, J . Indian Chem. Soc., 63, 914 (1986). 534. K. Breuker, H . van der Plas, and A. van Veldhuizen, Isr. J . Chem., 27, 67 (1986). 535. R. H. Wiley, J . Macrumol. Sci. Chem., A24, 1183 (1987). 536. J.-M. Delacotte, H. Parrot-Lopez, J. Renault, and S. Cros, J . Heterocycl. Chem., 24,571 (1987). 537. R. A. Zhuk, A. S. Ludzisha, and R. G. Kostyanocskii, Khim. Geterotsikl Soedin., 1987, 90. 538. L. T. Kaulinya and M. Y. Lidak, Khim. Geterotsikl. Soedin., 1987, 94.

References

1199

539. M. H. Elnagdi, M. R. H. Elmoghayar, and G. E. H. Elgemeie, Adu. Heterocycl. Chem., 41,319 (1987). 540. M. H. Elnagdi, M. R. H. Elmoghayar, and G. E. H. Elgemeie, Synthesis, 1984, 1. 541. M. H. Elnagdi, S. M. Sherif, and R. M. Mohareb, Heterocycles, 26, 497 (1987). 542. W. Ried and H. Nenninger, Chem.-Ztg., 111, 113 (1987). 543. N. S. Ibrahim, H. Z. Shams, F. A. E. M. Abd El-Aal, and M. H. Elnagdi, J . Prakt. Chem., 329, 552 (1987). 544. M. A. Armitage, M. M. Cashyap, and D. Saunders, J . Label. Compd. Radiopharrn, 24, 431 (1987). 545. G. Szilagyi, H. Wamhoff, and P. Sohar, Chem.-Ztg., 111, 144 (1987). 546. I . V. Semushkina, 0.A. Zagulyaeva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1987,663. 547. B. GaSpert and V. Skaric, Croat. Chem. Acta, 35, 171 (1963). 548. R. 0. Kochkanyan and S. S. Lukanyan, Khim. Geterotsikl. Soedin., 1987, 677. 549. A. Mo, Yiyao Gongye, 18, 267 (1987); Chem. Ahstr., 108, 94492 (1988). 550. F. J. Walker and K. G. Kraus, J . Heterocycl. Chem., 24, 1485 (1987). 551. A. V. El’tsov, K. L. Muravich-Aleksandr, and I. Y. Tsereteli, Zh. Org. Khim., 4, 110 (1968). 552. R. P. Holysz, R. V. Heinzelman, D. A. Shepherd, and P. H. Seay, US Pat. 2,987,516 (1961); Chem. Ahstr., 55, 23569 (1961). 553. D. Briel and G. Wagner, Z.Chem., 25, 364 (1985). 554. D. Briel and G. Wagner, Pharmazie, 40, 799 (1985). 555. B. Roth, B. S. Rauckman, R. Ferone, D. P. Baccanari, J. N. Champness, and R. M. Hydc, J . Med. Chem., 30, 348 (1987). 556. B. Roth and E. Aig, J . Med. Chem., 30, 1998 (1987). 557. B. Roth, D. P. Baccanari, C. W. Sigel, J. P. Hubbell, J. Eaddy, J. C. Kao, M. E. Grace, and B. S. Rauckman, J . Med. Chem., 31, 122 (1988). 558. B. GlunEii-, and K. KovaEcviC, Rad. Jugosl. Akad. Znan. Umjet., Kem., 5, 27 (1986). 559. B. Gluni-ii-, K. KovaEevii-, and N. Kujundiii-, Rad. Jugosl. Akad. Znan. Umjet., Kern., 5, 33 (1986). 560. L. A. Grigoryan, M. A. Kaldrikyan, Y. Z. Ter-Zakharyan, and R. V. Paronikyan, Arm. Khim. Zh., 40, 443 (1987); Chem. Ahstr., 108, 131739 (1988). 561. J. L. Kelley, M. P. Krochmal, J. A. Linn, E. W. McLean, and F. E. Soroko, J . Med. Chem., 31, 606 ( I 988). 562. L. Strekowski, R. A. Watson, and M. A. Faunce, Synthesis, 1987, 579. 563. S. A. L. Abdel-Hady, M. A. Badawy, A. M. Kadry, and M. A. N. Mosselhi, J . Heterocycl. Chem., 24, 1587 (1987). 564. H. Pischel, A. Holy, J. Vesely, G. Wagner, and D. Cech, Collect. Czech. Chem. Commun., 52, 2061 (1987). 565. K. Takagi, M. Tanaka, Y. Murakami, K. Ogura, K. Ishii, H. Morita, and T. Aotsuka, J . tieterocycl. Chem., 24, 1003 (1987). 566. C. Kashima, K. Harada, A. Katoh, M. Shimizu, and Y. Omote, Nippon Kagaku Kaishi,1987, 1194. 567. L. Strekowski, J. L. Mokrosz, F. A. Tanious, R. A. Watson, D. Harden, M. Mokrosz, W. D. Edwards, and W. D. Wilson, J . Med. Chem., 31, 1231 (1988). 568. J. Knabe and P. Lampen, Arch. Pharm. (Weinheim,Ger.), 320, 756 (1987). 569. J. Knabe and P. Lampen, Arch. Pharm. (Weinheirn, Ger.), 320, 719 (1987). 570. J. Knabe, H. P. Buch, and G. A. Kirsch, Arch. Pharm. (Weinheim, Ger.), 320, 323 (1987).

1200

References

571. L. Ernst, K. Gorlitzer, and C. Heinrici, Arch. Pharm. (Weinheim, Ger.), 320, 289 (1987). 572. J. Bagli, T. Bogri, B. Palameta, S. Rakhit, S. Peseckis, J. McQuillan, and D. K. H. Lee, J . Med. Chem., 31, 814 (1988). 573. W. B. Cowden, I. A. Clark, and N. H. Hunt, J . M e d . Chem., 31, 799 (1988). 574. E. L. Khanina, E. E. Liepin’sh, D. K. Mutsenietse, and G. Y. Dubur, Khim. Geterotsikl. Soedin., 1987, 668. 575. G. Westphal and H.-H. Stroh, Liehigs Ann. Chem., 711, 124 (1968). 576. H. Biltz and L. Loewe, J . Prakt. Chem., 121, 141, 225 (1934). 577. J. G . Nairn and H. Tieckelmann, J . Org. Chem., 25, 1127 (1960). 578. R. Hull, J . Chem. Soc., 1956, 2033. 579. K. Ikeda, T. Sumi, K. Yokoi, and Y. Mizuno, Chem. Pharrn. Bull., 21, 1327 (1973). 580. S. Bien, G . Salemnik, L. Zamir, and M. Rosenblum, J . Chem. Soc. (C), 1968, 496. 581. J. H. Chesterfield, D. T. Hurst, J. F. W. McOmie, and M. S. Tute, J . Chem. Soc., 1964, 1001. 582. D. T. Hurst, Aust. J . Chem., 36, 1659 (1983). 583. B. Graham, A. M. Griffith, C. S. Pease, and B. E. Christensen, J . A m . Chem. Soc., 67, 1294 (1 945). 584. M. Horiuchi and Y. Sawa, Yakuyaku Zasshi, 78, 137 (1958); Chem. Abstr., 52, 11072 (1958). 585. H.-G. Kaamirowski, G. Dietz, and E. Carstens, J . Prakt. Chem. [4], 19, 150 (1963). 586. J. H. Speer and A. L. Raymond, J . Am. Chem. Soc., 75, 114 (1953). 587. H. Bredereck, I. Hennig, and 0. Miiller, Chem. Ber., 86, 850 (1953). 588. E. S. Golovchinskaya, Zh. Obshch. Khim., 24, 136 (1954). 589. H. Bredereck, I. Hennig, W. Pfleiderer, and G. Weber, Chem. Ber., 86, 333 (1953). 590. E. S. Golovchinskaya and F. L. Kolodkin, Zh. Obshch. Khim., 29, 1650 (1959). 591. M. Sekiya and Y. Ozaki, Jap. Pat. 8621 (1967); Chem. Abstr., 67, 54153 (1967). 592. K. Fink, W. S. Adams, and W. Pfleiderer, J . B i d . Chem., 239, 4250 (1964). 593. T. Ueda, T. Tsuji, and H. Momona, Chem. Pharm. Bull., 11, 912 (1963). 594. K. Sirakawa, Yakugaku Zasshi, 73, 643 (1953); Chem. Abstr., 48, 9364 (1954). 595. K . Tanaka, T. Sugawa, R. Nakimori, Y. Sanno, Y. Ando, and K. Imai, Chem. Pharm. Bull., 12, 1024 (1964). 596. 597. 598. 599. 600.

B. R. Baker and K. Sachdev, J . Pharm. Sci., 53, 1020 (1964). D. S. Acker and J. E. Castle, J . Org. Chem., 23, 2010 (1958). H. Bredereck, I. Hennig, and W. Pfleiderer, Chem. Ber., 86, 321 (1953). V. I. Khmelevskii, Zh. Obshch. Khim., 31, 3123 (1961).

H. Bredereck, G. Kolb, W. Saum, and K. J. Schmidt, Rea. Chim., Acad. Repub. Pop. Roum., 7,

705 (1962); Chem. Abstr., 61, 4353 (1964). 601. D. J. Brown, R. L. Jones, A. M. Angyal, and G . W. Grigg, J . Chem. Soc., Perkin Trans. 1, 1972, 1819. 602. M. Ishidate and A. Yuki, Chem. Pharm. Bull., 8, 131 (1960). 603. G. L. Tong, W. W. Lee, and L. Goodman, J . Am. Chem. Soc., 86, 5664 (1964). 604. G. B. Elion, I. Goodman, W. Lange, and G. H. Hitchings, J . Am. Chem. Soc., 81, 1898 (1959). 605. C. V. Z. Smith, R. K. Robins, and R. L. Tolman, J . Chem. Sue., Perkin Trans. 1, 1973, 1855. 606. C:E. Liau, K. Yamashita, and M. Matsui, Agric. Biol. Chem., 26,624 (1962); Chem. Abstr., 59, 3921 (1963). 607. C. Temple, R. L. McKee, and J. A. Montgomery, J . Org. Chem., 30, 829 (1965). 608. D. T. Browne, J. Eisinger, and N. J. Leonard, J . Am. Chem. Soc., YO, 7302 (1968). 609. D. B. Lake and T. E. Londergan, J . Org. Chem., 19, 2004 (1954).

References

1201

610. J. F. W. Keana and F. P. Mason, J . Org. Chem., 35, 838 (1970). 61 1. D. T. Browne, in Synthetic P&cedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 96. 612. J. J. Traverso, E. B. Robbins, and C. W. Whitehead, J . Med. Pharm. Chem., 5, 808 (1962). 613. B. R. Baker and P. I. Almaula, J . Heterocycl. Chem., 1, 263 (1964). 614. R. Hull, B. J. Lovell, H. T. Openshaw, and A. R. Todd, J . Chem. Soc., 1947, 41. 615. Y. Nitta, K. Okui, and K. Ito, Chem. Pharm. Bull., 13, 557 (1965). 616. J. Nakazawa and M. Watatani, Takamine Kenkyusho Nempo, 12, 32 (1960); Chem. Ahstr., 55, 6491 (1961). 617. J. H. Lister, J . Chem. Soc., 1963, 2228. 618. E. W. Parnell, J . Chem. Soc., 1962, 2856. 619. G. D. Daves, R. K. Robins, and C. C . Cheng, J . Am. Chem. Soc., 84, 1724 (1962). 620. C. Temple, B. H. Smith, and J. A. Montgomery, J . Org. Chem., 40, 3141 (1975). 621. R. Duschinsky, in Nucleic Acid Chemistry, Part 1 (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 43. 622. J. A. Montgomery and C. Temple, J . Org. Chem., 25, 395 (1960). 623. Y. T. Ku and M. T. Tsah, J . Chin. Chem. Soc., 18, 202 (1951); Chem. Abstr., 46, 9106 (1952). 624. K.-Y. Zee-Cheng and C. C. Cheng, J . Med. Chem., 11, I107 (1968). 625. M. Ishidate and H. Yuki, Chem. Pharm. Bull., 8, 137 (1960). 626. S. Inoue, Chem. Pharm. Bull., 6, 346 (1958). 627. W. Traube, Liebigs Ann. Chem., 432, 266 (1923). 628. W. Wilson, .I. Chem. Soc., 1948, 1157. 629. W. Pfleiderer and M. Shanshal, Liebigs Ann. Chem., 726, 201 (1969). 630. C. Temple, B. H. Smith, and J. A. Montgomery, in Nucleic Acid Chemistry, Part I (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 47. 631. H. Kugita, M. Takeda, and T. Oine, Jap. Pat. 22,887 (1963); Chem. Ahstr., 60, 2966 (1964). 632. C. Temple, R. L. McKee, and J. A. Montgomery, J . Org. Chem., 28, 923 (1963). 633. S. Inoue, Chem. Phurm. Bull., 6, 343 (1958). 634. E. von Meyer, J . Prakt. Chem., [2], 30, 115 (1884). 635. J. I . DeGraw and V. H. Brown, J . Heterocycl. Chem., 13, 439 (1976). 636. J. Wojciechowski, Acta Pol. Pharm., 19, 121 (1962); Chem. Ahstr., 59, 1633 (1963). 637. Y. Nitta, K. Okui, and K. Ito, Jap. Pat. 220 (1965); Chem. Ahstr., 62, 11826 (1965). 638. F. E. Kempter, H. Rokos, and W. Pfleiderer, Chem. Ber., 103, 885 (1970). 639. E. A. Falco, G. B. Elion, E. Burgi, and G. H. Hitchings, J. A m . Chem. Soc., 74, 4897 (1952). 640. B. R. Baker, R. E. Schaub, and J. P. Joseph, J . Org. Chem., 19, 638 (1954). 641. W. Pfleiderer and F. E. Kempter, Chem. Ber., 103, 908 (1970). 642. E. S. Golovchinskaya, Zh. Obshch. Khim., 24, 146 (1954). 643. E. S. Golovchinskaya, Z h . Ohshch. Khim., 29, 1213 (1959). 644. W. Pfleiderer and K.-H. Schundehutte, Liebigs Ann. Chem., 612, 158 (1958). 645. F. L. Rose, J . Chem. Soc., 1952, 3448. 646. F. D. Asplin, E. Boyland, S. Sargent, and G. Wolf, Proc. R. Soc. London, Ser. B, 139,358 (1952). 647. M. Ruccia, N. Vivoni, and G. Cusmano, J . Heterocycl. Chem., 11, 829 (1974). 648. T. L. Cairns, A. W. Larchar, and B. C. MeKusick, J . Am. Chem. Soc., 74, 5633 (1952). 649. E. C. Taylor and R . W. Morrison, Angew. Chem., 76, 342 (1964). 650. H. Yamanaka, M. Komatsu, K. Tanji, S. Ogawa, S. Konno, and M. Mizugaki, Yukugaku Zasshi, 99, 342 (1979).

1202

References

R. Urban and 0. Schnider, Helv. Chim. Acta, 41, 1806 (1958). W. J. Irwin and D. G. Wibberley, J . Chem. Soc. ( C ) , 1967, 1745. W. Pfleiderer and G. Strauss, Liebigs Ann. Chem., 612, 173 (1958). V. F. Sedova, T. Y. Mustafina, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1981, 1515. H. Biltz and K. Strufe, Liebigs Ann. Chem., 426, 246 (1922). M. Ichiba, S. Nishigaki, and K. Senga, J . Org. Chem., 43, 469 (1978). E. G. Antonovich and M. A. Prokof’ev, Vestn. Mosk. Uniu., 10, No. 3, Ser. Fiz.-Mat. Estest. Nauk, No. 2, 57 (1955); Chem. Abstr., 49, 10972 (1955). 658. I. A. Brownlie, J . Chem. Soc., 1950, 3062. 659. W. Pfleiderer and E. Liedek, Liebigs Ann. Chem., 612, 163 (1958). 660. K. W. Merz and P. H. Stahl, Beitr. Biochem. Physiol. Naturstoflen, Festschr., 1965, 285; Chem. Abstr., 65, 3877 (1966). 661. N. E. Britikova, L. A. Belova, K. A. Chkhikvadze, and 0. Y. Magidson, Khim. Ceterotsikl. Soedin., 1973, 270. 662. C. D. Nenitzescu, M. Avram, and E. Sham, Rev. Chem., Acad. Repub. Pop. Roum., 1,73 (1956); Chem. Abstr., 51, 1973 (1957). 663. G. Sunagawa and M. Watatani, Jap. Pat. 5187 (1962); Chem. Abstr., 59, 642 (1963). 664. M. D. Fenn and J. H. Lister, J . Chem. Soc., Perkin Trans. I , 1974, 1300. 665. D. R. Osborne, W. T. Wieder, and R. Levine, J . Heterocycl. Chem., 1, 145 (1964). 666. R. Duschinsky, T. Gabriel, M. Hoffer, J. Berger, E. Titsworth, and E. Grunberg, J . M e d . Chem., 9, 566 (1966). 667. B. R. Baker and C . E. Morreal, J . Pharm. Sci., 52, 840 (1963). 668. B. R. Baker and H. S. Shapiro, J . Med. Chem., 6, 664 (1963). 669. B. R. Baker and C. E. Morreal, J . Pharm. Sci., 51, 596 (1962). 670. B. W. Bycroft, D. Cameron, and A. W. Johnson, J . Chem. Sue. (C), 1971, 3040. 671. A. Fujita, T. Yamamoto, S. Minami, and H. Takamatsu, Chem. Pharm. Bull., 13, 1183 (1965). 672. B. K. Snell, J . Chem. Soc. (C), 1968, 2358. 673. Schering A . G . , Neth. Pat. Appl. 299,218 (1965); Chem. Abstr., 64, 8202 (1966). 651. 652. 653. 654. 655. 656. 657.

674. T. S. Safonova, M. P. Nemeryuk, A. F. Keremov, N. I. Traven’, and L. A. Myshkina, Khim. Geterotsikl. Soedin., 1971, 423. 675. H. Bredereck, G. Kupsch, and H. Wieland, Chem. Ber., 92, 583 (1959). 676. 677. 678. 679. 680. 681. 682. 683. 684. 685. 686. 687. 688. 689.

D. J. Brown, W. C. Dunlap, G. W. Grigg, and J. Kelly, Aust. J . Chem., 30, 1775 (1977). T. Nishino, M. Kiyokawa, Y. Miichi, and K. Tokuyama, Bull. Chem. Soc. Jpn., 45,2010 (1972). H. Morimoto, N. Hayashi, T. Naka, and S. Kato, Chem. Ber., 106, 893 (1973). N. Katagiri, A. Koshihara, S. Atsuumi, and T. Kato, J . Org. Chem., 47, 167 (1982). A. R. Todd, F. Bergel, H. L. Fraenkel-Conrat, and A. Jacob, J . Chem. Soc., 1936, 1601. A. Albert and D. J. Brown, J . Chem. Soc., 1954, 2060. R. Hull, J . Chem. SOC.,1957, 4845. G. W. Miller and F. L. Rose, J . Chem. Soc., 1965, 3357. M. E. C. Biffin, D. J. Brown, and T.-C. Lee, Aust. J . Chem., 20, 1041 (1967). R. F. Evans and A. V. Robertson, Aust. J . Chem., 26, 1599 (1973). B. J. Whitlock, S. H. Lipton, and F. M. Strong, J . Org. Chem., 30, 115 (1965). K. Miura, Belg. Pat. 638,220 (1964); Chem. Abstr., 62, 9106 (1965). V. P. Mamaev and A. L. Vais, Khim. Geterotsikl. Soedin., 1975, 1555. H. J. den Hertog, H. C. van der Plas, M. J. Pieterse, and J. W. Streef, Recl. Trau. Chim. PaysBas, 84, 1569 (1965).

References 690. 691. 692. 693. 694. 695. 696. 697. 698. 699. 700. 701. 702. 703. 704. 705. 706. 707. 708. 709. 710. 711. 712. 713. 714. 715. 716. 717. 718. 719. 720. 721. 722.

1203

P. Lardenois, M. Stlim, and M. Selim, Bull. Soc. Chim. Fr., 1971, 1858. M . P. L. Caton, J . Chem. Soc. (C), 1969, 1269. R. Behrend, Liehigs Ann. Chem., 231, 248 (1885). W. J. Serfontein and H. H . E. Schroder, J . S. Afr. Chem. Inst., 19, 38 (1966); Chem. Ahstr., 65, 13700 (1966). J. L. Shim, R. Niess, and A. D. Broom, J . Org. Chem., 37, 578 (1972). T. Matsukawa and K. Sirakawa, Yakugaku Zasshi, 72, 913 (1952); Chem. Ahstr., 47, 6425 (1953). G. W. Kenner, C. B. Reese, and A. R . Todd, J . Chem. Soc., 1955, 855. T. Ueda and J. J. Fox, J . Org. Chem., 29, 1762 (1964). M. PrystaS and F. $ o m , Collect. Czech. Chem. Commun., 34, 2316 (1969). J. Baddiley, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1943, 571. G. A. Howard, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1945, 556. P. Nantka-Namirski and J. Wojcieschowski, Acta Pol. Pharm., 27, 341 (1970); Chem. Ahstr., 74, 141675 (1971). M. P. V. Boarland and J. F. W. McOmie, J . Chem. Soc., 1952, 4942. W. J. Hale and H. C. Brill, J . Am. Chem. Soc., 34, 82 (1912). R. 0. Roblin, P. S. Winnek, and J. P. English, J . Am. Chem. Soc., 64, 567 (1942). S. Tozaki, Rep. Sci. Res. Inst. (Tokyo),27, 401 (1951); Chem. Abstr., 47, 2181 (1953). J. Korman, US Pat. 2,944,057 (1960); Chem. Ahstr., 55, 587 (1961). J. J. Traverso and C. W. Whitehead, US Pat. 2,874,157 (1959); Chem. Abstr., 53, 12319 (1959).

D. J. Brown and L. N. Short, J . Chem. Soc., 1953, 331. A. P. Phillips and J. Mentha, J . Am. Chem. Soc., 76, 6200 (1954). H. L. Wheeler, J . Biol. Chem., 3, 285 (1907). N. Whittaker, J . Chem. Soc., 1951, 1565. R. F. Evans and J. S. Shannon, J . Chem. Soc., 1965, 1406. K. R. Huffman, F. C. Schaefer, and G. A. Peters, J . Org. Chem., 27, 551 (1962). R. Behrend and R. Grunewald, Liehigs Ann. Chem., 309, 256 (1899). 0. Piloty and C. Finckh, Liehigs Ann. Chem., 333, 71 (1904). M. Ridi and P. Papini, Gazz. Chim. Ital., 78, 13 (1948). L. F. Cavalieri, V. E. Blair, and G. B. Brown, J . Am. Chem. Soc., 70, 1240 (1948). J. F. W. McOmie and A. B. Turner, J . Chem. Soc., 1963, 5590. H. L. Wheeler and T. B. Johnson, Am. Chem. J., 29, 492 (1903). D. M. Brown, A. R. Todd, and S. Varadarajan, J . Chem. Sue., 1956, 2384. I. Wempen, G. B. Brown, T. Ueda, and J. J. Fox, Biochemistry, 4, 54 (1965). J. F. Codington, R. Fecher, M. H. Maquire, and R. Y. Thompson, and G. B. Brown, J . Am. Chem. Soc., 80, 5164 (1958). R . Nery, J . Chem. Soc. (C), 1969, 1860. A. D. Ward and B. R. Baker, J . M e d . Chem., 20, 88 (1977). P. Singh and L. Berlinquet, Can. J . Chem., 42, 605 (1964). H. Kaye and S.-H. Chang, Tetrahedron, 26, 1369 (1970). K. Yanagiya, M. Yasumoto, and M. Kurabayashi, Bull. Chem. Soc. Jpn., 46, 2804 (1973). W. Ried and J. Valentin, Liehigs Ann. Chem., 707, 250 (1967).

723. 724. 725. 726. 727. 728. 729. M. Robba, Ann. Chim. (Paris), 5, 351 (1960). 730. E. Bisagni, J.-P. Marquet, and J. Andre-Louisfert, Bull. Soc. Chim. Fr., 1969, 803. 731. J.-P. Marquet, J. Andre-Louisfert, and E. Bisagni, Bull. Soc. Chim. Fr., 1969, 4344.

1204

References

732. E. Bisagni, J.-P. Marquet, and J. Andre-Louisfert, Bull. Soc. Chim. Fr., 1969, 4338. 733. M. Gacek, L. Ongstad, and K. Undheirn, Acta Chem. Scand., Ser. B, 33, 150 (1979). 734. K. Takagi, G. Bastian, M. Hubert-Habart, and R. Royer, Eur. J . M e d . Chem-Chim. Ther., 9, 255 (1974). 735. V. M. Cherkasov, G. Y. Rernennikov, and E. A. Rornanenko, Khim. Geterotsikl. Soedin., 1978, 1389. 736. V. M. Cherkasov, G. Y, Rernennikov, and E. A. Rornanenko, Khim. Geterotsikl. Soedin., 1981, 823. 737. S. Niitsuma, T. Sakamoto, and H. Yamanaka, Heterocycles, 10, 171 (1978). 738. H. Yarnanaka, S. Konno, T. Sakamoto, S. Niitsuma, and S. Noji, Chem. Pharm. Bull., 29,2837 (1981). 739. H. Yamanaka, S. Ogawa, and S. Konno, Chem. Phurrn. Bull., 29, 98 (1981). 740. H. Wolfers, U. Kraatz, and F. Korte, Chem. Ber., 106, 874 (1973). 741. M. Gacek and K. Undheirn, Acta Chem. Scand., Ser. B, 33, 515 (1979). 742. K.-H. Lee, Y.-S. Wu, and I. H. Hall, J . M e d . Chem., 20, 911 (1977). 743. M. Hubert-Habart, C. P h e , and R. Royer, Chim. Ther., 8, 194 (1973). 744. B. Roth, R. Laube, M. Y. Tidwell, and B. S. Rauckman, J . Org. Chem., 45, 3651 (1980). 745. S. I. Zav’yalov, N. I. Aronova, N. N. Makhova, V. I. Gunar, L. F. Ovcchkina, N. A. Radionova, and E. P. Gracheva, Izv. Akud. Nauk SSSR, Ser. Khim., 1970, 11 19. 746. P. Lemaitre, G. Bastian, M. Hubert-Habart, and R. Royer, Eur. J . M e d . Chem-Chim. Ther., 11, 381 (1976). 747. B. A. Otter, I. M. Sasson, and R. P. Gagnier, J . Org. Chem., 47, 508 (1982). 748. W. Klotzer, Monatsh. Chem., 95, 1729 (1964). 749. H. Biltz and H. Paetzold, Liebigs Ann. Chem., 452, 67 (1927). 750. H. Andersag and K. Westphal, Err. Dtsch. Chem. Ges., 70, 2035 (1937). 751. R. Dohmori, R. Yoshirnura, S. Kitahara, Y. Tanaka, and T. Naito, Chem. Pharm. Bull., 18, 1908 (1970). 752. V. Krchiiak and Z. Arnold, Collect. Czech. Chem. Commun., 40, 1390 (1975). 753. B. K. Snell and R. Ghosh, S. Afr. Pat. 6701,8701 (1968); Chem. Abstr., 71, 3399 (1969). 754. Y. Kondo and B. Witkop, J . Am. Chem. Soc., 91, 5264 (1969). 755. R. Behrend and C. Hufschmidt, Liebigs Ann. Chem., 343, 155 (1905). 756. 0. Hoebel, Liebigs Ann. Chem., 353, 242 (1907). 757. L. G. Tirnoshinina and V. M. Vvedenskii, Khim. Geterotsikl. Soedin., 1973, 267. 758. R. Brossmer and E. Rohm, Hoppe-Seyler’s Z . Physiol. Chem., 348, 1431 (1967). 759. T. Stensrud, E. Bernatek, and M. Johnsgaard, Acta Chem. Scand., 25, 523 (1971). 760. D. V. Santi and A. L. Pogolotti, J . Heterocycl. Chem., 8, 265 (1971). 761. R. Brossmer and V. Eschenfelder, Liebigs Ann. Chem., 1974, 967. 762. K. Hirota, Y. Yamada, Y. Kitade, and S. Senda, J . Chem. Soc., Perkin Trans. I , 1981, 2943. 763. A. Y. Tikhonov, L. B. Volodarskii, 0.A. Vakolova, and M. I. Podgornaya, Khim. Geterotsikl. Soedin., 1981, 110. 764. R. R. Hunt, J. F. W. McOmie, and E. R. Sayer, J . Chem. Soc., 1959, 525. 765. D. V. Santi and A. L. Pogolotti, Tetrahedron Lett., 1968, 6159. 766. T. B. Johnson and L. H. Chernoff, J . Am. Chem. Soc., 35, 585 (1913). 767. T. B. Johnson and L. H. Chernoff, J . Biol. Chem., 14, 307 (1913). 768. R. S. Shadbolt and T. L. V. Ulbricht, J . Chem. Soc. (C), 1968, 1203. 769. R. Behrend and R. Griinnewald, Liebigs Ann. Chem., 323, 178 (1902).

References

1205

770. K. L. Nagpal, J . M e d . Chem., 15, 121 (1972). 771. R. Behrend and 0. Roosen, Ber. Dtsch. Chem. Ges., 21,999 (1888);Liebigs Ann. Chem., 251,235 ( I 889). 772. R. Behrend and H. Friedrich, Liebigs Ann. Chem., 344, 1 (1906). 773. H. Biltz, Liebigs Ann. Chem., 404, 180 (1914). 774. D. T. Hurst, J. F. W. McOmie, and J. B. Searle, J . Chem. Soc., 1965, 7116. 775. J.-L. Bcrnicr, A. Lefcbvre, J.-P. Henichart, R. Houssin, and C. Lespagnol, Bull. Soc. Chim. Fr., 1976, 616. 776. R. Marumoto and Y. Furukawa, Chem. Pharm. Bull., 25, 2974 (1977). 777. E. C. Taylor and E. E. Garcia, J . Org. Chem., 29, 2116 (1964). 778. R. S. Vartanyan and Z . V. Kazaryan, Arm. Khim. Zh., 34, 1023 (1981);Chem. Abstr., 96,181237 (1982). 779. R. S. Vartanyan, Z . V. Kazaryan, and S. A. Vartanyan, Khim. Geterotsikl. Soedin., 1982, 1558. 780. R. W. Luckenbaugh and E. J. Soboczenski, US Pat. 3,360,520 (1967); Chem. Ahstr., 69, 19201 (1968). 781. Hoffman-La Roche, Neth. Pat. Appl. 6,514,743 (1966); Chem. Ahstr., 65, 10597 (1966). 782. M. Fytelson and T. B. Johnson, J . Am. Chem. Soc., 64, 306 (1942). 783. M. Ridi, P. Papini, and S.Checchi, Gazz. Chim. Ital., 91, 973 (1961). 784. J. H. Dewar and G. Shaw, J . Chem. Soc., 1961, 3254. 785. T. Kato, H. Yamanaka, J. Kawamata, and H. Shimomura, Chem. Pharm. Bull., 17, 1889 ( 1969). 786. P. J. Barr, L. RohBEek, A. S. Jones, and R. T. Walker, .I. Label. Compd. Radiopharm., 16, 909 (1979). 787. J. Clark, 9. Parvizi, and R. Colman, J . Chem. Soc., Perkin Trans. I , 1976, 1004. 788. B. W. Langley, J . Am. Chem. Suc., 78, 2136 (1956). 789. H. Biltz and H. Wittek, Ber. Dtsch. Chem. Ges., 54, 1035 (1921). 790. R. Hull, J . Chem. Soc., 1958, 3742. 791. J. Goerdcler and D. Wieland, Chem. Ber., 100, 47 (1967). 792. T. Sakamoto, T. Ono, T. Sakasai, and H. Yamanaka, Chem. Pharm. Bull., 28, 202 (1980). 793. 1. I. Naumenko, M. A. Mikhalcva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1981, 958. 794. S. Senda, K. Hirota, and J. Notani, Cheni. Pharm. Bull., 20, 1380 (1972). 795. R. Lofthousc, G. Mackenzie, G. Shaw, and N. J. Cusack, J . Chem. Res., Synop. 56, Minipr. 664 (1978). 796. R. W. Lamon, J . Heterocycl. Chem., 6, 261 (1969). 797. M. Uher, D. Ilavsky, J. Foltin, and K. Skuarminova, Collect. Czech. Chem. Commun., 46,3128 ( 1 98 1). 798. M. Swierkowski and D. Shugar, J . M e d . Chem., 12, 533 (1969). 799. Hoffmann-La Roche, Br. Pat. 875,971 (1961); Chem. Ahstr., 57, 15221 (1962). 800. M. Tada, Chem. Lett., 1975, 129. 801. D. J. Brown and T. Sugimoto, J . Chem. Soc., Perkin Trans. I , 1972, 237. 802. J. B. Polya and G. F. Shanks, J . Chem. Soc., 1964, 4986. 803. D. J. Brown and T. Sugimoto, J . Chem. Soc. (C), 1971, 2616. 804. D. J. Brown and T. Sugimoto, Aust. J . Chem., 24, 633 (1971). 805. W. Kirkor and E. Koziowska-Gramsz, Rocz. Chem., 44, 137 (1970). 806. H. Maehr, M. Leach, and V. Toome, J . Hetrrocycl. Chem., 9, 1389 (1972). 807. M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 29, 121 (1964).

1206

References

808. G . Amiard and V. Torelli, Fr. Pat. 1,336,866 (1963); Chem. Abstr., 60, 3082 (1964). 809. C. W. Whitehead and J. J. Traverso, J . Am. Chem. Soc., 78, 5294 (1956). 810. M. Bobek, J. FarkaS, and F. Sorm, Collect. Czech. Chem. Cornmun., 34, 1690 (1969). 811. H. Ballweg, Tetrahedron Lett., 1968, 2171. 812. J. L. Wong and D. S. Fuchs, J . Org. Chem., 35, 3786 (1970). 8 13. A. Novatek and I. Hedrlin, Collect. Czech. Chem. Cornmun., 32, 1045 (1 967). 814. T. Sakamoto, T. Sakasai, and H. Yamanaka, Heterocycles, 9, 481 (1978). 815. L. B. Spector and E. B. Keller, J . Biol. Chem., 232, 185 (1958). 816. M. Hoffer, Chem. Ber., 93, 2777 (1960) 817. L. R. Buerger and T. B. Johnson, J . Am. Chem. Soc., 56, 2754 (1934). 818. A. Stein, H. P. Gregor, and P. E. Spoerri, J . Am. Chem. Soc., 78, 6185 (1956). 819. T. Benneche and K. Undheim, Acta Chem. Scand., Ser. B, 36, 529 (1982). 820. E. Ziegler and E. Steiner, Monutsh. Chem., 96, 548 (1965). 821. J. Goerdeler and J . Gnad, Chem. Ber., 98, 1531 (1965). 822. J. Goerdeler and H. W. Pohland, Chem. Ber., 96, 526 (1963). 823. P. Battesti, 0. Battesti, and M. Stlim, Bull. Soc. Chim. Fr., 1976, 1543. 824. P. Battesti, 0. Battesti, and M. Selim, Bull. Soc. Chim. Fr., 1976, 1549. 825. R. H. Lindsay, H. Y. Aboul-Enein, D. Morel, and S. Bowen, J . Pharm. Sci., 63, 1383 (1974). 826. H. Bredereck, G. Simchen, and P. Speh, Liebigs Ann. Chem., 737, 39 (1970). 827. I. K. Fel'dman, A. I. Berlin, and G. S. Semicheva, Mechenye Biol. Akt. Veshchestoa, Sb. Statei, No. 2, 43 (1966); Chem Ahsfr.,66, 65800 (1967). 828. E. Wittenburg, Chem. Ber., 101, 2132 (1968). 829. W. Bergmann and T. B. Johnson, Ber. Dtsch. Chem. Ges., 66, 1492 (1933). 830. N. V. Makarov and E. G. Popova, Sintez Prirodn. Soedin. ikh Analogol; i Fragmentov, Akad. Nauk SSSR,Otd. Obshch. i Tekhn. Khim., 273 (1965); Chem. Ahstr., 65, 2256 (1966). 831. R. C. Bleackley, A. S. Jones, and R. T. Walker, Tetrahedron, 32, 2795 (1976). 832. N. G. Kundu and S. A. Schmitz, J . Heterocycl. Chem., 19, 463 (1982). 833. L. 0.Ross, E. M. Acton, W. A. Skinner, L. Goodman, and B. R. Baker, J . Org. Chem.,26,3395 (1961). 834. M. Conrad and M. Guthzeit, Ber. Dtsch. Chem. Ges., 15, 2844 (1982). 835. N. S. Vul'fson and R. B. Zhurin, Zh. Obshch. Khim., 31, 281 (1961). 836. H. Bredereck, R. Gompper, and H. Herlinger, Chem. Ber., 91, 2832 (1958). 837. J. A. Baker and P. V. Chatfield, J . Chem. Soc. (C), 1970, 2478. 838. T. J. Bardos, M. P. Kotick, and C. Szantay, Tetrahedron Lett., 1966, 1759. 839. M. P. Kotick, C. Szantay, and T. J. Bardos, J . Org. Chem., 34, 3806 (1969). 840. R. Gompper, H. Euchner, and H. Kast, Liebigs Ann. Chem., 675, 151 (1964). 841. A. Giner-Sorolla and L. Medrek. J . Med. Chem., 9, 97 (1966). 842. H.-J. Lee and P. W. Wigler, Biochemistry, 7, 1427 (1968). 843. D. J. Brown and B. T. England, J . Chem. Soc. (C), 1967, 1922. 844. T. Benneche and K. Undheim, Acta Chem. Scand., Ser. B, 37, 115 (1983). 845. W. T. Caldwell and G. E. Jaffe, J . Am. Chem. Sac., 81,5166 (1959). 846. H. J. Minnemeyer, P. B. Clarke, and H. Tieckelmann, J . Org. Chem., 31, 406 (1966). 847. E. C. Taylor, R . J. Knopf, R. F. Meyer, A. Holmes, and M. L. Hoefle, J. Am. Chem. Soc., 82, 5711 (1960). 848. M. L. Hoefle and R. F. Meyer, US Pat. 2,949,466 (1960); Chem. Ahstr., 55, 589 (1961). 849. V. Papesch, US Pat. 3,299,066 (1967); Chem. Abstr., 66, 76028 (1967).

References

1201

850. C. W. Noell and R. K. Robins, .I. M e d . Pharm. Chem., 5, 558 (1962). 851. H. J. Thomas, C. Temple, and J. A. Montgomery, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorhach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 22. 852. J. Clark, B. Parvizi, and I. W. Southon, J . Chem. Soc., Perkin Trans. I , 1976, 125. 853. W. Stoll, Get. Pat. 938,846 (1956); Chem. Ahstr., 53, 6273 (1959). 854. B. A. Otter, A. Taube, and J. J. Fox, J . Ory. Chem., 36, 1251 (1971). 855. G. Strauss, Liebigs Ann. Chem., 638, 205 (1960). 856. V. Papesch, US Pat. 2,650,924 (1953); Chem. Ahstr., 48, 10786 (1954). 857. E. F. Schroeder, US Pat. 3,162,635 (1964); Chem. Abstr., 62, 13162 (1965). 858. V. Papesch, US Pat. 2,650,923 (1953); Chem. Ahstr., 48, 10784 (1954). 859. H. Fuchs and W. Pfleidercr, Heterocycles, 11, 247 (1978). 860. J. Reiter and L. Toldy, Acta Chim. Acad. Sci. Hung., 82, 99 (1974). 861. R. Majima, Ber. Dtsrh. Chem. Ges., 41, 176 (1908) 862. V. Hach, Chem. Listy, 45, 459 (1951); Chem. Abstr., 46, 7573 (1952). 863. B. K. Snell, R. S. Elias, and P. F. H. Freeman, S. Ajr. Pat. 67 01,373 (1968); Chem. Ahstr., 71, 91517 (1969)

C. W. Whitehead and J. J. Traverso, .I. Am. Chem. Soc., 77, 5867 (1955). Cilag-Chemie, Br. Pat. 859,716 (1961); Chem. Ahsrr., 55, 17669 (1961). C. W. Whitehead and J. J. Traverso, J . Am. Chem. Soc., 80, 2185 (1958). J. Goerdeler and W. Roth, Chem. Ber., 96, 534 (1963). V. A. Portnyagina and V. K. Karp, Ukr. Khim. Zh., 31, 215 (1965); Chem. Ahstr., 63, 1785 (1965). 869. W. T. Caldwell, W. Fiddler, and N. J. Santora, J . Med. Chem., 6, 58 (1963). 870. L. Doub, U. Krolls, J. M. Vandenbelt, and M. W. Fisher, J . Med. Chem., 13, 242 (1970). 871. D. L. Helfer, R. S. Hosmane, and N. J. Leonard, J . Org. Chem., 46, 4803 (1981). 872. H. J. Minnemeyer, J. A. Egger, J. F. Holland, and H. Tieckelmann, J . Org. Chem., 26, 4425 (1961). 873. Bayer, Ger. Pat. 156,055 (1904); Frdl., 7, 684 (1902-1904). 874. J. A. Montgomery and K. Hewson, J , Heterocycl. Chem., 2, 313 (1965). 875. K. K. Gauri, Ger. Pat. 1,248,665 (1967); Chem. Ahstr., 68, 21948 (1968). 876. K. K. Gauri, Arch. Pharm (Weinheim, Ger.), 306, 622 (1973). 877. K. K. Gauri, Br. Pat. 1,177,874 (1970); Chem. Ahstr., 72, 79080 (1970). 878. R. G. Melik-Ogandzhanyan, A. S. Gapoyan, V. E. Khachatryan, and V. S. Mirzoyan, Khim. Geterotsikl. Soedin., 1982, 118. 879. K. K. Gauri, Ger. Pat. 1,259,340 (1968); Chem. Abstr., 69, 27455 (1968). 880. G. W. Miller and F. L. Rose, J . Chem. Soc., 1963, 5642. 881. B. R. Baker, C. E. Morreal, and B.-T. Ho, J . Med. Chem., 6, 658 (1963). 882. H. Fuchs, M. Gottlieb, and W. Pfleiderer, Chem. Ber., 111, 982 (1978). 883. M . Gacek and K. Undheim, Acta Chem. Scand., Ser. B, 35,69 (1981). 884. M. J. Kalm, US Pat. 2,931,812 (1960); Chem. Abstr., 54, 17433 (1960). 885. M. J. Kalm, J . Org. Chem., 26, 2925 (1961). 886. E. F. Schroeder, US Pat. 3,361,745 (1968); Chem Abstr., 68, 114632 (1968). 887. V. N. Sokolova and 0. Y. Magidson, Khim. Geterotsikl. Snedin., 1968, 519. 888. J . A. Montgomery and K. Hewson, J . Med. Chem., 10, 665 (1967). 889. R. G. Melik-Ogandzhanyan, A. S. Gapoyan, V. 8. Khachatryan, and V. S. Mirzoyan, Khim. Geterotsikl. Soedin., 1982, 1686. 864. 865. 866. 867. 868.

1208

References

895. 896. 897. 898. 899. 900.

S. Giambrone, Boll. Sci. Fac. Chim. Ind. Bologna, 11, 86 (1953); Chem. Ahstr., 49, 4662 (1955). S. Senda, M. Honda, K. Maeno, and H. Fujimura, Chem. Pharm. Bull., 6, 490 (1958). S. Senda and H. Fujimura, Jap. Pat. 11,966 (1961); Chem. Ahstr., 56, 5978 (1962). S. Scnda and H. Fujimura, Jap. Pat. 8,177 (1961); Chem. Abstr., 58, 13968 (1963). J. P. English, J. H. Clark, J. W. Clapp, D. Seeger, and R. H. Ebel, J . Am. Chem. Soc., 68, 453 (1946). R. Behrend and 0. Biickendorf, Liebigs Ann. Chem., 385, 314 (191 I). J.-L. Fourrey, E. Estrabaud, and P. Jouin, J . Chem. Soc., Chem. Commun., 1975, 993. V. Papesch, US Pat. 2,673,848 (1954): Chem. Abstr., 49, 4016 (1955). B. R. Baker and G. D. F. Jackson, J . Pharm. Sci., 54, 1758 (1965). N. G. Kundu and S. A. Schmitz, J . Pharm. Sci., 71, 935 (1982). G. W. Miller and F. L. Rose, Br. Pat. 864,731 (1961); Chem. Abstr., 55, 24798 (1961).

901. 902. 903. 904. 905. 906. 907. 908.

V. Eschenfelder and R. Brossmer, Liehigs Ann. Chem., 1977, 1969. D. J. Brown, B. T. England, and J. S. Harper, J . Chem. Soc. (C), 1966, 1165. I. W. Southon and W. Pfleiderer, Chem. Her., 111, 1006 (1978). C. W. Whitehead, J . Am. Chem. Soc., 74, 4267 (1952). T. Ajello and A. Miraglia, Gazz. Chim. Ital., 78, 921 (1948). T. B. Johnson and A. J. Hill, J . Am. Chem. Soc., 36, 364 (1914). K. K. Gauri, Ger. Pat. 1,248,664 (1967); Chem. Abstr., 68, 21945 (1968). R. L. Shone, J . lieterocycl. Chem., 9, 1175 (1972).

909. 410. 911. 912. 913. 914.

K. Sasse, Leibigs Ann. Chem., 1976, 768. F. J. Dinan, H. J. Minnemeyer, and H. Tieckelmann, J . Urg. Chem., 28, 1015 (1963). B. Agai, G. Hornyik, and K . Lempert, Period. Polytech., Chem. Eny., 18, 47 (1974). H. Singh, S. Singh, and R. K. Mehta, Indian J . Chem., Sect. B, 14, 215 (1976). A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 12, 1418 (1964). A. Takamizawa and K. Hirai, Jap. Pat. 4343 (1967): Chem. Abstr., 67, 21925 (1967).

890. 891. 892. 893. 894.

915. R. Kitamurd, Yukugaku Zusshi, 57, 807; Supplement, p. 209 (1937).

A. Grussner, M. Montavon, and 0. Schnider, Monatsh. Chem., 96, 1677 (1965). T. B. Johnson and H. W. Haggard, J . Am. Chem. Soc., 37, 177 (1915). S. Basterfield, F. B. S. Rodman, and J. W. Tomecko, Can. J . Res., Sect. B, 17, 390 (1939). J. K. Elwood and J. W. Gates, J . Urg. Chem., 32, 2956 (1967). H. J. Minnemeyer, H. Tieckelmann, and J. F. Holland, J . M e d . Chem., 6, 602 (1963). M. de Nardo and F. Rubessa, Farmuco, Ed. Sci., 24, 512 (1969). M. V. Nadkarni and J. W. Jones, J. Am. Pharm. Assoc., Sci. Ed., 39, 297 (1950). D. J. Brown and M. N. Paddon-Row, J . Chem. Soc. (C), 1967,903. K. Nakashima and S. Akipama, Yakugaku Zasshi, 100, 515 (1980). M. Yoshimura, T. Hatdada, M. Deki, and M. Sugii, Yakugaku Zasshi, 96, 1094 (1976). Z. Budtiinski, L. Bruna, A. Svib, and A. eapek, Collect. Czech. Chem. Commun., 40, 1078 (1975). 927. K. Berg-Nielsen, T. Stensrud, and E. Bernatek, Acta Chem. Scand., 26, 15 (1972). 928. T. Sakuragi, Arch. Biochem. Riophys., 74, 362 (1958). 916. 917. 918. 919. 920. 921. 922. 923. 924. 925. 926.

929. J. HadaEek and E. RabuSic, Publ. Fac. Sci. Univ. Masaryk, 366, 323 (1955); Chem Ahstr., 50, 12066 (1956). 930. J. Lee, J . Am. Chem. Soc., 60, 993 (1938). 931. F. J. Dinan and T. J. Bardos, J . Med. Chem., 23, 569 (1980).

References

1209

932. G . D. Daves, C. W. Noell, R. K. Robins, H. C. Koppel, and A. G. Beaman, J . Am. Chem. Soc., 82, 2633 ( I 960). 933. G . M. Kheifets, N. V. Khromov-Rorisov, and L. A. Gavrilova, Zh. Org. Khim., 7, 199 (1971). 934. W. J. Croxal and M. F. Fegley, J . Am. Chem. Soc., 72, 2888 (1950). 935. H. Gershon, R. Parmegiani, and R. D’Ascoli, J . Med. Chem., 10, 113 (1967). 936. N. E. Britikova, K. A. Chkhikvadze, and 0. Y . Magidson, Khim. Geterotsikl. Soedin., 1966, 783; Chem. Ahstr., 61, 64344 (1967). 937. F. E. King and T. J. King, J . Chcm. Soc., 1947, 943. 938. H. Suter and E. Habicht, US Pat. 2,698,326 (1954); Chem. Ahstr., 50, 1093 (1956). 939. S. K. Chatterji and N. Anand, J . Sci. Ind. Res. (India),Seer. B, 18, 272 (1959); Chem. Abstr., 54, 6745 (1960). 940. D. M. Brown and C. M. Taylor, J. Chem. Soc., Perkin Trans. I , 1972, 2385. 941. D. M. Brown, P. F. Coe, and D. P. L. Green, J . Chem. Soc. (C), 1971, 867. 942. B. R. Baker and J. K. Coward, J . Pharm. Sci., 54, 714 (1965). 943. W. A. Summers, J. Y. Lee, and J. G. Burr, J . Orq. Chem., 40, 1559 (1975). 944. 0. E. Polansky and M. A. Grassberger, Monatsh. Chem., 94, 662 (1963). 945. D. M. W. Anderson, F. Bell, and J. L. Duncan, J . Chem. Soc., 1961, 4705. 946. M. E. C. Biffin, J. Miller, A. G. Moritz, and D. B. Paul, Aust. J . Chem., 22, 2561 (1969). 947. J. W. Ducker and M. J. Gunter, Aust. J . Chem., 26, 2567 (1973). 948. W. J. Middleton and V. A. Engelhardt, J . Am. Chem. Soc., 80, 2829 (1958). 949. G. N. Mitchell and R. E. McKee, J . Org. Chem., 39, 176 (1974). 950. D. E. Worrall, J . Am. Chem. Soc., 65, 2053 (1943). 951. T. B. Johnson and C. 0. Johns, Am. Chem. J., 34, 175 (1905). 952. Wellcome Foundation, Br. Pat. 990,857 (1965); Chem. Ahstr., 63, 4310 (1965). 953. E. F. Schroeder, US Pat. 2,731,465 (1956); Chem. Ahstr., 51, 1257 (1957). 954. R. Granados, F. Marquez, and M. Melgarejo, An. R . Soc. Esp. Fis. Quim., Ser. B, 58, 479 ( 1 962). 955. V. S. Reznik and Y . S. Shvetsov, I z u . Akad. Nauk SSSR, Ser. Khim.,1970, 1646. 956. G. R. Barker and N. G. Luthy, J . Chem. Soc., 1956, 917. 957. J. Wojciechowski, Acta Pol. Pharm., 18, 409 (1961); Chem. Abstr., 57, 11193 (1962). 958. H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, J . Org. Chem., 26, 792 (1961). 959. J. Jaeger, Liehigs Ann. Chem., 262, 365 ( 1 891). 960. C. C. Price, N. J. Leonard, and R. H. Reitsema, J . Am. Chem. Soc., 68, 766 (1946). 961. T. Nishiwaki, Chem. Pharm. Bull., 9, 38 (1961). 962. K. Hirota, K. A. Watanabe, and J. J. Fox, J . Org. Chem., 43, 1193 (1978). 963. T. B. Johnson and S. H. Clapp, J . Biol. Chem., 5, 49 (1908). 964. G. R. Barker, N. G. Luthy, and M. M. Dhar, J . Chem. Soc., 1954, 4206. 965. T. Hirayama, M. Kamada, M. Mimura, and H. Tsurumi, Chem. Pharm. Bull., 24, 507 (1976). 966. T. Hirayama, M. Kamada, M. Mimura, and H. Tsurumi, Heterocycles, 2, 461 (1974). 967. H. L. Wheeler and T. B. Johnson, Am. Chem. J., 31, 591 (1904). 968. D. J. Brown and J. S. Harper, J . Chem. Soc., 1961, 1298. 969. H. L. Wheeler and H. S. Bristol, Am. Chem. J., 33, 448 (1905). 970. T. B. Johnson, C. 0. Johns, and F. W. Heyl, Am. Chem. J., 36, 160 (1906). 971. H. Taguchi and S. Y .Wang, J . Org. Chem., 44,4385 (1979). 972. T. Hirayama, M. Kamada, H. Tsurumi, and M. Mimura, Chem. Pharm. Bull., 24, 26 (1976).

1210

References

973. T. Hirayama, M. Kamada, H. Tsurumi, and M. Mimura, Heterocycles 2, 451 (1974). 974. S. David and H. Hirshfeld, J . Chem. Soc. (C), 1969, 133. 975. T. Matsukawa, Yakugaku Zasshi, 62, 417; Supplement, p. 122 (1942); Chem. Ahstr., 45, 4723 (1951). 976. T. B. Johnson and C. F. Speh, Am. Chem. J., 38, 602 (1907). 977. M. A. Prokof’ev and Y. P. Shvachkin, Zh. Obshch. Khim., 25, 1218 (1955). 978. M. A. Prokof’ev, E. G. Antonovich, and Y. A. Shvachkin, Dokl. Akad. Nauk S S S R , 87, 783 (1952); Chem. Abstr., 48, 169 (1954). 979. D. I. Biskupskaya, V. N. Mikhilova, and I . K. Fel’dman, Khim.Geterotsikl. Soedin., 1968,159. 980. V. Rericha and M. Protiva, Chem. Listy, 44, 232 (1950); Chem. Zentr., 4138 (1952); Chem. Abstr., 45, 8017 (1951). 981. B. R. Baker, D. V. Santi, P. 1. Almaula, and W. C. Wekheiser, J . Med. Chem., 7, 24 (1964). 982. R. B. Angier and W. V. Curran, J . Org. Chem., 26, 1891 (1961). 983. K. Kondo, T. Sato, and K. Takemoto, Chem. Lett., 1973, 967. 984. B. E. Mandrichenko, 1. A. Mazur, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1974, 1140. 985. T. B. Johnson and F. W. Heyl, Am. Chem. J . , 38, 659 (1907). 986. A. Schrage and G. H. Hitchings, J . Org. Chem., 16, 1153 (1951). 987. Z. Foldi, G. von Foder, I. Demjtn, H. Szekeres, and I. Halmos, Ber. Dtsch. Chem. Ges., 75,755 (1942). 988. D. E. Worrall, J . Am. Chem. Soc., 40, 1133 (1918). 989. Bayer, Ger. Pat. 224,491 (1910); Frdl., 10, 1289 (1910-1912). 990. T. B. Johnson and E. F. Kohmann, Am. Chem. J . , 49, 184 (1913). 991. T.-C. Lee, G. Salemnick, and G. B. Brown, J . Org. Chem., 39, 2963 (1974). 992. M. Beran, A. tern?, J. Kiepelka, and J. Vachek, Collect. Czech. Chem. Commun., 48, 292 (1983). 993. M. M. Stimpson and M. A. Reuter, J . Am. Chem. Soc., 67, 2191 (1945). 994. A. S. Jones, P. Lewis, and S. F. Withers, Tetrahedron, 29, 2293 (1973). 995. R. S. Goody and R. T. Walker. J . Org. Chem., 36, 727 (1971). 996. T. B. Johnson, H. T. Peck, and J. A. Ambler, J . Am. Chem. Soc., 33, 758 (1911). 997. E. Allenstein and R. Fuchs, Chem. Ber., 101, 1244 (1968). 998. P. Schmidt, K. Eichenberger, and M. Wilhelm, Anyew. Chem., 73, 15 (1961). 999. W. Pfleiderer and H. Walter, Liehigs Ann. Chem., 677, 113 (1964). 1000. T. K. Liao and C. C. Cheng, J . Heterocycl. Chem., 1, 212 (1964). 1001. H. Rembold and H. J. Schramm, Chem. Ber., 96, 2786 (1963). 1002. E. C. Taylor, J. E. Loeffler, and B. Mencke, J . Org. Chem., 28, 509 (1963). 1003. T. Matsukawa and S. Yurugi, Yakugaku Zasshi, 72, 1885 (1952); Chem. Abstr., 47,9330 (1953). 1004. H. Kristinsson, J . Chem. Soc., Chem. Commun., 1974, 350. 1005. K. A. Chkhikvadze and 0. Y . Magidson, Zh. Obshch. Khim., 34, 2577 (1964). 1006. L. Doub and U. Krolls, J . Heterocycl. Chem., 7, 527 (1970). 1007. 2. BudESinsky, V. Bydiovsky, J. Kopeck?, J. Piikryl, and A. Svab, Cesk. Farm., 10, 14 (1961); Chem. Abstr., 55, 25972 (1961). 1008. H. Bredereck, G. Simchen, and M. Kramer, Chem. Ber., 106, 3743 (1973). 1009. M. A. Perez and J. L. Soto, Synthesis, 1981, 955. 1010. Z. BudESinsky and J. Kopeck?, Chem. Listy, 48, 1364 (1954); Collect. Czech. Chem. Commun., 20, 52 (1955). 1011. D. T. Hurst, Aust. J . Chem., 36, 1285 (1983).

References

1211

D. T. Hurst, lfeterocycles, 22, 79 (1984). R. Brossmer and E. Rijhm, Angew. Chem., 77, 260 (1965). T. Nishiwaki, Tetrahedron, 22, 2401 (1966). W. Pfleiderer and H. Fink, Liebigs Ann. Chem., 657, 149 (1962). F. L. Rose and D. J. Brown, J . Chem. Soc., 1956, 1953. A. F. Keremov, E. M. Peresleni, T. F. Vlasova, Y. N. Sheinker, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1977, 398. 1018. W. Klotzer and M. Herberz, Monatsh. Chem., 96, 1721 (1965). 1019. W. Klijtzer and M. Herberz, Monatsh. Chem., 96, 1567 (1965). 1020. A. A. Santilli, D. H. Kim, and S. W. Wanser, J . Heterocycl. Chem., 8, 445 (1971). 1021. J. Davoll and D. D. Evans, J . Chem. Soc., 1960, 5041. 1022. A. Stuart and H. C. S. Wood, J . Chem. Soc., 1963,4186. 1023. A. Stuart, D. W. West, and H. C. S. Wood, J . Chem. Soc., 1964, 4769. 1024. R. Lohrmann and H. S. Forrest, J . Chem. Sou., 1964,460. 1025. D. T. Browne, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 94. 1026. L. Bell, H. M. McGuire, and G. A. Freeman, J . Heterocycl. Chem., 20, 41 (1983). 1027. H. Bredereck, G. Simchcn, and A. A. Santos, Chem. Ber., 100, 1344 (1967). 1028. H. Bredereck, G. Simchen, H. Wagner, and A. A. Santos, Liebigs Ann. Chem., 766, 73 (1972). 1029. 0. P. Shkurko and V. P. Mamacv, Khim. Geterotsikl. Soedin., 1977, 821. 1030. G. D. Daves, F. Biocchi, R. K. Robins, and C. C. Cheng, J . Org. Chem., 26, 2755 (1961). 1031. H. 0. Hooper and P. G. Bray, J . Chem. Phys., 30, 957 (1959). 1032. J.-P. Gallemaers, D. Christophe, and R. Promel, Tetrahedron Lett., 1976, 693. 1033. R. B. Angier, J. W. Mowat, J. H. Boothe, C. W. Waller, J. Semb, B. L. Hutchings, E. L. R. Stokstad, and Y. Subba-Row, J . Am. Chem. Soc., 70, 1274 (1948). 1034. E. F. Schroeder, US Pat. 3,080,364 (1963); Chem. Ahstr., 59, 6420 (1963). 1035. V. A. Portnyagina and V. K. Karp, Ukr. Khim. Zh., 32, 1306; (1966); Chem. Ahstr., 67, 3058 ( 1 967). 1036. S. Inoue, Chem. Pharm. Bull., 6, 349 (1958). 1037. L. Marchal, R. Promel, R. H. Martin, and A. Cardon, Bull. Soc. Chim. Bely., 69, 177 (1960). 1038. E. C. Taylor, J. W. Barton, and W. W. Paudler, J . Org. Chem., 26, 4961 (1961). 1039. L. Marchal and R. Promel, Bull. Sue. Chim. Belg., 66, 406 (1957). 1040. I. Wempen and J. J. Fox, J . Med. Chem., 6, 688 (1963). 1041. W. R. Boon and T. Leigh, J . Chem. Sou., 1951, 1497. 1042. H. S. Forrest, R. Hull, H. J. Rodda, and A. R. Todd, J . Chem. Sue., 1951, 3. 1043. G. B. Elion and G. H. Hitchings, J . Am. Chem. Soc., 74, 3877 (1952). 1044. D. L. Ross, C. G. Skinner, and W. Shive, J . Org. Chem., 26, 3582 (1961). 1045. L. F. Ovechkina, V. I. Gunar, and S. I. Zav’yalov, Izu. Akad. Nauk S S S R , Ser. Khim., 1969. 2035. 1046. H. L. Wheeler and G. S. Jamieson, Am. Chem. J., 32, 342 (1904). 1047. J. Clark and I. W. Southon, J . Chem. Soc., Perkin Trans. I , 1974, 1814. 1048. Bayer, Ger. Pat. 206,453 (1909); Frdl., 9, 1005 (1908-1910). 1049. Merck, Ger. Pat. 162,336 (1905); Frdl., 8, 1145 (1905-1907). 1050. Merck, Ger. Pat. 158,591 (1903); Frdl., 7, 663 (1902-1904). 1051. R. Hugi and W. Pfleiderer, Liehigs Ann. Chem., 759, 76 (1972). 1052. G. Scarlat, Bul. Soc. Stiinti Bucuresci, 13, 155 (1904); Chem. Zentr., 1904, 11, 1497.

1012. 1013. 1014. 1015. 1016. 1017.

1212

References

1053. F. Comte, US Pat. 2,781,344 (1957); Chem. Ahstr., 51, 13942 (1957). 1054. J. Ruttink, Recl. Trav. Chim. Pays-Bas, 65, 751 (1946). 1055. Y. Furukawa and S. Shima, Chem. Pharm. Bull., 24, 979 (1976). 1056. V. Papesch, US Pat. 3,056,781 (1962); Chem. Ahstr., 58, 5702 (1963). 1057. D. Szlompek-Nesteruk, L. Znojek, and P. Kamimierczak, Przem. Chem., 42,226 (1963); Chem Abstr., 60, 4144 (1964). 1058. Y. Furukawa, 0. Miyashita, and S. Shima, Chem. Pharm. Bull., 24, 970 (1976). 1059. Y.-F. Chi and Y. C. Ling, Sci. Sin.,6, 633 (1957). 1060. J. Lifschitz, Ber. Dtsch. Chem. Ges., 55, 1619 (1922). 1061. J. Lifschitz and G. Beck, Helu. Chim Actu, 2, 133 (1919). 1062. V. Papesch and E. F. Schroeder, J . Org. Chern., 16, 1879 (1951). 1063. W. Stoll, US Pat. 2,749,343 (1956); Chem. Ahstr., 51, 1258 (1957). 1064. K. Sembritzki, Ber. Dtsch. Chem. Ges., 30, 1814 (1897). 1065. S. Ogawa and S. Kasahard, Vitamins, 28, 238 (1963); Chem. Ahstr., 60, 5494 (1964). 1066. S. Nishigaki, K. Senga, and F. Yoneda, Chem. Phurm. Bull., 19, 2259 (1971). 1067. V. Papesch and E. F. Schroeder, US Pat. 2,615,020 (1952); Chem. Abstr., 47, 10013 (1953). 1068. V. Papesch, US Pat. 3,190,881 (1965); Chem. Abstr., 63, 9964 (1965). 1069. S. Senda, K. Hirota, M. Suzuki, T. Asao, and K. Maruhashi, J. Chem. Soc., Chem. Commun., 1976, 731. 1070. H. Bredereck, H. Herlinger, and W. Resemann, Chem. Ber., 93, 236 (1960). 1071. H.-G. Kazmirowski, G. Dietz, and E. Carstens, J . Prakt. Chem. [4], 35, 136 (1967). 1072. H.-G. Kazmirowski, G. Carstens, and J. Donat, DDR Pat. 25,960 (1963); Chem. Ahstr., 62, 4041 (1965). 1073. W. Pfleiderer and K. Deckert, Chem. Ber., 1962, 95, 1597. 1074. H. Hirdno and H. Yonemoto, Yukuyaku Zasshi, 76,230 (1956); Chem. Ahstr., 50, 13042 (1956). 1075. H. Hirano and H. Yonemoto, Jap. Pat. 2222 (1957); Chem. Abstr., 52, 5489 (1958). 1076. H. Rokos and W. Pfleiderer, Chem. Ber., 104, 739 (1971). 1077. M. G. Tamari and J. Awruch, Tetrahedron, 24, 2611 (1968). 1078. Ciba, Br. Pat. 901,749 (1962); Chem Ahstr., 59, 1660 (1963). 1079. L. A. Gutorov and E. S. Golovchinskaya, Khim.-Farm. Zh., I, 23 (1967); Chem. Abstr., 66, 115688 (1967). 1080. M. D. Fenn and J. H. Lister, J . Chem. Soc., Perkin Truns. 2, 1976, 29.

1081. P. B. Russell, G. B. Elion, and G. H. Hitchings, J . Am. Chem. Soc., 71, 474 (1949). 1082. E. C. Taylor and A. McKillop, J . Ory. Chem., 30, 3153 (1965). 1083. B. Roth, J. M. Smith, and M. E. Hultquist, J . Am. Chem. Soc., 73, 2864 (1951). 1084. S. Yamada, I. Chibata, and D. Kiguchi, Tanabe Seiyaku Kenkyir Nempci, 2, 13 (1957); Chem. Ahstr., 52, 1177 (1958). 1085. Ciba, Br. Pat. 933,158 (1963); Chem. Ahstr., 61, 5665 (1964). 1086. A. Holy and Z. Arnold, Collect. Czech. Chem. Commun., 38, 1371 (1973). 1087. E. Habicht, Swiss Pat. 358,424 (1962); Chem. Abstr., 58, 3444 (1963). 1088. Ciba, Br. Pat. 893,235 (1962); Chem. Abstr., 58, 12581 (1963). 1089. D. G. Saunders, J . Chem. Soc., 1956, 3232. 1090. W. Pfleiderer, Chem. Ber., 92, 3190 (1959). 1091. K. J. M. Andrews, N. Anand, A. R. Todd, and A. Topham, J . Chem. Soc., 1949, 2490. 1092. B. Roth, US Pat. 2,577,039 (1951); Chem. Ahstr., 46, 5620 (1952). 1093. W. V. Curran and R. B. Angier, J . Ory. Chem., 28, 2672 (1963).

References

1213

1094. T. Sugimoto and S. Matsuura, Res. Bull. Nagoya Unit.., 12. 24 (1968). 1095. E. Carstens, H.-G. Kazmirowski, and J. Donat, DDR Pat. 23,546 (1962); Chem. Ahsrr., 58, 9103 (1963). 1096. E. Carstens, H.-G. Kazmirowski, and J. Donat, Ger. Pat. 1,130,812 (1962); Chem. Ahsrr., 57, 13781 (1962). 1097. J. Clark and M. S . Morton, J . Chem. Soc., Perkin Trans. I , 1974, 1812. 1098. G. B. Bennett, W. R. J. Simpson, R. B. Mason, R. J. Strohschein, and R. Mansukani, J . Org. Chem., 42, 221 (1977). 1099. R. Beythien, Liehiys Ann. Chem., 389, 214 (1912). 1100. F. G. Fischer, W. P. Neumann, and J. Roch, Lirhigs Ann. Chem., 633, 158 (1960). 1101. H. M. Gilow and J. Jacobus, J . Org. Chem., 28, 1994 (1963). 1102. H. Bredereck and U. Gotsmann, Chem. Ber., 95, 1902 (1962). 1103. Z. Kazimierczuk and W. Pfleiderer, Chem. Ber., 112, 1499 (1979). 1104. W. Pfleiderer, Liehigs Ann. Chem., 747, 11 1 (1971). 1105. C. 0. Johns and E. J. Baumann, J . B i d . Chem., 16, 135 (1913-1914). 1106. W. Traube, Ber. Dtsch. Chem. Ges., 33, 3035 (1900). 1107. F. F. Blicke and H. C. Godt, J . Am. Chem. Soc., 76, 2798 (1954). 1108. K. A. Chkhikvadze and 0. Y. Magidson, Med. Prom. S S S R , 12, No. 9,16 (1958);Chem. Ahstr., 53, 16146 (1959). 1109. G . E. K. Branch, J . Am. Chrm. Soc., 38, 2466 (1916). 1110. E. 1. Abramova and V. I. Khmelevskii, Med. Prom. S S S R , 18, No. 3, 35 (1964); Chem. Ahstr., 61, 1865 (1964). 1 1 1 1 . A. Lespagnol, M. Debaert, and N. Minard-Vaillant, Bull. Chim. Ther., 1970, 321. 11 12. C. Valenzuela-Calahorro, R. Galisteo-Tirado, and J. de D. Lopez-Gonzalez, An. Quim., 73, 1124 (1977). 1 1 13. K. Nakashima, Y. Nakano, and S . Akiyama, Yakuyuku Zasshi, 98, 1072 (1978). 1 1 14. E. Dyer, T. J. Nycz, and M. B. Long, J . Heterocycl. Chem., 9, 1267 (1972). 11 15. W. R. H. Wooldridge and R. Slack, J . Chem. Soc., 1962, 1863. 1116. H.-J. Schreider and W. Pfleiderer, Chem. Ber., 107, 3377 (1974). 1117. G. W. Kenner, B. Lythgoe, A. R. Todd, and A. Topham, J . Chem. Soc., 1943, 388. 1118. W. Huber and H. A. Holscher, Ber. Dtsch. Chem. Ges., 71, 87 (1938). 1 119. M . Horiuchi, Yakugaku Zasshi, 78, 1224 (1958); Chem. Ahstr., 53, 5272 (1959). 1120. E. Ochiai, K. Yanai, and T. Naito, Yakugaku Zasshi, 63, 25 (1943); Chem. Ahsir., 45, 609 (1 95 1). 1121. J. Biggs and P. Sykes, J . Chem. Soc., 1961, 2595. 1122. M. Ochiai, E. Mizuta, Y. Asahi, and K. Morita, Tetruhedron, 24, 5861 (1968). 1123. H. Graboyes, G. E. Jaffe, I . J. Pachter, J. P. Rosenbloom, A. J. Villani, J. W. Wilson, and J. Weinstock, J . Med. Chem., 11, 568 (1968). 1124. T. Kato and N. Katagiri, Chem. Pharm. Bull., 18, 2278 (1970). 1125. T. B. Johnson and I. Matsuo, J . Am. Chem. Soc., 41, 782 (1919). 1126. H. Bredereck and A. Edenhofer, Chem. Ber., 88, 1306 (1955). 1127. W. Pfleiderer and E. Liedek, Liebigs Ann. Chem., 612, 184 (1958). 1128. M. Maeda and Y. Kawazoe, Tetrahedron Lett., 1973, 2751. 1129. T. C. Thurber and L. B. Townsend, J . Heterocycl. Chem., 12, 711 (1975). 1130. R. Behrend and P. Henkel, Liehigs Ann. Chem., 378, 170 (1911). 1131. T. Ukai, Y. Yamamoto, and S . Kanetomo, Yakuyaku Zasshi, 74, 678 (1954); Chem Ahstr., 48, 10743 (1954).

1214

References

1132. S. Senda, K . Hirota, and T. Asao, Tetrahedron Lett., 1973, 2647. 1133. S. Senda, K. Hirota, and T. Asdo, Chem. Pharm. Bull., 23, 1708 (1975). 1134. K. Senga, M. Ichiba, and S. Nishigaki, J . Org. Chem., 43, 1677 (1978). 1135. J. Schlenker, Ber. Dtsch. Chem. Ges., 34, 2812 (1901). 1136. F. H. S. Curd and D. N. Richardson, J . Chem. Soc., 1955, 1853. 1137. G. P. Hager and C. Kaiser, J . Am. Pharm. Assoc., Sci. Ed., 44, 193 (1955). 1138. H. Biltz and P. Damm, Ber. Dtsch. Chem. Ges., 46, 3662 (1913). 1139. W. Pfleiderer and H. Ferch, Liebigs Ann. Chem., 615, 52 (1958). 1140. W. Techow, Ber. Dtsch. Chem. Ges., 27, 3082 (1894). 1141. F. F. Blicke, and R. L. Schaaf, J . Am. Chem. Soc., 78, 5857 (1956). 1142. R. G. Dickinson, N. W. Jacobsen, and I. H. Pitman, Aust. J . Chem., 31, 2023 (1978). 1143. A. D. Ainley, F. H. S. Curd, W. Hepworth, A. G. Murray, and C. H. Vasey, J . Chem. Soc., 1953, 59. 1144. G. J. Stacey, Br. Pat. 674,259 (1952); Chem. Abstr., 47, 4920 (1953). 1145. R. N. Lacey. J . Chem. Soc., 1954, 839. 1146. R. N. Lacey, Br. Pat. 699,812 (1953); Chem. Abstr., 49, 2527 (1955). 1147. K. Ganapathi, C. V. Deliwala, and M. V. Shirsat, Proc. Indian Acud. Sci., Sect. A , 16, 115 (1942); Chern. Abstr., 37, 1403 (1943). 1148. T. Kato, N. Oda, and I. Ito, Chem. Pharm. Bull., 25, 215 (1977). 1149. W. Braker, E. J. Pribyl, J. T. Sheehan, E. R. Spitzmiller, and W. A. Lott, J . Am. Chem. Soc., 69, 3072 (1947). 1150. F. Pohl, J . Prakt. Chem. [Z]. 77, 533 (1908). 1151. B. R. Baker, B.-T. Ho, and D. V. Santi, J . Pharm. Sci., 54, 1415 (1965) 1152. M. Muraoka, A. Takada, and T. Ueda, Chem. Pharm. Bull., 18, 261 (1970). 1153. T. Kulikowski, B. Zmudzka, and D. Shugar, Acta Biochim. Pol., 16, 201 (1969). 1154. F. H. S. Curd and D. N. Richardson, J . Chem. Soc., 1955, 1850. 1155. Y.-F. Chi and Y. C. Ling, Sci. Sin., 6, 643 (1957). 1156. Y.-F. Chi and Y. S. Kao, J . Am. Chem. Soc., 58, 772 (1936). 1157. F. L. Rose, J . Chem. Soc., 1954, 4116. 1158. H. Hirano and H. Yonemoto, Yakugaku Zasshi, 76,234 (1956); Chem. Ahstr., 50, 13043 (1956). 1159. H. R. Henze, W. J. Clegg, and C. W. Smart, J . Org. Chem., 17, 1320 (1952). 1160. F. Korte, W. Paulus, J. Vogel, and H. Weitkamp, Liebigs Ann. Chem., 648, 124 (1961). 11/51, F. Eiden and G. Gaughlitz, Arch. Pharm. (Weinheim, Ger.), 302, 297 (1969). 1162. K. Senga, F. Yoneda, and S. Nishigaki, J . Org. Chem., 36, 1829 (1971). 1163. E. Fischer and L. Ach, Liebigs Ann. Chem., 288, 157 (1895). 1164. T. J. Delia and R. Otteman, Heterocycles, 20, 1805 (1983). 1165. J. C. Davis, H. H. Ballard, and J. W. Jones, J . Heterocycl. Chem., 7, 405 (1970). 1166. M. R. Atkinson, G. Shaw, and R. N. Warrener, J . Chem. Soc., 1956, 4118. 1167. Geigy, Br. Pat. 1,136,686 (1968); Chem. Ahstr., 70, 68418 (1969). 1168. T. Nishikawa and H. Kawasaki, Rep. Res. Diu. Chem., Sci. Dept. Kyushu Uniu., 1, 191 (1950); Chem. Abstr., 46, 3950 (1952). 1169. H. Gehlen and B. Simon, Arch. Pharm. (Weinheim, Ger.), 303, 501 (1970). 1170. F. G. Fischer and J. Roch, Liebigs Ann. Chem., 572, 217 (1951). 1171. R. Behrend, Liehigs Ann. Chem., 240, 1 (1887). 1172. A. Kohler, Liebigs Ann. Chem., 236, 32 (1886). 1173. H. Goldner and L. Trampau, DDR Pat. 39,698 (1965); Chem. Abstr., 64, 2103 (1966).

References

1215

1174. K. Okui and M. Mizoguchi, Yakuyuku Zasshi, 92, 785 (1972). 1175. S. H. Chang, J. S. Kim, and T. S. Huh, Daehan Hwahuk Wwoejee,13, 177 (1969); Chem. Abstr., 71, 112880 (1969). 1176. F. G. Fischer, W. P. Neumann, and J. Roch, Chem. Ber., 85, 752 (1952). 1177. Boehringer, Br. Pat. 753,317 (1956); Chem. Ahstr., 51, 7441 (1957). 1178. F. G. Fischer, J. Roch, and W. P. Neumann, Ger. Pat. 927,631 (1955); Chem. Abstr., 52, 3874 (1958). 1179. R. J. Badger and G. B. Barlin, J . Chem. Soc., Perkin Trans. I, 1976, 151. 1180. Armour, Br. Pat. 831,067 (1960); Chem. Abstr., 54, 19727 (1960). 1181. V. Papesch and E. F. Schroeder, US Pat. 2,598,936 (1952); Chem. Abstr., 46, 10196 (1952). 1182. 1183. 1184. 1185. 1186. 1187. 1188.

B. R. Baker and H. J. Jordaan, J . Heterocycl. Chem., 3, 324 (1966). S. Borodkin, S. Jonsson, G. H. Cocolas, and R. L. McKee, J . Med. Chem., 10, 248 (1967). H. F. Mower and C. L. Dickinson, J . Am. Chem. Soc., 81, 4011 (1959). Schering, Br. Pat. 943,489 (1963); Chem. Ahstr., 60, 5518 (1964). H. Baganz, J. Ruger, and J. Kohtz, Chem. Ber., 98, 2576 (1965). T. Takahashi, T. Naito, and S. Inoue, Chem. Pharm. Bull., 6, 334 (1958). T. B. Johnson and E. V. McCollum, .I. B i d . Chem., 1,437 (1905-1906).

1189. M. Snyers, M. Donnez, D. Isbecque, T. Kakhanisky, and R. Promel, Bull. Soc. Chim. Bely., 82, 357 (1973). 1190. Bayer, Ger. Pat. 155,732 (1904); Frdl., 7, 683 (1902-1904). 1191. R. J. Badger, D. J. Brown, and J. H. Lister, J . Chem. Soc., Perkin Trans. I , 1974, 152. 1192. C. 0. Johns and E. J. Baumann, J . Biol. Chem., 15, 119 (1913). 1193. C. 0. Johns and E. J. Baumann, J . B i d . Chem., 15, 515 (1913). 1194. Y. Okumura, M. Konagai, and M. Shimomura, Rep. Fac. Sci., Shizuoka U n i ~ .4,, 43 (1969); Chem. Abstr., 73, 87893 (1970). 1195. S. Sugiura, E. Suzuki, T. Naito, and S. Inoue, Chem. Pharm. Bull., 16, 745 (1968). 1196. C. 0. Johns and B. M. Hendrix, J . B i d . Chem., 19, 25 (1914). 1197. J.-L. Bernier, A. Lefebvre, C. Lespagnol, J. Navarro, and A. Perio, t‘ur. J . Med. Chem.-Chim. Ther., 11, 381 (1976). 1198. L. Schuler and L. Surayni, Ger. Pat. 1,117,128 (1961); Chem. Ahstr., 56, 11600 (1962). 1199. R. N. Warrener, Chem. Ind. (London),381, 556 (1966). 1200. A. Y. Berlin and I. A. Korbukh, Khim. Geterotsikl. Soedin., 1971, 397. 1201. E. D. Bergmann, S. Cohen, and I. Shahak, J . Chem. Soc., 1959, 3278. 1202. J. A. Montgomery and K. Hewson, J . Ory. Chem., 26, 4469 (1961). 1203. R. W. Morrison, W. R. Mallory, and V. L. Styles, J . Org. Chem., 43, 4844 (1978). 1204. V. Papesch and E. F. Schroeder, US Pat. 2,602,795 (1952); Chem. Abstr., 47,4920 (1953). 1205. V. Papesch, US Pat. 2,596,041 (1952); Chem. Abstr., 47, 3353 (1953). 1206. M. V. Wagle and T. B. Panse, Pmc. Indian Acad. Sci., Sect. A, 68, 277 (1968). 1207. H. Bredereck, R. Gompper, F. Effenberger, K. H. Popp, and G . Simchen, Chem. Ber., 94, 1241 (1961). 1208. A. A. Ramsey, US Pat. 3,830,812 (1974); Chem. Ahstr., 81, 136174 (1974).

1209. J. Biggs and P. Sykes, J . Chem. Soc., 1959, 1849. 1210. M. A. Volodina, A. P. Terent’ev, V. A. Kudryashova, and V. G. Mishina, Zh. Obshch. Khim., 34, 473 (1964). 121 1. M. A. Volodina, A. P. Terent’ev, and V. A. Kudryashova, Khim. Geterutsikl. Soedin., Sb. 1, 1967, 369; Chem. Abstr., 70, 87719 (1969).

1216

References

1212. K. Ikawa and F. Takami, Ger. Pat. (Offen.) 2,152,742 (1972); Chem. Ahstr., 77, 34546 (1972). 1213. T. Ukai, Y. Yamamoto, and S. Kanetomo, Yukuguku Zusshi, 74, 674 (1954); Chem. Ahstr., 48, 10743 (1954). 1214. M. Conrad. Ger. Pat. 177,768 (1906); Frdl., 8, 1148 (1905-~1907). 1215. A. Byk, Ber. Dtsch. Chem. Ges., 36, 1915 (1903). 1216. L. N. Short and ’I W. Thompson, J . Chem. Soc., 1952, 168. 1217. J. M. Sprague, L. W. Kissinger, and R. M. Lincoln, J . Am. Chem. Soc., 63, 3028 (1941). 1218. T. B. Johnson and G. C. Bailey, J . Am. Chem. Soc., 35, 1007 (1913). 1219. T. D. Kulikowski and D. Shugar, Actu Biochim. Pol., 18, 209 (1971). 1220. S. Watanabe, T. Tsuji, and S. Toyoshima, Chem. Pharm. Bull., 11, 495 (1963). 1221. D. J. Brown, J . A p p l . Chem., 9, 203 (1959). 1222. H. Biltz and E. Peukert, Ber. Dtsch. Chem. Ges., 58, 2190 (1925). 1223. M. A. Perez, J. L. Soto, and J. R. Carrillo, Synthesis, 1983, 402. 1224. S. Borodkin, S. Jonsson, G. H. Cocolas, and R. L. McKee, J . M e d . Chem., 10, 290 (1967). 1225. R. G. Jones, E. C. Kornfeld, and K. C. McLaughlin, J . Am. Chem. Soc., 72, 3539 (1950). 1226. 0. Cervinka and P. Malod, Collect. Czech. Chem. Commun., 42, 3464 (1977). 1227. M. Delepine and K. A. Jensen, Bull. Soc. Chim. Fr. [ S ] , 6, 1663 (1939). 1228. A. von Merkatz, Ber. Dtsch. Chem. Ges., 52, 869 (1919). 1229. Schering, Ger. Pat. 174,940 (1906); Frdl., 8, 1112 (1905-1907). 1230. J. P. Jonak, S. F. Zakrzewski, L. H. Mead, and M. T. Hakala, J . Med. Chem., 13, 1170 (1970). 1231. W. Logemann, L. Caprio, and D. Artini, Farmuco, Ed. Sci., 12, 586 (1957); Chem. Abstr., 53, 18052 (1959). 1232. H. Ballweg, Liehigs Ann. Chem., 673, 153 (1964). 1233. 0:E. Schult’z and P. Warnecke, Arzneim.-Forsch., 17, 1060 (1967). 1234. T. B. Johnson and C. 0. Johns, J . Bid. Chem., 1, 305 (1905-1906). 1235. T. Nishikawa, Mem. Ryojun Coll. Eng. (lnouye Commem. Vol.),389 (1934); Chem. Abstr., 29, 2913 (1935). 1236. G. H. Hitchings and P. B. Russell, US Pat. 2,682,542 (1954); Chem. Abstr., 50, 8748 (1956). 1237. Wellcome Foundation, Br. Pat. 671,927 (1952); Chem. Ahstr., 47, 5457 (1953). 1238. N. W. Jacobsen, B. L. McCarthy, and S. Smith, Ausl. J . Chem., 32, 161 (1979). 1239. A. R. Todd, F. Bergel, and X. Karimullah, J . Chem. Soc., 1936, 1557. 1240. W. T. Caldwell and W. M. Ziegler, J . Am. Chem. Soc., 58, 287 (1936). 1241. D. H. Tedeschi, Belg, Pat. 657,135 (1965); Chem. Abstr., 64, 19637 (1966). 1242. T. B. Johnson and G. A. Menge, J . B i d . Chem., 2, 105 (1906). 1243. H. R. Henze and J. L. McPherson, J . Org. Chem., 18, 653 (1953). 1244. F. Craveri and G. Zoni, Boll. Sci. Fac. Chim. l n d . Bologna, 16, 138 (1958). 1245. E. A. Oostveen and H. C. van der Plas, Reel. Trau. Chim. Pays-Bus, 96, 183 (1977). 1246. M. Pesson, Bull. Soc. Chim. Fr., 1948, 963. 1247. R. G. Jarque and C. V. Sala, An. Fis. Quim., 42, 349 (1946); Chem. Ahstr., 41, 4797 (1947). 1248. W. Steinbuch, Helu. Chim. Actu, 31, 2051 (1948). 1249. A. Dornow and G. Petsch, Liehigs Ann. Chem., 588, 45 (1954). 1250. s. K. Chatterjee and N. Anand, J . Sci. lnd. R e x , Sect. B, 17, 63 (1958). 1251. Tanabe Seiyaku, Fr. Pat. 1,470,072 (1967); Chem. Ahstr., 68, 12990 (1968). 1252. S. G. Cottis and H. Tieckelmann, J . Org. Chem., 26, 79 (1961). 1253. H. L. Wheeler and C. 0. Johns, Am. Chem. J., 40, 233 (1908). 1254. H. L. Wheeler and C. 0. Johns, Am. Chem. J., 38, 594 (1907).

References

1217

1255. T. B. Johnson, Am. Chem. J., 34, 191 (1905). 1256. K. A. Watanabe, H. A. Friedman, R. J. Cushley, and J. J. Fox, J . Org. Chem., 31, 2942 (1966). 1257. Y. A. Levin, R. N. Platonova, and V. A. Kukhtin, Izu. Akad. Nauk S S S R , Ser. Khim., 1964, 1475. 1258. T. B. Johnson and N. A. Shepard, J . Am. Chem. Soc., 35, 994 (1913). 1259. A. S. Jones, P. Serafinowski, and R. T. Walker, Tetrahedron Lett., 1977, 2459. 1260. G. J. Durr, J . M e d . Chem., 8, 253 (1965). 1261. P. J. Atkins and C. D. Hall, J . Chem. Soc., Perkin Trans. 2, 1983, 155. 1262. Z. BudCSinsky, V. Jelinek, and J. Piikryl, Collect. Czech. Chem. Commun., 27, 2550 (1962). 1263. P. Langen, G. Etzold, D. Barwolf, and B. Preussel, Biochem. Pharmacol., 16, 1833 (1967). 1264. M . G. Biressi, M. Carissimi, and F. Ravenna, Gazz. Chim. Ital., 93, 1268 (1963). 1265. W. Klotzer and M. HerberL, Monatsh. Chem., 99, 847 (1968). 1266. Hoffmann-La Roche, Br. Pat. 806,584 (1958); Chem. Ahstr., 53, 16171 (1959). 1267. K. Undheim and M. Gacek, Acta Chem. Scand., 23, 294 (1969). 1268. S. Domb and W. Haevsermann, Ger. Pat. (Offen.) 2,436,149 (1975); Chem. Abstr., 83, 43374 ( 1 975). 1269. Y. Y. Polis, Zh. Org. Khim., 5, 580 (1969). 1270. F. Comte, US Pat. 2,542,395 (1951); Chem. Ahstr., 46, 1035 (1952). 1271. J. Hebky and J. Kejha, Chem. Listy, 48, 1709 (1954). 1272. B. Bobranski and Z . Synowiedski, J . Am. Pharm. Assoc., Sci. Ed., 37, 62 (1948); Chem. Ahstr., 42, 4124 (1948). 1273. Bayer, Ger. Pat. 148,208 (1903); Frdl., 7, 682 (1902-1904). 1274. J. Swidinsky and M. M. Baizer, US Pat. 2,785,162 (1957); Chem. Ahstr., 51, 12159 (1957). 1275. J. Swidinsky and M. M. Baizer, US Pat. 2,785,163 (1957); Chem. Abstr., 51, 12158 (1957). 1276. Y. Ozaki, Yukugaku Zasshi, 80, 1798 (1960); Chem. Ahstr., 55, 10456 (1961). 1277. G . Blankenhorn and W. Pfleiderer, Chem. Ber., 105, 3334 (1972). 1278. R. M. Cresswell, H. K. Maurcr, T. Strauss, and G. B. Brown, .1. Ory. Chem., 30, 408 (1965). 1279. W. Pfleidcrer, R. Mengel, and P. Hemmerich, Chem. Ber., 104, 2273 (1971). 1280. N. J. M. Birdsall, T.-C. Lee, T. J. Delia, and J. C. Parham, J . Org. Chem., 36, 2635 (1971). 1281. W. Pfleiderer and M. Rukwied, Chem. Ber., 94, 1 (1961). 1282. T. Sugimoto and S. Matsuurd, Res. Bull. Nagoya Uniu., 11, 87 (1967). 1283. G. B. Elion, J . Org. Chem., 27, 2478 (1962). 1284. W. Traube and F. Winter, Arch. Pharm. (Weinheim,Ger.), 244, 1 1 (1906); Chem. Zentr., I, 1336 (1906). 1285. H. Langner and V. Lebedew, Ger. Pat. 873,701 (1953); Chem. Zentr., 2917 (1954). 1286. W. Pfleiderer and W. Hutzenlaub, Chem. Ber., 106, 3149 (1973). 1287. M. Engelmann, Ber. Dtsch. Chem. Ges., 42, 177 (1909). 1288. W. Pfleiderer, Chem. Ber., 90, 2272 (1957). 1289. C. 0. Johns, J . B i d . Chem., 11, 73 (1912). 1290. C. 0. Johns, Am. Chem. J . , 41, 58 (1909). 1291. A. Albert, J . Chem. Soc. ( B ) ,1966, 438. 1292. L. B. Townsend and R. K. Robins, J . Orq. Chem., 27, 990 (1962). 1293. W. Traube, Ber. Dtsch. Chem. Ges., 33, 1371 (1900). 1294. K. L. Dille and B. E. Christensen, J . Am. Chem. Soc., 76, 5087 (1954). 1295. G. H. Hitching and G. B. Elion, US Pat. 2,724,711 (1955); Chem. Abstr., SO, 8748 (1956). 1296. C. 0. Johns, J . Bid. Chem., 11, 67 (1912).

1218

References

1297. L. F. Cavalieri and A. Bendich, J . Am. Chem. Soc., 72, 2587 (1950). 1298. W. Traube, Liebigs Ann. Chem., 331, 64 (1904). 1299. M. Y . Lidak, R. A. Paegle, M. G. Plata, and Y. P. Shvachkin, Khim. Geterotsikl. Soedin., 1971, 530. 1300. C . E. Morreal, J. H. Hall, and K. Eskins, J . Med. Chem., 10, 1176 (1967). 1301. C. Temple, C. L. Kussner, and J. A. Montgomery, J . Org. Chem., 36, 3502 (1971). 1302. E. Peters, H. J. Minnemeyer, A. W. Spears, and H. Tieckelmann, J . Org. Chem., 25, 2137 ( 1 960). 1303. K. Sirakawa and T. Tsujikawa, Takeda Kenkyusho Nempo, 22, 27 (1963). 1304. M. Miihlstadl, H. Krausmann, and G. Fischer, J . Prakt. Chem., 312, 254 (1970). 1305. C. Temple, C. L. Kussner, and J. A. Montgomery, J . Org. Chem., 34, 3161 (1969). 1306. Imperial Chemical Industries, Br. Pat. 876,601 (1959); Chem. Ahstr., 56, 4781 (1962). 1307. F. Yoneda, T. Nagdmura, and M. Kawamura, J. Chem. Soc., Chem. Commun., 1976, 658. 1308. E. Tenor and C.-F. Kroger, Chem. Ber., 97, 1373 (1964). 1309. A. V. Ivashchenko and V. M. Dziomko, Khim. Geterotsikl. Soedin.,1977, 1404. 1310. R. M. Cresswell and T. Strauss, J . Org. Chem., 28, 2563 (1963). 1311. V. Papesch, US Pat. 2,517,410 (1950); Chem. Ahstr., 45, 646 (1951). 1312. V. S. Reznik and N. G. Pashkurov, Izu. Akud. Nauk SSSR, Ser. Khim., 1966, 1613. 1313. M. V. Wagle and K. D. Kulkarni, Indian J . Chem., 1, 449 (1963). 1314. H. Wamhoff and C. Materne, Liebigs Ann. Chem., 754, 113 (1971). 1315. T. Imai, J . Biochem. (Tokyo), 25, 95 (1937); Chem. Abstr., 31, 4373 (1937). 1316. R. Lohrmann, J. M. Lagowski, and H. S. Forrest, J . Chem. Soc., 1964, 451. 1317. E. Uhlmann and W. Pfleiderer, Heterocycles, 15, 437 (1981). 1318. G. Shaw and R. N. Warrener, J . Chem. Soc., 1959, 50. 1319. A. Svab, Z. BudESinsky, and J. Vaviina, Collect. Czech. Chem. Commun., 32, 1582 (1967). 1320. A. H. Nathan and M. T. Bogert, J . Am. Chem. Soc., 63, 2567 (1941). 1321. J. D. Fissekis, A. Myles, and G . B. Brown, J . Org. Chem., 29, 2670 (1964). 1322. Y. Inaki, H. Futagdwa, and K. Takemoto, Org. Prep. Proced. Int., 12, 275 (1980). 1323. N. Ueda, K. Kondo, M. Kono, K. Takernoto, and M. Imoto, Makromol. Chem., 120,13 (1968). 1324. J. Davoll and D. H. Laney, J . Chem. Soc., 1956, 2124. 1325. A. D. McNaught and G. B. Brown, J . Org. Chem., 32, 3689 (1967). 1326. T. Okuda and C. C. Price, J . Org. Chem., 23, 1738 (1958). 1327. R. Hull, Br. Pat. 756,189 (1956); Chem. Ahstr., 51, 8812 (1957). 1328. N. Oda, Y. Kanie, and I. Ito, Yukugaku Zusshi, 93, 817 (1973). 1329. C. S. Miller, J . Am. Chem. Soc., 77, 752 (1955). 1330. F. Weygand and 0. P. Swoboda, Z . Naturforsch., Teil B, 11, 369 (1956); Chem. Zentr., 4072 (1957). 1331. T. L. V. Ulbricht and C. C. Price, J . Org. Chem., 21, 567 (1956). 1332. G. B. Barlin and W. V. Brown, J . Chem. Soc. (B),1967, 736. 1333. H. Iida, K. Shibazaki, and T. Imaizurni, Tokyo Yukka Daigaku Kenkyu Nempo, 11, 38 (1961); Chem. Ahstr., 58, 2450 (1963). 1334. T. L. V. Ulbricht, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1. (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 66. 1335. Y. P. Shvachkin and L. A. Syrtsova, Zh. Ohshch. Khim., 33, 3805 (1963). 1336. V. S. Reznik, N. G. Pashkurov, 0.A. Raevskii, and Y. S. Shvetsov, IZG.Akad. Nauk S S S R , Ser. Khim., 1969, 919.

References

1219

P. Chang and S.-L. Wu, Sci. Sin., 6, 279 (1957); Chem. Ahstr., 52, 2022 (1958). W. Klotzer, Monatsh. Chem., 95, 265 (1964). D. Davidson and M. T. Bogert, Proc. Natl. Acad. Sci. U S A , 18, 490 (1932). P. Chang and K.-C. Chiang, Sci. Sin., 6, 293 (1957); Chem. Ahstr., 52, 2023 (1958). J. F. W. McOmie and J. H. Chesterfield, Chem. Ind. (London), 1956, 1453. T. B. Johnson and C. 0. Johns, Am. Chem. J., 34, 554 (1905). J. H. Chesterfield, J. F. W. McOmie, and M. S. Tute, J . Chem. Soc., 1960, 4590. A. Cier, A. Lefier, M. A. Ravier, and C. Nofre, C. R . Acad. Sci., 254, 504 (1962). R. C . Moschel and E. J. Behrman, J . Org. Chem., 39, 1983 (1974). D. J. Brown and M . N. Paddon-Row, J . Chem. SOC.(C), 1966, 164. E. Hannig and E. Baselt, Pharmazie, 23, 614 (1968). Y. M. Abu-Zeid, Z. Abu-Elala, and K. M. Ghoneim, J . Pharm. Sci. U A R , 4,41 (1963); Chem. Ahstr., 63, 18078 (1965). 1349. E. Biittner, Ber. Dtsch. Chem. Ges., 36, 2227 (1903). 1350. P. K. Chang and A. D. Welch, J . Med. Chem., 6,428 (1963).

1337. 1338. 1339. 1340. 1341. 1342. 1343. 1344. 1345. 1346. 1347. 1348.

1351. T. Maeda, I. Watanabe, I. Kamoi, M. Kojima, K. Kudo, and K. Nagao, Radioisotopes, 19, 190 (1970); Chem. Ahstr., 74, 39059 (1971). 1352. K. A. Watanabe, T.-L. Su, R. S. Klein, C. K. Chu, A. Matsuda, M. W. Chun, C. Lopez, and J. J. Fox, J . Med. Chem., 28, 152 (1983). 1353. W. Pfleiderer and R. Mengel, Chem. Ber., 104, 3842 (1971). 1354. Merck, Br. Pat. 911,551 (1962); Chem. Abstr., 58, 10214 (1963). 1355. E. C. Taylor and R. W. Morrison, J . Org. Chem., 32, 2379 (1967). 1356. B. Roth, E. Aig, K. Lane, and B. S. Rauckman, J . Med. Chem., 23, 535 (1980). 1357. N. Yamaoka, Y. Tsukamoto, and K. Aso, Nippon Nogei Kagaku Kaishi, 37,626 (1963); Chem. Ahstr., 63, 9942 (1 965). 1358. T. Tsuji, S. Watanabe, Y. Nakadai, and S. Toyoshima, Chem. Pharm. Bull., 10, 9 (1962). 1359. H. Wamhoff and F. Korte, Chem. Ber., 99, 872 (1966). 1360. H. Bretschneider, W. Richter, and W. Klotzer, Monatsh. Chem., 96, 1661 (1965). 1361. T. Naito, M. Hirata, and T. Kobayashi, Jap. Pat. 7766 (1965); Chem. Ahstr., 63, 1801 (1965). 1362. M. Hirata, S. Nagasaki, S. Isoda, N. Nakazawa, T. Kobayashi, Y. Oshima, and T. Naito, Yukugaku Zasshi, 87, 410 (1967). 1363. Bayer, Ger. Pat. 208,639 (1908); Frdl., 9, 1006 (1908-1910). 1364. E. Buhler and W. Pfleiderer, Chem. Ber., 99, 2997 (1966). 1365. A. F. Keremov, M. P. Nemeryuk, 0. L. Aparnikova, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1977, 1332. 1366. N. Okuda and I. Kuniyoshi, Yakugaku Zasshi, 82, 1035 (1962). 1367. E. A. Falco, P. B. Russell, and G. H. Hitchings, J . Am. Chem. Soc., 73, 3753 (1951). 1368. Z. Budtiinsky, J. Kopecky, and J. Piikryl, Czech. Pat. 104,969 (1962); Chem. Ahstr., 60, 8043 ( 1 964). 1369. B. Alhede, Dan. Pat. 116,591 (1970); Chem. Abstr., 73, 109792 (1970). 1370. K. Katsuno and K. Kubo, Jap. Pat. 12,424 (1967); Chem. Abstr., 68, 21949 (1968). 1371. W. Pfleiderer and H. Zondler, Chem. Ber., 99,3008 (1966). 1372. T. Rowan and H . C. S. Wood, J . Chem. Soc. (C), 1968,452. 1373. D. J. Brown and N. W. Jacobsen, J . Chem. Soc., 1961, 4413. 1374. W. E. Fidler and H. C. S. Wood, J . Chem. Soc., 1957, 4157. 1375. H. J. Borowitz, S. M. Bloom, J. Rothschild, and D. B. Sprinson, Biochemistry, 4, 650 (1964).

1220 1376. 1377. 1378. 1379. 1380. 1381.

References W. Pfleiderer and G. Niibel, Liebigs Ann. Chem., 631, 168 (1960). A. J. Birch and C. J. Moye, J . Chem. Soc., 1958, 2622. W. Pfleiderer and F. Sagi, Liebigs Ann. Chem., 673, 78 (1964). D. J. Brown, J . Appl. Chem., 7, 109 (1957). N. W. Jacobsen, J . Chem. Soc. (C), 1966, 1065. R. K. Robins and H. H. Lin, J . Am. Chem. Soc., 79, 490 (1957).

1382. R. Kotva, A. & m y , M. Semonsk?, J. Vachek, and V. Jelinek, Collect. Czech. Chem. Commun., 34, 21 14 (1969). 1383. D. J. Brown, J . Appl. Chem., 5, 358 (1955). 1384. C. 0. Johns, J . Biol. Chem., 9, 161 (1911). 1385. J. J. Fox and D. van Praag, J . Org. Chem., 26, 526 (1961). 1386. F. Bergmann, M. Kleincr, Z. Neiman, and M. Rashi, Isr. J . Chem., 2, 185 (1964). 1387. C . D. May and P. Sykes, J . Chem. Sue. (C), 1966, 649. 1388. H. Andersag and K. Westphal, US Pat. 2,377,395 (1945); Chem. Abstr., 40, 98 (1946). 1389. A. H. Goldberg and W. Kelly, J . Chem. Soc., 1947, 1372. 1390. Kodak, Belg. Pat. 587,287 (1960); Chem. Abstr., 56, 2320 (1961). 1391. J. W. Clark-Lewis and M. J. Thompson, J . Chem. Soc., 1959, 2401. 1392. H. Bredereck, F. Effenberger, and R. Sauter, Chem. Ber., 95, 2049 (1962). 1393. S. Hiinig, Liebigs Ann. Chem., 574, 106 (1951). 1394. S. D. Verma and A. N. Dey, J . Indian Chem. Soc., 40, 283 (1963). 1395. A. Litzinger and T. B. Johnson, J . Am. Chem. Soc., 58, 1936 (1936). 1396. W. Hutzenlaub and W. Pfleiderer, Liehigs Ann. Chem., 1979, 1847. 1397. W. Pfleidercr and G. Nubel, Liebigs Ann. Chem., 647, 155 (1961). 1398. G. Nubel and W. Pfleiderer, Chem. Ber., 98, 1060 (1965). 1399. J. Wojciechowski, Pol. Pat. 42,976 (1960); Chem. Abstr., 55, 27382 (1961). 1400. D. J. Brown, P. W. Ford, and K. H. Tratt, J . Chem. Soc. (C), 1967, 1445. 1401. A. Vincze and S. Cohen, Isr. J . Chem., 4, 23 (1966). 1402. C. 0. Johns, J . B i d . Chem., 14, l(1913). 1403. D. J. Brown and L. G. Stephanson, Aust. J . Chem., 27, 1371 (1974). 1404. C . 0. Johns, J . Biol. Chem., 11, 393 (1912). 1405. D. J. Brown, B. T. England, and J. M. Lyall, J . Chem. Soc. (C), 1966, 226. 1406. P. Nesbitt and P. Sykes, J . Chem. Soc., 1954, 3057. 1407. R. E. Bowman and D. J. Tivey, J . Chem. Soc., 1954, 4548. 1408. W. Huber, J . Am. Chem. Soc., 66, 876 (1944). 1409. M. Sekiya, Yakuguku Zasshi, 70, 62 (1950); Chem. Ahstr., 44, 5368 (1950). 1410. K. Miyatake and M. Tsunoo, Yakugaku Zasshi, 72, 630 (1952); Chem. Abstr., 47,2177 (1953). 1411. A. Wenz, G. Gottmann, and H. Koop, Liebigs Ann. Chem., 680, 82 (1964). 1412. A. Edenhofer, H. Spiegelberg, and W. E. Oberhansli, Helu. Chim. Acta, 58, 1230 (1975). 1413. H. Nakao, M . Ito, and S. Muramatsu, Sankyo Kenkyusho Nempo, 18,33 (1966); Chem. Abstr., 66, 115678 (1967). 1414. H. Neef, K.-D. Kohnert, and A. Schellenberger, J . Prakt. Chem., 315, 701 (1973). 1415. W. T. Caldwell and W. M. Ziegler, J . Am. Chem. Soc., 58, 1749 (1936). 1416. E. Vargha and I. Balazs, Stud. Unit.. Babes-Bolyia, Ser. Chem., 10, 79 (1965); Chem. Abstr., 64, 19606 (1 966). 1417. M. Mengelberg, Chem. Ber., 93, 2230 (1960).

References

1221

1418. L. P. Cerecedo and F. D. Pickel, J . Am. Chem. Soc., 59, 1714 (1937). 1419. Y. M. Slobodin and M. S . Ziegler, Zh. Ohshch. Khim., 11, 1019 (1941); Chem. Ahstr., 36, 6542 ( 1 942). 1420. A. Takamizawa, K . Tokuyama, and H. Satoh, Yukugaku Zasshi, 79, 664 (1959). 1421. T. J. Schwan and H. Ticckelmann, J . Iieterocycl. Chem., 2, 202 (1965). 1422. N. Yamaoka and K. Aso, Nippon Nogei Kagaku Kaishi, 35,280 (1961); Chem. Ahstr., 60, 520 ( 1 964). 1423. E. J . Birr, Ger. Pat. 763,389 (1952); Chem. Ahstr., 49, 5178 (1955). 1424. E. Hoggarth and H. P. D. Paget, Br. Pat. 716,327 (1954); Chem. Ahstr., 49, 5177 (1955). 1425. R. L. Tolman, G. L. Tolman, R. K. Robins, and L. B. Townsend, J . Heterocycl. Chem., 7, 799 (1970). 1426. C. 0. Johns and B. M. Hendrix, J . Biol. Chem., 20, 153 (1915). 1427. M. Polonovski and H. Scbmitt, Bull. Soc. Chim. Fr., 1950, 616. 1428. R. N. Prasad, C. W. Noell, and R. K. Robins, J . Am. Chem. Sue., 81, 193 (1959). 1429. K. Sirakawa, Yakugaku Zasshi, 73, 635 (1953); Chem. Ahstr., 48, 9363 (1954). 1430. D. Shiho and N. Takahayashi, Nippon Kugaku Zasshi, 76, 877 (1955); Chem. Ahstr., 51, 17930 (1957). 1431. Y. P. Shvachkin, L. A. Syrtsova, M. K. Berestenko, and M. A. Prokofev, Vestn. M o s k . Unic., Ser. I I , Khim.,17, No. 5, 75 (1962); Chem. Ahstr., 58, 5669 (1963). 1432. D. J. Brown, E. Hoerger, and S. F. Mason, .1. Chem. Sor., 1955, 211. 1433. C. 0. Johns, J . Biol. Chem., 17, 1 (1914). 1434. R. K. Robins, K. J. Dille, C. H. Willits, and B. E. Christensen, J . Am. Chem. Soc., 75, 263 (1953). 1435. E. Dyer, J. M. Reitz, and R. E. Farris, J . Med. Chem., 6, 289 (1963). 1436. R. S . Karlinskaya, N. V. Khromov-Borisov, and V. A. Ivanova, Zh. Ohshch. Khim., 34, 3734 (1964). 1437. D. J. Brown and J. S. Harper, J . Chem. Soc., 1965, 5542. 1438. Merck, Ger. Pat. 227,390 (1910); Frdl., 10, 1177 (191C1912). 1439. V. M. Nestcrov, L. M. Semikolennykh. M. K. Zhukova, M. N. Ivanova, and M. G. Katsnel'son, Med. Prom. SSSR, 20, 12 ( 1 966); Chem. A bstr., 65, 709 ( 1 966). 1440. G. Zvilichovsky and J. Feingers, J . Chem. Soc., Perkin Trans. I , 1976, 1507. 1441. W. Traubc, F. Schottlander, C. Goslich, R. Peter, F. A. Meyer, H. Schluter, W. Steinbach, and K. Bredow, Liehigs Ann. Chem., 432, 266 (1923). 1442. B. M . Turkevich and Y. D. Kovaliv, Ukr. Khim. Zh., 31, 607 (1965); Chem. Ahstr., 63, 7006 ( 1 965). 1443. G. Levin, and A. Kalmus, and F. Bergmann, .I. Org. Chem., 25, 1752 (1960). 1444. R. G. Dickinson and N. W. Jacobsen, Aust. J . Chem., 28, 2741 (1975). 1445. 1. W. Southon and W. Pfleiderer, Chem. Ber., 111, 971 (1978). 1446. R. Hull, Br. Pat. 741,667 (1955); Chem. Ahstr., 51, 2063 (1957). 1447. I . Ito, N. Oda, T. Kato, and K. Ota, Chem. Pharm. Bull., 23, 2104 (1975). 1448. B. R. Baker and J. H . Jordaan, J . Heterocycl. Chem., 2, 162 (1965). 1449. N. V. Khromov-Borisov and R. S. Karlinskaya, Zh. Ohshch. Khim., 24, 2212 (1954); Chem. Ahstr., 50, 355 (1956). 1450. N. V. Khromov-Borisov and R. S . Karlinskaya, Zh. Obshch. Khim., 27, 2518 (1957). 1451. A. Takamizdwa and K. Hirai, Chem. Pharm. Bull., 12, 393 (1964). 1452. C. A. R. Hurt and H. Stephen, Tetrahedron, Suppl., 7, 227 (1966). 1453. Y.-F. Chi and Y.-C. Ling, Actu Chim. Sin., 22, 3 (1956). 1454. Y.-F. Chi and Y.-C. Ling, Sci. Sin.,5. 205 (1956).

1222

References

Y.-F. Chi and K.-C. Chapg, J . Am. Chem. Soc., 60, 1721 (1938). H. R. Henze and S. 0. Winthrop, J . Am. Chem. Soc., 79, 2230 (1957). P. Karrer, R. Schwyzer, and K. Kostie, Helu. Chim. Acta, 33, 1482 (1950). D. Price, E. L. May, and F. D. Pickel, J . Am. Chem. Soc., 62, 2818 (1940). M. Delepine, Bull. Soc. Chim. Fr., 151 5, 1539 (1938). A. Gerecs, 0. Feher, and 0. Fuchs, Magy. Kem. Foly., 61, 112 (1955); Chem. Abstr., 50, 7809 (1956). 1461. M. Yamagishi, Yukuyaku Zasshi, 74, 599 (1954); Chem. Abstr., 48, 10749 (1954). 1462. S. Mizukami and E. Hirdi, J . Org. Chem., 31, 1199 (1966). 1463. A. Takamizawa, K. Hirai, and T. Ishiba, Chem. Pharm. Bull., 14, 1450 (1966).

1455. 1456. 1457. 1458. 1459. 1460.

1464. G. Cavallini, E. Massarani, F. Mazzucchi, and F. Ravenna, Farm. Sci. Tee., 7, 138 (1952); Chem. Abstr., 47, 6943 (1953). 1465. D. J. Brown and M. N. Paddon-Row, J . Chem. Soc. (C), 1967, 1928. 1466. R. Grewe, Hoppe-Seyler’s Z . Physiol. Chem., 242, 89 (1936); Chem. Abstr., 30, 8225 (1936). 1467. F. Korte and H. Weitkamp, Liebigs Ann. Chem., 622, 121 (1959). 1468. M. Ohta, Yukuyaku Zasshi, 67, 161 (1947); Chem. Ahstr., 45, 9545 (1951) 1469. Y. Sawa, F. Osawa, and H. Kaneko, Yakugaku Zasshi, 67, 204 (1947); Chem. Ahstr., 45,9063 (1951). 1470. I. Nabih and H. Zoroob, Experientia, 27, 143 (1971). 1471. A. Dornow and E. Hinz, Chem. Ber., 91, 1834 (1958). 1472. A. R. Todd and F. Bergcl, J . Chem. SOC., 1937, 364. 1473. Z . Foldi and A. Salamon, Ber. Dtsch. Chem. Ges., 74, 1126 (1941). 1474. S. Isoda, H. Yamaguchi, Y. Satoh, T. Miki, and M. Hirata, Chem. Pharm. Bull., 28,1408 (1980). 1475. P. C. Mitter and N. Palit, Q. J . Indian Chem. Soc., 2, 61 (1925); Chem. Zentr., I, 118 (1926). 1476. K. Tsuda and Y. Ogawa, Yakugaku Zasshi, 70, 73 (1950); Chem. Abstr., 44, 5323 (1950). 1477. T. Matsukawa, B. Ohta, and K. Sirakawa, Yakuyaku Zasshi, 70,283 (1950); Chem. Abstr., 45, 2894 (1951). 1478. S. David and B. Estramareix, Bull. Soc. Chim. Fr., 1960, 1731. 1479. Z . BusESinsky, Collect. Czech. Chem. Commun., 14, 223 (1949). 1480. W. Huber, J . Am. Chem. Soc., 65, 2222 (1943). 1481. H. Tieckelmann, R. Guthrie, and J. G. Nairn, J . Org. Chem., 25, 1257 (1960). 1482. T. Tsuji and Y. Otsuka, Chem. Pharm. Bull., 26, 2765 (1978). 1483. W. Klotzer and M. Herberz, Monatsh. Chem., 96, 1731 (1965). 1484. W. R. Boon, J . Chem. Soc., 1957, 2146. 1485. 0. Gerngross, Ber. Dtsch. Chem. Ges., 38, 3394 (1905). 1486. W. Klotzer, Monatsh. Chem., 97, 1117 (1966). 1487. B. Simon and K.-H. Uteg, Z . Chem., 12, 20 (1972). 1488. T. Tsuji and Y. Otsuka, Heterocycles, 14, 197 (1980). 1489. T. B. Johnson and A. Litzinger, J . Am. Chem. Soc., 58, 1940 (1936). 1490. J. A. Burckhalter, R. J. Seiwald, and H. C. Scarborough, J . Am. Chem. Soc., 82, 991 (1960). 1491. S.-I. Yamada and K. Achiwa, Chem. Pharm. Bull., 9, 119 (1961). 1492. R. Behrend and M. Lehmann, Liebigs Ann. Chem., 253, 77 (1889). 1493. B. Lythgoe, A. R. Todd, and A. Topham, 1.Chem. Soc., 1944, 315. 1494. R. K. Robins, F. W. Furcht, A. D. Grauer, and J. W. Jones, J . Am. Chem. Soc., 78,2418 (1956). 1495. R. Behrend and H. Osten, Liebigs Ann. Chem., 343, 133 (1905).

References

1223

1496. C.-N. Chang and C.-Y. Yuan, Yao Hsiieh tlsiieh Puo, 6, 139 (1958); Chem. Abstr., 53, 14108 (1959). 1497. I. K. Fel'drnan, G. S. Sernicheva, and N. G. Zhokhovets, Mechenye Biol. A k t . Veshchestva, Sb. Statei, 1962, 26; Chem. Ahstr., 59, 8745 (1963). 1498. J. Klosa, Arzneim.-Forsch., 30, 228 (1980). 1499. M. Conrad, Liebigs Ann. Chem., 340, 310 (1905). 1500. Merck, Ger. Pat. 165,561 (1905); Frdl., 8, 1139 (1905-1907). 1501. Merck, Ger. Pat. 170,657 (1906); Frdl., 8, 1142 (1905-1907). 1502. Merck, Ger. Pat. 170,555 (1906); Frdl., 8, 1143 (1905-1907). 1503. M. Polonovski, R. Vieillefosse, S. Guinand, and H. Jtrome, Bull. Soc. Chim. Fr., 1946, 80. 1504. G. Niibel and W. Pfleiderer, Chem. Ber., 95, 1605 (1962). 1505. W. Bergmann and T. B. Johnson, J . Am. Chem. Soc., 55, 1733 (1933). 1506. H. G. Mautner, S.-H. Chu, J. J. Jaffe, and A. C. Sartorelli, J . M e d . Chem., 6, 36 (1963). 1507. D. J. Brown and T. Teitei, Aust. J . Chem., 18, 559 (1965). 1508. D. J. Brown and B. T. England, J . Chem Soc. (C), 1971, 2507. 1509. S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 32, 2921 (1899). 1510. I. K. Fel'dman, Tr. Leninyr. Khim.-L'arm. Inst., No. 16, 25 (1962); Chem. Ahstr., 60, 10680 (1964). 151 1. B. Chatamra and A. S. Jones, J . Chem. Soc., 1963, 811. 1512. M. Kroger, M. Spinzl, and F. Cramer, Liebigs Ann. Chem., 1976, 1395. 1513. T. Ueda, Y. Iida, K. lkeda, and Y. Mizuno, Chem. Pharm. Bull., 16, 1788 (1968). 1514. G. H. Hitchings, G. B. Elion, E. A. Falco, and P. B. Russell, J. Biol. Chem., 177, 357 (1949). 1515. P. B. Russell, G. B. Elion, E. A. Falco, and G. H. Hitchings, J . Am. Chem. Soc., 71,2279 (1949). 1516. M. Polonovski, M. Pesson, and H. Schmitt, Bull. Soc. Chim. Fr. [S], 15, 392 (1948). 1517. S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 32, 1525 (1899). 1518. N. W. Jacobsen and B. L. McCarthy, Aust. J . Chem., 32, 153 (1979). 1519. E. Fischer and H. Clemrn, Ber. Dtsch. Chem. Ges., 30, 3089 (1897). 1520. D. J. Brown and N. W. Jacobsen, J . Chem. SOC.,1962, 3172. 1521. M. Hirata, Chem. Phurm. Bull., 16, 430 (1968). 1522. H. W. Scherp, J . Am. Chem. Soc., 68, 912 (1946). 1523. T. Curatolo, Gazz. Chim. Ital., 20, 585 (1890). 1524. R. Behrend and A. Kohler, Ber. Dtsch. Chem. Ges., 19, 220 (1886). 1525. A. Michael, J . Prakt. Chem. 121, 49, 26 (1894). 1526. K. Sugino, K. Odo, K. Shirai, and Y. Sugito, Koyyo Kayaku Zasshi, 53, 219 (1950); Chem. Ahstr., 47, 5946 (1953). 1527. M. A. Prokofev and Z. A. Rumyantseva, Dokl. Akad. Nauk SSSR,75,399 (1950); Chem. Abstr., 45, 7125 (1951). 1528. I. K. Fel'dman, V. M. Merlis, and Y. M. Rozanova, Zh. Obshch. Khim., 19, 1683 (1949). 1529. L. E. Brady and R. M. Herbst, J . Org. Chem., 24, 922 (1959). 1530. U. von Gizycki, Anyew. Chem., 83,406 (1971). 1531. E. H. Flynn, J. W. Hinrnan, E. L. Caron, and D. 0.Woolf, J . Am. Chem. Soc., 75, 5867 (1953). 1532. G. A. Stein, W. L. Sampson, J. K. Cline, and J. R. Stevens, J . Am. Chem. Soc., 63, 2059 (1941). 1533. J. J. Fox, D. van Praag, I. Wempen, 1. L. Doerr, L. Cheong, J. E. Knoll, M. L. Eidinoff, A. Bendich, and G. B. Brown, J . Am. Chem. Soc., 81, 178 (1959). 1534. A. R. Katritzky and A. W. Waring, J . Chem. SOC.,1963, 3046. 1535. K. Yarnauchi, K. Nakarnura, and M. Kinoshita, J . Org. Chem., 43, 1593 (1978).

1224

References

1536. K. K. Ogilvie, S. L. Beaucage, and M. F. Gillen, Tetruhedron Lett., 1978, 1663. 1537. W. Szer and D. Shugar, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S.Tipson, Eds.), Wiley, New York, 1968, p. 61. 1538. H. Hayatsu and M. Yano, Tetrahedron Lett., 1969, 755. 1539. M. Yano and H. Hayastu, Biochim. Biophys. Acta, 199, 303 (1970). 1540. R. S. Hosrnane and N. J. Leonard, Synthesis, 1981, 118. 1541. 0. S. Tee, M . J. Kornblatt, and C. J. Berks, J . Org. Chem., 47, 1018 (1982). 1542. T. Ueda and J. J. Fox, J . Org. Chem., 29, 1770 (1964). 1543. Y.-F. Chi and S.-F. Chen, Zh. Obshch. Khirn., 28, 1483 (1958); Chem. Ahstr., 53, 1362 (1959). 1544. J. M. Sprague and T. B. Johnson, J . Am. Chem. Soc., 58,423 (1936). 1545. A. Pullman and B. Pullman, Bull. Soc. Chim. Fr., 1959, 594. 1546. D. Shugdr and J. J. Fox, Biochim. Biophys. Acta, 9, 199 (1952). 1547. C. 0. Johns, Am. Chem. J . , 40, 348 (1908). 1548. Wellcome Foundation, Br. Pat. 663,567 (1951); Chem. Ahstr., 47, 616 (1953). 1549. C. Janion and D. Shugdr, Acta Biochim. Pol., 12, 337 (1965). 1550. M. W. Winkley and R. K. Robins, J. Ory. Chem., 33, 2822 (1968). 1551. T. Kitagawa, S. Mizukami, and E. Hirai, Chem. Phurm. Bull., 22, 1239 (1974). 1552. M. E. C. Biffin, D. J. Brown, and T. Sugimoto, J . Chem. SOC.(C), 1970, 139. 1553. W. Traube, Ger. Pat. 135,371 (1902); Frdl., 6, 1192 (190G1902). 1554. A. Maggiolo, A. P. Phillips, and G . H. Hitchings, J . Am. Chem. Soc., 73, 106 (1951). 1555. F. Craveri and G. Zoni, Boll. Chim.Farm., 97, 393 (1958); Chem. Ahstr., 53, 2240 (1959). 1556. S. Nishigaki, K. Ogiwara, K. Senga, S. Fukazawa, K. Aida, Y. Machida, and F. Yoneda, Chem. Pharm. Bull., 18, 1385 (1970). 1557. J. Baddiley, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1944, 318. 1558. J. Baddiley, B. Lythgoe, D. McNeil, and A. R. Todd, J. Chem. Soc., 1943, 383. 1559. C . 0. Johns and E. J. Baumann, J . B i d . Chem., 14, 381 (1913). 1560. N. Inukai, K . Katuno, Y. Ishii, Y. Ishii, M. Uda, and M. Murakami, Chem. Pharm. Bull., 24, 1506 (1 976). 1561. M. Murakami, T. Osono, K. Yano, S . Kawahard, S. Ishida, and H. Horiguchi, Jap. Pat. 29,666 (1970); Chem. Ahstr., 74, 22869 (1971). 1562. T. S. Gardner, E. Wenis, and J. Lee, J . Org. Chem., 19, 753 ( I 954). 1563. T. L. V. Ulbricht and C. C. Price, Chem. Ind. (London), 1955, 1221. 1564. G. A. Grant, C. von Seemann, and S. 0. Winthrop, Can. J . Chem., 34, 1444 (1956). 1565. T. S. Safonova, M. P. Nemeryuk, L. A. Myshkina, and N. I. Traven’, Khim. Geterotsikl. Soedin., 1972, 944. 1566. H. Bretschneider and W. Richter, Swiss Pat. 395,106 (1965); Chem. Ahstr., 64, 15896 (1966). 1567. H. Egg, W. Richter, and H. Bretschneider, Monatsh. Chem., 100, 518 (1969). 1568. M. Israel, H. K. Protopapa, H. N. Schlein, and E. J. Modest, J . Med. Chem., 7, 5 (1964). 1569. B. R. Baker, 3. P. Joseph, and R. E. Schaub, J . Org. Chem., 19, 631 (1954). 1570. C.-T. Chang, W.-W. Chang, and S.-H. Lin, Kung Yeh Chi Shu, 38, 1 (1977); Chem. Ahstr., 92, 181120 (1980). 1571. D. J. Brown and K. Ienaga, Aust. J . Chem., 28, 119 (1975). 1572. A. H. Cook, I. Heilbron, S. F. Macdonald, and A. P. Mahadevan, J. Chem. Soc., 1949, 1064. 1573. T. Tsuji and T. Ueda, Chem. Pharm. Bull., 19, 2530 (1971). 1574. E. B. Knott, J . Soc. Chem. Ind. (London), 60, 313 (1941). 1575. R. G. Dickinson and N. W. Jacobsen, Aust. J . Chem., 28, 2435 (1975).

References 1576. 1577. 1578. 1579. 1580. 1581. 1582. 1583. 1584. 1585. 1586. 1587. 1588. 1589. 1590. 1591. 1592. 1593. 1594. 1595. 1596. 1597.

1225

T. Nishikawa, Nippon Kayaku Zasshi, 65, 936 (1935); Chem. Abstr., 29, 7947 (1935). S. Hoffmann, W. Witkowski, and A. Gyulbudagyan, Z.Chem., 17, 101 (1977). W. Traube, Ber. Dtsch. Chem. Ges., 26, 2551 (1893). J. A. Carbon, J . Org. Chem., 26, 455 (1961). S. Nishigaki, K. Ogiwara, and F. Yoneda, Chem. Pharm. Bull., 19,418 (1971). P. Bitterli and H. Erlenmeyer, Helo. Chim. Acta, 34, 835 (1951). T. Naito and S. Inoue, Chem. Pharm. Bull., 6, 338 (1958). A. V. El'tsov, K. L. Muravich-Aleksandr, and L. M. Roitshtein, Z h . Org. Khim., 3,205 (1967); Chem. Ahstr., 66, 104986 (1967). D. J. Brown, J . Chem. Soc., 1959, 3647. C. 0. Johns, Am. Chem. J . , 45, 79 (1911). E. C. Taylor and M. J. Thompson, J . Org. Chem., 26, 5224 (1961). T.-C. Lee, J . Ory. Chem., 38, 703 (1973). Y. Mizuno, T. Ueda, M. Kobayashi, Y. Shimizu, and T. Murakami, Yakuyaku Zasshi, 77,686 (1957); Chem. Abstr., 51, 15494 (1957). J. Clark, I. Gelling, 1. W. Southon, and M. S. Morton, J . Chem. Soc. ( C ) , 1970, 494. E. C. Taylor and C. K. Cain, J . Am. Chem. Soc., 71, 2282 (1949). J. A. Sprung, US Pat. 2,635,960 (1953); Chem. Ahstr., 47, 8565 (1953). F. Korte, W. Paulus, and K. Steriko, Liehigs Ann. Chem., 619, 63 (1958). G. Zvilichovsky, Tetrahedron, 33, 2259 (1977). G. Zvilichovsky and G. B. Brown, J . Org. Chem., 37, 1871 (1972). E. C. Taylor and C. C. Cheng, J . Org. Chem., 25, 148 (1960). M. G. Nair, L. H. Boyce, and M. A. Berry, J . Ory. Chem., 46, 3354 (1981). R. E. Cline, R. M. Fink, and K . Fink, J . Am. Chem. Soc., 81,2521 (1959).

1598. F. Andreeff and M. Privat de Garilhe, Bull. Soc. Chim. Biol., 50, 435 (1968); Chem. Abstr., 69, 59176 (1968). 1599. T. B. Johnson and L. A. Mikeska, J . Am. Chem. Soc., 41, 810 (1919). 1600. S. Nishigaki, K. Senga, K. Aida, T. Takabataki, and F. Yoneda, Chem. Pharm. Bull., 18, 1003 (1970). 1601. S. Nishigaki, K. Aida, K. Senga, and F. Yoneda, Tetrahedron Lett., 1969, 247. 1602. M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 31, 3990 (1966). 1603. T. R. Ovsepyan and R. G. Melik-Ogandzhanyan, Sint. Geterotsikl. Soedin., No. 9, 81 (1972); Chem. Abstr. 79, 126440 (1973). 1604. H. L. Yale, K. Losee, J. Martins, M. Hoking, F. M. Perry, and J. Bernstein, J . Am. Chem. Soc., 75, 1933, (1953). 1605. K. A. Chkhikvadze, N . E. Britikova, and 0. Y. Magidson, Zh. Ohshch. Khim., 34, 161 (1964). 1606. S. Ruhemann and H. E. Stapleton, J . Chem. Soc., 77, 804 (1900). 1607. S. David and A. Lubineau, Fr. Pat. 1,566,554 (1969); Chem. Ahstr., 72, 79082 (1970) 1608. L. S. German, V. R. Polishchuk, M. N. Preobrazhenskaya, and S. Y. Mel'nik, Khim. Geterotsikl. Soedin, 1974, 858. 1609. L. Kaess and J. Gruszkiewicz, Ber. Dtsch. Chem. Ges., 35, 3600 (1902). 1610. L.-T Chen, Huu Hsueh Tung Pao, No. 3, 61 (1964); Chem. Abstr., 61, 5508 (1964). 1611. H. R. Sullivan and W. T. Caldwell, J . Am. Chem. Soc., 77, 1559 (1955). 1612. K. Zauer, K. Lempert, and K. Harsinyi, Period. Polytech., Chem., Eng., 20, 69 (1976). 1613. D. T. Browne, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 98.

1226

References

1614. H. Bredereck, G. Simchen, and H. Traut, Chem. Ber., 100, 3664 (1967). 1615. H. Bredereck, F. Effenberger, and E. H. Schweizer, Chem. Ber., 95, 956 (1962). 1616. J. P. English, J. H. Clark, R. G. Shepherd, H. W. Marson, J. Krapcho, and R. 0.Roblin, J . Am. Chem. Soc., 68, 1039 (1946). 1617. A. Takamizawa, K. Hirai, Y. Sato, and K. Tori, J . Org. Chem., 29, 1740 (1964). 1618. A. Takamizawa, K. Hirai, and Y. Sato, Jap. Pat. 26,733 (1964); Chem. Abstr., 62, 10448 (1965). 1619. J. Baddiley, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1943, 386. 1620. A. Kreutzberger and C. Grundmann, J . Org. Chem., 26, 1121 (1961). 1621. H. G. Mautner, J . Org. Chem., 23, 1450 (1958). 1622. E. C. Taylor, R. J. Knopf, J. A. Cogliano, J. W. Barton, and W. Pfleiderer, J . Am. Chem. Soc., 82, 6058 (1960). 1623. V. Krchiiik and Z. Arnold, Collect. Czech. Chem. Commun., 40, 1396 (1975). 1624. S. Sugasawa, S. Akahoshi, S. Toda, and H. Tomisawa, YakugukuZasshi, 72,192 (1952); Chem. Abstr., 47, 6418 (1953). 1625. H. Bredereck, G. Simchen, and H. Traut, Chem. Ber., 98, 3883 (1965). 1626. H . Bredereck, H. Ulmer, and H. Waldmann, Chem. Ber., 89, 12 (1956). 1627. T. Matsukawa and K. Sirakawa, Yukugaku Zasshi, 72, 909 (1952); Chem. Abstr., 47, 6425 (1953). 1628. G. D. Daves, D. E. O’Brien, L. R. Lewis, and C. C. Cheng, J . Heterocycl. Chem., 1, 130 (1964). 1629. H.-R. Schiitte and W. Woltersdorf, Liebigs Ann. Chem., 684, 209 (1965). 1630. G. D. Daves, D. E. O’Brien, L. R. Lewis, and C. C. Cheng. in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 80. 1631. E. Ballard and T. B. Johnson, J . Am. Chem. Soc., 64, 794 (1942). 1632. A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 12, 804 (1964). 1633. F. C. Schaefer, H. R. Huffman, and G. A. Peters, J . Org. Chem., 27, 548 (1962). 1634. H. Bredereck, F. Effenberger, and W. Resemann, Chem. Ber., 95, 2796 (1962). 1635. R. G. Jones and C. W. Whitehead, J . Org. Chem., 20, 1342 (1955). 1636. A. Michael, Am. Chem. J., 9, 219 (1887). 1637. H. L. Wheeler and H. S. Bristol, Am. Chem. J., 33, 437 (1905). 1638. E. B. Brown and T. B. Johnson, J . Am. Chem. Soc., 46, 702 (1924). 1639. D. M. Besby and A. A. Goldberg, J . Chem. Soc., 1957, 4997. 1640. G. B. Barlin and W. Pfleiderer, J . Chem. Soc. (B), 1971, 1425. 1641. H. von Hahn, B. Prijs, and H. Erlenmeyer, Helu. Chim. Acta., 39, 341 (1956). 1642. J. K. Wood and E. A. Anderson, J . Chem. Soc., 95, 979 (1909). 1643. Merck, Ger. Pat. 165,562 (1905); Frdl., 8, 1141 (1905-1907). 1644. M. Israel, H. K. Protopapa, H. N. Schlein, and E. J. Modest, J . Med. Chem., 7, 792 (1964). 1645. E. Cingolani, G. Bellomonte, and A. Sordi, Farmaco, Ed. Sci., 19, 1050 (1964). 1646. R. D. Drinkard, US Pat. 2,804,459 (1957); Chem. Ahstr., 52, 2096 (1958). 1647. M. Polonovski and H. Schmitt, C. R . Acad. Sci., 230, 754 (1950). 1648. D. J. Brown, J . Appl. Chem. 4, 72 (1954). 1649. G. B. Elion, W. H. Lange, and G. H. Hitchings, J . Am. Chem. Soc., 78, 2858 (1956). 1650. D. J. Brown, J . Soc. Chem. Ind. (London),69, 353 (1950). 1651. M. Dymicky and W. T. Caldwell, J . Org. Chem., 27, 4211 (1962). 1652. B. W. Arantz and D. J. Brown, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 55. 1653. J. de Lannoy, A. Gysen, and R. Nasielski-Hinkens, Bull. Soc. Chim. Belg., 79, 329 (1970).

References

1227

1654. M. Benedek-Vamos and R. Promel, Tetrahedron Lett., 1969, 1011. 1655. N. Okuda, 1. Kuniyoshi, Y. Oshima, and S. Nagasaki, Yakugaku Zasshi, 82, 1039 (1962). 1656. F. Wohler and J. Liebig, Liehigs. Ann. Chem., 26, 241 (1838). 1657. A. Baeyer, Liebigs Ann. Chem., 127, 199 (1863). 1658. H. C. Koppel and R. K. Robins, J . Am. Chem. Soc., 80, 2751 (1958). 1659. D. Davidson and H. Soloway, J . Org. Chem., 3, 365 (1938). 1660. G. Pellizari, Guzz. Chim. Ital., 17, 254 (1887). 1661. Ciba, Br. Pat. 815,977 (1959); Chem. Abstr., 54, 3464 (1960). 1662. W. T. Caldwell and H. B. Kime, J . Am. Chem. Soc., 62, 2365 (1940). 1663. S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 36,3379 (1903). 1664. G. E. Hilbert, J . Am. Chem. Sac.,, 56, 190 (1934). 1665. G. E. Hilbert, E. F. Jansen, and S. B. Hendricks, J . Am. Chem. Soc., 57, 552 (1935). 1666. D. Isbecque, R. Promel, R. C. Quinaux, and R. H. Martin, f f e l c . Chim. Acta, 42, 1317 (1959). 1667. M. M. Stimpson, J . Am. Chem. Soc., 71, 1470 (1949). 1668. R. 0. Roblin and J. P. English, US Pat. 2,224,836 (1940); Chem. Ahstr., 35,2160 (1941). 1669. M. M. Stimpson and M. J. O’Donnell, J . Am. Chem. Soc., 74, 1805 (1952). 1670. H. Tabocska and S. Biniecki, Diss. Phurm., 15, 389 (1963). 1671. R. S. Karlinskaya and N. V. Khromov-Borisov, Zh. Obshch. Khim., 27, 2113 (1957). 1672. N. Vivona and G. Cusmano, Heterocycles, 6, 107 (1977). 1673. M. Mikohjczyk and J. tuczak, Synthesis, 1974, 491. 1674. P. J. Tarsio and L. Nicholl, J . Org. Chem., 22, 192 (1957). 1675. G. E. Hilbert and T. B. Johnson, J . Am. Chem. Soc., 52, 1152 (1930). 1676. Y.-F. Chi and S.-F. Chen, Sci. Sin., 6, 111 (1957). 1677. J. A. Hill and W. J. Le Quesne, J . Chem. Soc., 1965, 1515. 1678. D. J. Brown and J. M. Lyall, Aust. J . Chem., 15, 851 (1962). 1679. M. lshidate and H. Yuki, Pharm. Bull., 5, 240 (1957). 1680. Q. Stahl, F. Lehmkuhl, and B. E. Christensen, J . Org. Chem., 36, 2462 (1971). 1681. W. Klotzer, Monatsh Chem., 96, 169 (1965). 1682. G. Scheuing and W. Konz, Ger. Pat. 834,993 (1952); Chem. Abstr., 48, 1445 (1954). 1683. B. Kokel, C. Lespagnol, and H. G. Viehe, Bull. Soc. Chim. Brlg., 89, 651 (1980). 1684. G. W. Anderson, I. F. Halverstadt, W. H. Miller, and R. 0.Roblin, J . Am. Chem. Soc., 67,2197 (1945). 1685. T. B. Johnson and J. A. Ambler, J . Am. Chem. Soc., 33, 978 (1911).

T. B. Johnson and B. H. Nicolet, J . Am. Chem. Soc., 36, 345 (1914). M. Ridi, P. Papini, and S. Checchi, Gazz. Chim. Ital., 84, 781 (1954). P. C. Mitter and J. C. Bardhan, J . Chem. Soc., 123, 2179 (1923). H. Vorbriiggen and P. Strehlke, Chem. Ber., 106, 3039 (1973). A. G. Beaman, J . Am. Chem. Soc., 76, 5633 (1954). K. Ganapathi and B. N. Palande, Proc. Indian Acad. Sci., Sect. A , 37,652 (1953);Chem. Abstr., 48, 7564 (1954). 1692. H. Yamasaki and T. Hashizume, Agric. Biol. Chem., 35, 122 (1971). 1693. S. Senda, A. Suzui, M. Honda, and H. Fujimura, Chem. Pharm. Bull., 6, 482 (1958). 1694. N. V. Khromov-Borisov and I. M. Yurist, Sh. Statei Obshch. Khim. Akad. Nauk S S S R , 1, 657 (1953); Chem. Abstr., 49, 1056 (1955). 1695. M. Hagen, Liebigs Ann. Chem., 244, 1 (1888).

1686. 1687. 1688. 1689. 1690. 1691.

1228 1696. 1697. 1698. 1699. 1700.

References W. Pfleiderer and H. Mosthaf, Chem. Ber., 90, 738 (1957). F. Perini and H. Tieckelmann, J . Org. Chem., 35, 812 (1970). P. A. Levene and J. K. Senior, J . B i d . Chem., 25, 607 (1916). R. Brossmer and E. Rohm, Liebigs Ann. Chem., 692, 119 (1966). R. E. Banks, A. Prakash, and N. D. Venayak, J . Fluorine Chem., 16, 325 (1980).

1701, C. Wentrup, Tetrahedron, 26, 4969 ( I 970). 1702. C. Temple, R. L. McKee, and J. A. Montgomery, J . Ory. Chem., 27, 1671 (1962). 1703. J. P. Horwitz and A. J. Tomson, J . Org. Chem., 26, 3392 (1961). 1704. F. Yoneda, Y. Sakuma, and M. Ueno, J . Heterocycl. Chem., 10, 415 (1973). 1705. F. Yoneda and Y. Sakuma, J . Heterocycl. Chem., 10, 993 (1973). 1706. C. Temple and J. A. Montgomery, J . Org. Chem., 30, 826 (1965). 1707. K. Sirakawa, Jap. Pat. 777 (1957); Chem. Abstr., 52, 4699 (1958). 1708. C. Temple and J. A. Montgomery, J . Am. Chem. Soc., 86, 2946 (1964). 1709. R. Huisgen and K. von Fraunberg, Tetrahedron Lett., 1969, 2595. 1710. V. F. Sedova, V. F. Krivopalov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1979, 986. 1711. D. J. Brown and J. A. Hoskins, J . Chem. Soc., Perkin Trans. I , 1972, 522. 1712. J. Farkai and F. Sorm, Collect. Czech. Chem. Commun., 26, 893 (1961). 1713. M. Kroger and F. Cramer, Liebiys Ann. Chem., 1977, 1668. 1714. R. H. Wiley, J. Lanet, and K. H. Hussung, J . Heterocycl. Chem., 1, 175 (1964). 1715. D. J. Brown and P. W. Ford, J . Chem. Soc. (C), 1967, 568. 1716. C. Temple, M. C. Thorpe, W. C. Coburn, and J. A. Montgomery, J . Org. Chem., 31,935 (1966). 1717. H. Reimlinger, Chem. Ber., 103, 1900 (1970). 1718. C. Riess, J . Prakt. Chem. [2]. 30, 145 (1884). 1719. E. von Meyer, J . Prakt. Chem. 121. 39, 262 (1889). 1720. V. S. Reznik, I. S. Salikhov, Y. S. Shvetsov, A. N. Shirshov, V. S. Bakulin, and B. E. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 880. 1721. V. S. Reznik, Y. S. Shvetsov, and N. G. Pashkurov, Zzu. Akad. Nauk S S S R , Ser. Khim., 1968, 2811. 1722. J. Pitha and P. 0. P. Ts’o, J . Ory. Chem., 33, 1341 (1968). 1723. R. B. Greenwald, J . Heterocycl. Chem., 13, 1135 (1976). 1724. J.-I. Yamashita, I. Yamawaki, S. Ueda, M. Yasumoto, N. Unemi, and S. Hashimoto, Chem. Pharm. Bull., 30, 4258 (1982). 1725. A. NoviEek and M. Lissnerova, Collect. Czech. Chem. Commun., 33, 604 (1968). 1726. R. W. Chambers, Biochemistry, 4, 219 (1965). 1727. H. Schroeder, E. Kober, H. Ulrich, R. Ritz, H. Agahigian, and C. Grundmann, J . Org. Chem., 27, 2580 (1962). 1728. R. E. Banks, D. S. Field, and R. N. Haszeldine, J . Chem. Soc. (C), 1967, 1822. 1729. A. E. El’tsov, K. L. Muravich-Aleksandr, and M. Z . Girshovich, Zh. Org. Khim., 5,2061 (1969); Chem Abstr., 72, 55327 (1970). 1730. 0. P. Shkurko, S. G. Baram, and V. P. Mamaev, Izv. Sib. Otcl. Akad. Nauk SSSR,Ser. Khim. Nauk, 6, 81 (1973). 1731. H. Neunhoeffer and B. Lehmann, Liebigs Ann. Chem., 1975, 1 1 13. 1732. E. A. Gray, R. M. Hulley, and B. K. Snell, J . Chem. Soc., (C), 1970, 986. 1733. G. Tennant and G . M. Wallace, J . Chem. Soc., Chem. Commun., 1982, 267. 1734. E. A. Arutyunyan, V. 1. Gunar, and S. I. Zav’yalov, Izv. Akad. Nauk SSSR, Ser. Khim., 1970, 904.

References

1229

1735. W. Pfleiderer and H. Mosthaf, Chem. Ber., 90, 728 (1957). 1736. E. A. Arutyunyan, V. I . Gunar, E. P. Gracheva, and S. I. Zav'yalov, Izt.. Akad. Nauk S S S R , Ser. Khim., 1969, 655. 1737. S. B. Gashev and L. D. Smirnov, Khim. Geterotsikl. Soedin., 1982, 393. 1738. W. E. Fidler and H. C. S. Wood, J . Chem. Soc., 1956, 3311. 1739. G. Konrad and W. Pfeiderer, Chem. Ber., 103, 722 (1970). 1740. S. Nishigaki, K. Senga, and F. Yoneda, Chem. Pharm. Bull., 19 1526 (1971). 1741. D. J. Brown and J. S. Harper, J . Chem. Soc., 1963, 1276. 1742. D. J. Brown and T. Teitei, J . Chem. Soc., 1965, 755. 1743. D. J. Brown and T. Teitei, Aust. J . Chem., 18, 199 (1965). 1744. R. Gompper and U. Heinemann, Anqew. Chem., 93, 298 (1981). 1745. D. T. Hurst, K. Biggadike, and J. J. Tibble, Heterocycles, 6, 2005 (1977). 1746. W. Pfleiderer and E. C. Taylor, J . Am. Chem. Soc., 82, 3765 (1960). 1747. H. Goldner and E. Carstens, J . Prakt. Chem. 141, 12, 242 (1961). 1748. J. M. Sprague and T. B. Johnson, J . Am. Chem. Soc, 57,2252 (1935). 1749. D. J. Brown and P. Waring, Aust. J . Chem., 31, 649 (1978). 1750. H. Bretschneider, W. Klotzer, G. Spiteller, and J. Dehler, Monatsh. Chem., 92, 75 (1961). 1751. Y.-F. Chi and S.-F. Chen, Acta Chim. Sin., 22, 194 (1956). 1752. D. J. Brown and T. Nagamatsu, Aust. J . Chem., 32, 1585 (1979). 1753. A. P. Martinez and W. W. Lee, J . Med. Chem., 10, 1192 (1967). 1754. V. K. Karp and V. A. Portnyagina, Khim.-Farm. Zh., 4, No. 7, 29 (1970). 1755. V. S. Reznik and N. G. Pashkurov, Izu. Akad. Nauk SSSR, Ser. Khim., 1968, 1327. 1756. M. PrystaS and J. Gut, Collect. Czech. Chem. Commun., 27, 1054 (1962). 1757. H. Tuppy and E. Kiichler, Monatsh. Chem, 95, 1698 (1964). 1758. G. E. Ustyuzhanin, V. V. Kolomeitseva, and N. S. Tikhomirova-Sidorova, Zh. Obshch. Khim., 43, 2093 (1973). 1759. G. E. McCasland and D. S. Tarbell, J . Am. Chem. Soc., 68, 2393 (1946). 1760. B. K. Andrews, US Pat. 3,105,075 (1963); Chem. Ahstr., 60, 1769 (1964). 1761. Ciba, Belg. Pat. 645,062 (1964); Chem. Abstr., 66, 37942 (1967). 1762. Hoffmann-La Roche, Belg. Pat. 620, 1 1 1 (1963); Chem. Ahstr., 60, 4160 (1964). 1763. Ciba, Belg. Pat. 641,253 (1964); Chem. Ahstr., 63, 9962 (1965). 1764. D. J. Brown and N. W. Jacobsen, J . Chem. Soc., 1965, 3770. 1765. A. D. Ainley, F. H. S. Curd, and S. Birtwell, Br. Pat. 658,202 (1951); Chem. Ahstr., 46, 9619 (1952). 1766. D. E. OBrien, C. W. Noell, R. K. Robins, and C. C. Cheng, J . M e d . Chem., 9, 121 (1966). 1767. I. J. Pachter and J. Weinstock, US Pat. 3,127,402 (1964); Chem. Ahstr., 60, 14523 (1964). 1768. J. Weinstock, R. Y. Dunoff, B. Sutton, B. Trost, J. Kirkpatrick, F. Farina, and A. S. Straub, J . M e d . Chem., 11, 549 (1968). 1769. G. B. Elion and G. H. Hitchings, J . Am. Chem. Soc., 75, 4311 (1953). 1770. D. J. Brown and N. W. Jacobsen, J . Chem. Soc., 1960, 1978. 1771. W. Winkelmann, J . Prakt. Chem. [N.F.], 115, 292 (1927). 1772. F. H. Case and A. J. Hill, J . Am. Chem. Soc., 51, 1590 (1929). 1773. A. Albert, D. J. Brown, and H. C. S. Wood, J . Chem. Soc., 1956, 2066. 1774. H. Bredereck, F. Effenberger, and H. G . Osterlin, Chem. Ber., 100, 2280 (1967). 1775. H. Blitz and H. Biilow, Liebigs Ann. Chem., 426, 246 (1922). 1776. I. M. Ovcharova and E. S. Golovchinskaya, Khim.-Farm. Zh., 1, No. 3, 32 (1967).

1230

References

1777. J. A. Montgomery and C. Temple, J . Am. Chem. Soc., 82, 4592 (1960). 1778. D. T. Hurst, Aust. J . Chem., 36, 1477 (1983). 1779. G. Sunagawa, J. Nakazawa, and M. Watatani, Jap. Pat. 18,745 (1962); Chem. Ahstr., 59,10075 (1 963). 1780. J. A. Bee and F. L. Rose, J . Chem. Soc. (C),1966, 2031. 1781. R. S. Shadbolt and T. L. V. Ulbricht, J . Chem. Soc. (C), 1967, 1172. 1782. L. Strekowski, Rocz. Chem., 49, 1693 (1975). 1783. B. Stanovnik, M. TiSler, A. Hribar, G. B. Barlin, and D. J. Brown, Aust. J. Chem., 34, 1729 (1981). 1784. W. E. Taft and R. G. Shepherd, J . Med. Pharm. Chem., 5, 1335 (1962). 1785. Agfa, Br Pat. 823,943 (1959); Chem. Ahstr., 54, 19243 (1960). 1786. H. Eilingsfeld, M. Patsch, and H. Scheuermann, Chem. Ber., 101, 2426 (1968). 1787. M. D. Mehta, D. Miller, and E. F. Mooney, J. Chem. Soc., 1965, 6695. 1788. M. P. L. Caton, M. S. Grant, D. L. Pain, and R. Slack, J . Chem. Soc., 1965, 5467. 1789. H. Bretschneider and H Egg, Monatsh. Chem., 98, 1577 (1967). 1790. K. L. Dille, M. L. Sutherland, and B. E. Christensen, J . Org. Chem., 20, 171 (1955). 1791. R. S. Fenton, J. K. Landquist, and S. E. Meek, J . Chem. Soc. (C), 1971, 1536. 1792. T. Nishimura, B. Shimizu, and I. Iwai, Chem. Pharm. Bull., 11, 1470 (1963). 1793. E. Wittenburg, Z . Chem., 4, 303 (1964). 1794. Sanko, Belg. Pat. 639,885 (1964); Chem. Abstr., 62, 16364 (1965). 1795. I. Iwai, T. Nishimura, and B. Shimizu, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 388. 1796. C. C. Price, N. J. Leonard, and R. L. Whittle, J . Ory. Chem., 10, 327 (1945). 1797. A. NovaEek, Collect. Czech. Chem. Commun., 36, 4066 (1971). 1798. A. NovaEek, Collect. Czech. Chem. Commun., 36, 1964 (1971). 1799. L. Strekowski, Rocz. Chem., 49, 1017 (1975). 1800. L. Pichat, J. Deschamps, B. Masse, and P. Dufay, Bull. Soc. Chim. Fr., 1971, 2110. 1801. M. Hasegdwa, Pharm. Bull., 1, 387 (1953). 1802. J. A. Elvidge and N. A. Zaidi, J. Chem. Soc., (C), 1968, 2188. 1803. D. Lloyd, H. McNab, and K. S. Tucker, J. Chem. Soc., Perkin Trans. I, 1977, 1862. 1804. R. Paegle, M. Plata, M. Lidaks, and Y. P. Shvachkin, Khim. Geterotsikl. Soedin., 1968, 912. 1805. P. Nantka-Namirski and J. Wojciechowski, Acta Pol. Pharm., 28,585 (1971); Chem. Ahstr., 76, 153696 (1 972). 1806. H. L. Wheeler and L. M. Liddle, J. Am. Chem. Soc., 30, 1152 (1908). 1807. S. Y. Wang, J. C. Nnadi, and D. Greenfeld, Tetrahedron, 26, 5913 (1970). 1808. P. Nantka-Namirski and J. Wojciechowski, Rocz. Chem., 41, 669 (1967); Chem. Ahstr., 67, 54099 (1967). 1809. P. Nantka-Namirski and J. Wojciechowski, Pol. Pat. 55,190 (1968); Chem. Abstr. 70, 106551 (1969). 1810. E. Ochiai and Y. Ito, Yukuyaku Zasshi, 57, 579 (1937); Supplement, p. 109. 1811. M. Hirata, S. Isoda, M. Kanao, and H. Shimizu, Yakuyaku Zasshi, 92, 288 (1972). 1812. W. PAeiderer and H. Deiss, Isr. J. Chem., 6, 603 (1968). 1813. G. Szilagyi and H. Wamhoff, Synthesis, 1981, 701. 1814. H. Bader and N. Spiere, J. Org. Chem., 28, 2155 (1963). 1815. L. Strqkowski, M. Dworniczak, and A. Kowalewski, Pol. J. Chem., 54, 1557 (1980). 1816. H. C. Koppel, R. H. Springer, and C. C. Cheng, J. Org. Chem., 26, 1884 (1961).

References

1231

F. R . Basford, F. H. S. Curd, and F. L. Rose, J . Chem. Soc., 1946, 713. T. Nishiwaki, Chem. Pharm. Bull., 10, 1029 (1962). D. D. Bly, J . Org. Chem., 29, 943 (1964). E. Cherbuliez and K. N. Stavritch, Helu. Chim. Actu, 5, 267 (1922). K. Undheim and J. Rere, Actu Chem. Scand., 23, 2437 (1969). H. C. van der Plas, Kecl. Truu. Chim. Pays-Bus, 84, 1101 (1965). L. Strqkowski, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 24, 17 (1976).

1817. 1818. 1819. 1820. 1821. 1822. 1823. 1824. 1825. 1826. 1827. 1828. 1829. 1830. 1831. 1832.

T. B. Johnson and A. W. Joyce, J . Am. Chem. Soc., 38, 1557 (1916). D. J. Brown and J. M. Lyall, Aust. J . Chem., 17, 794 (1964). B. W. Ardntz and D. J. Brown, J . Chem Soc. (C), 1971, 1889. J. Chesterfield, J. F. W. McOmie, and E. R. Sayer, J . Chem. Soc., 1955, 3478. W. Barbieri, L. Bernardi, F. Luini, and G. Palamidessi, Farrnaco, Ed. Sci., 25, 694 (1970). E. Wittenburg, Collect. Czech. Chem. Commun., 36, 246 (1971). A. P. Phillips, N. B. Mehta, and J. Z. Strelitz, J . Org. Chem., 28, 1488 (1963). A. P. Phillips and N. B. Mehta, Ger. Pat. 1,148,556 (1963); Chem. Abstr., 59, 11525 (1963). N. V. Khromov-Borisov and G. M. Kheifets, Zh. Obshch. Khim., 34, 1321 (1964).

1833. 1834. 1835. 1836. 1837.

C. G. Overberger, I. C. Kogon, and W. J. Einstman, J . Am. Chem. Soc., 76, 1953 (1954). T. Matsukawa and B. Ohta. Yukuyaku Zasshi, 70, 134 (1950); Chem. Abstr., 44, 5885 (1951). T. Nishiwaki and T. Goto, Bull. Chem. Soc. Jpn., 33, 26 (1960). R. C. Elderfield and A. N. Prasad, J . Org. Chem., 25, 1583 (1960). G. E. Hilbert and E. F. Jansen, J . Am. Chem. Soc., 56, 134 (1934).

1838. D. M. Mulvey, R. D. Babson. S. Zawoiski, and M. A. Ryder, J . Heterocycl. Chem., 10, 79 (1973). 1839. J. D. Bryant and N. J. Leonard, J . Org. Chem., 43, 511 (1978). C. Riess and E. von Meyer, J . Prakt. Chem. 121. 31, 112 (1985). G. E. Hilbert and T. B. Johnson, J . Am. Chem. Soc., 52, 2001 (1930). H. Biltz and T. Hamburger, Ber. Dtsch. Chem. Ges., 49, 635 (1916). B. A. Ivin, V. I. Slcsarcv, and E. G. Sochilin, Zh. Obshch. Khim., 34, 4120 (1964). H. C. Koppel, R. H. Springer, G. D. Daves, and C. C. Cheng, J . Phurm. Sci., 52, 81 (1963). R . W. Luckenbaugh and E. J. Soboczenski, Br. Pat. 968,666 (1964); Chem. Abstr., 61, 13327 (1 964). 1846. J. Esche and H. Wojahn, Arch. Pharm. (Weinheim, Ger.), 299, 56 (1966). 1847. L. Strqkowski, Rocz. Chem., 48, 2157 (1974). 1848. K. Westphal, US Pat. 2,219,858 (1941); Chem. Abstr., 35, 1805 (1941). 1849. B. Roth and L. A. Schloemer, J . Org. Chem., 28, 2659 (1963). 1850. J. Nasielski, A. Kirsch-Demesmaeker, and R. Nasielski-Hinkens, Tetrahedron, 28,3767 (1972). 1851. K. A. Chkhikvadze, N. E. Britikova, and 0. Y. Magidson, B i d . Akt. Soedin., Akad. Nauk SSSR, 1965, 22; Chem. Abstr., 63, 18081 (1965). 1852. E. von Meyer, J . Prukt. Chem. 121, 27, 152 (1883). 1853. A. G. Bayer, Ber. Dtsch. Chem. Ges., 4, 176 (1871). 1854. P. Keller, J . Prakt. Chem. 121, 31, 363 (1885).

1840. 1841. 1842. 1843. 1844. 1845.

1855. 1856. 1857. 1858.

M. P. V. Boarland and J. F. W. McOmie, J . Chem. Soc., 1952, 3722. M. P. L. Caton, D. T. Hurst, J. F. W. McOmie, and R. R. Hunt, J . Chem. Soc. (C),1967, 1204. K . Edo, T. Sakamoto, and H. Yamanaka, Chem. Pharm. Bull., 26, 3843 (1978). S. Y. Wang, Nature (London),180, 91 (1957).

1232

References

1859. S. Y. Wang, M. Apicella, and B. R. Stone, J . Am. Chem. Soc., 78, 4180 (1956). 1860. S. Y. Wang, J . Am. Chem. Soc., 80,6196 (1958). 1861. S. Y. Wang, J . Ory. Chem., 24, 11 (1959). 1862. A. M. Moore and S. M. Anderson, Can. J . Chem., 37, 590 (1959). 1863. S. Senda, K. Hirota, and K. Banno, J . M e d . Chem., 15, 471 (1972). 1864. K. Schmedes, Liehiys Ann. Chem., 441, 192 (1925). 1865. P. Henkel, Liebigs Ann. Chem., 378, 170 (1911). 1866. A. Pinner, Ber. Dtsch. Chem. Ges., 20, 2361 (1887). 1867. 0. Stark, Liebigs Ann. Chem., 381, 143 (1911). 1868. R. Brossmer and D. Ziegler, Hoppe-Seyler’s Z.Physiol. Chem., 350, 457 (1969). 1869. R. S. Klein and J. J. Fox, J . Ory. Chem., 37, 4381 (1972). 1870. C. I. Hong, C. Piantadosi, and J. L. Irvin, J . Pharm. Sci.,59, 1637 (1970). 1871. C. I. Hong, C. Piantadosi, C.-B. Chae, and J. L. Irvin, J . M e d . Chem., 11, 1182 (1968). 1872. D. G . Crosby and R. V. Berthold, J . Ory. Chem., 23, 1377 (1958). 1873. J. Moravek and J. Filip, Collect. Czech. Chem. Commun., 25, 2697 (1960). 1874. S. Angerstein, Ber. Dtsch. Chem. Ges., 34, 3956 (1901). 1875. H. Gershon. R. Brdun, A. Scala, and R. Rodin, J . M e d . Chem., 7, 808 (1964). 1876. S. Basterfield and E. C. Powell, Can. J . Rex, 1, 285 (1929); Chem. Ahstr., 24, 618 (1930). 1877. G . E. McCasland, D. S. Tarbell, A. B. Carlin, and N. Shakespeare, J . Am. Chem. Soc., 68,2390 (1945). 1878. H. Yamanaka, S. Niitsuma, T. Sakamoto, and M. Mizugaki, Chem. Phurm. Bull., 27, 2291 (1979). 1879. D. J. Brown and T.-C. Lee, Aust. J . Chem., 21, 243 (1968). 1880. F. Bergmann, G. W. Chen, and M. Rahat, J . Chem. Soc., Perkin Trans. I , 1976, 90. 1881. A. Y. Berlin and I. A. Korbukh, Khim. Geterotsikl. Soedin., 1971, 1004. 1882. I. G. Farbenindustrie, Fr. Pat. 816,432 (1937); Chem. Abstr., 32, 1869 (1938). 1883. S. Senda, K. Hirota, and T. Asao, Yukugaku Zusshi, 95, 1250 (1975). 1884. T. Hirayama, M. Kamada, and M. Mimura, Heterocycles, 2, 457 (1974). 1885. V. S. Reznik, 1. S. Salikhov, Y. S. Shvetsov, and B. E. Ivanov, Izv. Akud. Nauk S S S K , Ser. Khim., 1980, 2568. 1886. T. B. Johnson and W. F. Storey, Am. Chem. J., 40, 131 (1908). 1887. A. P. Martinez, W. E. Lee, and L. Goodman, J , M e d . Chem., 11, 60 (1968). 1888. K. Sirakawa, T. Tsujikawa, and T. Tsuda, US Pat. 3,041,339 (1962); Chem. Ahstr., 57, 13774 ( 1962). 1889. D. H. Kim and R. L. McKee, J . Ory. Chem., 35, 455 (1970). 1890. K. Edo, T. Sakamoto, and H. Yamanaka, Heterocycles, 12, 383 (1979). 1891. H. C . Bucha, W. E. Cupery, J . E. Harrod, H. M. Loux, and L. M. Ellis, Science, 137,537 (1962). 1892. W. W. Thompson and R. H. Wallick, US Pat. 3,274,196 (1966); Chem. Ahstr., 65, 16981 (1966). 1893. J. E. Gearien and S. B. Binkley, J . Ory. Chem., 23, 491 (1948). 1894. A. R. Katritnky and A. J. Waring, J . Chem. Soc., 1962, 1540. 1895. M. Gacek and K. Undheim, Actu Chem. Scund., Ser. B, 36, 15 (1982). 1896. C. A. H. Rasmussen, H. C. van der Plas, P. Grotenhuis, and A. Koudijs, J . Heterocycl. Chem., 15, 1121 (1978). 1897. Z . BudESinski and J. Vaviina, Collect. Czech. Chem. Commun., 37, 1721 (1972). 1898. H. C. van der Plas and G. Geurtsen, Tetruhedron Lett., 1964, 2093. 1899. L. Strekowski, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 24, 29 (1976).

References

1233

1900. G. M. Kheifets and N. V. Khromov-Borisov, Zh. Org. Khim., 2, 1511 (1966). 1901. J . P. Geerts, C. A. H. Rasmussen, H. C. van der Plas, and A. van Veldhuizen, Reel. Trac. Chim. Pays-Bas, 93, 231 (1974). 1902. E. von Meycr, J . Prakt. Chem. [2], 26, 337 (1882). 1903. T. L. Cupps, D. S. Wise, and L. B. Townsend, Tetrahedron Lett., 1982, 4759. 1904. A. Schellenberger and K. Winter, Hoppe-Seyler’s Z . Physiol. Chem., 344, 16 (1966). 1905. S. Senda, K. Hirota, T. Asao, and Y. Yamada, Heterocycles, 4, 1765 (1976). 1906. K. Hirota, Y. Yamada, T. Asao, and S. Senda, J . Chem. Soc., Perkin Trans. I , 1981, 1896. 1907. D. J. Brown and P. Waring, Aust. J . Chem., 31, 1391 (1978). 1908. D. J. Brown and P. Waring, Aust. J . Chem., 30, 1785 (1977). 1909. W. J. Robbins and F. Kavanagh, Proc. Natl. Acad. Sci. U S A , 24, 229 (1938). 1910. G . Leichssenring, DDR Pat. 11,159 (1956); Chem. Ahstr., 52, 17295 (1958). 1911. I. Saikawa and T. Maeda, Yakugaku Zasshi, 84, 131 (1964). 1912. A. Schellenberger and K. Winter, Hoppe-Seyler’s Z . Physiol. Chem., 322. 164 (1960). 1913. F. H. S. Curd, D. N. Richardson, and F. L. Rose, J . Chem. Soc., 1946, 378. 1914. H. W. Barrett, I. Goodman, and K. Dittmer, J . Am. Chem. Soc., 70, 1753 (1948). 1915. G. Hornyik and K. Lempert, Acta Chim. Acad. Sci. Hung., 68, 277 (1971). 1916. Du Pont, Br. Pat. 968,661 (1964); Chem. Ahst., 61, 13326 (1964). 1917. I. G. Farbenindustrie, Br. Pat. 475,507 (1937); Chem. Ahstr., 32, 3420 (1938). 1918. A. I. Gravin, Z h . Prikl. Khim., 16, 105 (1943); Chem. Abstr., 38, 1239 (1944). 1919. R. F. Raffauf, lielc. Chim. Acta, 33, 102 (1950). 1920. J. K. Cline, R. R. Williams, and J. Finkelstein, J . Am. Chem. Soc., 59, 1052 (1937). 1921. 1. K. Fel’dman, L. A. Petrova, Z. Y. Drok, and G. S. Semicheva, Mechenye Biol. Akt. Veschestua, Sh. Statei, 1962, 20; Chem. Ahstr., 59, 10041 (1963). 1922. V. M. Tursin, Tr. Vses. Nauchno-Issled. Vitam. Inst., 6, 22 (1959); Chem. Abstr., 55, 11428, 12411 (1961) 1923. I . M. Lisnyanskii and E. S. Zhdanovich, Tr. Vses. Nauchno-Issled. Vitam. Inst., 7, 48 (1961); Chem. Abstr., 59, 1637 (1963). 1924. J. C. Soyfer, G. Giovannangeli, B. Cristau, and P. Audibert, Chim. Ther., 1973, 71. 1925. Y. P. Shvachkin and L. A. Syrtsova, Zh. Ohshch. Khim., 34, 2159 (1964). 1926. Y. P. Shvachkin and L. A. Syrtsova, Vestn. Mosk. Uniu., Ser. II, Khim., 18, No. 4, 88 (1963); Chem. Ahstr., 5 9 , 10229 (1963). 1927. B. Blank and W. T. Caldwell, J . Org. Chem., 24, 1137 (1959). 1928. D. R. V. Golding and A. E. Senear, J . Org. Chem., 12, 293 (1947). 1929. T. Nishino, M. Kiyokawa, Y. Miichi, and K. Tokuyama, Bull. Chem. Soc. Jpn., 45, 1127 (1927). 1930. E. Benary, Ber. Dtsch. Chem. Ges., 63, 2601 (1930). 1931. C. Ziegler, US Pat. 2,609,372 (1952); Chem. Abstr., 48, 746 (1954). 1932. S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 34, 1234 (1901). 1933. D. J. Brown and P. Waring, Aust. J . Chem., 27, 2251 (1974). 1934. W. J. Haggerty, R. H. Springer, and C. C. Cheng, J . Heterocycl. Chem., 2, l(1965). 1935. J. W. F. McOmie and 1. M. White, J . Chem. Soc., 1953, 3129. 1936. G . M. Kosolapoff and C. H. Roy, J . Org. Chem., 26, 1895 (1961). 1937. L. T. Weinstock, D. E. O‘Brien, and C. C. Cheng, J . M e d . Chem., 11, 1238 (1968). 1938. V. M. Berezovskii, G. D. Glebova, E. M. Birinberg, and N. A. Andreeva, Khim.-Farm. Zh., 1, NO. 6, 5 (1967); Chem. Ahstr., 68, 49546 (1968). 1939. S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 35, 1569 (1902).

1234 1940. 1941. 1942. 1943. 1944. 1945.

References J. A. Carbon, J . Org. Chem., 25, 1731 (1960).

A. Benitez, L. 0. Ross, L. Goodman, and B. R. Baker, J . Am. Chem. Soc., 82, 4585 (1960). T. B. Johnson and F. W. Heyl, Am. Chem. J., 37, 628 (1907). R. Behrends, Liebigs Ann. Chem., 229, 1 (1885). R. Behrends, Liebigs Ann. Chem., 236, 57 (1886). B. Kurtev and M. Kirolov, Bulgar. Akad. Nauk Otdel. Geo1.-Geograf Khim. Nauk, Izv. Khim. Inst., 1, 277 (1951); Chem. Abstr., 47, 1607 (1953).

1946. H. Dubicki, F. Zielinski, and F. W. Starks, J . Pharm. Sci., 53, 1422 (1964). 1947. G. V. Konrat’eva, V. I. Gunar. G. A. Kogan, and S . I. Zav’yalov, Izu. Akad. Nauk SSSR, Ser. Khim., 1966, 1219. 1948. N. G. Chernova and A. S. Khokhlov, Zh. Obshch. Khim., 30, 1281 (1960). 1949. T. Sasaki and M. Ando, Bull. Chem. Soc. Jpn., 41, 2215 (1968). 1950. M. R. Truter and B. L. Vickery, J . Chem. Soc. ( A ) , 1971, 2077. 1951. D. J. Brown and R. V. Foster, Aust. J . Chem., 19, 2321 (1966). 1952. 0. S. Tee and S . Banerjee, Can. J . Chem., 55, 3800 (1977). 1953. R. Promel, A. Cardon. M. Daniel, G. Jacques, and A. Vandersmissen, Tetrahedron Lett., 1968, 3067. 1954. S . C. Bennur and V. V. Badiger, Arch. Pharm. (Weinheim, Ger.), 303, 971 (1970). 1955. G. A. Grant, C. von Seemann, and S . 0. Winthrop, US Pat. 2,876,224 (1959); Chem. Abstr., 53, 16170 (1959). 1956. S. C. Bennur and V. V. Badiger, Monatsh. Chem., 100, 2136 (1969). 1957. H. W. Barrett, US Pat. 2,585,615 (1952); Chem. Abstr., 46, 8148 (1952). 1958. H. Gershon. K. Dittmer, and R. Braun, J. Org. Chem., 26, 1874 (1961). 1959. K. Golankiecwicz and L. Strqkowski, Bull. Acud. Pol. Sci., Ser. Sci Chim.,18, 449 (1970). 1960. K. Golankiecwicz and L. Strqkowski, Rocz. Chem., 45, 3 (1971). 1961. F.-S. Tjoeng, and E. Kraas, E. Breitmaier, and G. Jung, Chem. Ber., 109, 2615 (1976). 1962. B. R. Baker and M. Kawazu, J . Med. Chem., 10, 316 (1967). 1963. T. V. Protopopova, V. K. Klimko, and A. P. Skoldinov, Khim. Nauka Prom., 4, 805 (1959); Chem. Abstr., 54, 11036 (1960). 1964. K. Yanai. Yakugaku Zasshi, 62, 315; Supplement, p . 95 (1942); Chem. Abstr., 45, 5150 (1951). 1965. T. J. Kress and L. L. Moore, J . Heterocycl. Chem., 10, 153 (1973). 1966. M. V. Jovanovic, Heterocycles, 20, 2011 (1983). 1967. D. D. Bly and M. G. Mellon, J . Org. Chem., 27, 2945 (1962). 1968. M. P. V. Boarland and J. F. W. McOmie, J . Chem. SOC.,1952, 3716. 1969. H. Bredereck, F. Effenberger, and E. H. Schweizer, Chem. Ber., 95, 803 (1962). 1970. T. Kauffmann, R. Nurnberg, and K. Udluft, Chem. Ber., 102, 1177 (1969). 1971. L. van der Does and H. J. den Hertog, Tetrahedron Lett., 1972, 2183. 1972. S. A. Krueger and W. W. Paudler, J . Org. Chem., 37,4188 (1972). 1973. M. Robba and R. Delaby, C. R. Acad. Sci., 248, 250 (1959). 1974. A. Holland and R. Slack, Chem. Ind. (London), 1954, 1203. 1975. C. J. B. Clews and W. Cochran, Acta Cryst., 2, 46 (1949); Chem. Abstr., 43, 6487 (1949). 1976. T. B. Johnson, J . Am. Chem. Soc., 62, 2269 (1940). 1977. T. B. Johnson and M. G. Winton, J . Am. Chem. Soc., 63, 2379 (1941). 1978. C. Parkanyi and F. Sorm, Collect. Czech. Chem. Commun., 28, 2491 (1963). 1979. S. H. Chang, I. K. Kim, D. S. Park, and B.-S. Hahn, Daehan Hwahuk Hwoejee, 9, 29 (1965); Chem. Abstr., 64, 15876 (1966).

References

1235

1980. 0. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Chem. Pharm. Bull. 29, 3181 (1981). 1981. D. J. Brown, J . Chem. Soc., 1956, 2312. 1982. S. Banerjee and 0. S. Tee, J . Org. Chem., 39, 3120 (1974). 1983. A. K. Macbeth, T. H. Nunan, and D. Traill, J . Chem, Soc,, 1926, 1248. 1984. W. Bock, Ber. Dtsch. Chem. Ges., 55, 3400 (1922). 1985. 0. Y. Neiland and D. E. Neiman, Zh. Org. Khim., 6, 2509 (1970). 1986. D. G. Crosby and R. V. Berthold, J . Org. Chem., 25, 1916 (1960). 1987. S. Senda, K. Hirota, and T. Asao, Chem. Pharm. Bull., 26, 3208 (1978). 1988. T. L. Hullar and W. C. French, J . Med. Chem., 12, 424 (1969). 1989. Y. P. Shvachkin, M. T. Azarova, and I. I. Rapanovich, Vestn. Mosk. Unio., Ser. IZ, Khim., 18, No. 5, 68 (1963); Chem. Abstr., 59, 15283 (1963). 1990. G . G. Massaroli and G. Signorelli, Boll. Chim. Farm., 105, 400 (1966); Chem. Abstr., 65, 8903 (1966). 1991. S. M. McElvain and B. E. Tate, J . Am Chem. Soc., 73, 2760 (1951). 1992. A. Dornow and M. Siebrecht, Chem. Ber., 93, 1106 (1960). 1993. M. Ridi, P. Papini, and S. Checchi, Gazz. Chim. Ital., 92, 209 (1962). 1994. K. Hirota, M. Suematsu, Y. Kuwabara, T. Asao, and S. Senda, J . Chem. Soc., Chem. Commun., 1981, 623. 1995. Y.-F. Chi and C. M. Ma, J . Am. Chem. Soc., 55, 4655 (1933). 1996. A. Albert and S. Matsuura, J . Chem. Soc., 1962, 2162. 1997. D. J. Brown and P. Waring, Aust. J . Chem., 30, 621 (1977). 1998. K. Washimi, Yakugaku Zasshi, 66, 62 (1946); Chem. Abstr., 45, 6207 (1951). 1999. A. Pinner, Ber. Dtsch. Chem. Ges., 28, 473 (1895). 2000. A. Dornow and E., Neuse, Arch. Pharm. (Weinheirn, Cer.), 287, 361 (1954). 2001. D. J. Brown, J. C. Gamble, and P. Waring, in Nucleic Acid Chemistry, Part 1 (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 67. 2002. F. Zymalkowski and E. Reimann, Arch. Pharm. (Weinheim, Ger.), 299, 362 (1966). 2003. Y. P. Shvachkin and M. T. Azarova, Zh. Obshch. Khim., 33, 590 (1963). 2004. Y. P. Shvachkin and M. T. Azarova, Vestn. Mosk. Univ., Ser. IZ, Khim., 18, No. 2, 53 (1963); Chem. Abstr., 59, 5159 (1963). 2005. Y. P. Shvachkin, M. K. Berestenko, and G. P. Mishin, Biol Akt. Soedin., Akad. Nauk SSSR, 72 (1965); Chem. Abstr., 64, 9720 (1966). 2006. J. Weinstock, H. Graboyes, G. E. Jaffe, I. J. Pachter, K. Snader, C. B. Karash, and R. Y. Dunoff,J . M e d . Chem., 11, 560 (1968). 2007. J. D. Fissekis and F. Sweet, Biochemistry, 9, 3136 (1970). 2008. J. Barluenga, M. Tomas, V. Rubio, and V. Gotor, J . Chem. Soc., Chem. Commun., 1979, 675. 2009. I. B. Toperman and 0. Y. Magidson, Khim.-Farm. Zh., 2,6; Chem. Abstr., 68, 114386 (1968). 2010. Y. P. Shvachkin and M. A. Prokof’ev, Zh. Obshch. Khim., 26, 3416 (1956). 201 I. R. Paegle, M. Lidaks, and Y. P. Shvachkin, Khim. Geterotsikl. Soedin., Akud. Nauk Latv. S S R , 1966, 316; Chem. Abstr., 65, 2256 (1966). 2012. P. F. Wiley and F. A. MacKellar, J . Am. Chem. Soc., 92, 417 (1970). 2013. M. Sato, H. Ogasawara, and T. Kato, J . Heterocycl. Chem., 20, 87 (1983). 2014. A. P. Martinez, W. W. Lee, and L. Goodman, J . Med. Chem., 8, 187 (1965). 2015. C. V. Greco and J. F. Warchol, J . Org. Chem., 36, 604 (1971). 2016. Y. P. Shvachkin, 1. I. Rapanovich, and M. T. Azarova, Vestn. Mosk. Univ., Ser. II, Khim., 20, No. 1, 73 (1965); Chem. Abstr., 62, 13002 (1965).

1236

References

2017. 2018. 2019. 2020. 2021.

T. B. Johnson and F. W. Heyl, Am. Chem. J., 38, 237 (1907). K. Takagi and T. Ueda, Chem. Phurrrr. Bull., 12, 607 (1964). R. A. Partyka, US Pat, 3,396,261 (1967); Chem. Ahstr., 66, 55508 (1967). R. A. Partyka, US Pat. 3,311,628 (1967); Chem. Abstr., 67, 64432 (1967). R. Smri, J. 0. Jilek, K. Sindelai, B. KakaE, E. Svitek, J. Holubek, J. Grimova, and M. Protiva, Collect. Czech. Chem. Commun., 41, 2771 (1976).

2022. 2023. 2024. 2025.

H. Pischel, A. Holy, G. Wagner, and D. Cech, Collect. Czech. Chem. Commun., 40,2689 (1975). M. Tada, Bull. Chem. Soc. Jpn., 48, 3427 (1975). J. L. Rabinowitz and S. Gurin, J . Am. Chem. Soc., 75, 5758 (1953). G. Hornyak, B. Agai, L. Szocs, and K. Lempert, Actu Chim. Acad. Sci. Hung., 88, 413 (1976).

2026. R. Destro and R. E. Marsh, Acta Crystallogr., Sect. B., 28, 2971 (1972); Chem. Abstr., 77, 170030 (1972). 2027. G. Shaw and R. N. Warrener, J . Chem. Soc., 1958, 153. 2028. H. L. Wheeler and L. M. Liddle, J . Am. Chem. Soc., 30, 1156 (1908). 2029. Imperial Chemical Industries, Fr. Pat. 1,491,242 (1967); Chem. Abstr., 69, 35586 (1968). 2030. B. R. Baker and G. B, Chheda, J . Pharm. Sci., 54, 25 (1965). 2031. M. W. Gray and B. G. Lane, Biochemistry, 7 , 3441 (1968). 2032. G. E. Hilbert, J . Am. Chem. Soc., 54, 2076 (1932). 2033. M. L. Tamayo, J. M. Gamboa, and E. F. Alvarez, An. R . Soc. Esp. Fis. Quim.,Ser. B., 48, 889 (1952); Chem. Ahstr., 48, 1278 (1954). 2034. U. Drehmann and H. J. Born, J . Prukt Chem, [4], 5, 200 (1957). 2035. R. N. Warrener and E. N. Cain, Chem. Ind. (London), 1964, 1989. 2036. H. Schueler, H. Grabhoefer, and H. Ulrich, Ger. Pat. 1,163,142 (1964); Chem. Ahstr., 60, 14518 (1964). 2037. V. P. Mamaev and E. A. Grdcheva, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1975, 123. 2038. W. K. Hagmann, F. Z. Basha, M. Hashimoto, R . B. Frye, S. Kojo, and S. M. Hecht, J . Org. Chem., 46, 1413 (1981). 2039. J. D. Fissekis and F. Sweet, J . Ory. Chem., 38. 264 (1973). 2040. H. C. J . Ottenheijm, S. P. J. M. van Nispen, and M. J. Sinnige, Tetrahedron Lett., 1976, 1899. 2041. D. Davidson and 0. Baudisch, J . Am. Chem. Soc., 48, 2379 (1926). 2042. E. C. Ressner, P. Fraher, M. S. Edelman, and M. P. Mertes, J . Med. Chem., 19, 194 (1976). 2043. T. B. Johnson and J. M. Sprague, J . Am. Chem. Soc., 60, 1622 (1938). 2044. W. R. Boon, J . Chem. Soc., 1952, 1532. 2045. M.-J. Langerman and C. K. Banks, J . Am. Chem. Soc., 73, 3011 (1951). 2046. J. Clark and W. Pendergast, J . Chem. Soc. ( C ) , 1969, 2780 2047. S. Matsumoto, 0. Shioyama, and K. Murata, Noyaku Seisan Gijutsu, 9, 17 (1963); Chem. Abstr., 61, 6300 (1964). 2048. R. Fusco, G. Losco, and N. Troiani, Ital. Pat. 662,501 (1964); Chem. Abstr., 65, 20147 (1966). 2049. L. Pichat and G. Chatelain, Bull. Soc. Chim. Fr., 1970, 1833. 2050. S. Yanagida, M. Ohoka, M. Okahara, and S. Komori, J . Ory. Chem., 34, 2972 (1969). 2051. K. A. Chkhikvadze, N. I. Koretskaya, N. S. Rodnyanskaya, and 0. Y. Magidson, Khim. Geterotsikl. Suedin., 1969, 138; Chem. Abstr., 71, 81300 (1969). 2052. N. I. Koretskaya, K. A. Chkhikvadze, N. S. Rodnyanskaya, and 0.Y. Magidson, Khim.-Farm. Zh., 2, No. 6, 5 (1968); Chem. Ahstr., 70, 115103 (1969). 2053. Y. Kuwayama, Yakugaku Zasshi, 82, 1028 (1962).

References

1237

2054. H. M. Loux, R. W. Luckenbaugh, and E. J. Soboczenski, Belg. Pat. 625,897 (1963); Chem. Ahstr., 60, 14519 (1964). 2055. Y. P. Shvachkin, L. A. Syrtsova, and M. A. Prokofev, Zh. Ohshch. Khim., 32, 2431 (1962). 2056. Y. P. Shvachkin and G. G. Krivtsov, Zh. Ohshch. Khim., 34, 2164 (1964). 2057. Y. P. Shvachkin, L. A. Syrtsova, and M. P. Filatova, Zh. Ohshch. Khim., 33, 2487 (1963). 2058. Y. P. Shvachkin, M. P. Filatova, and L. A. Syrtsova, Vestn. Musk. Unic., Ser. ZZ, Khim., 18, No. 2, 55 (1963); Chem. Ahstr., 59, 6404 (1963). 2059. V. P. Shvachkin, M. A. Novikova, M. B. Reznikova, and N. S. Padyukova, Biol. Akt. Soedin., Akad. Nauk S S S R , 1965, 25; Chem. Ahstr., 63, 16453 (1965). 2060. J. W. Cornforth and H. T. Huang, J . C'hem. Soc., 1948, 1988. 2061. E. von Meyer, J . Prakl. Chem. 121, 22, 261 (1880). 2062. D. J. Brown and T. Nagamatsu, Aust. .I. Chem., 30, 2515 (1977). 2063. R. E. Banks, D. S. Field, and R. N. Haszeldinc, J . Chem. Soc. (C), 1970, 1280. 2064. C. W. Tullock, R. A. Carboni, R. J. Harder, W. C. Smith, and D. D. CotTman, J . Am. Chem. Soc., 82, 5107 (1960). 2065. I. Hirao, T. Fujimoto, Y. Kato, and H. Okazaki, Kogyo Kagaku Zasshi, 66,1682 (1963); Chem. Ahstr., 60, I2008 ( 1 964). 2066. C. Piantadosi, C. S. Kim, and J. L. Irvin, J . Pharm. Sci., 58, 821 (1969). 2067. Geigy, Belg. Pat. 626,639 (1967); Chem. Ahstr., 60, 8043 (1964). 2068. R. Nutiu and A. J. Boulton, J . Chem. Soc., Perkin Trans. I, 1976, 1327. 2069. D. Baldwin and P. van den Broek, J . Chem. Soc., Perkin Truns. I, 1975, 375 2070. 2071. 2072. 2073. 2074. 2075. 2076. 2077. 2078. 2079. 2080. 2081. 2082. 2083. 2084. 2085. 2086. 2087. 2088. 2089. 2090. 2091.

S. B. Greenbaum, .I. A m . Chem. Soc., 76, 6052 (1954). S . B. Greenbaum and W. T. Holmes, J . Am. Chem. Soc., 76, 2899 (1954). N. Okuda and I. Kuniyoshi, Yakugaku Zasshi, 82, 1031 (1962). Hoffmann-La Roche, Fr. Pat, 1,341,774 (1963); Chem. Abstr., 60, 10698 (1964). A. Albert, J . Chem. Soc., Perkin 7ran.s. I , 1978, 513. G. Grundmann and R. Richter, J . Org. Chem., 32, 2308 (1967). H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, J . Org. Chem., 27, 181 (1962). K. Westphal, Ger. Pat. 703,068 (1941); C'hem. Ahstr., 36, 911 (1942) C. G. Overberger and I. C. Kogon, J . Am. Chem. Soc., 76, 1879 (1954). H.-G. Kazmirowski and E. Carstcns, J . Prukt. Chem. 141, 26, 101 (1964). W. Pfleidcrer and G. Nubel, Chem. Ber., 95,1615 (1962). P. Nantka-Namirski and J. Wojciechowski, Pol. Pat, 59,331 (1970); Chem. Ahstr., 74, 31766 (1971). J. Almog, A. Y. Meyer, and H. Shanan-Atidi, J . Chem. Soc., Perkin Trans. 2, 1972, 451. C. G. Overberger and I. C. Kogon, J . Am. Chem. Soc., 76, 1065 (1954). H. C. van der Plas and B. Zuurdeeg, Recl. Trati. Chim. Paya-Bas, 88, 426 (1969). P. Schmidt, K. Eichenberger, M. Wilhelm, and J. Druey, Helt;. Chim. Acta, 42, 763 (1959). L. P. Prikazchikova, B. M. Khutova, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1982, 974. S. Senda, K. Hirota, G:N. Yang, and M. Shirahashi, Yukugaku Zasshi, 91, 1372 (1971). I. M. Goldman, J . Org. Chem., 34, 3285 (1969). S. Senda, K. Hirota, and G.-N. Yang, Chem. Pharm. Bull., 20, 399 (1972). A. F. Crother, F. H. S. Curd, B. J. Lovell, H. T. Openshaw, and A. R. Todd, Br. Pat. 600,337 (1948); Chem. Ahstr., 42, 82 16 (1948). H. Biltz and K. Sedlatscheck, Ber. Dtsch. Chem. Ges., 57, 339 (1924).

1238 2092. 2093. 2094. 2095. 2096.

2097. 2098. 2099. 2100. 2101. 2102. 2103. 2104. 2105. 2106. 2107. 2108. 2109. 2110. 21 11.

References R. Andreasch, Sitzungsher. Akad. Wiss. Wien, Math.-Naturwiss. Kl., Aht. 28, 104, 648 (1895). T. Okano, S. Goya, and H. Matsumoto, Yakugaku Zasshi, 87, 1315 (1967). E. Brand, P. Richter, and K. Rieckhoff, Br. Pat. 988,398 (1965); Chem. Ahstr., 62, 16267 (1965). E. Brand, P. Richter, and K. Rieckhoff, Ger. Pat, 1,241,833 (1967); Chem. Ahstr., 68, 39644 (1 968). N. L. Drake, C. M. Eaker, J. A. Garman, K. E. Hamlin. R. A. Hayes, S. T. Haywood, R. M. Peck, R. K. Preston, J. Sterling, J. A. van Hook, and E. Walton, J . Am. Chem. Soc., 68, 1602 (1946). S. Sugasawa, S.-I. Yamada, and M. Narahashi, Yakugaku Zasshi, 71, 1345 (1951); Chem. Abstr., 46, 8034 (1952). T. Matsukawa and B. Ohta, Yukugaku Zasshi, 69, 491 (1949); Chem. Abstr., 44, 3456 (1950). R. Andrisano and G. Modena, Gazz. Chim. Ital., 81, 405 (1951). L. E. Lyons, J . Chem. Phys., 20, 1814 (1952). D. J. Brown and J. M. Lyall, Aust. J . Chem., 18, 1811 (1965). M. E. Kuehne, J . Am. Chem. Soc., 84, 837 (1962). R. R. Williams, US Pat. 2,194,190 (1939); Chem. Ahstr., 34, 4866 (1940). R. E. Busby, M. A. Khan, M. R, Khan, J . Parrick, C. J. G. Shaw, and M. Iqbal, J . Chem. Soc., Perkin Trans. I , 1980, 1427. K. F. M. J. Schmidt, Ber. Dtsch. Chem. Ges., 35, 1575 (1902). H. Vanderhaeghe and M. Claesen, Bull. Soc. Chim. Belg., 68, 30 (1959). T. Kato, H. Yamanaka, and H. Hiranuma, Chem. Pharm. Bull., 16, 1337 (1968).

R. R. Williams, A. E. Ruehle, and J. Finkelstein, J . Am. Chem. Soc., 59, 526 (1937). A. Brossi, Arch. Pharm. (Weinheim, Ger.), 296, 299 (1963). H. J. Fisher and T. B. Johnson, J . Am. Chem. Soc., 54, 727 (1932). E. Bergmann and H. Heimhold, J . Chem. Soc., 1935, 955.

2112. K. Tanabe, Y. Asahi, M. Nishikawa, T. Shima, Y. Kuwada, T. Kanzawa, and K. Ogata, Takeda Kenkyusho Nempo, 22, 133 (1963); Chem. Abstr., 60, 13242 (1964). 21 13. Z. Kazimierczuk and D. Shugar, Acta Biochim. Pol., 17, 325 (1970). 2114. D. J. Brown and B. T. England, J . Chem. Soc. (C), 1971, 250. 2115. D. J. Brown and T. Teitei, J . Chem. Soc., 3535 (1963); 832 (1965). 2116. E. von Meyer, Ber. Verhandl. K . Siichs. Ges. Wiss.Math. Phys. K I . , 57, 324 (1905); Chem. Zentr., 1906, I, 941; J . Chem. Soc., Ahstr., 1906, I, 411. 2117. E. Falch, J. Weis, and T. Natvig, J . Med. Chem., 11, 608 (1968). 2118. F. R. Basford, F. H. S. Curd, E. Hoggarth, and F. L. Rose, J . Chem. Soc., 1947, 1354. 2119. T. B. Johnson, J . Am. Chem. Soc., 65, 1218 (1943). 2120. T. B. Johnson, J . Am. Chem. Soc., 66, 146 (1944). 2121. H. Gershon, J . Org. Chem., 27, 3507 (1962). 2122. S. Murakami and N. Kondo, Jap. Pat. 32,265 (1970); Chem. Abstr., 74, 76442 (1971). 2123. T. B. Johnson and W. T. Caldwell, J . Am. Chem. Soc., 51, 873 (1929). 2124. I. I. Kuz’menko and L. D. Protsenko, Khim. Geterotsikl. Soedin., 1973, 117. 2125. W. R. Boon and W. G. M. Jones, J . Chem. Sac., 1951, 591. 2126. K. Takagi and T. Ueda, Chem. Pharm. Bull., 11, 1382 (1963). 2127. E. Profft and H. Raddatz, Arch. Pharm. (Weinheim, Ger.), 295, 649 (1962). 2128. R. H. Wiley and Y . Yamarnoto, J . Org. Chem., 25, 1906 (1960). 2129. T. B. Johnson and H. H. Guest, Am. Chem. J . , 42, 271 (1909). 2130. F. L. Rose and G. A. P. Tuey, J . Chem. Soc., 1946, 81.

References 2131. 2132. 2133. 2134. 2135. 2136. 2137. 2138. 2139. 2140. 2141. 2142. 2143. 2144. 2145. 2146. 2147. 2148. 2149. 2150. 2151. 2152. 2153. 2154. 2155. 2156. 2157. 2158. 2159. 2160. 2161. 2162. 2163. 2164. 2165. 2166. 2167. 2168. 2169. 2170. 2171. 2172.

1239

W. Klotzer and J. Schantl, Monatsh. Chem., 94, 1178 (1963). Y. Nitta and K. Okui, Jap. Pat. 10,335 (1962); Chem. Abstr., 59, 5176 (1963). T. B. Johnson and A. W. Joyce, J . Am. Chem. SOC., 37, 2151 (1915). N. K. Kochetkov, V. N. Shibaev, and A. A. Kost, Tetrahedron Lett., 1971, 1993. J. Clark and T. Ramsden, J . Chem. Soc. (C), 1971, 679. H. Kropf and M. Ball, Liebigs Ann. Chem., 1976, 2331. Y. F. Shealy, R. F. Struck, J. D. Clayton, and J. A. Montgomery, J . Org. Chem., 26,4433 (1961). J. A. Montgomery and C. Temple, J . Am. Chem. Soc., 79, 5238 (1957). C. Temple and J. A. Montgomery, J . Org. Chem., 31, 1417 (1966). Y.-1:. Chi and Y.-L. T'ien, J . Am. Chem. SOC.,57, 215 (1935). K. K. Gauri, Ger. Pat. 1,232,153 (1967); Chem. Abstr., 66, 95080 (1967). E. Habicht and R. Zubiani, Swiss Pat. 443,341 (1967); Chem. Ahstr., 68, 114627 (1968). D. Lipkin and E. G. Lovett, J . Org. Chem., 40, 1713 (1975). S. S. Berg and E. W. Parnell, J . Chem. Soc., 1961, 5275. Y. A. Tota and R. C. Elderfield, J . Org. Chem., 7, 309 (1942); Chem. Abstr., 36, 6161 (1942). S. Yanagida, M . Ohoka, M. Okahara, and S. Komori, Tetruhedron Lert., 1968, 2351. B. Camerino, G. Palamidessi, and R. Sciaky, Gazz. Chim. [tul., 90, 1830 (1960). R. Robertson and M. L. Tomlinson, J . Chon. Soc., 1935, 1283. H. C. van der Plas, B. Haase, B. Zuurdeeg, and M. C. Vollering, Reel. Trai:. Chim.Puys-Bas, 85, 1101 (1966). W. T. Caldwell and W. M. Ziegler, J . Am. Chem. Soc., 58, 78 (1936). H. Gershon, R. Braun, and A. Scala, J . Med. Chem., 6, 87 (1963). K. K. Gauri, Ger. Pat. 1,139,505 (1962); Chem. Abstr., 58, 7952 (1963). L. D. Protsenko and Y. I Bogodist, Ukr. Khim. Zh., 32, 378 (1966); Chem. Abstr., 65, 3869 ( 1 966). Y.-F. Chi and S.-F. Chen, Sci. Rec. (Peking),I, 31 (1957). Y.-F. Chi and S.-F. Chen, Sci. Rec. (Peking),1, 49 (1957). Y,-F. Chi and S.-F. Chen, Sci. Sin., 6, 477 (1957). Y.-F. Chi and Y. S. Kao, J . Am. Chem. Soc., 58, 769 (1936). R. Duschinsky, E. Pleven and C. Heidelberger, J . Am. Chem. Soc., 79, 4559 (1957). B. A. Ivin and V. G. Nemets, Zh. Obshch. Khim.,35, 1303 (1965). Z. BudtSinsky, J. Piikryl, and E. Svatek, Collect. Czech. Chem. Commun., 30, 3895 (1965). C. Heidelberger and R. Duschinsky, US Pat. 2,802,005 (1957); Chem. Abstr., 52, 2100 (1958). E. Wittenburg. J . Prakt. Chem. (41, 33, 165 (1966). R. K. Glushkov, B. A. Ivin, and E. G. Sochilin, Khim. Geterotsikl. Soedin., 1968, 914. G. Spiteller and H. Bretschneider, Monatsh. Chem., 92, 183 (1961). A. Dornow, F. Boberg, and L. Schurer, Arch. Pharm. (Weinheim, Ger.), 286, 494 (1953). J . Polis, Khim. Geterotsikl. Soedin., 1970, 571. R. Dohmori, S. Nagasaki, Y. Tanaka, N. Nakazawa, Y. Oshima, and T. Naito, Yukuguku Zasshi, 87, 419 (1967). Hoffmann-La Roche, Br. Pat. 877,318 (1960); Chem. Abstr., 56, 8724 (1962). G. J. Durr. in Synthetic Procedures in Nucleic Acid Chemistry,Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 92. G. D. Daves, R. K. Robins, and C. C. Cheng, J . Am. Chem. Soc., 83, 3904 (1961). H. Brocas-Neuwels and R. Promel, Bull. Soc. Chim. Belg., 77, 103 (1968). C:T. Chang and W.-W. Chang, J . Chin. Chem. Soc. (Taipei),26, 105 (1979).

1240 2173. 2174. 2175. 2176. 2177. 2178. 2179. 2180. 2181. 2182. 2183. 2184. 2185. 2186. 2187. 2188. 2189.

References C. Temple, C. L. Kussner, and J. A. Montgomery, J . Org. Chem., 34, 2102 (1969).

D. L. Ladd, J . Heterocycl. Chem., 19, 917 (1982). 1. Y. Postovskii and N. B. Smirnova, Dokl. Akad. Nauk SSSR, 166, 1136 (1966). W. B. Cowden and N. W. Jacobsen, Aust. J . Chem., 32, 2049 (1979). T. Sakamoto, Y. Kondo, and H. Yamanaka, Chem. Pharm. Bull., 30, 2410 (1982). M. Yanai and T. Naito, Yakugaku Zasshi, 61,99; Supplement, p. 46 (1941) Chem. Zentr., 1942, 1483; Chem. Ahstr., 36, 479 (1942). R. J . Dubois, C.-C. L. Lin, and B. L. Michel, J . Pharm. Sci., 64, 825 (1975). D. W. Allen, D. J. Buckland, B. G. Hutley, A. C. Oades, and J. B. Turner, J . Chem. Soc., Perkin Truns. I , 1977, 621. E. C. Taylor and F. Sowinski, J.Am. Chem. Soc., 91, 2143 (1969). W. Pfleiderer and R. Lohrmann, Chum. Ber., 94, 2708 (1961). M. Israel, S. K. Tinter, D. H. Trites, and E. J. Modest, J . Heterocycl. Chem., 7, 1029 (1970). G . K. Helmkamp and N. S. Kondo, Biochim. Biophys. Acta, 157, 242 (1968). R. Schneider, Ger. Pat. (Offen.), 2,006,145 (1970); Chem. Abstr., 74, 22877 (1971). D. J. Brown and T. Teitei, J . Chem. Suc., 1964, 3204. N. Yamaoka and K. Aso, J . Org. Chem., 27, 1462 (1962). Y.-F. Chi and Y.-H. Chen, J . Chem. Eng. (China), 5, 35 (1938); Chem. Zentr., 1939, I, 4955. G. K . Rogul'chenko and I. A. Mazur, Farm. Zh. (Kiev),30, No. 4, 27 (1975); Chem. Ahstr., 84, 43966 (1976). D. Shiho, S. Tagami, N. Takahayashi, and R. Honda, Yakuguku Zasshi, 76, 804 (1956).

2190. 2191. Hoffmann-La Roche, Belg. Pat. 665,446 (1965); Chem. Ahstr., 65, 728 (1966). 2192. Z . BudiSinsky, J. Piikryl, S. VaniEk, and E. Svatek, Collect. Czech Chem. Commun., 33, 2266 (1968). 2193. C. C. Price, N. J. Leonard, and D. Y. Curtin, J . Org. Chem., 10, 318 (1945). 2194. T. Naito, M. Hirata, and T. Kotake, Jap. Pat. 7,281 (1965); Chem. Abstr., 63, 617 (1965). 2195. Hoffmann-La Roche, Br. Pat. 953,875 (1964); Chem. Abstr., 61, 8321 (1964). 2196. Ciba, Belg. Pat. 641,252 (1964); Chem. Abstr., 63, 617 (1965). 2197. K. Sirakawa, S. Ban and M. Yoneda, Yakugaku Zasshi, 73, 598 (1953); Chem. Abstr., 48,9362 (1954). 2198. Z . BudESinsky, V. Bydiovsky, J. Kopecky, A. Svab, and J. Vaviina, Czech. Farm., 10, 241 (1961); Chem. Ahstr., 55, 25973 (1961). 2199. T. Yasushige, Y. Tsuruta, M. Aida, K. Noda, and S. Hyoto, Jap. Pat. 28,776 (1964); Chem. Ahstr., 62, 11828 (1965). 2200. T. Naito, M. Hirata, and T. Kobayashi, Jap. Pat. 7,513 (1965); Chem. Ahstr., 63, 1802 (1965). 2201. Takeda, Jap. Pat. 19,143 (1963); Chem. Abstr., 60, 2965 (1964). 2202. Geigy, Fr. Pat. 1,339,747 (1963); Chem. Abstr., 60, 5518 (1964). 2203. H. C. Koppel, R. H. Sringer, R. K. Robins, and C. C. Cheng, J . Org. Chem., 27, 3614 (1962). 2204. J. L. Fedrick, R. G. Shepherd, and S. G. Svokos, Fr. Pat. M2325 (1964); Chem. Ahstr., 61, 667 ( I 964). 2205. Hoffmann-La Roche, Br. Pat. 914,417 (1963); Chem. Ahstr., 58, 12579 (1963). 2206. V. A. Zasosov, T. N. Nikulina, L. S. Blinova, V. S. Onoprienko, V. N. Sycheva, G. N. Sokolova, K. S, Borodina, and K. V. Denisova, Khim.-Farm. Zh., 6, No. 3, 29 (1972); Chem. Abstr., 77, 5421 (1972). 2207. K. Kitani and H. Sedeoka, Nippon Kagaku Zasshi, 74, 624 (1953); Chem. Abstr., 48, 13693 (1954). 2208. H. Yuki and S. Hayakawa, Yakuyaku Zasshi, 87,458 (1967).

References 2209. 2210. 221 1. 2212. 2213. 2214.

1241

W. Klotzer and J. Schantl, Monatsh. Chem., 94, 1190 (1963). Hoffmann-La Roche, Fr. Pat. 1,343,491 (1963); Chem. Ahstr., 64, 3567 (1966). H. Yamanaka, Chem. Pharm. Bull., 7, 297 (1959). B. Lythgoe and L. S. Rayner, J . Chem. Soc., 1951, 2323. D. M. Belu and S. Cilianu, Rom. Pat. 53,975 (1972); Chem. Ahstr., 72, 152217 (1972). Hoffmann-La Roche, Br. Pat. 914,929 (1963); Chem. Abstr., 59, 1659 (1963).

W. C. Schneider, J . Am. Chem. Soc., 70, 627 (1948). G . B. Barlin, J . Chem. Soc. (B), 1967, 954. D. Authenrieth, H. Schmid, M. Ott, and W. Pfleiderer, Liehigs Ann. Chem., 1977, 1194. D. E. O’Brien, F. Baiocchi, R. K. Robins, and C. C. Cheng, J . M e d . Chem., 6, 467 (1963). R. J. Badger and G . B. Barlin, J . Chem. Soc., Perkin Trans. 2, 1974, 1854. M. P. Nemeryuk and T. S. Safonova, Khim. Geterotsikl. Soedin., Akad. Nauk Latc. SSR, 1966, 470; Chem. Ahstr., 65, 8903 (1966). 2221. H. Schroeder, US Pat. 3,118,889 (1964); Chem. Ahstr., 60, 12027 (1964).

2215. 2216. 2217. 2218. 2219. 2220.

2222. T. Sakamoto. K.-I. Tanji, S. Niitsuma, T. Ono, and H. Yarnanaka, Chem. Pharm. Hull., 28, 3362 (1980). 2223. F. Yoneda and Y. Sakuma, J . Chem. Soc., Chem. Commun., 1976, 203. 2224. F. Yoneda, Y. Sakuma, S. Mizumoto, and R. Ito, J . Chem. Soc., Perkin Trans. I , 1976, 1805. 2225. Merck, Br. Pat. 902,392 (1962); Chem. Ahstr., 57, 15128 (1962). 2226. T. Sakamoto, S. Kaneda, Y. Hama. H. Yosjizawa, and H. Yamanaka, Heterocycles, 20, 991 (1983). 2227. Merck, Br. Pat. 884,772 (1961); Chem. Ahstr., 57, 2231 (1962). 2228. K. Bhushan, D. J. Brown, J. H. Lister, L. G . Stephanson, and F. Yoneda, Aust. J . Chem., 28, 2553 (1975). 2229. T. B. Johnson and K. G . Mackenzie, Am. Chem. J., 42, 353 (1909). 2230. T. Hoshino and M . Ohta, Proc. Imp. Acad. (Tokyo), 13, 101 (1937); Chem. Zentr., 11, 3894 ( 1 937). 2231. A. Dornow and G . Petsch, Chem. Ber., 86, 1404 (1953). 2232. L. Suranyi and H. Wilk, Ger. Pat. 1,150,987 (1963); Chem. Ahstr., 60, 2971 (1964). 2233. M . M. Endicott and T. B. Johnson, J . Am. Chem. Soc., 63, 2063 (1941). 2234. A. Y. Berlin and M. N. Vasil’eva, Zh. Ohshch. Khim., 28, 1063 (1958). 2235. T. Kato, H. Yamanaka, and J . Kawamata, Yukugaku Zasshi, 89,460 (1969). 2236. 2237. 2238. 2239. 2240. 2241. 2242. 2243. 2244. 2245. 2246.

T. Okuda and C. C. Price, J . Org. Chem., 24, 14 (1959). H. C. Carrington, F. H. S, Curd, and D. N. Richardson, J . Chem. Soc., 1955, 1858. T. Matsukawa and B. Ohta, Yakugaku Zasshi, 69, 489 (1949); Chem. Ahstr., 44, 3455 (1950). J. D. Brooks, P. T. Charlton,. P. E. Macey, D. A. Peak, and W. F. Short, J . Chem. Soc., 1950, 452. J . F. W. McOmie, E. R. Sayer, and J. Chesterfield, J . Chem. Soc., 1957, 1830. H. L. Wheeler and D. F. McFarland, Am. Chem. J., 42, 431 (1909). S. Senda and A. Suzui, Chem. Pharm. Bull., 6, 479 (1958). R. A. West and H. W. Barrett, J . Am. Chem. Soc., 76, 3146 (1954). S. Cohen, E. Thom, and A. Bendich, J . Org. Chem., 27, 3545 (1962). C. W. Woenckhaus, Chem. Ber., 97, 2439 (1964). W. R. Boon, W. G. M. Jones, and G. R. Ramage, J . Chem. Soc., 1951, 96.

2247. R. S. Karlinskaya and N. V. Khrornov-Borisov, Zh. Ohshch. Khim., 30, 1485 (1960). 2248. J. P. Jonak, S. F. Zakrzewski, and L. H. Mead, J . Med. Chem., 15, 662 (1972).

1242

References

2255. 2256. 2257. 2258. 2259. 2260. 2261. 2262. 2263. 2264. 2265. 2266.

J. R. Marshall and J. Walker, J . Chem. Soc., 1951, 1004. K. Ueno, M. Kinoene, and T. Minami, Jap. Pat. 5,394 (1968); Chem. Ahstr., 69, 87009 (1968). Z . Proba and K. L. Wierzchowski, Acta Biochim. Pol., 22, 131 (1975). F. Craveri and G. Zoni, Boll. Sci. Fac. Chim. Ind. Bologna, 16, 132 (1958); Chem. Ahstr., 53, 13161 (1959). F. Craveri and G. Zoni, Boll. Sci. Fuc. Chim. Ind. Bologna, 16, 126 (1958); Chem. Ahstr., 53, 13161 (1959). F. R. Basford, F. H. S. Curd, F. L. Rose, H. T, Openshaw, R. Hull, and A. R. Todd, Br. Pat., 590,706 (1947); Chem. Ahstr., 42, 228 (1948). K. L. Howard, US Pat. 2,477,409 (1949). M. Seefelder and D. Leuchs, Br. Pat. 913,910 (1962); Chem. Abstr., 59, 2836 (1963). D. T. Hurst, Tetrahedron Lett., 1970, 979. D. J. Brown and P. Waring, Aust. J . Chem., 26, 443 (1973). S. Gabriel, Ber. Dtsch. Chem. Ges., 37, 3638 (1904). N. B. Chapman and C. W. Rees, J . Chem. Soc., 1954, 1190. M . Ohta, Yakuyaku Zasshi, 67, 175 (1947); Chem. Abstr., 45, 9545 (1951). M. Calligaris, P. Linda, and G. Marino, Tetrahedron, 23, 813 (1967). D. J. Brown and J. A. Hoskins, J . Chem. Soc. (B),1971, 2214. H. Vanderhaeghe and M. Claesen, Bull. Soc. Chim. Belg., 66, 276 (1957). M. Forchiassin, G. Illuminati, and G. Sleiter, J . Heterocycl. Chem,. 6, 879 (1969). Z. BudESinskji and F. Roubinek, Collect. Czech. Chem. Commun., 26, 2871 (1961).

2267. 2268. 2269. 2270.

A. J. Boulton, D. T. Hurst, J. F. W. McOmie, and M. S. Tute, J . Chem. Sue. (C),1967, 1202. H. Yamanaka, Chem. Pharm. Bull., 7, 508 (1959). S. Matsuura and T. Goto, J . Chem. SOC., 1965, 623. . W. A. Skinner, M. G. M. Schelstraete, and B. R. Baker, J . Org. Chem., 25, 149 (1960).

2249. 2250. 2251. 2252. 2253. 2254.

2271. A. Giner-Sorolla and L. Medrek, in Nucleic Acid Chemistry, Part 1 (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 83. T. B. Johnson, J . Am. Chem. SOC.,65, 1220 (1943). W. Schoenauer, Swiss Pat. 372,679 (1963); Chem. Ahstr., 60, 13257 (1964). T. B. Johnson and L. H. Chernoff, J . Am. Chem. Soc., 36, 1742 (1914). P. Rambacher and N. Kaniss, Angew. Chem., 80, 405 (1968). H. Goldner, G. Dietz, and E. Carstens, Liehigs Ann. Chem., 691, 142 (1966). 1. Wempen and J. J. Fox, J . Am. Chem. Soc., 86, 2474 (1964). K. K. Gauri. Ger. Pat, 1,185,617 (1965); Chem. Abstr., 62, 13159 (1965). B. W. Langley, Br. Pat. 845,378 (1960); Chem. Ahstr., 55, 6505 (1961). K. K. Gauri and H. Partenheimer, Ger. Pat. 1,250,829 (1967); Chem. Abstr., 68, 105226 (1968). M. M. Endicott and T. B. Johnson, J . Am. Chem. Soc., 63, 1286 (1941). 2. BudESinsk?, V. Jelinek, and J. Piikryl, Czech. Pat. 107,166 (1963); Chem. Abstr., 60, 9291 (1964). 2283. B. A. S. F. Br. Pat. 1,174,165 (1967); Chem. Ahstr., 72, 90504 (1970). 2284. F. Yoneda, M . Kawamura, S. Matsumoto, and M. Higuchi, J . Chem. Soc., Perkin Trans. I , 1977, 2285. 2272. 2273. 2274. 2275. 2276. 2277. 2278. 2279. 2280. 2281. 2282.

2285. 2286. 2287. 2288.

S. Yanagida, H. Hayama, and S. Komori, J . Org. Chem., 34, 4180 (1969). M. Hashimoto, Y. Saito, H. Seki, and T. Kamiya, Chem. Pharm. Bull., 20, 1186 (1972). J. Baddiley and A. Topham, J . Chem. Soc., 1944, 678. T. Ueda and J. J. Fox, J . Med. Chem., 6, 697 (1963).

References

1243

2289. W. H. Nyberg and C. C. Cheng, J . Heterocycl. Chem., 1, 1 (1964). 2290. P. Schmidt and M. Wilhelm, US Pat. 3,014,035 (1961); Chem. Abstr., 56, 14304 (1962). 2291. Z . BudESinsky, J. Vaviina, L. LangBidl, and J. Holubek, Collect. Czech. Chem. Commun., 45, 539 ( 1 980). 2292. Y. I. Bogodist and L. D, Protsenko, U k r . Khim. Zh., 31, 1309 (1965); Chem. Abstr., 64, 12670 (1 966). 2293. H. Yamanaka, K. Edo, F. Shoji, S. Konno, T. Sakamato, and M. Mizugaki, Chem. Phurm. Bull., 26, 2160 (1978). 2294. D. E. O’Brien, C. C. Cheng, and W. Pfleiderer, J . Med. Chem., 9, 573 (1966). 2295. D. J. Brown, J . Appl. Chem., 2, 239 (1952). 2296. 0. Isay, Rer. Dtsch. Chem. Ges., 39, 250 (1906). 2297. R. G. W. Spicket and G. M. Timmis, Chem. Ind. (London), 1951, 937. 2298. F. S. Okumura, H. Kusaka, and T. Takematsu, Bull. Chem. Soc. Jpn., 33, 1471 (1960). 2299. M. G . Harris and R. Stewart, Can. J . Chem., 55, 3800 (1977). 2300. S. M. Greenberg, L. 0. Ross, and R. K. Robins, J . Org. Chem., 24, 1314 (1959). 2301. H. Segal and D. Shapiro, J . Med. Chem., 1, 371 (1959). 2302 H. Goldner, Z . Chem., I, 16 (1961). 2303. N. J. Leonard and T. R. Henderson, J . Am. Chem. Soc., 97,4990 (1975). 2304. R. Andrisano and G. Modena, Boll. Sci. Fac. Chim. Ind. Bologna, 10, 156 (1952); Chem. Ahstr., 47, 4737 (1953). 2305. M . P. L. Caton and J . F. W. McOmie, J . Chem. Soc. (C), 1968, 836. 2306. A. Signor, E. Scoffone, L. Biondi, and S. Bezzi, Guzz. Chim. Ital., 93, 65 (1963). 2307. R. K. Robins, K. L. Dille, and B. E. Christensen, J . Org. Chem., 19, 930 (1954). 2308. D. E. O’Brien, C. C. Cheng, and W. Pfleiderer, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorback and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 78. 2309. R. M. Cresswell and H. C. S. Wood, J . Chem. Soc., 1960, 4768. 2310. W. Klotzer and M. Herberz, Monatsh. Chem., 96, 1573 (1965). 231 1. S. Gabriel, Ber. Dtsch. Chem. Ges., 38, 1689 (1905). 2312. H. L. Wheeler and T. B. Johnson, J . B i d . Chem., 3, 183 (1907). 2313. M. E. Hultquist and E. Kuh. Br. Pat. 559,455 (1944); Chem. Abstr., 39, 5410 (1945). 2314. J. P. English, US Pat. 2,224,811 (1940); Chem. Abstr., 35, 2160 (1941). 2315. M. E. Hultquist, US Pat. 2,436,360 (1948); Chem. Ahstr., 42, 3438 (1948). 2316. M. Yanagita, Yukugaku Zasshi, 72, 1383 (1952). 2317 V. N. Sokolova and 0. Y. Magidson, Muter. Obmenu Peredouym Opytom Nauchn. Dostizh. Khim.-Farm. Prom., No. 1, 129 (1958); Chem. Abstr., 55, 25956 (1961). 2318. R. M. Wagner and C. Jutz, Chem. Ber., 104, 2975 (1971). 2319. C. W. Whitehead and J. J. Traverso, US Pat. 2345,425 (1958); Chem. Ahstr., 53, 2262 (1959). 2320. H. Goldner, Chem. Tech. (Leipzig), 12, 495 (1960); Chem. Abstr., 55, 5517 (1961). 2321. M. P. V. Boarland and J. F. W. McOmie, J . Chem. Suc., 1951, 1218. 2322. J. W. Copenhaver and R. F. Kleinschmidt, Br. Pat. 663,302 (1951); Chem. Abstr., 46, 10212 (1952). 2323. I. C . Kogon, R. Minin, and C. G. Overberger, Org. Synth., 35, 34 (1955). 2324. N. Sperber, D. Papa, E. Schwenk, M. Sherlock, and R. Fricano, J . Am. Chem. Soc., 73, 5752 (1951). 2325. J. F. W. McOmie and M. P. V. Boarland, Chem. Ind. (London), 1950, 602. 2326. V. M. Cherkasov, L. P. Prikazchikova, and L. I. Rybchenko, Khim. Geterotsikl. Soedin., 1972, 558.

1244

References

2327. A. Albert, D. J. Brown, and G. W. H. Cheeseman, J . Chem. Soc., 1951, 474. 2328. W. G. M. Jones, Nature (London), 162, 524 (1948). 2329. J. A. Montgometry, J . Am. Chem. Soc., 78, 1928 (1956). 2330. A. Nagel, H. C. van der Plas, and A. van Veldhuizen, Reel. Trav. Chim.Pays-Bas, 94,45(1975). 2331. B. Roth and J. Z. Strelitz, J . Org. Chem., 34, 821 (1969). 2332. S. Gabriel, Ber. Dtsch. Chem. Ges., 34, 3362 (1901). 2333. T. J. Delia and D. L. Venton, J . Heterocycl. Chem., 9, 73 (1972). 2334. A. Albert, D. J. Brown, and G. W. H. Cheeseman, J . Chem. Soc., 1952, 4219. 2335. A. Bendich, P. J. Russell, and J. J. Fox, J . Am. Chem. Soc., 76, 6073 (1954). 2336. H. Ballweg, Leibigs Ann. Chem., 657, 141 (1962). 2337. H. H. Lin and C. C. Price, J . Org. Chem., 26, 264 (1961). 2338. L. R. Lewis, F. H. Schneider, and R. K. Robins, J . Org. Chem., 26, 3837 (1961). 2339. B. Bobranski and K. Stankiewicz, Rocz. Chem., 45, 277 (1971). 2340. T. B. Johnson, Am. Chem. J . , 40, 19 (1908). 2341. M. Wrona and B. Czochrolska, Acta Biochim. Pol., 17, 351 (1970). 2342. G. M. Kheifets and N. V. Khromov-Borisov, Zh. Obshch. Khim., 34, 3851 (1964). 2343. T, Masuda, Pharm. Bull., 5, 28 (1957). 2344. W. R. Boon and T. Leigh, Br. Pat. 677,342 (1952); Chem. Abstr., 47, 9369 (1953). 2345. W. S. McNutt, J . Am. Chem. Soc., 82, 217 (1960). 2346. R. B. Silvcrman, R. E. Radak, and N. P. Hacker, J . Org. Chem., 44, 4970 (1979). 2347. J. W. Clapp and R. 0. Roblin, US Pat. 2.577,231 (1951); Chem. Ahstr., 46, 5619 (1952). 2348. R. 0. Roblin and J. W. Clapp, J . Am. Chem. Soc., 72, 4890 (1950). 2349. J. P. English and E. B. Leffler, J . Am. Chem. Soc., 72, 4324 (1950). 2350. S. J. Childress and R. L. McKee, J . Am. Chem. Soc., 72, 4271 (1950). 2351. S. J. Childress and R. L. McKee, J . Am. Chem. Soc., 73, 3862 (1951). 2352. Y. F. Shealey, J. D. Clayton, C. A. ODell, and J. A. Montgomery, J . Org. Chem., 27, 4518 (1962). 2353. W. Bock, Ber. Dtsch. Chem. Ges., 56, 1222 (1923). 2354. E. Ziegler, R. Salvador, and T. Kappe, Monatsh. Chem., 93, 1376 (1962). 2355. Z . BudESinsky, J. Piikryl, A. Svab, and V. Jelinek, Czech. Pat. 108,806 (1963); Chem. Abstr., 61, 5664 (1964). 2356. T. B. Johnson and G. de Siito-Nagy, J . Am. Chem. Soc., 63, 261 (1941). 2357. A. E. Lanzilotti, A. C. Shabica, and J. B. Ziegler, US Pat. 2,666,764 (1954); Chem. Abstr., 49, 6995 (1955). 2358. R. L. Jones and C. W. Rees, J . Chem. Soc. (C), 1969, 2251. 2359. R. Hull, B. J. Lovell, H. T. Openshaw, L. C. Payman, and A. R. Todd, J . Chem. Soc., 1946,357. 2360. G. Strauss, Ger. Pat. 1,141,287 (1962); Chem. Abstr., 58, 12578 (1963). 2361. P. J. Barr, A. S. Jones, and R. T. Walker, Nucleic Acid Res., 3, 2845 (1976). 2362. S. Birtwell, J . Chem. Soc., 1953, 1725. 2363. L. Fabbrini, Gazz. Chem. Ital., 87, 1293 (1957). 2364. C. W. Thornber, J. M. Farrell, and D. S. Clarke, Synthesis, 1983, 222. 2365. T. B. Johnson and E. V. McCollum. Am. Chem. J., 36, 136 (1906). 2366. M. A. Kirillova, I. A. Maretina, and A. A. Petrov, Zh. Org. Khim., 7, 14 (1971). 2367. H. Maisack, D. Peukert, and W. Schonleben, Br. Pat. 860,423 (1961); Chem. Abstr., 55, 17664 (1961). 2368. E. Fischer and H. Tullner, Ber. Dtsch. Chem. Ges., 35, 2563 (1902).

References

1245

2369. E. Mulder, Ber. Dtsch. Chem. Ges., 6, 1015 (1873). 2370. A. Novitek and M. Lissnerova, Collect. Czech. Chem. Commun., 33, 1003 (1968). 2371. U. Valcavi and L. Gaudenzi, Farmaco, Ed. Sci., 18, 847 (1963); Chem. Abstr., 60, 4142 (1964). 2372. D. W. Kaiser, US Pat. 3,036,075 (1962); Chem. Abstr., 58, 1477 (1963). 2373. W. Ried and P. Stock, Liebigs Ann. Chem., 700, 87 (1966). 2374. T. Sakamoto, H. Arakida, K. Edo, and H. Yamanaka, Heterocycles, 16, 965 (1981). 2375. T. Sakamoto, H. Arakida, K. Edo, and H. Yamanaka, Chem. Pharm. Bull., 30, 3647 (1982). 2376. K. Edo, T. Sakamoto, and H. Yamanaka, Chem. Pharm. Bull., 27, 193 (1979). 2377. G . A. Howard, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1944, 416. 2378. 1. J . Pachter, P. E. Nemeth, and A. J. Villani, J . Org. Chem., 28, 1197 (1963). 2379. I. J. Pachter, US Pat. 3,159,629 (1964); Chem. Ahstr., 62, 6496 (1965). 2380. V. I. Khmelevskii and 0. I. Durnitsyna, Z h . Ohshch. Khim., 26, 755 (1956); Chem. Abstr., 50, 14777 (1956). 2381. Bayer, Ger. Pat. 144,761 (1902); F‘rdl., 7, 681 (1902-1904). 2382. Boehringer, Ger. Pat. 126,797 (1901); frdl., 6, 1185 (1900- 1902). 2383. U. Sanyal, S. Dutta, S. Banerjee, and S. K. Chakraborti, Indian J . Chcm., Sect. B, 21, 565 (I982). 2384. A. Bendich and G . C . Clements, Biochim. Biophys. Acta, 12, 462 (1953). 2385. M. Horiuchi, Chem. Pharm. Bu//., 7, 393 (1959). 2386. A. Bendich, Trans. N . Y. Acad. Sci., 15, 58 (1952); Chern. Ahstr., 47, 12394 (1953). 2387. J. A. Baker and P. V. Chatfield, J . Chem. Soc. (C), 1969, 603. 2388. D. E. O’Brien, L. T. Weinstock, and C. C. Cheng, J . Med. Chern., 11, 387 (1968). 2389. H. Gold and 0. Bayer, Chem. Ber., 94, 2594 (1961). 2390. W. Pfleiderer and H. Fink, Chem. Ber., 96, 2950 (1963). 2391. W. Pfleiderer, E. Liedek, R. Lohrmann, and M. Rukwied, Chem. Ber., 93, 2015 (1960). 2392. K. N. Campbell and B. K. Campbell, US Pat. 2,523,496 (1950); Chem. Ahstr., 45, 6657 (1951). 2393. M. Ishidate, M. Sekiya, Y. Osdki, and Y. Harada, Yakugaku Zasshi, 76, 1107 (1956); Chem. Ahstr., 51, 3614 (1957). 2394. H. Goldner, G. Dietz, and E. Carstens, Lichiys Ann. Chem., 692, 134 (1966). 2395. S. M. S. Chauhan and H. Junjappa, Tetrahedron, 32, 1779 (1976). 2396. J. Clark, W. Pendergast, F. S. Yates, and A. E. Cunliffe, J . Chem. Soc. (C), 1971, 375. 2397. Bayer, Ger. Pat. 158,621 (1904); Frdl., 7, 666 (1902-1904). 2398. M. Furukawa, Y. Seto, and S. Toyoshima, Chem. Pharm. Bull., 9,914 (1961). 2399. M. Polonovski, R. Vieillefosse, and M. Pesson, Bull. Soe. Chim. Fr., 1945, 78. 2400. D. C. Suster, G. Botei, I. V. Feyns, V. Dobre, and 1. Niculescu-Duvsz, Rev. Roum. Chim., 22, 257 (1 977). 2401. W. Traube and H. W. Dudley, Ber. Dtsch. Chem. Ges., 46 3839 (1913). 2402. A. Bendich, J. F. Tinker, and G. B. Brown, J . Am. Chem. Sue., 70, 3 I09 ( 1 948). 2403. S. 1. Zav’yalov and G. V. Pokhvisneva, Izc. Akad. Nauk S S S R , Ser. Khim.,1973, 2363. 2404. S. Matsuura, M. Yamamoto, and Y. Kaneko, Bull. Chem. Soc. Jpn., 45,492 (1972). 2405. M. Sprecher and D. B. Sprinson, Biochemistry, 4, 655 (1965). 2406. J. A. Haines, C. B. Reese, aqd A. R. Todd, J . Chem. Soc., 1962, 5281. 2407. H. Zondler and W. Pfleiderer, Chem. Ber., 99,2984 (1966). 2408. W. R. Boon and G. Bratt, J . Chem. Soc., 1957, 2159. 2409. K. Hartka and L. Peshkar, Phurm. Zentralhalle, 107, 348 (1968). 2410. S. Trofimenko, E. L. Little, and H. F. Mower, J . Org. Chem., 27, 433 (1962).

1246

References

2411. W. Bohm, W. Peschke, and E. Rabald, Ger. Pat. 834,994 (1952); Chem. Abstr., 47, 1733 (1953). 2412. A. Schafer and H. Miksch, Ger. Pat. 824,945 (1951); Chem. Abstr., 47, 6990 (1953). 2413. A. Albert, D. J. Brown, and H. C. S. Wood, J . Chem. SOC.,1954, 3832. 2414. M. Seefelder. Ger. Pat. 1,112,982 (1959); Chem. Abstr., 56, 5810 (1962). 2415. H. J. Bielig and A. Loeser, Ger. Pat. 859,168 (1952); Chem. Abstr., 50, 9452 (1956). 2416. T. Ueda, N. Oda, and I. Ito, Heterocycles, 8, 263 (1977). 2417. T. Ueda, N. Oda, and I. Ito, Chem. Phurm. Bull., 28, 2144 (1980). 2418. R. S. Karlinskaya and N. V. Khromov-Borisov, Zh. Obshch. Khim., 32, 1858 (1962). 2419. G. T. Rogers and T. L. V. Ulbricht, J . Chem. SOC.(C), 1971, 2364. 2420. D. J. Brown and N. W. Jacobsen, J . Chem. SOC.,1965, 1175. 2421. P. D. Landauer and H. N. Rydon, J . Chem. SOC.,1953, 3721. 2422. J. Clark and G. Neath, J . Chem. SOC.(C), 1968, 919. 2423. A. A. Santilli and D. H. Kim, J . Med. Soc., 15, 442 (1972). 2424. A. Kalmus and F. Bergmann, J . Chem. Soc., 1961, 760. 2425. F. Bergmann and M. Tamari, J . Chem. SOC., 1961, 4468. 2426. W. B. Cowden and N. W. Jacobsen, Aust. J . Chem., 33. 131 (1980). 2427. A. Albert and H. S. C. Wood, J . Appl. Chem., 3, 521 (1953). 2428. A. Kostolansky and J. Mokry, Chem. Z w s t i , 10, 170 (1956); Chem. Abstr., SO, 15546 (1956). 2429. P. R. Pal, J . Indian Chem. SOC.,31, 673 (1954). 2430. F. L. Hahn, Ber. Dtsch. Chem. Ges., SO, 705 (1917). 2431. E. C. Taylor, 0. Vogl, and C. C. Cheng, J . Am. Chem. Soc., 81, 2442 (1959). 2432. 0. Vogl and E. C. Taylor, J . Am. Chem. Soc., 79, 1518 (1957). 2433. H. Wieland and R. Liebig, Liebiys Ann. Chem., 555, 146 (1944). 2434. Merck, Ger. Pat. 165,693 (1905); Frdl., 8, 1082 (1905-1907). 2435. J. Clark, J . Chem. Soc. (C), 1967, 1543. 2436. C. K. Cain, M. F. Mallette, and E. C. Taylor, J . Am. Chem. SOC.,68, 1996 (1946). 2437. M. Ishidate, M. Sekiya, Y. Osaki, I. Kurita, and Y. Harada, Pharm. Bull., 3, 224 (1955). 2438. E. S. Golovchinskaya and N. N. Uryupina, Zh. Prikl. Khim., 19, 1340 (1946); Chem. Abstr., 42, 1207 (1948). 2439. W. R. Sherman and E. C. Taylor, Org. Synth., 37, 15 (1957). 2440. W. Pfleiderer, Chem. Ber., 92, 2468 (1959). 2441. R. M. Evans, P. G. Jones, P. J. Palmer, and E. F. Stephens, J . Chem. Soc., 1956,4106. 2442. G. B. Elion and G. H. Hitchings, J . Am. Chem. Soc., 69, 2553 (1947). 2443. S. F. Mason, J . Chem. SOC., 1954, 2071. 2444. M. Hoffer, in Jubilee Volume, Emil Barell, Hoffmann-La Roche, Basel, 1946, p. 428; Chem. Ahstr., 41, 4108 (1947). 2445. J. Clark, B. Parvizi, and I. W. Southon, Chem. Ind. (London),1974, 661. 2446. G. B. Elion and G. H. Hitchings, J . Am. Chem. SOC.,76, 4027 (1954). 2447. G. H. Hitchings and G. B. Elion, US Pat. 2,721,866 (1955); Chem. Ahstr., 50, 8748 (1956). 2448. Y . F. Shealey, J. D. Clayton, and J. A. Montgomery, J . Org. Chem., 27, 2154 (1962). 2449. F. Bergmann and A. Kalmus, J . Chem. SOC.,1962, 860. 2450. J. A. van Allan, Ory. Synth., 32, 45 (1952). 2451. H. Heinrich and W. F. Buth; US Pat. 2,673,204 (1954); Chem. Abstr., 49, 1825 (1955). 2452. W. Pfleiderer and R. Lohrmann, Chem. Ber., 94, 12 (1961). 2453. H. G. Garg and R. A. Sharma, J . Phurm. Sci., 59, 1691 (1970).

References

1247

2454. V. G. Nemets, B. A. Ivin, and V. I. Slesarev, Zh. Obshch. Khim., 35, 1429 (1965). 2455. R. 0.Roblin, J. 0.Lampen, J. P. English, Q. P. Cole, and J. R. Vaughan, J . Am. Chem. Soc., 67, 290 (1945). A. Carr, E. Sawicki, and F. E. Ray, J . Org. Chem., 23, 1940 (1958). G. B. Elion, E. Burgi, and G. H. Hitchings, J . Am. Chem. Soc., 74, 411 (1952). C. 0. Johns and A. G. Hogan, J . Biol. Chem., 14, 299 (1913). F. R. Benson, L. W. Hartzel, and E. A. Otten, J . Am. Chem. Soc., 76, 1858 (1954). G. A. Reynolds, J. A. van Allan, and J. F. Tinker, J . Org. Chem., 24, 1205 (1959). W. D. Guither, D. G. Clark, and R. N. Castle, J . Heterocycl. Chem., 2, 67 (1965). F. G. Fischer and E. Fahr, Liebigs Ann. Chem., 651, 64 (1962). J. M. Pabiot, L. Pichat, A. Esanu, J. Pommier, and J. P. Laurent, J . Label. Compd. Radiopharm., 19, 195 (1982). 2464. Geigy, Fr. Pat. 1.377,696 (1964); Chem. Ahstr., 62, 7776 (1965). 2465. S. Yanagida, T. Fujita, M. Ohoka, R. Kumagai, and S. Komori, Bull. Chem. Soc. Jpn., 46, 299 (1973).

2456. 2457. 2458. 2459. 2460. 2461. 2462. 2463.

2466. 2467. 2468. 2469. 2470. 2471. 2472. 2473. 2474. 2475. 2476. 2477. 2478. 2479. 2480. 2481. 2482. 2483. 2484. 2485. 2486. 2487. 2488. 2489. 2490. 2491. 2492. 2493.

W. Klotzer and H. Bretschneider, Monatsh. Chem., 87, 136 (1956). A. Bowman, J . Chem. Soc., 1937, 494.

Y. P. Shvachkin and L. A. Syrtsova, Zh. Obshch. Khim., 33, 2848 (1963). A. L. Cossey, R. L. N. Harris, J. L. Huppatz, and J. N. Phillips, Angew. Chem., 86, 898 (1974). B. Stelander and H. G. Viehe, Anyew. Chem., 89, 182 (1977). G. Mattioda, P. Obellianne, H. Gauthier, G. Loiseau, R. Milliseher, A.-M. Donadieu, and M. Mestre, J . Med. Chrm., 18, 553 (1975). J. A. Hendry, R. F. Homer, and F. L. Rose, Br. Pat. 683,414 (1952); Chem. Abstr., 48, 746 (1 954). G. Girault, S. Coustal, and P. Rumpf, Bull. Soc. Chim. Fr., 1972, 2787. F. E. King and T. J. King, J . Chem. Soc., 1947, 726. W. R. Boon, Br. Pat. 763,041 (1956); Chem. Ahstr., 51, 15612 (1957). C. Grundmann and R. Richter, J . Org. Chem., 33, 476 (1968). H. Bretschneider and E. Fitz, Swiss Pat. 423,786 (1967); Chem. Ahstr., 68, 2910 (1968). Y.-F. Chi and T.-K. Chin, J . Chem. Eng., (China), 5, 19 (1938); Chem. Zentr., 1939, I , 413. L. D. Protsenko and Y. 1. Bogodist, Zh. Obshch. Khim., 33, 537 (1963). R. A. Paegle, M . G. Platta, M. Y. Lidak, and Y. Y. Popel, Khim.Geterotsikl. Soedin., 1971,258. F . Bergel and A. R. Todd, J . Chem. Soc., 1937, 1504. I. V. Boldyrev, I. F. Vladimirtsev, E. A. Romanenko, N. G. Korzhenevskaya, E. V. Titov, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1977, 1248. Y. I. Bogodist, U k r . Khim. Zh., 33, 87 (1967); Chem. Abstr., 66, 94989 (1967). C. J. Moye, Aust. J . Chem., 17, 1309 (1964). H. Bretschneider, J. Dehler, and W. Klotzer, Monatsh. Chem., 95, 207 (1964). H. Bretschneider and W. Klotzer, US Pat. 3,091,610 (1963); Chem. Abstr., 59, 3934 (1963). P. D. Landor and H. N. Rydon, J . Chem. Soc., 1955, 1 1 13. M. Pesson, Bull. Soc. Chim. Fr., 1951,428. Y.-F. Chi, S.3. We], and M.-S. Liang, J . Am. Chem. Soc., 61, 3377 (1939). R. L. N. Harris and J. L. Huppatz, Angew. Chem., 89, 816 (1977). S. Nishigaki, K. Senga, and F. Yoneda, Chem. Pharm. Bull., 18, 1925 (1970). W. Schmidt-Nickels and T. B. Johnson, J . Am. Chem. Soc., 52, 4511 (1930). H. Steudel and A. Kossel, Woppe-Seyler’s Z . Physiol. Chem., 29, 303 (1900).

1248

References

2494. C. C. Bhat and H. R. Munson, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 83. 2495. Y.-F. Chi and Y.-C. Ling, Sci. Sin., 4, 119 (1955). 2496. T. Kato and H. Hayashi, Yakugaku Zasshi, 88, 458 (1968). 2497. A. A. Abou Ouf, M. M. El-Kerdawy, and A. A. Missalem, Egypt. J . Pharm. Sci., 14,189 (1973); Chem. Ahstr., 80, 133374 (1974). 2498. Y. Maki, M. Suzuki, T. Furuta, T. Hiramitsu, and M. Kuzuya, Tetrahedron Lett., 1974,4107. 2499. V. M. Cherkasov, G. S. Tret’yakova, and N. N. Aleksandrova, Ukr. Khim. Zh., 36,694 (1970); Chem. Abstr., 74, 3577 (1971). 2500. R . Hull, J . Chem. Soc., 1959, 481. 2501. 1. K. Fel’dman and V. I. Zlobina, Mechenye Biol. Akt. Veshchestua, Sh. Statei, 53 (1962); Chem. Ahstr., 59, 7527 (1963). 2502. L. R. Davidenkov, Med. Prom. SSSR, 16, No. 1, 25 (1962); Chem. Abstr., 58, 4565 (1963). 2503. A. J. Montgomery, W. E. Fitzgibbon, V. Minic, and C. A. Krauth, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 75. 2504. 2505. 2506. 2507. 2508.

H. Bretschneider, W. Klotzer, and G. Spiteller, Monatsh. Chem., 92, 128 (1961). J. P. English and J. H. Clark, US Pat. 2,506,351 (1950); Chem. Ahstr., 44, 6883 (1950). R. Hull, J . Chem. Soc., 1951, 2214. G. W. Kenner, B. Lythgoe, A. R. Todd, and A. Topham, J . Chem. Soc., 1943, 574. C. Hennart and E. Merlin, Bull. Soc. Chim. Fr., 1959, 741.

2509. E. F. Godefroi, J . Org. Chem., 27, 2264 (1962). 2510. J. Wojciechowski, Pol. Pat. 71,235 (1974); Chem. Ahstr., 83, 79280 (1975). 251 I . E. L. Stogryn, J. Med. Chem., 15, 200 (1972). 2512. Geigy, Br. Pat. 1,182,086 (1970); Chem. Ahstr., 72, 100736 (1970). 2513. V. H. Smith and B. E. Christensen, J . Org. Chem., 20, 829 (1955). 2514. E. C. Taylor and P. Drenchko, J . Am. Chem. Soc., 74, 1101 (1952). 2515. K. Seitz, US Pat. 3,086,020 (1963); Chem. Ahstr., 59, 10084 (1963). 2516. K. Seitz, H. Riat, and M. Staeuble, Swiss Pat., 467,847 (1969); Chem. Ahstr., 71, 92639 (1969). 2517. K. Berg-Neilsen, Acta Chem. Scand., Ser. B, 29, 1092 (1975). 2518. G. J. Durr, J . Med. Chem., 8, 140 (1965). 2519. J. iemlii-ka, Collect. Czech. Chem. Commun., 28, 1060 (1963). 2520. T. Ueda and H. Ohtsuka, Chem. Pharm. Bull., 21, 1451 (1973). 2521. H. C. van der Plas and H. Jongjan, Recl. Trau. Chim. Pays-Bas, 89, 680 (1970). 2522. H. Yamanaka, H. Abe, H. Hiranuma, and T. Sakamoto, Chem. Pharm. Bull., 26, 842 (1978). 2523. Y. Nitta and K. Okui, Jap. Pat. 10,336 (1962); Chem. Ahstr., 59, 5177 (1963). 2524. D. G. McMinn, Synthesis, 1976, 824. 2525. T. Kato, H. Yamanaka, and H. Hiranuma, Yukugaku Zasshi, 90, 877 (1970). 2526. G. A. Neville, Can. J . Chem., 50, 1253 (1972). 2527. H. L. Wheeler, T. B. Johnson, and C. 0. Johns, Am. Chem. J., 37, 392 (1907). 2528. C. H. Eldredge and J. D. Mee, US Pat. 3.674,782 (1972); Chem. Ahstr., 77, 128093 (1972). 2529. Y. Kanaoka, E. Sato, M. Aiura, 0. Yonemitsu, and Y. Mizuno, Tetrahedron Lett., 1969, 3361. 2530. S. Yurugi, M. Hieda, T. Fushimi, Y. Kawamatsu, H. Sugihara, and M. Tomimoto, Chem. Pharm. Bull., 20, 15I 3 ( I 972). 2531. M. Boctius, B. Marchand, and G. Dietz, J . Prakt. Chem. [4], 7, 135 (1959). 2532. A. Kreutzberger and U.-H. Tesch, Chem. Ber., 109, 3255 (1976).

References 2533. 2534. 2535. 2536. 2537. 2538. 2539. 2540. 2541. 2542. 2543. 2544. 2545. 2546. 2547. 2548. 2549. 2550. 2551. 2552. 2553. 2554. 2555. 2556. 2557. 2558. 2559. 2560. 2561. 2562. 2563. 2564. 2565. 2566. 2567. 2568. 2569. 2570. 2571. 2572. 2573.

1249

G. A. Neville and H. W. Avdovich, Can. J . Chem., 50, 880 (1972). E. Frankland and H. Kolbe, Liebigs Ann. Chem., 65, 269 (1848). E. von Meyer, J . Prakt. Chem., [2], 38, 336 (1888). G. A. Reynolds, W. H. Humphlett, F. W. Swamer, and C. R. Hauser, J . Org. Chem., 16, 165 (1951). K. Takeda and K. Tokuyarna, Yukuyaku Zasshi, 76,77 (1956);Chem. Ahstr., 50, 13035 (1956). R. T. Markiw and E. S. Canellakis, J . Ory. Chem., 34, 3707 (1969). R. N. Lacey, J . Chem. Soc., 1954, 845. R. Behrend and J. Hoffmann, Liebigs Ann. Chem., 253, 68 (1889). R. N. Lacey, Br. Pat. 738,581 (1955); Chem. Ahstr., 50, 14004 (1956). H. Egg and I. Volgger, Synthesis, 1982, 1071. A. Pinner, Ber. Dtsch. Chem. Ges., 22, 1612 (1889). E. von Meyer, J . Prakt. Chem. 121, 39, 156 (1889). E. von Meyer, J . Prakt. Chem. 121, 40, 303 (1889). T. L. Cairns, J. C. Sauer, and W. K. Wilkinson, J . Am. Chem. Soc., 74, 3989 (1952). C. W. Whitehead, US Pat. 2.774,760 (1956); Chem. Ahstr., 51, 7440 (1957). K. Fickentscher and E. Giinther, Arch. Pharm. (Weinheim, Ger.), 308, 118 (1975). K. K. Ogilvie, S. L. Beaucage, and M. F. Gillen, Tetrahedron Lett., 1978, 3203. E. Frass, M. Draminski, and B. Fiszer, Rocz. Chem., 48, 971 (1974). J. P. Jonak, G. C. Hopkins, H. J. Minnerneyer, and H. Tieckelmann, J . Ory. Chem., 35, 2512 ( 1 970). L. G. S. Brooker, G. H. Keyes, R. H. Sprague, R. H. van Dyke, E. van Lare, G. van Zandt, and F. L. White, J . Am. Chem. Soc., 73, 5326 (1951). D. Shugar and J. J. Fox, Bull. Soc. Chim. Belg., 61, 293 (1952). A. Kreutzberger and H. Schimmelpfenning, Arch. Pharm. (Weinheim, Ger.),313, 260 (1980). R. E. Banks, D. S. Field, and R. N. Haszeldine, J . Chem. Soc. (C), 1969, 1866. A. G. Beaman and R. K. Robins, J . M e d . Pharm. Chem., 5, 1067 (1962). T. Okano, A. Takadate, and H. Matsumoto, Yakuguku Zasshi, 88, 439 (1968). 0. P. Shkurko, S. G. Baram, and V. P. Marnaev, Khim. GeterotsikL Soedin., 1972, 1281. D. J. Brown and T. Sugimoto, J . Chem. Soc. (C), 1970, 2661. M. E. C. Biffin, D. J. Brown, and T.-C. Lee, J . Chem. Soc. (C), 1967, 573. R. Andrisano, Boll. Sci. Fac. Chim.Ind. Bologna, 5, 52 (1944-1947); Chem. Ahstr., 44, 3905 (1950). A. Sugihara and M. Ito, Yukugaku Zusshi, 85,418 (1965). I. K. Fel’dman and C.-C. Chih, Zh. Ohshch. Khim., 30, 3835 (1960); Chem. Ahsrr., 55, 21 137 (1961). M. A. Krackov and B. E. Christensen, J . Org. Chem., 28, 2677 (1963). W. Kunze, Ger. Pat. 962,165 (1957); Chem. Abstr., 53, 10262 (1959). M. P. V. Boarland, J. F. W. McOrnie, and R. N. Timms, J . Chem. Soc., 1952, 4691. T. K. Liao, E. G. Podrebarac, and C. C. Cheng, J . Am. Chem. Soc., 86, 1869 (1964). K. Rohde and H. Nahme, Ger. Pat. 738,497 (1943); Chem. Abstr., 38, 4273 (1944). M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 31, 1035 (1966). D. J. Brown and K. lenaga, J . Chem. Soc.. Perkin Trans. 1, 1974, 372. E. Buschmann and W. Steglich, Angew. Chem., 86, 414 (1974). R. N. Lacey and W. R. Ward, J . Chem. Soc., 1958, 2134. A. Kreutzberger and H. Schimmelpfennig, Arch. Pharm. (Weinheim, Ger.), 314, 391 (1981).

1250 2574. 2575. 2576. 2577. 2578. 2579. 2580. 2581. 2582. 2583. 2584. 2585. 2586. 2587. 2588. 2589. 2590.

References J. C. Sauer and W. K. Wilkinson, US Pat. 2,524,479 (1950); Chem. Abstr., 45, 1168 (1951). T. Kato, H. Yamanaka, and S. Konno, Yakugaku Zasshi, 91, 1004 (1971). H. Biltz and H. Paetzold, Liebigs Ann. Chem., 433, 64 (1923). 0. Nagase, M. Hirata, and M. Inaoka, Yakugaku Zasshi, 82, 528 (1962). C. Piantadosi, V. G. Skulason, J. L. Irvin, J. M. Powell, and L. Hall, J . Med. Chem., 7, 337 (1964). T. Naito, 0.Nagase, and M. Hirata, Jap. Pat. 10,793 (1962); Chem. Ahstr., 59, 3939 (1963). S. Mizukami and E. Hirai, Chem. Pharm. Bull., 14, 1321 (1966). H. J. Backer and A. B. Grevenstuk, R e d . Trau. Chim. Pays-Bas, 64, 115 (1945). S. Senda, H. Izumi, M. Kano, and J. Tsubota, Cifu Yakku Daigaku Kiyo, 11,62 (1961); Chem. Abstr., 57, 11194 (1962). T. Natio, M. Hirata, and T. Kobayashi, Jap. Pat. 7,900 (1965); Chem. Ahstr., 63, 1802 (1965). G. Maury, J.-P. Paugam, and R. Paugarn, J . Heterocycl. Chem., 15, 1041 (1978). H. Yamanaka, Chem. Pharm. Bull., 6, 633 (1958). M. Prystai and F. Sorrn, Collect. Czech. Chem. Commun., 32, 1298 (1967). M. Prystag, Collect. Czech. Chem. Commun., 32, 4241 (1967). E. A. Oostveen and H. C. van der Plas, Recl. Trau. Chim. Pays-Bas, 96, 64 (1977). A. Karnpf, C. J. Pillar, W. J. Woodford, and M. P. Mertes, J . Med. Chem., 19, 909 (1976). E. C. Ressner, A. Kampf, and M. P. Mertes, in Nucleic Acid Chemistry, Part 1 (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 89. G. Ritzrnann, K. Ienaga, L. Kiriasis, and W. Pfleiderer, Chem. Ber., 113, 1535 (1980).

2591. 2592. J. Nakazawa and M. Watatani, Takamine Kenkyusho Nempo, 12, 37 (1960), Chem. Ahstr., 55, 6491 (1961). 2593. G. Sunagawa and J. Nakazawa, Jap. Pat. 4,893 (1962); Chem. Abstr., 59, 642 (1963). 2594. G. Sunagawa, J. Nakazawa, and M. Watatani, Jap. Pat. 10,697 (1962); Chem. Abstr., 59, 5177 (1963). 2595. H. Brctschneider and W. Klotzer, Swiss Pat. 369,454 (1963); Chem. Abstr., 60, 14517 (1964). 2596. G. A. P. Tuey, Br. Pat. 571,014 (1945); Chem. Abstr., 40, 7238 (1946). 2597. N. Okuda and I. Kuniyoshi, Jap. Pat. 3,142 (1963); Chem. Abstr., 59, 11528 (1963). 2598. Hoffrnann-La Roche, Br. Pat. 946,488 (1964); Chem. Abstr., 64, 3568 (1966). 2599. Z . BudGinskS;, J. Piikryl, and E. Svatek, Collect. Czech. Chem. Commun., 32, 1637 (1967). 2600. R. G. Shepherd, W. E. Taft, and H. M. Krazinski, J . Org. Chem., 26, 2764 (1961). 2601. E. L. Stogryn, J . Heterocycl. Chem., 11, 251 (1974). 2602. W. Klotzer, Monatsh. Chem., 87, 536 (1956). 2603. W. Klotzer, Monatsh. Chem., 87, 526 (1956). 2604. Osterreichische Stickstoffwerke, Austrian Pat. 186,638 (1956); Chem. Abstr., 51, 2886 (1957). 2605. R. W. Lamon, Tetrahedron Lett., 1970, 3957. 2606. F. L. C. Baranyovits and R. Ghosh, Chem. Ind. (London), 1969, 1018. 2607. F. G. Fischer, H. Eilingsfeld, and W. P. Neurnann, Liebigs Ann. Chem., 651, 49 (1962). 2608. A. V. El’tsov and K. L. Muravich-Alexandr, Tetrahedron Lett., 1968, 739. 2609. W. H. Dekker, Recl. Trau. Chim. Pays-Bas, 92, 705 (1973). 2610. W. Klotzer, Monatsh. Chem., 87, 131 (1956). 2611. T. Kato, H. Yarnanaka, and H. Hiranuma, Yakugaku Zasshi, 90, 870 (1970). 2612. S. R. James, J . Chem. Res., Synop. 125, Minipr. 664 (1979). 2613. H. Biltz and G. Zellner, Liebigs Ann. Chem., 423, 297 (1921). 2614. K. Bredereck and S. Humburger, Chem. Ber., 99, 3227 (1966).

References

1251

2615. G. Tennant and C. W. Yacomeni, J . Chem. Soc., Chem. Commun., 1982, 60. 2616. Y. Nitta, K. Okui, and K. Ito, Jap. Pat. 13,878 (1965); Chem. Abstr., 63, 13285 (1965). 2617. B. R. Baker, J. P. Joseph, R . E. Schaub, and J. H. Williams, J . Org. Chem., 19, 1780(1954). 2618. W. R. Boon, Br. Pat. 763,120 (1956); Chem. Ahstr., 51, 15612 (1957). 2619. T. Kulikowski and D. Shugar, Acta Biochim. Pol., 26, 145 (1979). 2620. E. C. Taylor, G. P. Beardsley, and Y. Maki, J . Org. Chem., 36, 3211 (1971). 2621. A. Schellenbergcr and V. Muller, Hoppe-Seyler’s Z . Physiol. Chem., 328, 220 (1962). 2622. B. K. Snell, J . Chem. Soc. (C), 1968, 2367. 2623. H. Rokos and W. Pfleiderer, Chem. Ber., 104, 770 (1971). 2624. W. Pfleiderer and E. Biihler, Chem. Ber., 99, 3022 (1966). 2625. D. So11 and W. Pfleidcrer, Chem. Ber., 96, 2977 (1963). 2626. W. Pfleiderer, D. Autenrieth, and M. Schranner, Chem. Ber., 106, 317 (1973). 2627. J. Okada, K. Nakano, and H. Miyake, Chem. Pharm. Bull., 29, 667 (1981). 2628. D. E. O’Brien, L. T. Weinstock, R. H. Springer, and C. C. Cheng, J . Heterocycl. Chem., 4, 49 ( I 967). 2629. Ciba, Fr. Pat. 1,549,237 (1968); Chem. Ahstr., 72, 31838 (1970). 2630. F. Yoneda, K. Senga, and S. Nishigaki, Chem. Pharm. Bull., 21, 260 (1973). 2631. K. Senga, F. Yoneda, and S. Nishigaki, Chem. Pharm. Bull., 19, 215 (1971). 2632. T. J. Delia, J. P. Scovill, W. D. Munslow, and J . H. Burckhalter, J . Med. Chem., 19, 344(1976). 2633. B. Roth, J. Z . Strelitz, and B. S. Rauckman, J . Med. Chem., 23, 379 (1980). 2634. G. H. Hitchings and P.B. Russell, US Pat. 2,676,965 (1954); Chem. Abstr., 49, 5534 (1955). 2635. T. Kunieda and B. Witkop, J . Am. Chem. Soc., 93, 3487 (1971). 2636. H. Maehr, J. Smallheer, and V. Toome, J . Heterocycl. Chem., 14, 687 (1977). 2637. M. Polonovski and M. Pesson, Bull. Soc. Chim.Fr. IS], 15, 688 (1948). 2638. W. Szer and D. Shugar, Acta Biochim. Pol., 13, 177 (1966). 2639. E. A. Arutyunyan, V. I. Gunar, and S. I . Zav’yalov, Izu. Akad. Nauk SSSR, Ser. Khim.,1970, 1198. 2640. H. Iwamura, N. J. Leonard, and J. Eisinger, Proc. Nutl. Acud. Sci. U S A , 65, 1025 (1970). 2641. C. L. Leese and G. M. Timmis, J . Chem. Soc., 1958,4104. 2642. L. Alrnirante, Ann. Chim. (Rome),49, 333 (1959). 2643. E. Waletzky, US Pat. 2,543,748 (1951); Chem. Ahstr., 45, 5371 (1951). 2644. Y. Rahamim, J. Sharvit, A. Mandelbaum, and M. Sprecher, J . Org. Chem., 32, 3856 (1967). 2645. E. C. Taylor and C. W. Jefford, J . Am. Chem. Soc., 84, 3744 (1962). 2646. B. Roth, J. M. Smith, and M. E. Hultquist, J . Am. Chem. Soc., 72, 1914 (1950). 2647. E. Habicht, Swiss Pat. 358,426 (1962); Chem. Abstr., 58, 3443 (1963). 2648. S. Minami, T. Shono, and J.-I. Matsumoto, Chem. Pharm. Bull., 19, 1426 (1971). 2649. H. Bredereck, G . Simchen, and W. Griebenow, Chem. Ber., 107, 1545 (1974). 2650. R. B. Angier and J. M. Marsico, J . Ory. Chem., 25, 759 (1960). 2651. C. G. Overberger, I. C. Kogon, and R. Minin, Org. Synth., 35, 58 (1955). 2652. S. Kobayashi, Bull. Chem. Soc. Jpn., 46, 2835 (1973). 2653. D. J. Brown, W. B. Cowden, and L. Strekowski, Aust. J . Chem., 34, 1353 (1981). 2654. T. Kato, N. Katagiri, T. Takahashi, and Y. Katagiri, J . Heterocycl. Chem., 16, 1575 (1979). 2655. C. Jutz and W, Muller, Anyew. Chem., 78, 1059 (1966). 2656. D. J. Brown, W. B. Cowden, S.-B. Lan, and K. Mori, Aust. J . Chem., 37, 155 (1984). 2657. R. B. Angier and J. W. Marsico, US Pat. 2,784,188 (1957); Chem. Ahstr., 51, 15614 (1957).

1252

References

2658. E. P. Studentsov, E. G. Sochilin, T. A. Chumak, and L. F. Starzhevskaya, Khim. Geterotsikl. Soedin., 1974, 1574. 2659. W. Pfleiderer, F. Sagi, and L. Grozinger, Chem. Ber., 99, 3530 (1966). 2660. B. R. Baker and W. Rzeszotarski, J . Med. Chem., 11, 639 (1968). 2661. Wellcome Foundation, Br. Pat. 671,926 (1952); Chem. Abstr., 47, 5457 (1953). 2662. H. M. Kissman and M. J. Weiss, J . Am. Chem. Soc., 80, 2575 (1958). 2663. H. Biltz and M. Heyn, Liebigs Ann. Chem., 413, 7 (1917). 2664. I. Wempen, R. Duschinsky, L. Kaplan, and J. J. Fox, J , Am. Chem. Soc., 83, 4755 (1961). 2665. W. Szer and D. Shugar, in Synthetic' Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 58. 2666. C. G. Overberger and F. W. Michelotti, J . Am. Chem. Soc., 80, 988 (1958). 2667. W. Pfleiderer and H. Deiss, Chem. Ber., 104, 780 (1971). 2668. R. Akantard and S. Y. Wang, Photochem. Photobid., 4, 465 (1965). 2669. R. €3. Silverman and M. P. Groziak, J . Am. Chem. Soc., 104, 6434 (1982). 2670. W. Liebenow and H. Liedtke, Chem. Ber., 105, 2095 (1972). 2671. S. Senda, K. Hirota, and T. Asao, J . Org. Chem., 40, 353 (1975). 2672. W. Klotzer and S. Romani, Liebigs Ann. Chem., 1981, 1429. 2673. J. J. Fox, N. Yung, and I. Wempen, Biochirn. Biophys. Acta, 23, 295 (1957). 2674. W. V. Curran and R. B. Angier, J . Org. Chem., 31, 201 (1966). 2675. S. Senda, K. Hirota, and T. Asao, Heterocycles, 3, 213 (1975). 2676. S. Senda, K. Hirota, and T. Asao, J . Org. Chem., 44, 970 (1979). 2677. 2678. 2679. 2680. 2681. 2682. 2683. 2684. 2685. 2686. 2687. 2688. 2689. 2690. 2691. 2692. 2693. 2694. 2695. 2696. 2697. 2698. 2699.

A. Guyot, J. Chopin, and C. Mentzer, Bull. Soc. Chim. Fr., 1960, 1596. R. U. Lemieux and I . Puskas, Can. J . Chem., 42, 2909 (1964). R. R. Herr, T. Enkoji, and T. J. Bardos, J . Am. Chem. Soc., 78,401 (1956). H.-G. Kazmirowski and E. Carstens, J . Prakt. Chem. [4], 32, 47 (1966). A. G. Panteleimonov and V. S. Mandrik, Ukr. Khim. Zh., 36,696 (1970);Chem. Abstr., 74,3576 (1 97 I). H. Biltz and D. Heidrich, Liebigs Ann. Chem., 426, 269 (1922). S. Senda, K. Hirota, T. Asao, and Y. Yamada, J . Chem. Soc., Chem. Comrnun., 1977, 556. W. Pfleiderer and F. E. Kempter, Chem. Ber., 103, 900 (1973). K. T. Potts and R. K. C. Hsia, J . Org. Chem., 38, 3485 (1973). C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, Chem. Pharm. Bull., 29, 2516 (1981). F. Yoneda and T. Nagamatsu, Bull. Chem. Sou. Jpn., 48, 1484 (1975). E. Fischer, Ber. Dtsch. Chem. Ges., 30, 549 (1897). R. Dohmori, Y.Nakai, R. Yosjimura, and T. Naito, Chem. Pharm. Bull., 17, 1479 (1969). Partenheimer, Ger. Pat. 1,186,466 (1965); Chem. Abstr., 62, 13159 (1965). F. Yoneda and T. Nagamatsu, Heterocycles, 2, 153 (1974). T. Sakasai, T. Sakamoto, and H. Yamanaka, Heterocycles, 13, 235 (1979). T. Sekiya, H. Hiranuma, M. Uchide, S. Hata, and S.-I. Yamada, Chem. Pharm. Bull., 29, 948 (1 98 1). I. Saikawa, Yukugaku Zasshi 84, 207 (1964). R. S. Shadbolt and T. L. V. Ulbricht, J . Chem. Soc. ( C ) , 1968, 733. T. Yoshikawa, Yakuyaku Zasshi, 76, 772 (1956); Chem. Abstr., 51, 1197 (1957). W. J. Hale and A. G. Williams, J . Am. Chem. Soc., 37, 594 (1915). H. L. Wheeler and D. F. McFarland, Am. Chem. J . , 43, 19 (1910). V. Uchytilova, A. Holy, D. Cech, and J. Gut, Collect. Czech. Chem. Commun., 40, 2347 (1975).

References

1253

2700. H. L. Wheeler and D. F. McFarland, Am. Chem. J., 42, 101 (1909). 2701. Z . A. Martirosyan, V. I. Gunar, and S. I. Zav’yalov, Iza. Akad. Nauk. S S S K , Ser. Khim., 1972, 404. 2702. T. Nishimura, Y. Miyamoto, and H. Fukuyasu, Yukugaku Zasshi, 96, 384 (1976). 2703. 2704. 2705. 2706. 2707. 2708. 2709. 2710. 2711. 2712. 2713. 2714. 2715. 2716. 2717. 2718. 2719. 2720.

A. Priisse, I,iehigs Ann. Chem., 441, 203 (1925). M. PrystaS and J. Gut, Collect. Czech. Chem. Commun., 28, 2501 (1963). G.-F. Huang and P. F. Torrence, J . Org. Chem., 42, 3821 (1977). H. U. Blank and J. J. Fox, J . Heterocycl. Chem., 7, 735 (1970). H. Goldner, G . Dietz, and E. Carstens, Liebigs Ann. Chem., 699, 145 (1966). P. A. Leermakers and W. A. Hoffman, J . Am. Chem. Soc., 80, 5663 (1958). E. Fischer and L. Ach, Ber. Dtsch. Chem. Ges., 28, 3135 (1895). H. Biltz, Ber. Dtsch. Chem. Ges., 45, 3659 (1912). E. Fischer, Ber. Dtsch. Chem. Ges., 14, 1905 (1881). E. Fischer, Liehigs Ann. Chem., 215, 253 (1882). H. Kwart, R. W. Spayd, and C. J. Collins, J . Am. Chem. Soc., 83, 2579 (1961). L. Heinisch, W. Ozegowski, and M. Miihlstadt, Chem. Ber., 97, 5 (1964). S. Kato and G. Dryhurst, Electroanal. Chem., 62, 415 (1975). S. Scnda and K. Hirota, Chem. Lett., 1972, 367. S. Senda and K. Hirota, Chem. Pharm. Bull., 22, 1459 (1974). T. D. Duffy and D. G. Wibberley, J . Chem. Soc., Perkin Trans. I, 1974, 1921. R. C. Elderfield and I. Serlin, .I. Org. Chrm., 16, 1669 (1951). J. H. Burckhalter and H. C. Scarborough, J . Am. Pharm. Assoc., Sci. Ed., 44, 545 (1955).

2721. K. E. Schulte, J. Reisch, A. Mock, and K. H. Kauder, Arch. Phurm. (Weinheim,Ger.), 296,235 (1 963). 2722. A. Pinner, Die Imidoiither und ihre Deriuute, Oppenheim, Berlin, 1892, p. 230ff. 2723. B. A. Otter, S. S. Saluja, and J. J. Fox, J . Org. Chem., 37, 2858 (1972). 2724. K . Edo, H. Yamanaka, and T. Sakamoto, Heterocycles, 9, 271 (1978). 2725. K. Tokuyama, Yakuguku Zasshi, 79, 814 (1959). 2726. K. Miyatake, G. Ohta, and H. Uchimaru, Yukugaku Zasshi, 75,1063; (1955); Chem. Ahstr., 50, 5634 (1956). 2727. A. Takamizawa, K. Ikawa, and M. Narisada, Yakugaku Zusshi,78, 632 (1958). 2728. G. E. Bonvicino and D. J. Hennessy, J . Org. Chem., 24, 451 (1959). 2729. N. Shimahara, N. Nakajima, and H. Hirano, Chem. Pharm. Bull., 22, 2081 (1974). 2730. A. R. Ronzio and W. B. Cook, Org. Synth., 24, 6 (1944). 2731. R. Holtzwart, .I. Prakt. Chem. [2], 39, 230 (1889). 2732. K. Tdkatori and S. Asano, Giju Yakku Duigaku K i p , 7, 60 (1957); Chem. Abstr., 52, 5422 (1958). 2733. V. A. Serzhanina, N. V. Khromov-Borisov, and R. S. Karlinskaya, Khim. Geterotsikl. Soedin., 1968, 527. 2734. H. Bredereck, F. Effenberger, and H. Botsch, Chem. Ber., 97, 3397 (1964). 2735. W. Wendelin and A. Harler, Monatsh. Chem., 106, 1479 (1975). 2736. W. J. Hale and F. C. Vibrans, J . Am. Chem. Soc., 40, 1046 (1918). 2737. J. Klosa, Arch. Pharm. (Weinheim,Ger.), 287, 62 (1954). 2738. A. Combes and C. Combes, Bull. Soc. Chim.Fr. [3], 7, 788 (1892). 2739. T. F. Scholz and G. M. Smith, US Pat. 2,660,579 (1953); Chem. Ahstr.. 48, 12184 (1954). 2740. C. A. C. Haley and P. Maitland, J . Chem. Soc., 1951, 3155.

1254 2741. 2742. 2743. 2744. 2745. 2746. 2747. 2748. 2749. 2750. 2751. 2752. 2753. 2754. 2755. 2756. 2757. 2758. 2759. 2760. 2761. 2762. 2763.

References A. Maschka, M. von Stein, and W. Trauer, Monatsh. Chem., 84, 1071 (1953). T. J. Batterham, D. J. Brown, and M. N. Paddon-Row, J . Chem. Soc. (B), 1967, 171. F . 3 . Tjoeng, E. Kraas, E. Stark, E. Breitmaier, and G. Jung, Chem. Ber., 108, 862 (1975). T. Kato, H. Yamanaka, and T. Shibata, Yakugaku Zasshi, 87, 1096 (1967). A. Holland, Chem. Ind. (London), 1954, 786. A. Holland, Br. Pat. 777,465 (1957); Chem. Abstr., 52, 1284 (1958). H. Bredereck, H. Herlinger, and E. H. Schweizer, Chem. Ber., 93, 1208 (1960). R. Kruse and E. Breitmaier, Chem.-Ztg,, 101, 305 (1977). H. Bredereck, H. Herlinger, and J. Renner, Chem. Ber., 93, 230 (1960). H. Bredereck, R. Gompper, and B. Geiger, Chem. Ber., 93, 1402 (1960). T. Koyama, T. Hirota, C . Bashou, Y. Satoh, Y. Watanabe, S. Matsumoto, Y. Shinohara, S. Ohmori, and M. Yamato, Chem. Pharm. Bull., 23, 2158 (1975). H. Bredereck, R. Gompper, and G. Morlock, Chem. Ber., 90, 942 (1957). C. R. Hauser and R. M. Manyik, J . Org. Chem., 18, 588 (1953). H. C . van der Plas and H. Jongejan, Recl. Trav. Chim. Pays-Bas, 87, 1065 (1968). M. Strul and I. Zugrlvescu, Reu. Roum. Chim., 16, 1877 (1971). H. Bredereck, R. Sell, and F. ElTenberger, Chem. Ber., 97, 3407 (1964). E. Ochiai and M. Yanai, Yakugaku Zasshi, 58, 397; Supplement, p. 76 (1938); Chem. Zentr., 1938, 11, 4242. E. A. Gracheva and V. P. Mamaev, Khim. Geterotsikl, Soedin., 1972, 1422. V. P. Mamaev and E. A. Gracheva, Khim. Geterotsikl. Soedin., 1971, 838. V. P. Mamaev and E. A. Gracheva, Khim. Geterotsikl. Soedin., 1969, 1086. T. J. Schwan, H. Tieckelmann, J. F. Holland, and B. Bryant, J . Med. Chem., 8, 750 (1965). E. Ochiai and H. Yamanaka, Pharm. Bull., 3, 175 (1955). E. Ochiai and H. Yamanaka, Pharm. Bull., 3, 173 (1955).

2764. V. P. Mamaev and V. P. Krivopalov, Khim. Geterotsikl. Soedin., Sb. I , 1967,145;Chem. Abstr., 70, 87721 (1969). 2765. I. B. Simon and I. 1. Levshina, Tr. Ukr. Nauchno-lssled. Inst. Eksp. Endokrinol., 20, 193 (1965); Chem. Abstr., 66, 85752 (1967). 2766. H. Yamanaka, Chem. Pharm. Bull., 6,638 (1958). 2767. Hoffmann-La Roche, Br. Pat. 800,776 (1958); Chem. Abstr., 53, 8178 (1959). 2768. F. H. Case and A. J. Hill, J . Am. Chem. Soc., 52, 1536 (1930). 2769. I. A. Mikhailopulo, V. I. Gunar, and S. I. Zav’yalov, Izu. Akad. Nauk SSSR,Ser. Khim., 1965, 1715. 2770. K. Yamauchi and M. Kinoshita, J . Chem. Soc., Perkin Trans. 1, 1973, 391. 2771. K. Harada and S. Suzuki, Tetrahedron Lett., 1976, 2321. 2772. K. J. Kolonko, R. H. Shapiro, R. M. Barkley, and R. E. Sievers, J . Org. Chem., 44, 3769 (1979). Chem. Soc., 1958, 157. 2773. G. Shaw and R. N. Warrener, .I. 2774. R. C. Smith and S. B. Binkley, J . Org. Chem., 24, 249 (1959). 2775. T. Naito, M. Hirata, T. Kawakami, and M. Sano, Chem. Pharm. Bull., 9, 703 (1961). 2776. T. T. Sakai, A. L. Pogolotti, and D. V. Santi, J . Heterocycl. Chem., 5, 849 (1968). 2777. G. M. Kheifets and N. V. Khromov-Borisov, Zh. Obshch. Khim., 34, 3134 (1964). 2778. R. K. Ralph, G. Shaw, and R. N. Naylor, J . Chem. Soc., 1959, 1169. 2779. R. Behrend and R. Thurm, Liebigs Ann. Chem., 323, 160 (1902). 2780. R. Behrend and G. Hartel, Liebigs Ann. Chem., 422, 74 (1921).

References

1255

2781. I. A. Mikhailopulo, V. I. Gunar, and S. I. Zav’yalov, I i u . Akad. Nauk SSSR, Ser. Khim., 1967, 1811. 2782. V. S. Reznik, V. S. Bakulin, and Y. S. Shvetsov, I i v . Akad. Nauk, SSSR,Ser. Khim., 1975, 1604. 2783. A. L. Cossey and J. N. Phillips, Chem. Ind. (London), 1970, 58. 2784. L. P. Ferris and A. R. Ronzio, J . Am. Chem. Soc., 62, 606 (1940). 2785. A. Guyot, J. Chopin, and C . Mentzer, C. R. Acad. Sci., 248, 3444 (1959). 2786. E. Wittenburg, Chem. Ber., 99, 2380 (1966). 2787. M. Ledvina and J. FarkaS, Collect. Czech. Chem. Commun., 47, 676 (1982). 2788. T. S. Ma and W. G. Zoellncr, J . Chin. Chem. Soc. (Taipei) 121, 4, 56 (1957); Chem. Ahstr., 53, 8158 (1959). 2789. T. B. Johnson and A. W. Joyce, J . Am. Chem. Soc., 38, 1854 (1916). 2790. K. Sirakawa, Yakugaku Zusshi, 79, 1477 (1959). 2791. V. S. Reznik, N. G. Pashkurov, and Y. M. Kargin, Khim. Geterotsikl. Soedin., 1968, 175. 2792. W. Kirchcr, Liebigs Ann. Chem., 385, 293 (1911). 2793. G. Poetsch and R. Behrend, Liebigs Ann. Chem., 448, 89 (1926). 2794. M. Draminski and B. Fiszer, Roci. Chem., 45, 1349 (1971). 2795. G. Pala, Farmaco, Ed. Sci., 13, 461 (1958). 2796. Omikron-Gagliardi, Br. Pat. 833,049 (1960); Chem. Ahstr., 55, 1665 (1961). 2797. E. Ochiai and T. Naito, Yakugaku Zusshi, 63, 317 (1943); Chem. Ahstr., 45, 5154 (1951). 2798. M. Ceresole, Ber. Dtsch. Chem. Ges., 16, 1133 (1883). 2799. H. Voigt, D. Heydenhauss, F. Hofmann, and G. Jaenecke, Z.Chem., 14, 436 (1974). 2800. E. Mulder, Ber. Dtsch. Chem. Ges., 12, 465 (1879). 2801. J. W. Clark-Lewis and M. J. Thompson, J . Chem. Soc., 1959, 1628. 2802. J. J. Fox and D. Shugar, Bull. Soc. Chim. Belg., 61, 44 (1952). 2803. F. Baum, Ber. Dtsch. Chem. Ges., 41, 532 (1908). 2804. K . Ito, K . Nishiie, and M. Sekiya, Yakugaku Zusshi, 90, 188 (1970). 2805. M. Yogo, K. Hirota, and S. Senda, J . Neterocycl. Chem., 18, 1095 (1981). 2806. H. Tsukamoto, H. Yoshimura, and S. Toki, Pharm. Bull., 4, 364 (1956). 2807. G. A. Neville, H. W. Avdovich , and A. W. By, Can. J . Chem., 48, 2274 (1970). 2808. M. Sekiya and C. Yanaihara, Chem. Pharm. Bull., 17, 738 (1969). 2809. A. Dornow and H. Hell, Chem. Ber., 93, 1998 (1960). 2810. 0. S. Tee and M. Endo, J . Heterocycl. Chem., 11, 441 (1974). 281 I . H. Baumann, G. Hansen, H.-R. Miiller, and M. Seefelder, Liebigs Ann. Chem., 717, 124 (1968). 2812. S. David, B. Estramareix, H. Hirshfeld, and P. Sinay, Bull. Soc. Chim. Fr., 1964, 936. 2813. S. David, B. Estramareix, and H. Hirshfeld, Biochim. Biophys. Acta, 148, 1 1 (1967). 2814. R. Wollner, J . Prakt. Chem. 121. 29, 131 (1884). 2815. H. Kano and Y. Makisumi, Pharm. Bull., 3, 270 (1955). 2816. Y. Iwakura, K. Nagakubo, and C. Hosoyane, Kogyo Kagaku Zasshi, 57, 947 (1954); Chem. Ahstr., 50, 1028 (1956). 2817. B. Ohta, Yukugaku Zasshi, 71, 305 (1951). 2818. H. Kano and Y. Makizumi, Jap. Pat. 5,722 (1957); Chem. Ahstr., 52, 11967 (1958). 2819. N. N. Mel’nikov, K. D. Shvetsova-Shilovskaya, and A. F. Grapov, Org. Insektofungitsidy Gerbitsidy, 1958, 108; Chem. Abstr., 55, 3600 (1961). 2820. T. Kato, H. Yamanaka, and S. Konno, Yakugaku Zasshi, 90, 509 (1970). 2821. V. D. Adams and R. C. Anderson, Synthesis, 1974, 286.

1256 2822. 2823. 2824. 2825. 2826. 2827. 2828.

References T. Kato, T. Chiba, and M. Sasaki, Heterocycles, 16, 577 (1981). A. Albert and F. Reich, J . Chem. Soc., 1960, 1370. M. T. de Hahn, Recl. Trau. Chim. Pays-Bas, 27, 162 (1908), W. J. Hale, J . Am. Chem. Soc., 36, 104 (1914). E. Kalatzis, J . Chem. Soc. (B), 1968, 96. R. 0. Hutchins and B. E. Maryanoff, J . Ory. Chem., 37, 1829 (1972). G. Zvilichovsky, Tetrahedron, 23, 353 (1967).

2829. C. Janion and D. Shugar, Acta Biochim. Pol., 15, 261 (1968). 2830. D. T. Hurst, Aust. J . Chem., 36, 2119 (1983). 2831. T. L. Gilchrist, C. J. Harris, D. G . Hawkins, C. J. Moody, and C. W. Rees, J . Chem. Soc., Perkin Trans. 1, 1976, 2166. 2832. K. Anzai and S. Suzuki, Agric. Biol. Chem., 30, 597 (1966). 2833. C. E. Malen, B. H. Danree, and X. B. L. Pascaud, J . Med. Chem., 14, 244 (1971). 2834. 2835. 2836. 2837.

V. Vosatka, A. Capek, and 2. Budtiinsky, Collect. Czech. Chem. Commun., 42, 3186 (1977). J. L. Soto, A. Lorente, and J. L. Garcia-Navio, An. Quim., Ser. C , 77, 255 (1981). R. G. Shepherd, J . Chem. Soc., 1964,4410. Z. Kazimierczuk, A. Psoda, and D. Shugar, Acta Biochim. Pol., 20, 83 (1973).

2838. H. Ogura, M. Sakaguchi, and K. Takeda, Chem. Pharm. Bull., 20, 404 (1972). 2839. 2840. 2841. 2842. 2843. 2844. 2845. 2846. 2847. 2848. 2849. 2850. 2851. 2852. 2853. 2854. 2855. 2856. 2857. 2858. 2859.

J. F. B. Mercer and R. N. Warrener, Chem. Ind. (London), 1970, 927. G. B. Elion and G. H. Hitchings, J . Am. Chem. Soc., 69, 2138 (1947).

R. Behrend and P. Hesse, Liebiys Ann. Chem., 329, 341 (1903). G. Barnikow and J. Bodeker, Z . Chem., 5, 62 (1965). K. Bredereck and R. Richter, Chem. Ber., 98, 131 1965. H. C. Scarborough, J . Org. Chem., 26, 3717 (1961). H. C. Scarborough and W. A. Gould, J . Org. Chem., 26, 3720 (1961). 0. Widman, Ber. Dtsch. Chem. Ges., 29, 1954 (1896). H. Biltz and K . Strufe, Liebiys Ann. Chem., 413, 124 (1917). M. Bachstez, Ber. Dtsch. Chem. Ges., 64, 2683 (1931). M. P. Mertes and S. E. Saheb. J . Med. Chem., 6, 619 (1963). A. Giner-Sorolla and A. Bendich, J . Ory. Chem., 31, 4239 (1966). R. Brossmer and D. Ziegler, Tetrahedron Lett., 5253 (1966). R. Brossmer and D. Ziegler, Chem. Ber., 102, 2877 (1969). B . 4 . Hahn and S. Y. Wang, J . Org. Chem., 41, 567 (1976). T. B. Johnson and L. H. Cretcher, J . Am. Chem. Soc., 37, 2144 (1915). T. B. Johnson and E. F. Schroeder, J . Am. Chem. Soc., 53, 1989 (1931). M. Claesen and H. Vanderhaeghe, Bull. Soc. Chim. Bely., 66, 292 (1957). E. Ludolphy, Chem. Ber., 84, 385 (1951). K.-Y. Zee-Cheng and C. C. Cheng, J . Heterocycl. Chem., 4, 163 (1967). F. J. Lopez-Aparicio, F. J. Lopez-Herrerd, and M. Valpuesta-Fernandez, Carhohydr. Res., 69, 235 (1979). 2860. K.-Y. Zee-Cheng and C. C. Cheng, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 70. 2861. I. A. Mikhailopulo, V. I. Gunar, and S. I. Zav’yalov, Izu. Akad. Nauk S S S R , Ser, Khim., 1967, 1388.

2862. R. G. Glushkov, E. G. Sochilin, and B. A. Ivin, Zh. Ohshch. Khim., 37, 1579 (1967).

References

1251

2863. T. B. Johnson, Am. Chem. J . , 42, 505 (1909). 2864. G . Shaw, J . Chem. Soc., 1955, 1834. 2865. .J. Gut, J. Moravek, C. Pirkanyi, M. PrystaS, J. Skoda, and F. Sorm, Collect. Czech Chem. Commun., 24, 3154 (1959). 2866. H. Meinert and D. Cech, Z.Chem., 12, 291 (1972). 2867. H. Meindl and H. Ackermann, Helo. Chim. Acta 55, 1039 (1972). 2868. W. K. Chung, C. K. Chu, K. A. Watanabe, and J. J. Fox, J . Org. Chem., 44,3982 (1979). 2869. K.-H. Heise and S. Noll, Isotopenpraxis, 15, 292 (1979). 2870. V. G. Nemets and B. A. Ivin, Zh. Obshch. Khim., 35, 1299 (1965). 2871. B. A. Ivin and V. G. Nemets, Zh. Obshch. Khim., 35, 1294 (1965). 2872. R. Behrend and K. Struve, Liehigs Ann. Chem., 378, 153. (1911). 2873. J. F. W. McOmie and I. M. White, J . Chem. Soc., 1953, 4175. 2874. A. A. Santilli, W. F. Bruce, and T. S. Osdene, J . M e d . Chem., 7, 68 (1964). 2875. H. K. Mitchell and J. F. Nyc, J . Am. Chem. Soc., 69, 674 (1947). 2876. H. L. Wheeler, Am. Chem. J., 38, 358 (1907). 2877. J. F. Nyc and H. K. Mitchell, J . Am. Chem. Sac., 69, 1382 (1947). 2878. S. Takeyama, T. Noguchi, Y. Miura, and M. Ishidate, Pharm. Bull., 4, 492 (1956). 2879. G. Biscaro and E. Belloni, Annu. Soc. Chim.Miluno, 11 18, 71 (1905); Chem. Zentr., 11, 63, 64. 2880. C. Heidelberger and R. B. Hurlbert, J . Am. Chem. Soc., 72, 4704 (1950). 2881. J. Baddiley and J. G. Buchanan, Annu. Rep. Prog. Chem., 54, 329 (1957). 2882. 2883. 2884. 2885. 2886. 2887. 2888. 2889.

2890. 2891. 2892. 2893. 2894. 2895. 2896. 2897. 2898. 2899. 2900. 2901. 2902.

K. L. Nagpal, K.L. Agarwal, and M. M. Dhar, Indian J . Chem., 3, 356 (1965). Rhone-Poulenc, Br. Pat. 800,700 (1958); Chem. Abstr., 53, 16172 (1959). L. Pichat, M. Audinot, and P. Carbonnier, Bull. Soc. Chim.Fr., 1959, 1798. K. A. Chkhikvadze and 0. Y. Magidson, Med. Prom. SSSR, 14, No. 10, 24 (1960); Chem. Ahstr., 55,6487 (1961). W. Barbieri, L. Bernardi, F. Luini, and G. Palamidessi, Farmaco, Ed. Sci., 25, 702 (1970). V. I. Gunar, L. F. Ovechkina, I. A. Mikhailopulo, and S. I. Zav’yalov, lzo. Akad. Nauk SSSR, Ser. Khim., 1968, 918. R. N. Warrener and E. N. Cain, Aust. J . Chem., 24, 785 (1971). G . D. Daves, F. Baiocchi, R. K. Robins, C. C. Cheng, and W. H. Nyberg, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 72. M. Ridi, Gazz. Chim.Ital., 79, 175 (1949). R. H. Wiley, K. F. Hussung, W. E. Hobbs, and S. Huh, J . M e d . Chem., 7, 358 (1964). A. W. Larchar, US Pat. 2,540,826 (1951); Chem. Ahstr., 45, 5726 (1951). E. Dyer, M. L. Gluntz, and E. J. Tanck, J . Org. Chem., 27, 982 (1962). A. Vincze, R. E. L. Henderson, J. J. McDonald, and N. J. Leonard, J . Am. Chem. Soc., 95,2677 (1973) A. Kreutzberger and S. Leyke-Rohling, Arch. Pharm. (Weinheim, Ger.), 314, 897 (1981). H. Yamanaka, S. Niitsuma, and T. Sakamoto, Chem. Phurm. Bull., 27, 2642 (1979). H. Biltz and E. Kramer, Liehigs Ann. Chem., 436, 154 (1924). H. R . Henze and E. N. Kahlenberg, J . Am. Chem. Soc., 80, 1664 (1958). H. Biltz and L. Loewe, Ber. Dtsch. Chem. Ges., 67, 1199 (1934). Bayer, Ger. Pat. 249,907 (1912); Frdl., 11, 929 (1912-1914). J. Pitha, J . Org. Chem., 35, 903 (1970). G. E. Hilbert, .I. Am. Chern. Soc., 59, 330 (1937).

1258

References

J. Pitha, P. M. Pitha, and P. 0. P. Ts’o, Biochim. Biophys. Acta, 204, 39 (1970). T. B. Johnson and D. B. Jones, J . Am. Chem. Soc., 31, 590 (1909). A. Margot and H. Gysin, Helu. Chim. Acta, 40, 1562 (1957). Y. Nitta, K. Okui, and K. 110, lap. Pat. 19,808 (1966); Chem. Ahstr., 66, 55500 (1967). G. Sunagawa, J. Nakazawa, and M. Watatani, Jap. Pat. 2,291 (1963); Chem. Ahstr., 59, 11525 (1963). 2908. Z. Budtginsky, V. Bydiovsky J. Kopecky, and J. Piikryl, Czech. Pat. 97,788 (1960); Chem. Ahstr., 55, 23568 (1961). 2909. L. Capuano, P. Boschat, H. W. Heyer, and G. Wachter, Chem. Eer., 106, 312 (1973). 2910. E. D. Bergrnann and S. Cohen, J . Chem. Soc., 1960, 463. 291 1. M. Y. Karpeiskii, S. M. Mikhailov, A. S. Tsieminya, A. A. Ziderrnan, I. M. Kravchenko, M. Y. Lidak, and R. A. Zhuk, Khim. Geterotsikl. Soedin., 1980, 1541. 2912. J. H. Clark, J. P. English, P. S. Winnek, H. W. Marson, Q. P. Cole, and J. W. Clapp, J . Am. Chem. Soc., 68, 96 (1 946). 2913. W. A. Lott and W. Braker, US Pat. 2,484,629 (1949); Chem. Ahstr., 44, 4030 (1950). 29 14. G. V. Chelintsev and Z. V. Benevolenskaya, Z h . Ohshch. Khim., 14, 1142 (1944); Chem. Ahstr., 40, 4069 ( 1 946). 2915. A. Takamizawa, K. Tokuyama, and K. Tori, Bull. Chem. Soc. Jpn., 32, 188 (1959). 2916. A. Takamizawa, K. Ikawa, and K. Tori, Yukugaku Zasshi,78, 647 (1958). 2917. A. Takarnizawa, S. Hayashi, and K. Tori, YukugakuZasshi, 78, 1166 (1958). 2918. A. Takamizawa and R. Maeda, Yakugaku Zasshi, 74, 746 (1954); Chem. Ahstr., 49, 11662 (1955). 2919. A. Takamizawa and K. Tokuyama, Yakugaku Zasshi, 79, 670 (1959). 2920. G. V. Chelintsev, B. M. Dubinin, and Z. V. Benevolenskaya, Zh. Ohshch. Khim., 17,273 (1947); Chem. Ahstr., 42, 866 (1948). 2921. G. Fodor, A. Gerech, I. Kishsh, Y. Kollonich, Y. Vein, and E. Kovach, Zh. Obshch. Khim.,21 1897 (1951); Chem. Ahstr., 46, 6654 (1952). 2922. M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 31, 1053 (1966). 2923. A. Takamizawa, YakugukuZasshi, 74, 756 (1954). 2924. G. A. Stein and J. R. Stevens, US Pat. 2,591,313 (1952); Chem. Ahstr., 47, 617 (1953). 2925. M. Polonovski and H. Schrnitt, C. R. Acad. Sci.,232, 2108 (1951); Br. Abstr., A2, 1952, 976. 2926. M. Polonovski, M. Pesson, and A. Puister, Bull. Sou. Chim Fr., 1951, 521. 2927. K. Sugino and K. Shirai, Nippon Kagaku Zasshi, 70, 111 (1949); Chem. Ahstr., 45,6641 (1951). 2928. T. Nishiwaki, Tetrahedron, 22, 3117 (1966).

2903. 2904. 2905. 2906. 2907.

2929. H. Priewe and K. Gutsche, US Pat. 3,331,841 (1967); Chem. Abstr., 68, 59603 (1968). 2930. T. Matsukawa and K . Sirakawa, Yakugaku Zasshi, 71, 1313; (1951); Chem. Ahstr., 46, 8123 (1952). 2931. A. Takamizawa, K. Hirai, and T. Seppa, Jap. Pat. 5,711 (1965); Chem. Abstr., 62, 16268 (1965). 2932. E. G. Lovett and D. Lipkin, J . Org. Chem., 40, 1722 (1975). 2933. G. L. Bubbar and V. S. Gupta, Can. J. Chem., 48, 3147 (1970). 2934. A. J. H. Nollet and U. K. Pandit, Tetrahedron, 25, 5989 (1969). 2935. W. M. Bruce, J . Am. Chem. Soc., 26, 449 (1904). 2936. G. Menichi, M. Hubert-Habart, and R. Royer, Eur. J . Med. Chem.-Chim.Ther., 10,633 (1975). 2937. T. B. Johnson and G. E. Hilbert, Science, 69, 579 (1929); Chem. Ahstr., 23, 3930 (1929). 2938. J.-L. Fourrey and P. Jouin, Tetrahedron Lett., 1977, 951. 2939. P. Newmark and I. Goodman, J . Am. Chem. Soc., 79, 6446 (1957).

References

1259

2940. P. L. Warner and T. J. Bardos, J . Med. Chem., 9, 977 (1966). 2941. G. C. Hopkins, J. P. Jonak, H. Tieskelmann, and H. J. Minnemeyer, J . Org. Chem., 31, 3969 (1966). 2942. P. Barczynski and H. C. van der Plas, J . Org. Chem., 47 1077 (1982). 2943. B. Roth, J. M. Smith, and M. E. Hultquist, J . Am. Chem. Soc., 73, 2869 (1951). 2944. P. F. Juby and T. W. Hudyma, Ger. Pat. (Offen). 2,418,285 (1974); Chem. Abstr., 82, 73045 (1975). 2945. H. Priewe and K. Gutsche, Ger. Pat. 1,145,622 (1963); Chem. Abstr., 59, 6421 (1963). 2946. K. Gutsche, E. Schroder, C. Rufer, and 0. Loge, Arzneim.-Forsch., 24, 1028 (1974). 2947. D. J. Brown and R. V. Foster, J . Chem. Soc., 1965, 4911. 2948. H. C. van der Plas and H. Jongejan, Recl. Trau. Chim. Pays-Bas, 91, 336 (1972). 2949. E. A. Kaczka and K. Folkers, US Pat. 2,584,024 (1952); Chem. Abstr., 46, 9621 (1952). 2950. S. Basterfield, J . Pharmacol., 20, 451 (1922). 2951. G. E. Hilbert and C. E. Rist, J . Biol. Chem., 117, 371 (1937). 2952. C.-N. Chang, S.-A. Yang, T.-T. Wang, and Y. Hu, Yao Hsueh Hsueh Pao, 10,600 (1963), Chem. Abstr., 60, 14504 (1964). 2953. J. Goerdeler and U. Keuser, Chem. Ber., 97, 3106 (1964). 2954. V. P. Mamaev, 0. A. Zagulyaeva, S. M. Shein, A. T. Shvets, and V. P. Krivopalov, Reakts. Sposobn. Org. Soedin., 5, 824 (1968). 2955. R. Muller, J . Prukt. Chem. 121, 56, 475 (1897). 2956. C. W. Whitehead and J. J. Traverso, J . Am. Chem. Sac., 80, 2182 (1958). 2957. 2958. 2959. 2960. 2961. 2962. 2963. 2964. 2965. 2966. 2967.

2968. 2969. 2970. 2971. 2972. 2973. 2974. 2975. 2976. 2977.

F. S. Yaks and I. Blair, J . Chem. Soc., Perkin Trans. I , 1974, 1565. K. Grohe and H. Heitzer, Liebigs Ann. Chem., 1973, 1025. J. Clark, W. Kernick, and A. J. Layton, J . Chem. Soc., 1964, 3221. M. Israel, M. M. Berman, and M. Muhammad, Org. Prep. Proced. Znt., 4, 83 (1972). F. Yoneda and M. Higuchi, Bull. Chem. Soc. Jpn., 46, 3849 (1973). F. Yoneda and M. Higuchi, J . Chem. Soc., Chem. Commun., 1972, 402. F. L. Rose, US Pat. 2,554,213 (1951); Chem. Abstr., 46, 7117 (1952). A. Kreutzberger and S. Leyke-Rohlings, Arch. Pharm. (Weinheim,Ger.), 311, 351 (1978). H. Biltz and H. Biilow, Liebigs Ann. Chem., 426, 299 (1922). H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, J . Org. Chem., 27, 1492 (1962). H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, in Synthetic Procedures in Nucleic Acid Chemistry, Vol 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 86. H. Bredereck, 0 . Christmann, W. Koser, P. Schellenberg, and R. Nast, Chem. Ber., 95, 1812 ( 1962). T. B. Johnson and Z. Z. Zee, Am. Chem. J . , 49, 287 (1913). Y.-F. Chi and Y.-L. Wu, Acta Chim. Sin., 23, 145 (1957); Sci. Sin., 6, 853 (1957). 0. Hromatka, Ger. Pat. 667,990 (1938); Frdl., 25, 432 (1942). M. Fikus, K. L. Wierzchowski, and D. Shugar, Photochem. Photobiol., 1, 325 (1962). J. Clark and W. Pendergast, J . Chem. Soc (C), 1968, 1124. T. L. V. Ulbricht, in Synthetic Procedures in Nucleic Acid Chemistry, Vol 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 88. T. Takahashi, Yakuguku Zasshi, 89, 591 (1969). C. W. Whitehead, J . Am. Chem. Soc., 75, 671 (1953). H. Bredereck, F. Etfenberger, and G. Rainer, Liebigs Ann. Chem., 673, 82 (1964).

1260

References

2978. I. C . Kogon, J . Org. Chem., 21, 1027 (1956). 2979. J. M. McCall, R. E. Ten-Brink, and J. J. Ursprung, J . Org. Chem., 40, 3304 (1975). 2980. 2981. 2982. 2983. 2984.

A. P. Phillips, J . Am. Chem. Soc., 73, 1061 (1951). 0. Piloty and K. Finckh, Liebigs Ann. Chem., 333, 22 (1904). J. Kinugawa, M. Ochiai, and H. Yamamoto, Yakugaku Zasshi, 83, 1086 (1963). T. L. V. Ulbricht, T. Okuda, and C. C. Price, Org. Synth., 39, 34 (1959). H. Arai, W. K. Hagmann, H. Suguna and S. M. Hecht, J . Am. Chem. Soc., 102, 6631 (1980).

2985. R. S. Shadbolt and T. L. V. Ulbricht, Chem. Ind. (London), 1966, 459. 2986. Y. Shuto, E. Taniguchi, K. Maekawa, Agric. B i d . Chem., 42, 1933 (1978). 2987. Y. Umezawa, H. Morishima, S.-I. Saito, T. Takita, H. Umezawa, S. Kobayashi, M . Otsuka, M. Narita, and N. Ohno, J . Am. Chem. Soc., 102, 6630 (1980). 2988. Y. Sawa, S. Maeda, H. Hishimura, K. Nakajima, and N. Shimaoka, Shionogi Kenkyusho Nempo, 2, 1 (1952); Chem. Abstr., 51, 10008 (1957). 2989. S. Yurugi, M. Hieda, T. Fushimi, and M. Tomimoto, Chem. Pharm. Bull., 19, 2354 (1971). 2990. K. J. M. Andrews and B. P. Tong, J . Chem. Soc. (C), 1968, 1753. 2991. C. W. Todd, J. H. Fletcher, and D. S. Tarbell, J . Am. Chem. Soc., 65, 350 (1943). 2992. E. Peters, J. F. Holland, B. Bryant, H. J. Minnemeyer, C. Hohenstein, and H. Tieckelmann, Cancer Res., 19, 516 (1959). 2993. 2994. 2995. 2996. 2997. 2998. 2999. 3000. 3001. 3002. 3003. 3004.

F. Eiden, Arch. Pharm. (Weinheim, Ger.), 295, 516 (1962). J. Clark and G. R. Ramage, J . Chem. Soc., 1958, 2821. A. Kreutzberger and U.-H. Tesch, J . Heterocycl. Chem., 14, 1197 (1977). K. Hirota, T. Sugiyama, Y. Kitadi, S. Senda, and Y. Maki, Synthesis, 1982, 1097. Z . BukaE and J. Sebenda, Collect. Czech. Chem. Commun., 32, 3537 (1967). A. Pinner, Ber. Dtsch. Chem. Ges., 22, 1600 (1889). A. Kreutzberger and B. Tichter, Chem.-Ztg., 105, 229 (1981). J. C. Roberts, J . Chem. Soc., 1952, 3065. T. Sakamoto, S. Niitsuma, M. Mizugaki, and H. Yamanaka, ffeterocycles, 8, 257 (1977). R. Schwarze, J . Prakt. Chem. 121, 42, 1 (1890). S. Kanetomo, T. Hase, and S. Nagai, Chem. Pharm. Bull., 29, 229 (1981). E. Dyer and H. Richmond, J . Med. Chem., 8, 195 (1965).

3005. 3006. 3007. 3008. 3009. 3010. 3011. 3012.

J. Klosa, J . Prakt. Chem. 141, 26, 43 (1964). E. Cingolani, G. Bellomonte, and A. Sordi, Farmaco, Ed. Sci., 20, 259 (1965). M. Hauser, E. Peters, and H. Tieckelmann, J . Org. Chem., 26, 451 (1961). M. Ridi, Gazz. Chim. Ital., 82, 23 (1952). T. Ueda and S. Kato, Jap. Pat. 14,625 (1961); Chem. Abstr., 56, 10170 (1962). C. Clerc-Bory and C. Mentzer, Bull. Soc. Chim. Fr., 1958, 436. R. Wache, J . Prakt. Chem. 121, 39, 245 (1889). E. von Meyer, J Prakt. Chem. 121, 37, 411 (1888).

3013. 3014. 3015. 3016. 3017. 3018. 3019.

H. Yamanaka, T. Sakamoto, Y. Bannai, and S. Ogawa, Chem. Pharm. Bull., 26, 3404 (1978). P. F. Juby, US Pat. 3,300,496 (1967); Chem. Abstr., 66, 115722 (1967). R. Riemschneider and H. Pehlmann, Z . Naturforsch., Teil B, 20, 540 (1965). T. B. Johnson and Y.-F. Chi, J . Am. Chem. Sac., 52, 1580 (1930). T. B. Johnson and Y.-F. Chi, Recl. Trau. Chim. Pays-Bas, 49, 197 (1930). T. B. Johnson and Y.-F. Chi, Recl. Trau. Chim. Pays-Bas, 49, 86 (1930). L. Rylski, F. Sorm, and Z. Arnold, Collect. Czech. Chem. Commun., 24, 1667 (1959).

References

1261

E. Dyer and T. B. Johnson, J . Am. Chem. Soc., 56, 222 (1934). F. Pochat, Synthesis, 1980, 379. W. C . Schneider and I. F. Halverstadt, J . Am. Chem. Soc., 70, 2626 (1948). Y.-E-. Chi and C.-M. Ma, Trans. Sci. Soc. China, 8, 91 (1934); Chem. Abstr., 29, 472 (1935). Y.-F. Chi and S.-Y. Ming, Trans. Sci. Soc. China, 8, 77 (1934); Chem. Abstr., 29, 472 (1935). S. Ozaki, Y. Ike, H. Mizuno, K. Ishikawa, and H. Mori, Bull. Chem. Soc. Jpn., 50,2406 (1977). R. Dusehinsky and C. Heidelberger, US Pat. 2,948,725 (1960); Chem. Ahstr., 55, 17663 (1961). T. Matsukawa and S. Yurugi, Yakugaku Zasshi, 70,331 (1950); Chem. Ahstr., 45,2952 (1951). T. Sasaki and M. Ando, Yuki Gosei Kayaku Kyokai Shi, 27,169 (1969); Chem. Ahstr., 71,22101 (1 969). 3029. R. K . Glushkov, E. G. Sochilin, and B. A. Ivin, Zh. Obshch. Khim., 39, 924 (1969). 3030. G. W. Miller and F. L. Rose, Br. Pat. 859,287 (1961); Chem. Ahstr., 55, 17665 (1961). 3031. V. P. Arya, J. David, R. S. Grewal, S. B. Marathe, and S. D. Patil, Indian J . Chem., Sect. B,15, 1129 (1977). 3032. A. V. Ivashchenko, 0. N. Garicheva, L. V. Shmelev, Y. S. Ryabokobylko, and G. M. Adamova, Khim. Geterotsikl. Soedin., 1980, 1673. 3033. M. Hauser, E. Peters, and H. Tieckelmann, J . Org. Chem., 25, 2570 (1960). 3034. R. W. Lamon, J. Heterocycl. Chrm., 5, 837 (1968). 3035. G. S. Skinner, E. Anderson, and R. F. Bogart, J . Am. Chem. Soc., 71, 1482 (1949). 3036. W. B. Cowden and N. W. Jacobsen, Aust. J . Chem., 31, 2517 (1978). 3037. Y. Maki, K. Izuta, and M. Suzuki, J . Chem. Sue., Chem. Commun., 1971, 1442. 3038. W. Pfleiderer and G. Blankenhorn, Tetrahedron Lett., 1969, 4699. 3039. I. A. Nasyr and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1976, 1409. 3040. F. Yoneda, K. Shinomura, and S. Nishigaki, Tetrahedron Lett., 1971, 851. 3041. F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 23, 2001 (1975). 3042. V. M. Vvedenskii, Khim. Geterotsikl. Soedin., 1969, 1092. 3043. T. J. Schwan and H. Tieckelmann, J . Heterocycl. Chem., 1, 201 (1964). 3044. A. E. Lanzilotti, J. B. Ziegler, and A. C. Shabica, .I. Am. Chem. Soc., 76, 3666 (1954). 3045. Z. A. Martirosyan, V. A. Gunar, and S. I. Zav’yalov, Izo. Akad. Nuuk S S S R , Ser. Khim., 1970, 1127. 3046. S. Yurugi, M. Tomimoto, and T. Fushimi, Takeda Kenkyusho Nempo, 28, 1 (1969); Chem. Abstr., 72, 55401 (1970). 3047. S. Senda and H. Izumi, Yakuyaku Zasshi, 89, 266 (1969). 3048. H. Yamanaka, K . Edo, and S. Konno, Yakuyaku Zasshi, 97, 726 (1977). 3049. G. H. Hitchings and P. B. Russell, US Pat. 2,671,087 (1954); Chem. Ahstr., 49, 3270 (1955). 3050. T. B. Johnson, J . Biol. Chem., 3, 299 (1907). 3051. C. Mentzer and D. Billet, C. R . Acad. Sci., 288, 402 (1949); Br. Abstr., A2, 1949, 841. 3052. R. C. Elderfield and R. N. Prasad, J . Org. Chem., 26, 3863 (1961). 3053. H. L. Wheeler and H. F. Merriam, Am. Chem J., 29, 478 (1903). 3054. H. Biltz and F. Max, Liebiys Ann. Chem., 414, 85 (1918). 3055. A. Takamizawa and K. Hirai, Jap. Pat. 2,264 (1967); Chem. Ahstr., 66, 95073 (1967). 3056. T. I. Greissman, M. J. Schlatter, I. D. Webb, and J. D. Roberts, J . Ory. Chem., 11, 741 (1946). 3057. R. Gompper, H. E. Noppel, and H. Schaefer, Anyew. Chem., 75, 918 (1963). 3058. M. Draminski and B. Fiszer, Rocz. Chem., 45, 19 (1971). 3059. G. H. Raiziss and M. Freifelder, J . Am. Chem. Soc., 64, 2340 (1942). 3060. P. Dizabo, J.-C. Monier, and A. Pompon, J . Label. Compd., 7, 399 (1971).

3020. 3021. 3022. 3023. 3024. 3025. 3026. 3027. 3028.

1262

References

3061. J. W. Copenhaver, Ger. Pat. 822,086 (1951); Chem. Abstr., 52, 2094 (1958). 3062. A. Schellenberger, W. Rodel, and H. Rodel, Hoppe-Seyler’s Z.Physiol. Chem., 339, 122 (1964). 3063. E. J. Modest, S. Chatterjee, and H. Kangur, J . Org. Chem., 27, 2708 (1962). 3064. V. I. Gunar and S. I. Zav’yalov, Dokl. Akad. Nauk SSSR, 158, 1358 ( I 964). 3065. T. Kato, T. Chiba, T. Shimizu, and H. Takahashi, Chem. Pharm. Bull., 29, 862 (1981). 3066. F. G . P. Rernfry, J . Chem. Soc., 99, 610 (1911). 3067. E. G. Lovett and D. Lipkin, J . Org. Chem., 42, 2574 (1977). 3068. M. Ohoka, S. Yanagida, and S. Komori, J . Org. Chem., 37, 3030 (1972). 3069. G . H. Hitchings and G. B. Elion, US Pat. 2,415,793 (1947); Chem. Abstr., 41, 3132 (1947). 3070. Wellcome Foundation, Br. Pat. 598,514 (1948); Chem. Abstr., 42, 5621 (1948). 3071. H. Aspelund, Acta Acad. Abo., Ser. B, 10, No. 2, 1 (1936); Chem. Abstr., 31, 6630 (1937). 3072. D. J. Brown and B. T. England, J . Chem. Soc. (C), 1971, 425. 3073. A. Pinner, Ber, Dtsch, Chem. Ges., 18, 2845 (1885). 3074. E. A. Oostveen and H. C. van der Plas, Recl. Trau. Chim.Pays-Bas, 96, 68 (1977). 3075. E. Habicht, Swiss Pat. 443,342 (1967); Chem. Abstr., 68, 114625 (1968). 3076. I. B. Simon and I. I. Kovtunovskaya, Zh. Obshch. Khim., 21,760 (1951); Chem. Abstr., 45,9484 (195 1). 3077. R. H. Baker and A. H. Schlesinger, J . Am. Chem. Soc., 70, 1652 (1948). 3078. H. Vanderhaeghe, Bull. Soc. Chim. Bely.,, 59, 689 (1950); Br. Abstr., A2, 1951, 1343. 3079. H. Biltz and K. Sedlatschek, Ber. Dtsch. Chem. Ges., 57, 175 (1 925). 3080. A. Pinner, Ber. Dtsch. Chem. Ges., 25, 1414 (1892). 3081. M. J. E. Ernsting and W. T. Nauta, R e d . Trau. Chim. Pays-Bas, 72, 527 (1953). 3082. H. Vanderhaeghe, Bull. Soc. Chim.Belg., 62, 611 (1953). 3083. M. Draminski and B. Fiszer, Bull. Acad. Pol. Sci., Ser. Sci. B i d , 15, 527 (1967); Chem. Abstr., 68, 59522 (1968). 3084. M. Draminski and B. Fiszer, Rocz. Chem., 43, 499 (1969); Chem. Abstr., 70, 115100 (1969). 3085. J. L. van Winkle, J. D. McClure, and P. H. Williams, J . Ory. Chem., 31, 3300 (1966). 3086. V. T. Klimko, V. A. Mikhalev, and A. P. Skoldinov, Zh. Obshch. Khim., 30, 1258 (1960). 3087. M. A. Kirillova, A. E. Tsil’ko, I. A. Maretina, and A. A. Petrov, Zh. Org. Khim.,6,2369 (1970). 3088. V. T. Klimko, T. V. Protopopova, N. V. Smirnova, and A. P. Skoldinov, Zh. Obshch. Khim., 32, 2961 (1962). 3089. K. Morita, S. Kobayashi, H. Shimadzu, and M . Ochiai, Tetrahedron Lett., 1970, 861. 3090. M. Tsuchiya, S. Morita, T. Tsukamoto, and J. Okada, Yakugaku Zasshi, 96, 1005 (1976). 3091. M. A. Kirillova, A. E. Tsil’ko, I. A. Maretina, and A. A. Petrov, Zh. Org. Khim., 6, 2374 (1970). 3092. M. A. Kirillova, I. A. Maretina, A. A. Petrov, and A. E. Lisitsyn, Zh. Org. Khim., 6, 1528 (1970). 3093. E. Breitmaier, Angew. Chem., 83, 287 (1971). 3094. P. Reynaud and R. C. Moreau, Bull. Suc. Chim.Fr., 1960, 2002. 3095. G. Carrara, F. M. Chiancone, V. DAmato, E. Ginoulhiac, C. Martinuzzi, U. M. Teotino, and N. Visconti, Gazz. Chim. Ital., 82, 652 (1952). 3096. T. V. Gortinskaya, K. M. Murav’eva, and M. N. Shchukina, Zh. Obshch. Khim., 25, 2313 (1955). 3097. H. Yamanaka, M. Mizugaki, M. Sagi, K. Edo, H. Miyazaki, H. Takayama, and Y. Minatogawa, Heterocycles, 12, 1323 (1979). 3098. J. K. Cline, R. R. Williams, A. E. Ruehle, and R. E. Waterman, J . Am. Chem. Soc., 59, 530 (1937). 3099. E. Falch, Acta Chem. Scand., 24, 137 (1970).

References 3100. 3101. 3102. 3103. 3104. 3105. 3106. 3107. 3108. 3109. 3110. 3111. 31 12. 3113. 3114. 311 5. 3116. 3117. 3118. 3119. 3120. 3121. 3122. 3123. 3124. 3125. 3126. 3127. 3128. 3129. 3130. 3131. 3132. 3133. 3134. 3135. 3136. 3137. 3138. 3139.

1263

A. Soemmer, Gcr. Pat. 1,200,308 (1965); Chem. Abstr., 63, 16364 (1965). T. L. V. Ulbricht, Tetrahedron, 6, 225 (1959). J. Tafel and H. B. Thompson, Ber. Dtsch. Chem. Ges., 40, 4489 (1907). A. Guyot and C. Mentzer, C. R. Acad. Sci.,246, 436 (1958). W. B. Whalley, E. L. Anderson, F. DuCan, J. R. Wilson, and G. E. Ullyot, J . Am. Chem. Soc., 77, 745 (1955). B. A. Feit and A. Teuerstein, J . Heterocycl. Chem., 11, 295 (1974). M. A. Kirillova, A. E. Tsil'ko, I. A. Maretina, and A. A. Petrov, Khim. Geterotsikl. Soedin., 1971, 843. Merck, Ger. Pat. 165,692 (1905); Frdl., 8, 1073 (1905-1907). P. B. Russell and G . H. Hitchings, J . Am. Chem. Soc., 74, 3443 (1952). E. Fischer and A. Dilthey, Liebiys Ann. Chem., 335, 334 (1904). E. H. Volwiler, J . Am. Chem. Soc., 47, 2236 (1925). K. Shimo and S. Wakamatsu, J . Org. Chem., 24, 19 (1959). K. Shimo and S. Wakamatsu, Yuki Gosei Kagaku Kyokai Shi,17, 232 (1959); Chem Abstr., 53, 18958 (1959). J. K. Wood, J . Chem. Soc., 89, 1831 (1906). H. Aspelund and L. Lindh, Acta Acud. Abo., Ser. B, 12, No. 10, 1 (1939); Chem. Zentr., 1942,II, 659. R. Giudicelli, H. Najer, P. Chabrier, and E. Joannic-Voisinet, Ann. Pharm. Fr., 15, 533 (1957); Chem. Ahstr., 52, 11081 (1958). B. M. Gatehouse and B. M. Craven, Acta Crystallogr., Sect. B, 27, 1337 (1971). L. Bauer, G. E. Wright, B. A. Mikrut, and C. L. Bell, J . Heterocycl. Chem., 2,447 (1965). K. Golankiewicz, M. Szajda and E. Wyrzykiewicz, Pol. J . Chern., 52, 1085 (1978). J. M. Carpenter and G. Shaw, J . Chem. Soc., 1965, 3987. W. Klotzer, Monatsh. Chem., 92, 1212 (1961). Z . BudEinsky, V. Bydiovsky, J. Kopecky, and J. Piikryl, Czech. Pat. 109,263 (1963); Chem. Abstr., 60, 15889 (1964). M. R. Atkinson, G. Shaw, and G. Sugowdz, J . Chem. Soc., 1957, 3207. K. Senga, M. Ichiba, H. Kanazawa, and S. Nishigaki, J . Heterocycl. Chem., 19, 77 (1982). J. Reiter and L. Toldy, Acta Chim. Acad. Sci. Hung., 82, 107 (1974). A. VystrEil and J. Vidlieka, Chem. Listy, 45, 407 (1951); Chem. Ahstr., 46, 7567 (1952). M. Kawanishi, Tanabe Seiyaku Kenkyu Nempo, 3, 4 (1958); Chem. Abstr., 52, 20183 (1958). A. Dornow and G. Petsch, Ger. Pat. 870,260 (1953); Chem. Abstr., 48, 2123 (1954). Y.-F. Chi and Y.-H. Chen, J . Am. Chem. Soc., 54, 2056 (1932). A. H. Pedersen and K. Undheim, Acta Chem. Scand., Ser. B, 36, 415 (1982). D. J. Brown and R. K. Lynn, J . Chem. Soc., Perkin Trans. I , 1974, 349. T. B. Johnson and L. H. Cretcher, J . Bid. Chem., 26, 99 (1916). Y.-F. Chi, C. Wei, and N.-S. Pan, J . Am. Chem. Soc., 60, 1719 (1938). K. Anzai, J . Heterocycl. Chem., 16, 567 (1979). H. L. Wheeler and T. B. Johnson, Am. Chem. J., 42, 30 (1909). R. List, Liebiys Ann. Chem., 236, 1 (1886). Kodak, Belg. Pat. 561,108 (1957); Chem. Abstr., 54, 4220 (1960). A. Maggiolo and G . H. Hitchings, J . Am. Chem. Soc., 73, 4226 (1951). S. Hoffmann, W. Witkowski, A. Gyulbudagyan, and H. Schubert, Z . Chem., 14, 475 (1974). T. B. Johnson and E. F. Schroeder, J . Am. Chem. Soc., 54, 2941 (1932).

1264

References

3140. A. Burger, J. B. Clements, N. D. Dawson, and R. B. Henderson, J . Ory. Chem., 20, 1383 (1955). 3141. R. E. Hagenbach and H. @sin, Experientia, 8, 184 (1952). 3142. E. R. Tucci, R. E. Doody, and N. C. Li, J . Phys. Chem., 65, 1570 (1961). 3143. T. B. Johnson and A. W. Joyce, J . Am. Chem. Soc., 38, 1385 (1916). 3144. D. J. Brown and R. V. Foster, Aust. J. Chem., 19, 1487 (1966). 3145. G. G. Skvortsova, Z. V. Stepanova, L. V. Andriyankova, and V. K. Voronov, Z h . Ohshch. Khim., 52, 1625 (1982). 3146. R. J. Badger, D. J. Brown, and J. H. Lister, J . Chem. Soc. Perkin Trans. I , 1973, 1906. 3147. L. V. Pavlova and F. Y . Rachinskii, Khim. GeterotsikL Soedin., 1969, 533. 3148. H. L. Wheeler and L. M. Liddle, Am. Chem. J., 40, 547 (1908). 3149. A. Einhorn, Liehigs Ann. Chem., 359, 145 (1908). 3150. G. de Stevens, B. Smolinsky, and L. Dorfman, J . Org. Chem., 29, 1115 (1964). 3151. R. S. Bhatt, N. G. Kundu, T. L. Chwang, and C. Heidelberger, J . Heterocycl. Chem., 18, 771 (1981). 3152. M. S. Shvartsberg, V. P. Mamaev, N. V. Orekhova, and I. L. Kotlyarevskii, Izu . Akad. Nauk SSSR, Ser. Khim., 1978, 2429. 3153. M. PrystaS and F. Sorm, Collect. Czech. Chem. Comrnun., 30, 1900 (1965). 3154. D. J. Brown and P. Waring, J . Chem. Soc., Perkin Trans. 2, 1974, 204. 31 55. M. Fikus, K. L. Wierchowski, and D. Shugar, Biochern. Biophys. Res. Commun., 16,478 (1964). 3156. B. A. Ivin and V. G. Nernets, Zh. Obshch. Khim., 34, 4120 (1964). 3157. D. H. R. Barton, W. A. Bubb, R. H. Hesse, and M. M. Pechet, J. Chem. Soc., Perkin Trans. I , 1974, 2095. 3158. D. Barwolff, G. Kowollik, and P. Langen, Collect. Czech. Chem. Commun., 39, 1494 (1974). 3159. Y . Ashani and S. Cohen, Isr. J . Chem., 3, 101 (1965). 3160. K. Halbritter, W.-D. Kermer, and C. Reichardt, Angew. Chem., 84, 68 (1972). 3161. C. Reichardt and K. Halbritter, Liehigs Ann. Chem., 1975, 470. 3162. K. L. Wierzchowski, E. Litonska, and D. Shugar, J . Am. Chem. Soc., 87, 4621 (1965). 3163. E. D. Bergrnann, S. Cohen, and I. Shahak, J . Chem. Soc., 1959, 3286. 3164. G. Etzold, D. BQrwolff,P. Langen, D. Cech, and H. Meinert, J . Prakt. Chem., 313, 602 (1971). 3165. D. Cech, H. Beerbaum, and A. Holy, Collect. Czech. Chem. Commun., 42, 2694 (1977). 3166. I. K. Fel’dman, A. I. Berlin, I. M. Nurova, I. A. Kuznetsova, E. N. Alekseeva, M. E. Lutts, K. A. Chkhikvadze, and 0. Y . Magidson, Med. Prom. SSSR, 19, No. 3, 12 (1965); Chem. Ahstr., 62, 16239 (1965). 3167. T. I. Yurasova, Zh. Obshch. Khim., 44, 956 (1974). 3168. D. H. R. Barton, R. H. Hesse, H. T. Toh, and M. M. Pechet, J . Ory. Chem., 37, 329 (1972). 3169. J. Stastny and J. Filip, Radiuisotopy, 8, 583 (1967); Chem. Ahstr., 71, 49889 (1969). 3170. E. D. Bergmann, I. Shahak, and I. Gruenwald, J . Chem. Soc. C , 1967, 2206. 3171. Y . Kobayashi, I. Kumadaki, and A. Nakazato, Tetrahedron Lett., 21, 4605 (1980). 3172. W. K. Chung and J. H. Chung, Yakhak Hoe Chi, 26,25 (1982); Chem. Ahstr., 98,4510 (1983). 3173. W. K. Chung, J. H. Chung, and K. A. Watanabe, J . Heterocycl. Chem., 20, 457 (1983). 3174. 1. Wempen and J. J. Fox, J . Med. Chem., 7, 207 (1964). 3175. M. TiBler, B. Stanovnik, and 2. ZrimSek, Heterocycles, 17, 405 (1982). 3176. D. J. Brown and S. F. Mason, J . Chem. Soc., 1957, 682. 3177. R. M . Cresswell, T. Neilson, and H. C. S. Wood, J . Chem. Soc., 1960, 4776. 3178. T. Matsukawa and S. Yurugi, Yakuyaku Zasshi, 69,508 (1949); Chem. Abstr., 44,4476 (1950). 3179. S. Sugasawa and H. Shigehara, YakuyakuZasshi, 62,531 (1942); Chem. Ahstr., 45,2861 (1951).

References 3180. 3181. 3182. 3183. 3184. 3185. 3186. 3187. 3188. 3189. 3190. 3191. 3192. 3193. 3194. 3195. 3196. 3197. 3198. 3199. 3200. 3201. 3202.

1265

M. Sekiya, Yakugaku Zasshi, 70, 524 (1950); Chem Ahstr., 45, 5640 (1951). A. Takamizawa and K. Hirai, Jap. Pat. 22,009 (1964); Chem. Ahstr., 62, 9150 (1965). T.-Y. Weng, Y u o Hsueh Hsueh Pao, 7, 253 (1959); Chem. Abstr., 54, 14256 (1960). R. Denayer, Bull. Soc. Chim. Fr., 1962, 1358. D. I. Magrath and G. B. Brown, J . Am. Chem. SOC.,79, 3252 (1957). E. Richter and E. C. Taylor, J . Am. Chem. Soc., 78, 5848 (1956). L. F. Cavalieri, J. F. Tinker, and A. Bendich, J . Am. Chem. Soc., 71, 533 (1949). V. M. Clark and H. M. Kalckar, J . Chem. Soc., 1950, 1029. W. Traube, Ber. Dtsch. Chem. Ges., 37, 4544 (1904). S. Senda and K. Hirota, Chem. Pharm. Bull., 22, 2593 (1974). S . Murahashi and A. Nishio, Yukugaku Zasshi, 73, 977 (1953); Chem. Ahstr., 48, 11426 (1954). P. Papini and R. Cimmarusti, Gazz. Chim. Ital., 77, 142 (1947). M . Ridi and S . Checchi, Gazz. Chim. Ital., 83, 36 (1953). B. R. Baker, B.-T. Ho, and T. Neilson, J . Heterocycl. Chem., 1, 79 (1964). K . Sirakawa, T. Tsujikawa, and T. Tsuda, Takeda Kenkyusho Nempo, 22, 27 (1963). T. K. Liao, F. Baiocchi, and C. C. Cheng, J . Org. Chem., 31, 900 (1966). M . T. Doel, A. S. Jones, and N. Taylor, Tetrahedron Lett., 1969, 2285. G. Shaw and J. H. Dewar, Proc. Chem. Soc., 1961, 216. A. P. Martinez and W. W. Lee, J . Org. Chem., 30, 317 (1965). J. H. Dewar and G. Shaw, J . Chem. Soc., 1962, 583. D. E. Bergstrom and W. C. Agosta, Tetrahedron Lett., 1974, 1087. K. Rackmann, Liebigs Ann. Chem., 376, 163 (1910). A. Schellenberger and W. Rodel, Angew. Chem., 76, 226 (1964).

3203. G. Cavallini, E. Massarani, F. Mazzucchi, and F. Ravenna, Farm. Sci. Tec., 7, 397 (1952); Chem. Ahstr., 47, 8015 (1953). 3204. 3205. 3206. 3207. 3208. 3209. 3210. 3211. 3212. 3213. 3214. 3215. 3216. 3217. 3218. 3219. 3220. 3221. 3222.

T. Naito, T. Yoshikawa, S.-I. Kitahara, and N.-E. Aoki, Chem. Phurm. Bull., 17, 1467 (1969). W. Plleiderer and K.-H. Schundehutte, Liebigs Ann. Chem., 615, 42 (1958). R. Giuliano and G. Leonardi, Farmaco, Ed. Sci., 11, 389 (1956); Chem. Zentr., 1957, 12756. D. J. Brown and T. Nagamatsu, Aust. J . Chem., 31, 2505 (1978). K. Sirakawa, Yakugaku Zasshi, 78, 1395 (1958). R. Behrend and P. Ernert, Liebigs Ann. Chem., 258, 347 (1890). M. Ganguly, D. Sen, and B. C. Guha, Naturwissenschaften, 48, 695 (1961). M. E. C. Biffin and D. J. Brown, Tetruhedron Lett., 1968, 2503. A. Dornow and K. Dehmer, Chem. Ber., 100, 2577 (1967). F. Baumbach, H . 4 . Henning, and G. Hilgetag, Z. Chem., 4, 67 (1964). D. Shiho and N. Takahayashi, Yukugaku Zasshi, 75,773 (1955); Chem. Abstr., 50,4976 (1956). T. Matsukawa, S. Ban, K. Sirakawa, and M. Yoneda, Yakugaku Zasshi, 73, 159 (1943). K. Sirakawa, Yakugaku Zasshi, 73, 640 (1953); Chem. Ahstr., 48, 9364 (1954). D. Shiho and T. Kanai, Nippon Kagaku Zasshi, 73, 862 (1952); Chem. Zentr., 1955, 6747; Chem. Ahstr., 48, 2070 (1954). J. D. Bower and F. P. Doyle, J . Chem. Soc., 1957, 727. D. Shiho, N. Takahayashi, and M. Kanaoka, Yakugaku Zasshi, 75, 898 (1955). B. Camerino, G. Palamidessi, and R. Skiaky, Gazz. Chim. Ital., 90,1821 (1960). D. Libermann and A. Rouaix, C. R. Acad. Sci., 240, 984 (1955); Chem. Zentr., 1956, 7535. D. Libermann, Fr. Pat. 1,170,115 (1959); Chem. Abstr., 54, 21147 (1960).

1266 3223. 3224. 3225. 3226. 3227. 3228. 3229. 3230. 3231. 3232. 3233. 3234. 3235. 3236. 3237. 3238. 3239. 3240. 3241. 3242. 3243. 3244. 3245. 3246. 3247. 3248. 3249. 3250. 3251. 3252. 3253. 3254. 3255. 3256. 3257. 3258. 3259. 3260. 3261.

References E.-J. Birr and W. Walther, Chem. Ber., 86, 1401 (1953). Y. A. Levin and V. A. Kukhtin, Zh. Obshch. Khim., 32, 1709 (1962). D. M. Brown, M. J. E. Hewlins, and P. Schell, J . Chem. Soc. (C), 1968, 1925. D. J. Brown and K. Shinozuka, Aust. J . Chem., 33, 1147 (1980). D. J. Brown and R. K. Lynn, Aust. J . Chem., 26, 1689 (1973). D. T. Hurst and J. Christophides, Heterocycles, 6, 1999 (1977). M. E. C. Biffin, D. J. Brown, and Q. N. Porter, Tetrahedron Lett., 1967, 2029. M. E. C. Biffin, D. J. Brown, and Q. N. Porter, J . Chem. Soc. (C), 1968, 2159. K. Sirakawa, Yakugaku Zasshi, 80, 952 (1960). G. B. Barlin and A. C. Young, J . Chem. Soc., Perkin Trans. 1, 1972, 1269. W. Kirkor, E. Kozlowska, and P. Grudzinska, Rocz. Chem., 43, 519 (1969); Chem. Abstr., 70, 115101 (1969). A. Spassov and N. Spassovska, C . R. Acad. Bulg. Sci., 24, 247 (1971). G. M. Kheifets, N. V. Khromov-Borisov, and A. I. Kol'tsov, Dokl. Akad. Nauk SSSR, 166,635 (1966); Chem. Abstr., 64, 11207 (1966). F. Lingens and H. Schneider-Bernlohr, Liebigs Ann. Chem., 686, 134 (1965). D. J. Brown and R. K. Lynn, Aust. J . Chem., 27, 1781 (1974). R. G. Dickinson, N. W. Jacobsen, and R. G. Gillis, Aust. J . Chem., 28, 859 (1975). D. M. Brown and P. Schell, J . Chem. Soc., 1965, 208. T. B. Johnson and N. A. Shepard, Am. Chem. J., 48, 279 (1912). P. K. Chang, J . Med. Chern., 8, 884 (1965). S. Y. Wang, J . Am. Chem. Soc., 81, 3786 (1959). R. Behrend and L. Fricke, Liebigs Ann. Chem., 327, 253 (1903). G. H. Hitchings and P. B. Russell, US Pat. 2,624,731 (1953); Chem. Abstr., 47, 10559 (1953). J. D. Fissekis and B. M. Creegan, J . Org. Chem., 32, 3595 (1967). E. Profft and H. Raddatz, Wiss. Z . Tech. Hochsch. Chem. Leuna-Merseburg, 2, 439 (1960); Chem. Abstr., 55, 11425 (1961). H. Mizuno, H. Okuyama, H. Hayatsu, and T. Ukita, Chem. Pharm. Bull., 12, 1240 (1964). H. M. Loux and E. J. Soboczenski, Belg. Pat. 620,174 (1962); Chem. Abstr., 59, 639 (1963). A. F. Vlasenko, B. E. Mandrichenko, G. K. Rogul'chenko, R. S. Sinyak, I. A. Mazur, and P. M. Kochergin, Khim. GeterotsikL Soedin., 1976, 834. G. Doleschall, M. Hornyak-Hamori, and K. Lempert, Acta Chim. Acad. Sci. Hung., 55, 319 ( 1968). A. Fujita and E. Hasegawa, Seikagaku, 22, 202 (1950); Chem. Abstr., 45, 9090 (1951). T. Ukita, H. Okuyama, and H. Hayatsu, Chem. Pharm. Bull., 11, 1399 (1963). T. B. Johnson and S. E. Hadley, J . Am. Chem. Soc., 39, 1919 (1917). C. C. Price and J. Zomlefer, J . Org. Chem., 14, 210 (1949). M . V. Wagle and K. D. Kulkarni, Indian J . Pharm., 30, 254 (1968); Chem. Abstr., 70, 57764 (1969). L. H. Cretcher, J. A. Koch, and W. H. Pittenger, J . Am. Chem. SOC.,47, 3083 (1925). U. Wolcke and G. B. Brown, J . Org. Chem., 34, 978 (1969). T. Sakamoto, K. Kanno, T. Ono, and H. Yamanaka, Heterocycles, 6, 525 (1977). T. J. Schwan, J. F. Holland, and H. Tieckelmann, J . Heterocycl. Chem., 1, 299 (1964). D. Ziegler and R. Brossmer, Tetrahedron Lett., 1973, 2055. K. A. Chkhivadze, N. E. Britikova, and 0.Y. Magidson, B i d . Akt. Soedin., Akad. Nauk S S S R , 1965, 16; Chem. Abstr., 63, 18080 (1965).

References 3262. 3263. 3264. 3265. 3266. 3267. 3268. 3269. 3270. 3271. 3272. 3273. 3274. 3275. 3276. 3277. 3278. 3279. 3280. 3281. 3282. 3283. 3284. 3285. 3286. 3287. 3288. 3289. 3290. 3291. 3292. 3293. 3294. 3295. 3296. 3297. 3298. 3299. 3300. 3301.

1267

F. Tanaka, S. Takeuchi, and H. Yonehara, J . Antibiot., Ser. A , 15, 197 (1962). K. Tokuyama, Yakugaku Zasshi, 79, 819 (1959). T. Matsukawa, T. Iwatsu, and S. Yurugi, Yakuyaku Zasshi, 71, 369 (1951). E. P. DiBella and D. J. Nennessy, J . Org. Chem., 26, 2017 (1961). T. Okuda and C. C. Price, J . Org. Chem., 22, 1719 (1957). H. Biltz and M. Heyn, Liebigs Ann. Chem., 413, 98 (1917). Z. Budtiinsky, J. Piikryl, and E. Svatek, Collect. Czech. Chem. Comrnun., 29, 2980 (1964). R. Behrend and E. Dietrich, Liebigs Ann. Chem., 309, 260 (1899). J. L. Wong, M. S. Brown, K. Matsumoto, R. Oesterlin, and H. Rapoport, J . Am. Chem. Soc., 93, 4633 (1971). R. Andreasch, Sitzungsber. Akad. Wiss. W e n , Math.-Naturwiss, KI., Abt. 28, 109, 166 (1900). Y. S. Shvetsov, A. N. Shirshov, and V. S. Reznik, Izv. Akad. Nauk S S S R , Ser. Khim., 1978, 2079. G. H. Denny and M. A. Ryder, J . Med. Chem., 17, 1230 (1974). R. N. Warrener and E. N. Cain, Anyew. Chern., 78,491 (1966). D. Davidson and 0. Baudisch, Ber. Dtsch. Chem. Ges., 58, 1685 (1925). D. Davidson and 0. Baudisch, J . Biol. Chem., 64, 619 (1925). N. E. Britikova, L. A. Belova, K. A. Chkhikvadze, and 0. Y. Magidson, Khim. Geterotsikl. Soedin., 1973, 273. E. M. Tanner, Spectrochim. Acta, 8, 9 (1956). R. S. Tipson, Org. Synth., 33, 3 (1953).

D. Davidson and E. Epstein, J . Org. Chem., 1, 305 (1936). R. S. Tipson and L. H. Cretcher, J . Org. Chem., 16, 1091 (1951). B. M. Craven and T. M. Sabine, Acta Crystallogr., Sect. B, 25, 1970 (1969). V. M. Nesterov and I. E. Chubova, Russ. Pat. 119,879 (1959); Chem. Abstr., 54, 2375 (1960). 0. 0. Orazi, R. A. Corral, and H. E. Bertorello, J . Org. Chem., 30, 1101 (1965). C. W. Noell and C. C. Cheng, J . Heterocycl. Chem., 5, 25 (1968). A. Takamizawa, K. Hirai, Y. Hamashima, and M. Hata, Chem. Pharm. Bull., 12, 558 (1964). R. Peereboom and H. C. van der Plas, R e d . Trau. Chim. Pays-Bas, 93, 284 (1974). R. S . Karlinskaya and N. V. Khromov-Borisov, Zh. Obshch. Khim., 30, 899 (1960). R. G. Shepherd and C. E. Fellows, J . Am. Chem. Soc., 70, 157 (1948). S. Gronowitz, B. Norrman, B. Gestblom, B. Mathiasson, and R. A. Hoffman, Arkiu. Kemi, 22, 65 (1964). W. H. Prusoff, W. L. Holmes, and A. D. Welch, Cancer Res., 13,221 (1953); Chem. Abstr., 47, 8876 (1953). T. Kato, H. Yamanaka, H. Fukumi, and M. Noda, Yakugaku Zusshi, 93, 1437 (1973). H. Aspelund, Acta Acad. Abo., Ser. B, 21, No. 10, l(1958); Chem. Abstr., 53, 21991 (1959). H. Aspelund, Acta Acad. Abo. Ser. B, 20, No. 12, 1 (1956); Chem. Abstr., 51, 9628 (1930). S. Basterfield and E. C. Powell, Can. J . Res., 1, 261 (1929); Chem. Abstr., 24, 1356 (1930). L. Birkofer, A. Ritter, and H.-P. Kiihlthau, Chem. Ber., 97, 934 (1964). E. Buhler and W. Pfleiderer, Chem. Ber., 100, 492 (1967). D. J. Brown and J. M. Lyall, Aust. J . Chem., 18, 741 (1965). R. W. Luckenbaugh and E. J. Soboczenski, US Pat. 3,235,363 (1966); Chem. Abstr., 65, 13733 (1966). Du Pont, Br. Pat. 968,664 (1964); Chem. Abstr., 61, 13327 (1964). H. Bredereck, A. Brauninger, D. Hayer, and H. Vollmann, Chem. Ber., 92, 2937 (1959).

1268

References

3302. A. Pompon, E. Picquenard, C. Coupry, J. Belloc, and P. Dizabo, J . Chem. Res., Synop. 238, Minipr. 2630 (1981). 3303. I. BaBnik and J. FarkaS, Collect. Czech. Chem. Commun., 44,2426 (1979). 3304. U. Niedballa and H. Vorbruggen, J . Org. Chem., 41, 2084 (1976). 3305. S. David and P. Sinay, Bull. Soc. Chim. Fr., 1965, 2301. 3306. H. R. Snyder and H. M. Foster, J . Am. Chem. Soc., 76, 118 (1954). 3307. A. Jurand and J. Niwelinski, Bull. Int. Acad. Pol. Sci. Lett., Cl. Med., 1949, 87; Chem Abstr., 44, 3156 (1950). 3308. J. M. Sprague and E. M. Schultz, US Pat. 2,650,921 (1953); Chem. Abstr., 48, 10784 (1954). 3309. H. Eilingsfeld, M. Seefelder, and H. Weidinger, Chem. Ber., 96, 2671 (1963). 3310. J. C. Martin, K. R. Barton, P. G. Gott, and R. H. Meen, J . Org. Chem., 31, 943 (1966). 3311. E. C. Taylor and J. G. Berger, Angew. Chem., 78, 144 (1966). 3312. E. V. Taylor and J. G. Berger, J . Org. Chem., 32, 2376 (1967). 3313. F. Fichter and H. Stenzl. Helo. Chim. Actu, 17, 665 (1934). 3314. W. Abraham and G. Barnikow, Tetrahedron, 29, 691 (1973). 3315. T. P. Johnston, G. S. McCaleb, P. S. Opliger, W. R. Laster, and J. A. Montgomery, J . M e d . Chem., 14, 600 (1971). 3316. G. R. Brown, J. Chem. Soc.. Perkin Trans. 1, 1973, 2022. 3317. Y. Sawa, H. Tanidd, and T. Ishida, Yakugaku Zasshi, 76, 1103 (1956); Chem. Ahstr., 51, 3607 (1957). 3318. R. Weiss, Mikrochim. Actu, 1961, I I . 3319. T. J. Bardos, R. R. Herr, and T. Enkoji, J . Am. Chem. Soc., 77, 960 (1955). 3320. W. Trzcinski, Ber. Dtsch. Chem. Ges., 16, 1057 (1883). 3321. M. Nencki, Ber. Dtsch. Chem. Ges., 4, 722 (1871). 3322. M. G. Stout and R. K. Robins, J . Heterocycl. Chem., 9, 545 (1972). 3323. Y. P. Shvachkin, M. k. Berestenko, and G. P. Mishin, Vestn. Mosk. Uniu., Ser. I / , Khim., 18, No. 3, 82 (1963); Chem. Abstr., 59, 7525 (1963). 3324. M. PrystaS, in Nucleic Acid Chemistry, Part 1 (L. 8. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 77. 3325. T. Naito, M. Hirata, and T. Kobayashi, Jap. Pat. 7,767 (1965); Chem. Abstr., 63, 1803 (1965). 3326. S. David and H. Hirshfeld, Bull. Soc. Chim. Fr., 1966, 527. 3327. R. Andrisano and G. Modena, Gazz. Chim. Ital.,81, 398 (1951). 3328. R. S. Karlinskaya, N. V. Khromov-Borisov, and 0. V. Maksimova, Khim. Geterotsikl. Soedin., 1970, 1573. 3329. J. L. Wong and D. S. Fuchs, J . Org. Chem., 36, 848 (1971). 3330. L. F. Cavalieri and B. A. Lowry, Arch. Biochem. Biophys., 35, 83 (1952). 3331. J. Brock, Z. Chem., 7, 343 (1967). 3332. J. D. Fissekis and F. Sweet, J . Org. Chem., 38, 1963 (1973). 3333. H. Yamanaka, S. Niitsuma, T. Sakamoto, and M. Mizugaki, Heterocycles, 5, 255 (1976). 3334. J. H. Lister and G. M. Timmis, J . Chem. Soc. (C), 1966, 1242. 3335. A. Takamizawa, Yakugaku Zasshi, 74, 759 (1954); Chem. Ahstr., 49, 11664 (1955). 3336. A. Takamizawa, Jap. Pat. 1,126 (1958); Chem. Abstr., 53, 1388 (1959). 3337. T. Matsukawa and K. Sirakawa, Yakugaku Zasshi, 71, 933 (1951); Chem. Abstr., 46, 4548 (1952). 3338. Ciba, Neth. Pat. Appl. 6,506,572 (1965); Chem. Abstr., 64, 19634 (1966). 3339. Y. Maki, M. Sako, and M. Suzuki, J . Chem. Soc., Chem. Commun., 1972, 999.

References 3340. 3341. 3342. 3343. 3344. 3345. 3346. 3347. 3348. 3349. 3350. 3351. 3352. 3353. 3354. 3355. 3356. 3357. 3358. 3359. 3360. 3361. 3362. 3363. 3364. 3365. 3366. 3367. 3368. 3369. 3370. 3371. 3372. 3373. 3374. 3375. 3376. 3377. '3378. 3379. 3380.

1269

S. Ghozi, Fr. Pat. 1,276,663 (1962); Chem. Ahstr., 57, 13779 (1962). Hoffmann-La Roche, Br. Pat. 953,876 (1964); Chem. Ahstr., 61, 8322 (1964). H. J. Backer and A. B. Grevenstuk, Reel. Trau. Chim. Pays-Bas, 61, 291 (1942).

K. Tsuda and Y. Ogawa, Yakuyuku Zasshi, 68, 103 (1948); Chem. Ahstr., 47, 7453 (1953). Schering, Br. Pat. 997,632 (1965); Chem. Ahstr., 63, 16365 (1965). H. Yamanaka, Chem. Pharm. Bull., 7, 158 (1959). W. Stadeli, W. von Philipsborn, A. Wick, and I. KompiS, Helv. Chim. Acta, 63, 504 (1980). J. Jonas and J. Gut, Collect. Czech. Chem. Commun., 27, 716 (1962). D. J . Brown and T. Tcitei, J . Chem. Soc., 1963, 4333. M. Ridi, A. Checchi, and P. Papini, Ann. Chim. (Rome),44, 769 (1954). D. J. Brown and T. Teitei, Aust. J . Chem., 17, 567 (1964). G. M. Kheifets, N. V. Khromov-Borisov, and A. I. Kol'tsov, Z h . O r y . Khim., 2, 1516 (1966). M. Sano, Chem. Pharm. Bull., 10, 308 (1962). G . Sunagawa and M. Watatani, Jap. Pat. 24,970 (1964); Chem. Ahstr., 62, 11826 (1965). W. H. Miller, A. M . Dessert, and G. W. Anderson, J . Am. Chem. Soc., 70, 500 (1948). V. M. Cherkasov, G. Y. Remennikov, A. A. Kisilenko, and E. A. Romanenko, Khim. Geterotsikl. Soedin., 1980, 239. H. Rokos and W. Pfleiderer, Chem. Ber., 104, 748 (1971). B. Roth, US Pat. 2,568,971 (1951); Chem. Ahstr., 46, 5093 (1952). K. Okui, K. Ito, and T. Kametani, J . Heterocycl. Chem., 9, 821 (1972). R. R. Adams and F. C. Whitmore, J . Am. Chem. Soc., 67, 735 (1945). K. Soda, T. Aka, K. Nishiide, Y. Watanabe, and S. Ono, Jap. Pat. 26,409 (1964); Chem. Ahstr., 62, 9148 (1965). T. Kato, H. Yamanaka, and H. Moriya, Yukugaku Zasshi, 84, 1201 (1964). R. Andrisano and G. Modena, Boll. Sci. Fac. Chim. Ind. Bologna, 9, 100 (1951); Chem. Ahstr.. 46, 9422 (1952). H. Brcdereck, R. Gompper, and G. Morlock, Chem. Ber., 91, 2830 (1958). I. Warczykowska and J. Wojciechowski, Pol. J . Chem., 54, 335 (1980). K. Stankiewicz and B. Bobranski, Farmuco, Ed. Sci., 33, 740 (1978). G. Zvilichovsky, Isr. J . Chem., 6, 123 (1968). T. Yasushige, Y. Tsuruta, M. Aida, S. Hyoto, and K . Noda. Jap. Pat. 27,259 (1964); Chem. Ahstr., 62, 11828 (1965). J. F. W. Keana, J. S. Bland, P. E. Eckler, and V. Nelson, J . Org. Chem., 41, 2124 (1976). A. S. Katner and E. A. Ziege, J . Chem. Soc., Chem. Commun., 1971, 864. M. Ridi, G . Franchi, and S. Mangiavacchi, Farmaco, E d . Sci., 23, 16 (1968). A. V. El'tsov and K. L. Muravich-Aleksandr, Zh. Ory. Khim., 6, 2612 (1970). J. Carbon, H. David, and M. H. Studier, Science, 161, 1146 (1968). J. H. Lister, Aust. J . Chem., 32, 2771 (1979). G . M. Blackburn and A. W. Johnson, J . Chem. SOC., 1960,4347. J. W. Daly and B. E. Christensen, J . Ory. Chem., 21, 177 (1956). J. W. Copenhaver and R. F. Kleinschmidt, Br. Pat. 663,303 (1951); Chem. Ahstr., 46, 10212 (1952). D. J. Brown, E. Hoerger, and S. F. Mason, J . Chem. SOC.,1955, 4035. D. J. Brown, Nature, 189, 828 (1961). D. D. Perrin and I. H. Pitman, Aust. J . Chem., 18, 763 (1965). S. Moiioz-Notari, An. Fac. Quim. Farm., UniL;. Chile, 1967, 76.

1270

References

3381. F. Bergmann, G. Levin, H. Kwietny-Govrin, and H. Ungar, Biochim. Biophys. Acta, 47, l(1961). 3382. A. Soemmer, E. Ger. Pat. 32,753 (1966); Chem. Abstr., 65, 727 (1966). 3383. M. D. Slimmer and J. Stieglitz, Am. Chem. J., 31, 661 (1904). 3384. H. Bredereck, G. Kupsch, and H. Wieland, Chem. Ber., 92, 566 (1959). 3385. G. I. Lavrenova and N. A. Poddubnaya, Zh. Obshch. Khim.,34, 2864 (1964). 3386. S. Cohen and A. Vincze, Isr. J . Chem., 2, 1 (1964). 3387. T. Nishimura and I. Iwai, Chem. Pharm. Bull., 12, 352 (1964). 3388. N. A. Chadaeva, G. K. Kamai, and K. A. Mamakov, Zh. Obshch. Khim., 37, 1402 (1967). 3389. R. K. Ralph and G. Shaw, J . Chem. Soc., 1956, 1877. 3390. K. Hirota, Y Kitade, and S. Senda, Tetrahedron Lett., 22, 2409 (1981). 3391. M. Bachstez, Ber. Dtsch. Chem. Ges., 63, 1000 (1930). 3392. M. R. Atkinson, M. H. Maguire, R. K. Ralph, G . Shaw, and R. N. Warrener, J . Chem. Scc., 1957, 2363. 3393. P. H. Laursen, W. A. Thews, and B. E. Christensen, J . Org. Chem., 22, 274 (1957). 3394. M. Ridi, Gazz. Chim. Ital., 82, 756 (1952). 3395. H. Biltz and H. Bullow, Liebigs Ann. Chem., 426, 283 (1992). 3396. T. Sugimoto and S. Matsuura, Bull. Chem. Soc. Jpn., SO, 1359 (1977). 3397. T. Nagamatsu, E. Matsumoto, and F. Yoneda, Chem. Lett., 1982, 1127. 3398. F. L. Lam and J . C. Parham, J . Am. Chem. Soc., 97, 2839 (1975). 3399. H. Iwasaki, Yukugaku Zasshi, 82, 1358-1395 (11 papers) (1962); Chum. Abstr., 59, 757 (1963). 3400. R. S. Klein, I. Wempen, K. A. Watanabe, and J. J. Fox, J . Org. Chem., 35, 2330 (1970). 3401. F. Yoneda and T. Nagamatsu, Synthesis, 1975, 177. 3402. F. Sweet and J. D. Fissekis, J . Am. Chem. Soc., 95, 8741 (1973). 3403. L. P. Prikazchikova, L. I. Rybchenko, and V. M. Cherkasov, Khim.Geterotsikl. Soedin., 1977, 831. 3404. E. Winterfeldt and J. M. Nelke, Chem. Ber., 100, 3671 (1967). 3405. C. C. Cheng and L. R. Lewis, J . HeterocycL Chem., 1, 260 (1964). 3406. T. Matsukawa and B. Ohta, Yukugaku Zasshi, 70, 137 (1950); Chem. Abstr., 44, 5886 (1951). 3407. S. F. Mason, J . Chem. Soc., 1960, 219. 3408. M. Ikehara, T. Ueda, and K. Ikeda, Chem. Pharm. Bull., 10, 767 (1962). 3409. J. Stantk, Collect. Czech. Chem. Commun., 23, 1154 (1958); Chem. Listy, 52, 357. 3410. A. N. Kost, R. S. Sagitullin, and G. G. Danagulyan, Khim. Geterotsikl. Soedin., 1978, 1400. 3411. E. C. Taylor and J. W. Barton, J . Org. Chem., 24, 127 (1959). 3412. Y. P. Shvachkin and M. K. Berestenko, Vestn.Mosk. Univ.,Ser. I I , Khim.,20, No. 3,91 (1965); Chem. Abstr., 63, 9943 (1965). 3413. R. Nutiu and I. Sebe, Rev. Roum. Chim., 16, 919 (1971). 3414. J. J. Fox, T.-L. Su, L. M. Stempel, and K. A. Watanabe, J . Ory. Chem., 47, 1081 (1982). 3415. F. Yoneda and T. Nagamatsu, J . Chem. Soc.. Perkin Trans. I , 1976, 1547. 3416. Y. Ashani and S. Cohen, J . Med. Chem., 13,471 (1970). 3417. B. C. Pal, M. Uziel, D. G. Doherty, and W. E. Cohn, J . Am. Chem. Sou., 91, 3634 (1969). 3418. H. Hayatsu and M. Inoue, J . Am. Chem. Soc., 93, 2301 (1971). 3419. E. Fischer and F. Ach, Ber. Dtsch. Chem. Ges., 32, 2721 (1899). 3420. H. B. Hill, Ber. Dtsch. Chem. Ges., 9, 1090 (1876). 3421. R. Maly and R. Andreasch, Monatsh. Chem., 3,92 (1882); J . Chem. Soc., Abstr., 42,629 (1882). 3422. V. G. Skulason, C. Piantadosi, B. F. Zambrana, and J. L. Irvin, J . Med. Chem., 8, 292 (1965).

References 3423. 3424. 3425. 3426. 3427. 3428. 3429. 3430. 3431. 3432. 3433. 3434. 3435. 3436. 3437. 3438. 3439. 3440. 3441. 3442. 3443. 3444. 3445. 3446. 3447. 3448. 3449. 3450. 3451. 3452. 3453. 3454. 3455. 3456.

1271

M . R. Atkinson, G . Shaw, K. Schaffner, and R. N. Warrener, J . Chem. Soc., 1956, 3847. F. Yoneda, k. Shinozuka, K. Tsukuda, and A. Koshiro, J . Heterocycl. Chem., 16, 1365 (1979). S. Senda and A. Suzui, Chem. Pharm. Bull., 6, 476 (1958). B. R. Baker, R. E. Schaub. J. P. Joseph, F. J. McEvoy, and J. H. Williams, J . Org. Chem., 18, 133 (1953). B. Singh and G. Y. Lesher, J . Heterocycl. Chem., 14, 1413 (1977). M. A. Mikhaleva, V. T. Lazareva, M. F. Grebenkin, V. A. Savel’ev, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1982, 1545. W. Franke and R. Kraft, Ger. Pat. 947,069 (1956); Chem. Zentr., 1957, 3347. M. Ishikawa and H. Kano, Yakugaku Zasshi, 70, 140 (1950); Chem. Abstr., 44. 5887 (1951). B. A. S. F., Br. Pat. 800,006 (1958); Chem. Ahstr., 53, 8179 (1959). D. M. Burness, J . Org. Chem., 21, 97 (1956). K. A. Jensen, P. Falkenberg, T. Thorsteinsson, and M. Lauridsen, Dan. Tidsskr. Farm., 16, 141 (1942); Chem. Zentr., 1943, I, 626. Lafage, Fr. Pat. 992,142 (1951); Chem. Abstr., 50, 15600 (1956). H. Veldstra and H. W. Wiardi, Recl. Trati. Chim. Pays-Bas, 61, 627 (1942). H. Bredereck, F. Effenberger, H. Botsch, and H. Rehn, Chem. Ber., 98, 1081 (1965). G . C. Tsatsaronis and A. H. Kehayoglou, J . Org. Chem., 35, 438 (!970). J. J. Donleavy and M . A. Kise, Org. Synth., Collect. Vol., 2, 422 (1943). R. H. Wiley and S. C. Slaymaker, J . Am. Chem. Soc., 79, 2233 (1957). G. W. Hearne, T. W. Evans, and H. L. Yale, US Pat. 2,455,172 (1948); Chem. Ahstr., 43, 1813 ( 1949). E. A. Oostveen, H. C. van der Plas, and H. Jongejan, Recl. Trati. Chim. Pays-Bas, 93, 114 (1 974). T. Miyaki and E. Kataoka, Yakugaku Zasshi, 60, 367 (1940); Chem. Abstr., 35, 1404 (1941). M. Ogata, H. Watanabe, K. Tori, and H. Kano, Tetrahedron Lett., 1964, 19. H, Bredereck, Org. Synth., 43, 77 (1963). M. V. Deichmeister and A. M. Platoshkin, Khim. Ceterotsikl. Soedin., Sb. 1, 1967, 333; Chem. Abstr., 70, 77900 (1969). J. L. Wong, M. S. Brown, and H. Rapoport, J . Org. Chem., 30, 2398 (1965). G. A. Archer, R. I. Kalish, R. Y. Ning, B. C. Sluboski, A. Stempel, T. V. Steppe, and L. H. Sternbach, J . Med. Chem., 20, 1312 (1977). R. Reiner and C. H. Eugster, Helu. Chim. Acta, 50, 128 (1967). E. Ochiai and M. Yanai, YakugakuZasshi, 59,18;Supplement,p. 97 (1939); Chem. Zentr., 1941, I, 1806. P. B. Russell, J . Chem. Soc., 1954, 2951. R. E. Gibson and B. R. Baker, J . Med. Chem., 17, 1290 (1974). L. STdbO, T. I. Kalman, and T. J. Bardos, J . Org. Chem., 35, 1434 (1970). R. J. de Pasquale, J . Org. Chem., 42, 2185 (1977). C. C. Cheng and L. R. Lewis, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 109. G. M. Kheifets and N . V. Khromov-Borisov, Zh. Org. Khim., 1, 1173 (1965). P. W. Wigler and H.-J. Lee, Biochemistry, 8, 1344 (1969).

3457. Z. A. Martirosyan, V. I. Gunar, and S. I . Zav’yalov, Izv. Akad. Nauk SSSR, Ser. Khim., 1970, 1841. 3458. L. L. Bennett, J . Am. Chem. Soc., 74, 2432 (1952). 3459. E. Fischer and G. Roeder, Ber. Dtsch. Chem. Crs., 34,3751 (1901).

1272 3460. 3461. 3462. 3463. 3464. 3465. 3466. 3467. 3468. 3469. 3470. 3471. 3472. 3473. 3474.

References A. Kossel and A. Neumann, Ber. Dtsch. Chem. Ges., 26, 2753 (1893). A. Kossel and A. Neumann, Ber. Dtsch. Chem. Ges., 27, 2215 (1894). M. M. Stimpson and M. A. Reuter, J . Am. Chem. Soc., 67, 847 (1945). V. Jezdic, Bull. Inst. Nucl. Sci. Boris Kidrich, 12, 121 (1961); Chem. Abstr., 57, 16605 (1963). K.-Y. Zee-Cheng, R. K. Robins, and C. C. Cheng, J . Org. Chem., 26, 1877 (1961). Y.-F. Chi and Y.-L. Wu, Acta Chim. Sin., 22, 188 (1956). I. K. Fel’dman and L. V. Shepshelevich, Mechenye B i d . Akt. Veshchestva, Sb. Statei, 1962, 65; Chem. Abstr., 59, 7528 (1963). A. Takamizawa, S. Hayashi, and H. Ito, Jap. Pat. 24,383 (1963); Chem. Abstr., 60, 2965 (1964). W. Klotzer, Monatsh. Chem., 104, 415 (1973). C. M. Redwine and T. W. Whaley, J , Label. Compd. Radiopharm., 16, 315 (1979). M . PrystaS, in Nucleic Acid Chemistry, Part I (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 73. P. Galimberti, V. Gerosa, and M. Melandri, Farmaco, Ed. Sci., 13,455 (1958); Chem. Abstr., 53, 6240 (1959). E. Ajello, T. Ajello, and V. Sprio, Ric. Sci., Parte 2,Sez. B, 4, 105 (1964); Chem. Abstr., 61, 5644 (1964). S. I. Zav’yalov, V. I. Gunar, I. A. Mikhailopulo, and L. F. Ovechkina, Tetrahedron, 22, 2003 ( 1 966). V. I. Gunar, L. F. Ovechkina, E. A. Arutyunyan, I. A. Mikhailopulo, S. I. Zav’yalov, and 0.N. Kulaeva, Izo. Akad. Nauk S S S R , Ser. Khim., 1969, 2772.

3475. V. I. Gunar, 1. A. Mikhailopulo, and S. 1. Zav’yalov, Izu. Akad. Nauk SSSR, Ser. Khim., 1968, 916. 3476. H. Singh, P. Singh, and N. Malhotra. J . Chem. Soc., Perkin Trans. I , 1981, 2647. 3477. K. S. Bhat and A. S. Rao, Ory. Prep. Proced. Int., 15, 303 (1983). 3478. R. N. Castle, K. Kaji, G. A. Gerhardt, W. D. Guither, C. Weber, M. P. Malm, R. R. Shoup, and W. D. Rhoades, J . Heterocycl. Chem., 3, 79 (1966). 3479. J. V. KoStii and V. Kr61, Chem. Listy, 43, 37 (1949); Chem. Abstr., 45, 562 (1951). 3480. A. Albert and G. B. Barlin, J . Chem. Soc., 1962, 3129. 3481. V. A. Serzhanina, N. V. Khromov-Borisov, and R. S. Karlinskaya, Khim. Geterotsikl. Soedin., 1968, 524. 3482. W. Franke and R. Kraft, Chem. Ber., 86, 797 (1953). 3483. T. Matsukawa and K. Sirakawa, Yakugaku Zasshi, 72, 486 (1952). 3484. E. M . Gal, J . Am. Chem. Soc., 72, 5315 (1950). 3485. D. Marotta and G. Rosanova, Atti Accad. Naz. Lincei, 1932, 15, 753; Chem. Zentr., 1932, 11, 1786. 3486. A. P. N. Franchimont and E. A. Klobbie, R e d . Trau. Chim. Pays-Bas, 7, 12 (1888). 3487. T. Nishikawa, Mem. Ryojun Coll. Eng., 3, 277 (1931); Chem. Abstr., 25, 5390 (1931). 3488. B. Arct, D. Prelicz, and H. Witek, Rocz. Chem., 41, 683 (1967); Chem. Abstr., 67, 54098 (1967). 3489. H. G. Biggs and B. Doumas, J . Biol. Chem., 238, 2470 (1963). 3490. R. Wagner and W. von Philipsborn, Helv. Chim. Acta, 53, 299 (1970). 3491. R. Miiller and H. Plieninger, Chem. Ber., 92, 3009 (1959). 3492. J. J. Fox and D. van Praag, J . Am. Chem. Soc., 82, 486 (1960). 3493. G. B. Barlin and J. A. Benbow, J . Chem. Sac., Perkin Trans. 2, 1975, 1385. 3494. E. H. Northey, US Pat. 2,417,318 (1947); Chem. Abstr., 41, 3823 (1947). 3495. A. Takamizawa, Jap. Pat. 8,031 (1954); Chem. Abstr., 50, 14002 (1956). 3496. S. Hiinig and K.-H. Oette, Liebigs Ann. Chem., 640, 98 (1961).

References 3497. 3498. 3499. 3500. 3501. 3502. 3503. 3504. 3505. 3506. 3507. 3508. 3509. 3510. 351 1. 3512. 3513. 3514. 3515. 3516. 3517. 3518. 3519. 3520. 3521. 3522. 3523. 3524. 3525. 3526. 3527. 3528. 3529. 3530. 3531. 3532. 3533. 3534. 3535. 3536. 3537. 3538.

1273

S. G. Laland and G. Serck-Hanssen, Biochem. J., 90,76 (1964). H. R. Synder, H. M. Foster, and G. A. Nussberger, J . Am. Chem. Soc., 76, 2441 (1954). H. M. Foster and H. R. Snyder, Ory. Synth., 35, 80 (1955). R. M. Dodson, E. R. Peterson, and J. K. Seyler, J . Am. Chem. Soc., 72, 3281 (1950). J. Maillard, R. M. Morin, M. M. J. Vincent, and M. M. Bernard, US Pat. 3,047,462 (1962); Chem. Abstr., 58, 1474 (1963). M. Khalifa, Bull. Fac. Phurm., Cairo Unia., 1, 149 (1961-1962); Chem. Abstr., 61, 5643 (1964). R. Peereboom and H. C. van der Plas, Reel. Traa. Chim. Pays-Bas, 93, 277 (1974). I. S. Levi, L. D. Graeva, and M . N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 1977,704. T. Kato and M. Noda, Chem. Pharm. Bull., 24, 303 (1976). J. Maillard, M. Benard, M. Vincent, V. van Tri, R. Jolly, R. Morin, C. Menillet and X. Benharkate, Chim. Ther., 2, 202 (1967); Chem. Ahstr., 68, 12949 (1968). H. G. Mautner, J . Am. Chem. Soc., 78, 5292 (1956). M. Sy and J. Oiry, Bull. Soc. Chim. Fr., 1969, 331. K. Anzdi, J . Ory. Chem., 44, 1737 (1979). R. R. Williams, US Pat. 2,153,016 (1939); Chem. Abstr., 33, 5131 (1939). H. Bretschneider and K. Biemann, Monatsh. Chem., 81, 647 (1950). G. E. Bonvicino and D. J. Hennessy, J . Am. Chem. Soc., 79, 6325 (1957). K. Masuda, Yukuyaku Zasshi, 81, 533 (1961). B. C. Pal and D. G. Schmidt, J . Org. Chem., 39, 1466 (1974). M. Saneyoshi and S. Nishimura, Biochim. Biophys. Acta, 204, 389 (1970). T. Tsuji and Y. Kamo, Chem. Lett., 1972, 641. T. Imai and K. Makino, Hoppe-Seyler’s Z . Physiol. Chem., 252, 76 (1938). P. Karrer and M. Schoeller, Helu. Chim. Acta, 34, 826 (1951). K. Westphal and H. Andersag, US Pat. 2,265,212 (1941); Chem. Abstr., 36, 1950 (1942). T. Matsukawa and S. Yurugi, Yakuyuku Zasshi, 71, 827 (1951). M. Jackman, A. J. Bergman, and S. Archer, J . Am. Chem. Soc., 70, 497 (1948). M. Israel, H. K. Protopapa, S. Chatterjee, and E. J. Modest, J . Phurm. Sci.,54, 1626 (1965). Z . BudESinsky, M. BudESinsky, and A. SvLb, Collect. Czech. Chem. Commun., 46,2254 (1981). W. L. F. Armarego, J . Chem. Soc., 1965, 2778. E. C. Taylor and C. K. Cain, J . Am. Chem. Soc., 74, 1644 (1952). H. N. Schlein, M. Israel, S. Chatterjee, and E. J. Modest, Chem. Ind. (London), 1964, 418. H. C. van der Plas, B. Zuurdeeg, and H. W. van Meeteren, Reel. Trau. Chim. Pays-Bas, 88, 1156 (1969). M. W. Winkley and R. K. Robins, J . Chem. Soc. (C), 1969, 791. M. S. Newman and H. A. Karnes, J . Ory. Chem., 31, 3980 (1966). A. Schrage and G. H. Hitchings, J . Ory. Chem., 16, 207 (1951). Y. Sato, T. Iwashige, and T. Nishimura, Jap. Pat. 6,537 (1962);Chem. Abstr., 58, 13967 (1963). M. Ott and W. Pfleiderer, Chem. Ber., 107, 339 (1974). G. M. Blaekburn and A. W. Johnson, J . Chem. Soc., 1960,4358. E. Ochiai and S. Kitagawa, Yakugaku Zasshi, 56,979; Supplement, p. 177 (1936); Chem. Zentr., 1937, I, 2974; Chem. Abstr., 32, 8418 (1938). Y. Usui, Annu. Rep. Takeda Res. Lab., 27, 96 (1968); Chem. Abstr., 70, 77845 (1969). B. Salvesen, Medd. N o r . Farm. Selsk., 25, 1 (1963); Chem. Abstr., 59, 3923 (1963). T. Ueda and J. J. Fox, J . Am. Chem. Soc., 85, 4024 (1963). M. Sano, Chem. Pharm. Bull., 10, 313 (1962).

1274

References

3539. F. Kuiban, S. Chilyanu, and F. Shcherbesku, M e d . Prom. S S S R , 12, NO. 10, 36 (1958); Chem. Abstr., 53, 16139 (1959). 3540. P. Brigl, Ber. Dtsch. Chem. Ges., 45, 1557 (1912). 3541. M. Sekiya and C . Yanaihara, Chem. Pharm. Bull., 17, 810 (1969). 3542. H. Feuer and J. P. Lawrence, J . Org. Chem., 37, 3662 (1972). 3543. S. Okurnura, Jap. Pat. 18,048 (1964); Chem. Abstr., 62, 5286 (1965). 3544. N. J. Leonard, J. J. McDonald, R. E. L. Henderson, and M. E. Reichmann, Biochemistry, 10, 3335 (1971). 3545. E. C. Taylor, C.-P. Tseng, and J. B. Rampal, J . Org. Chem., 47, 552 (1982). 3546. H. C. van der Plas, H. Jongejan, and A. Koudijs, J . Heterocycl. Chem., 15, 485 (1978). 3547. Y . Fujimoto and N. Ono, Yakugaku Zasshi, 85, 364 (1965). 3548. Y. Fujimoto and N. Ono, Yukugaku Zasshi, 85, 367 (1965). 3549. T. J. Delia, D. E. Portlock, and D. L. Venton, J . Heterocycl. Chem., 5, 449 (1968). 3550. E. Grimaux, Bull. Soc. Chim. Paris 121, 31, 146 (1879). 3551. A. F. Holleman, R e d . Trau. Chim. Pays-Bas, 16, 162 (1897). 3552. W. W. Hartman and 0. E. Sheppard, Org. Synth., Collect. Vol., 2, 440 (1943). 3553. A. Baeyer, Liebigs Ann. Chem., 130, 129 (1864). 3554. G. B. Barlin and A. C. Young, J . Chem. Soc. (B), 1971, 1675. 3555. I. Wempen, H. U. Blank, and J. J. Fox, J . Heterocycl. Chem., 6, 593 (1969). 3556. G . Simchen, Angew Chem., 76, 860 (1964). 3557. T. S. Osdene, US Pat. 3,180,869 (1965); Chem. Abstr., 63, 1807 (1965). 3558. T. S. Osdene, A. A. Santilli, L. E. McCardle, and M. E. Rosenthale, J . Med. Chem., 9, 697 (1966). 3559. H. Sato, M. Nakajima, and H. Tanaka, Nippon Kagaku Zasshi, 72, 866 (1951); Chem. Abstr., 47, 5946 (1953). 3560. Laboratories Lurniere et Institut Merieux, Fr. Pat. 1,364,734 (1964); Chem. Abstr., 62, 572 (1965). 3561. J. Guinchard, Ber. Dtsch. Chem. Ges., 32, 1723 (1899). 3562. F. G. Donnan, Z . Phys. Chem., 19,465 (1896). 3563. P. C. C. Isherwood, Proc. Chem. Soc., 25, 120 (1909). 3564. R. La1 and S . Dutt, Proc. Natl. Inst. Sci., India, 3, 377 (1937); Chem. Abstr., 32, 2908 (1938). 3565. R. P. Parker and J. S. Webb, US Pat. 2,574,155 (1951); Chem. Abstr., 46, 9614 (1952). 3566. R. G. Jones, J . Org. Chem., 25, 956 (1960). 3567. M Sono and H. Hayatsu, Chem. Pharm. Bull., 21, 995 (1973). 3568. D Nightngale, Org. Synth., 23, 6 (1943). 3569. W. W. Hartman and 0. E. Sheppard, Org. Synth., 23, 3 (1943). 3570. A. V. Holmgren and W. Wenner, Org. Synth., 32, 6 (1952). 3571. E. Ziegler and T. Kappe, Monatsh. Chem., 95, 1057 (1964). 3572. W. Bolton, Acta Crystallcgr., 17, 147 (1964). 3573. F. Pochon, M. Herbert, and L. Pichat, Commis. Energ. At. (Fr.),Rapp., No. 1822 (1961); Chem. Abstr., 55, 25967 (1961). 3574. R. Ducolornb, J. Cadet, and R. Teoule, Bull. Soc. Chrm. Fr., 1973, 1167. 3575. B. M. Visinski and G. Dryhurst, J . Electroanal. Chem., 70, 199 (1976). 3576. M. Bachstez, Ber. Dtsch. Chem. Ges., 64, 322 (1931). 3577. H. Moriyama, Yakugaku Zasshi, 83, 169 (1963). 3578. Wellcome Foundation, Br. Pat. 980,854 (1965); Chem. Abstr., 62, 14695 (1965).

References

1275

3579. V. M. Cherkasov, L. P. Prikazchikova, and L. I. Rybchenko, Khim. Geterotsikl. Soedin., 1972, 561. 3580. U. Lippold, Ger. Pat. 859,893 (1952); Chem. Abstr., SO, 7851 (1956). 3581. B. Stanovnik and M. TiSler, Arzenim.-Forsch., 14, 1004 (1964). 3582. J. Moravek and Z. Nejedly, Chem. Ind. (London), 1967, 1788. 3583. I. Iwai and T. Hiraoka, Chem. Pharm. BuLl., 12, 813 (1964). 3584. R. W. Price and A. Moos, J . Am. Chem. Soc., 67, 207 (1945). 3585. A. M. Grigorovskii and V. S. Federov, Russ. Pat. 104,411 (1956); Chem. Abstr., 51,6709 (1957). 3586. K. Sugino et al., Jap. Pat. 7,485 (1954); Chem. Abstr., SO, 4236 (1956). 3587. E. T. Tisza, B. F. Duesel, and H. L. Friedman, US Pat. 2,332,615 (1944); Chem. Abstr., 38, 1754 (1 944). 3588. E. Kuh and M. E. Hultquist, Br. Pat. 551,677 (1943); Chem. Abstr., 38, 2972 (1942). 3589. E. Ochiai and M. Yanai, Yakugaku Zasshi, 60,493; Supplement, p . 192 (1940); Chem. Zentr., 1941, 11, 199; Chem. Abstr., 35, 743 (1941). 3590. 3591. 3592. 3593. 3594. 3595.

E. Kuh and T. W. Clapper, US Pat. 2,425,248 (1947); Chem. Abstr., 41, 7420 (1947). T. Tsukamoto, Jap. Pat. 6,433 (1954); Chem. Abstr., SO, 7883 (1956). T. V. Protopopova and A. P. Skoldinov, Zh. Obshch. Khim., 26, 3355 (1956). E. Kobayashi, Yakugaku Zasshi, 82, 445 (1962). T. V. Protopopova and A. P. Skoldinov, Zh. Obshch. Khim., 28, 240 (1958). T. V. Protopopova and A. P. Skoldinov, Zh. Obshch. Khim.,27, 1276 (1957).

3596. S. Gabriel, Brr. Dtsch. Chem. Ges., 33, 3666 (1900). 3597. 3598. 3599. 3600. 3601. 3602. 3603. 3604. 3605. 3606. 3607. 3608. 3609. 3610. 361 1. 3612. 3613. 3614. 3615. 3616. 3617. 3618. 3619. 3620.

W. 0. Emery, Ber. Dtsch. Chem. Ges., 34, 4178 (1901). N. Whittaker, J . Chem. Soc., 1953, 1646. H. Bredereck and G. Simchen, Angew. Chem., 75, 1102 (1963). H. Bredereck, G. Simchen, A. Santos, and H. Wagner, Angew. Chem., 78, 717 (1966). Y. Ashani, H. Edery, J. Zahavy, W. Kiinberg, and S. Cohen, Isr. J . Chem., 3, 133 (1965). F. H. Case and E. Koft, J . Am. Chem. Soc., 81, 905 (1959). V. KrchAak and 2. Arnold, C o l l e c t . Czech. Chem. Commun., 40, 1384 (1975). F. H. Case, J . Org. Chem., 30, 931 (1965). H. Bredereck, W. Jentzsch, and G. Morlock, Chem. Ber., 93, 2405 (1960). S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 37, 3643 (1904). S. Gronowitz and J. Roe, Acta Chem. Scand., 19, 1741 (1965). J. P. English and J. W. Clapp, US Pat. 2,416,617 (1947); Chem. Abstr., 41, 3493 (1947). W. B. Cowden and P. Waring, Aust. J . Chem., 34, 1539 (1981). H. R. Hensel, Chem. Ber., 97, 96 (1964). D. Cohen, M. Koenigsbuch, and M. Sprecher, Isr. J . Chem., 6, 615 (1968). R. F. Evans, J . Chem. Soc., 1964, 2450. A. G. Beaman, J. F. Gerster, and R. K. Robins, J . Org. Chem., 27, 986 (1962). I. G. Farbenindustrie, Br. Pat. 475,559 (1937); Chem. Ahstr., 32, 3421 (1938). V. M. Berezovskii and A. M. Yurkevich, Zh. Obshch. Khim., 32, 1655 (1962). K. L. Nagpal and M. M. Dhar, Indian J . Chrm., 3, 126 (1965). W. Ried and R. M. Gross, Chem. Ber., 90,2646 (1957). S. Gabriel and J. Colman, Ber. Dtsch. Chem. Ges., 37, 3657 (1904). C. Parkanyi, Chem. Listy, 56, 652 (1962). K. P. Chakraborty and H. S . Loring, J . B i d . Chem., 235, 2122 (1960).

1276

References

G. Ehrensvard and J. Liljekvist, Acta Chem. Scand., 13, 2070 (1959). J. T. KuSmierek and D. Shugar, Acta Biochim. Pol., 17, 259 (1970). K. Takemoto and Y. Yamamoto, Synthesis, 1971, 154. C. Runti, L. Sindellari, and C. Nisi, Ann Chim. (Rome), 49, 1649 (1959). C. Runti, V. d’Osualdo, and F. Ulian, Ann. Chim. (Rome),49, 1668 (1959). A. Y. Tikhonov and L. B. Volodarskii, Khim. Geterotsikl. Soedin., 1977, 259. L. B. Volodarskii and A. Y. Tikhonov, Izu. Akad. Nauk SSSR, Ser. Khim., 1975, 1212. E. Shefter, M. N. G. James, and H. G. Mautner, J . Pharm. Sci., 55, 643 (1966). H. L. Yale, J . Am. Chem. Soc., 75, 675 (1953). E. Shefter and H. G . Mautner, J . Am. Chem. Soc., 89, 1249 (1967). I. Ozala and U. Mikstais, Khim.-Farm. Zh., 12, No. 9, 85 (1978). C. F. Koelsch and W. H. Gumprecht, J . Org. Chem., 23, 1603 (1958). H. Shindo, Chem. Pharm. Bull., 8, 33 (1960) M. F. Mallette, E. C. Taylor, and C. K. Cain, J . Am. Chem. Sue., 69, 1814 (1947). K. Tdnaka, E. Omura, T. Sugawa, Y. Sanno, Y. Ando, K.-I. Imai, and M. Kawashima, Chem. Pharm. Bull., 7, 1 (1959). 3636. H. Pasedach and M. Seefelder, US Pat. 2,778,821 (1957); Chem. Abstr., 51 9715 (1957). 3637. H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 90. 3638. A. F. Lewis, A. G . Beaman, and R. K. Robins, Can. J . Chem., 41, 1807 (1963).

3621. 3622. 3623. 3624. 3625. 3626. 3627. 3628. 3629. 3630. 3631. 3632. 3633. 3634. 3635.

3639. E. L. Bennett, J . Am. Chem. Soc., 74, 2420 (1952). 3640. H. Kondo and M. Yanai, Yakugaku Zasshi, 57, 747; Supplement, p. 173 (1937); Chem. Zentr., 1938, 11, 585. 3641. J. B. Dickey and A. R. Gray, Org. Synth., Collect. Vol., 2, 60 (1943). 3642. F. Cacaca and G. Montefinale, Ric. Sci., 28, 1419 (1958); Chem. Ahstr., 53, 6240 (1959). 3643. K. Shimo and S. Wakamatsu, Kogyo Kagaku Zasshi, 60, 1141 (1957). 3644. F. Korte and G. Ludwig, Liebiys Ann. Chem., 615, 94 (1958). 3645. J. Dick and C. Drugarin, Acad. Repuh. Pop. Rorn., Baza Cercet. Stiint., Timisoara, Stud. Cercet., Stiinte Chim., 8, 225 (1961); Chem. Ahstr., 58, 3431 (1963). 3646. L. B. Dashkevich and V. M. Siraya, Zh. Obshch. Khim., 32, 2330 (1962). 3647. K. Shimo, T. Kawasaki, and S. Wakamatsu, K o g y o Kagaku Zasshi, 65, 1370 (1962). 3648. I. K. Fel’dman and L. V. Shepshelevich, Mechenye Biol. Akt. Veshchestua, Sb. Statii, 1962, 85; Chem. Ahstr., 59, 7525 (1963). 3649. V. M. Vvedenskii and N. M. Turkevich, Dopou. Akad. Nauk Ukr. R S R , Ser. B, 32, 60 (1970); Chem. Ahstr., 72, 132658 (1970). 3650. D. J. Brown, Nature, 165, 1010 (1950). 3651. G. Maemoto, Jap. Pat. 7,030 (1951); Chem. Abstr., 48, 744 (1954). 3652. H. G. Mautner and E. M. Clayton, J . Am. Chem. Soc., 81, 6270 (1959). 3653. G. Ciamician and P. Magnaghi, Ber. Dtsch. Chem. Ges., 18, 3444 (1885); Gazz. Chim. Ital., 16, 173 (1886). 3654. J . Benz, US Pat. 3,075,980 (1963); Chem. Ahstr., 59, 1660 (1963). 3655. R. Braden, K. Findeisen, and H. Holtschrnidt, Angew. Chem., 82, 79 (1970). 3656. H. Schroeder, J . Am. Chem. Soc., 82,4115 (1960). 3657. R. D. Chambers, J. A. H. MacBride, and W. K. R. Musgrave, Chem. Ind. (London), 1966,1721. 3658. R. D. Chambers and C. R. Sargent, J . Chem. Soc., Chem. Commun., 1979, 446.

References

1277

3659. A,-M. Lamazouere and J. Sotiropoulos, Tetrahedron, 37, 2451 (1981). 3660. E. Picquenard and P. Dizabo, C a n . J . Chem., 59, 1270 (1981). 3661. 3662. 3663. 3664. 3665. 3666. 3667. 3668. 3669. 3670. 3671. 3672. 3673. 3674. 3675. 3676. 3677. 3678. 3679. 3680. 3681. 3682. 3683. 3684. 3685. 3686. 3687. 3688.

Wellcome Foundation, Br. Pat. 681,712 (1952); Chem. Abstr., 48, 1445 (1954). G. F. d’Alelio and J. W. Underwood, US Pat. 2,295,563 (1942); Chem. Ahstr., 37, 1130 (1943). Boehringer, Ger. Pat. 141,974 (1903); F r d l . , 7, 668 (1902-1904). A. Michael, J . Prakt. Chem. 121, 35,449 (1887). A. W. Dox and G. P. Plaisance, J . Am. Chem. Soc., 38, 2156 (1916). J. B. Ziegler, A. C. Shabica, and M. Sonenberg, J . O r g . Chem., 23, 1546 (1958). Y. P. Shvachkin, I. K. Shprunka, and G. V. Kazakova, Zh. Ohshch. Khim., 34, 3846 (1964). B. H. Clampitt and A. P. Mueller, J . Polymer Sci., 62, 15 (1962). W. V. Curran and R. B. Angier, J . Am. Chem. Soc., 80, 6095 (1958). J. J. McCormack and H. G. Mautner, J . Org. Chem., 29, 3370 (1964). E. P. Studentsov and V. G. Nemets, Khim. GeterotsikL Soedin., 1968, 732. V. M. Berezovskii and Y . P. Sobolev, Zh. Obshch. Khim., 28, 261 (1958). F. R. Benson, L. W. Hartzel, and W. L. Savell, J . Am. Chem. Soc., 72, 1816 (1950). Merck, Br. Pat. 648,904 (1951); Chem. Ahstr., 45, 8563 (1951). M. Yamashita, Koyyo Kayaku Zasshi, 55, 406 (1952); Chem. Ahstr., 48, 10027 (1954). F. Korte and H. Barkemeyer, Chem. Ber., 90, 392 (1957). F. Korte and H. Barkemeyer, Chem. Ber., 89, 2400 (1956). N. Roy and N. Kundu, Nature, 188, 581 (1960). D. Kazimierczak and P. Kazimierczak, Pol. Pat. 49,065 (1965); Chem. Abstr., 63, 1811 I (1965). G. B. Barlin and W. Pfleiderer, Chem. Ber., 104, 3069 (1971). W. L. F. Armarego, P. Waring, and B. Paal, Aust. J . Chem., 35, 785 (1982). W. Hentrich and E. Schirm, US Pat. 2,394,306 (1946); Chem. Ahstr., 40, 2328 (1946). H. F. Andrew and V. D. Poole, US Pat. 3,097,910 (1963); Chem. Ahstr., 62, 1768 (1965). Y. I. Bogodist, Russ. Pat. 178,383 (1966); Chem. Ahstr., 65, 2278 (1966). H. Ackermann and P. Dussy, Nelc. Chim. Acta, 45, 1683 (1962). F. E. King, T. J. King, and P. C. Spensley, J . Chem. Soc., 1947, 1247. M. M . Robinson, J . Am. Chem. Soc., 80, 5481 (1958). T. J. Delia, T. M. Wilcox, and R. R. Otteman, J . Heterocycl. Chem., 16, 1647 (1979).

3689. E. Hrehorowicz, Pol. Pat. 48,293 (1964); Chem. Abstr., 62, 7775 (1965). 3690. M. M. Boudakian, E. H. Kober, and E. R. Shipkowski, US Pat. 3,280,124(1966); Chem. Ahstr., 66, 2582 (1967). 3691. V. M. Cherkasov, G . Y . Remennikov, and A. A. Kisilenko, Khim. Geterotsikl. Soedin., 1982, 691. 3692. H. Bretschneider and W. Richter, Swiss Pat. 391,714 (1965); Chem. Ahstr., 66, 37940 (1967). 3693. B. A. Feit and A. Teuerstein, J . Heterocycl. Chem., 10, 47 (1973). 3694. P. Oxley and W. F. Short, J . Chem. Soc., 1948, 1514. 3695. V. S. Reznik and N. G. Pashkurov, Khim. Geterotsikl. Soedin., 1969, 129. 3696. R. Urban, L. H. Chopard-dit-Jean, and 0. Shcnider, Gazz. Chim. Ital., 93, 163 (1963). 3697. S. C. Bell and W. T. Caldwell, J . Org. Chem., 26, 3534 (1961). 3698. A. Pompon, E. Picquenard, C. Coupry, and P. Dizabo, J . Chim. Phys., 76, 351 (1979). 3699. H. Steudel, Hoppe-Seyler’s 2. Physiol. Chem., 30, 539 (1900). 3700. R. Behrend, F. C. Meyer, and Y. Buchholz, Liehigs Ann. Chem., 314, 200 (1901). 3701. R. Behrend, Liehrgs A n n . Chem., 253, 65 (1889).

1278

References

R. Behrend and F. C. Meyer, Ber. Dtsch. Chem. Ges., 33, 621 (1900). V. D. Davydov, f c z . Akad. Nauk SSSR, Ser. Khim., 1963, 571. J. Sotiropoulos and A.-M. Lamazoutre, C. R. Acad. Sci., Ser. C, 271, 1592 (1970). A. Katoh, C. Kashima, and Y. Omote, Heterocycles, 19, 2283 (1982). A. C. Cope, D. Heyl, D. Peck, C. Eide, and A. Arroyo, J . Am. Chem. Soc., 63, 356 (1941). G. Gastaldi and Q. Talu, Gazz. Chim. ftal., 58, 664 (1928). R. Gompper, Chem. Ber., 93, 198 (1960). A. Asai, Yakugaku Zasshi, 83, 471 (1963). K. Bremer, Liebiys Ann. Chem., 378, 188 (1911). R. Behrend and H. Hennicke, Liebigs Ann. Chem., 344, 19 (1906). M. Ridi and G. Feroci, Gazz. Chim. ftal., 78, 932 (1948). A. Baeyer, Liebigs Ann. Chem., 135, 312 (1865). M. Nencki, Ber. Dtsch. Chem. Ges., 5, 886 (1872). T. Curtius, Ber. Dtsch. Chem. Ges., 56, 1577 (1923). Osterreichische Stickstoffwerke, Austrian Pat. 174,377 (1953); Chem. Abstr., 47, 12422 (1953). A Baeyer, Liebigs Ann. Chem., 127, 1 (1863). E. Grimaux, Bull. Soc. Chim. Paris [2], 31, 535 (1879); J . Chem. Sac., Abstr., 36, 784 (1879). A. S. Jones, G. P. Stephenson, and R. T. Walker, Nucleic Acid Res., 1, 105 (1974). S. Y. Skachilova, Z. I. Shramova, V. G. Voronin, N. P. Petrugova, G. A. Ermakova, E. I. Oblapenko, and A. I. Ermakov, Khim.-Farm. Zh., 21, 1372 (1987); Chem. Ahstr., 109, 22940 ( 1 988). 372 1. N. A. Frolova. Z. A. Yugai, K. M. Makhkamov, and E. A. Sapozhnikova, Khim.-Farm. Zh., 22, 67 (1988); Chem. Abstr., 109, 73392 (1988).

3702. 3703. 3704. 3705. 3706. 3707. 3708. 3709. 3710. 3711. 3712. 3713. 3714. 371 5. 3716. 3717. 3718. 3719. 3720.

3722. L. Dong, S. Liu, L. Zhang, and X. Wang, Gaodeny Xuexiao Huaxue Xuebao, 8, 885 (1987); Chem. Ahstr., 109, 92924 (1988). 3723. A. Alberola, C. Andres, A. Gonzilez-Orgtega, R. Pedrosa, and M . Vicente, Synth. Commun., 17, 1309 (1987). 3724. V. K. Ahluwalia, R. Chandra, R. Aggarwal, and S. B. Singh, Synth. Commun., 17, 1435 (1987). 3725. M. Debi, J . Indian Chem. Soc., 64, 612 (1987). 3726. G. Stajer, A. E. Szabb, G. Bernath, and P. Sohir, Magy. Kem. Foly., 93, 28 (1987). 3727. R. M. Moriarty, 1. Prakash, D. E. Clarisse, R. Penmasta, and A. K. Awasthi, J . Chem. Soc., Chem. Commun., 1987, 1209 3728. T. Nishio, M. Fujisawa, and Y. Omote, J . Chem. Soc., Perkin Trans. I , 1987, 2523. 3729. T. Benneche, P. Strande, and K. Undheim, Acta Chem. Scand., Ser. B, 41, 448 (1987). 3730. N. G. Kundu, B. Das, A. Majumdar, and L. N. Choudhuri, Tetrahedron Lett., 28,5543 (1987). 3731. T. Ueda, H. Yoshida, and J. Sakakibara, Tetrahedron Lett., 28, 4579 (1987). 3732. K. Tanaka, X. Chen, and F. Yoneda, Tetrahedron, 44, 3241 (1988). 3733. K. Tanaka, X. Chen, T. Kimura, and F. Yoneda, Chem. Pharm. Bull., 36, 60 (1988). 3734. D. B. Harden, M. J. Mokrosz, and L. Strekowski, J . Org. Chem., 53, 4137 (1988). 3735. S. M. Hussain, A. M. El-Reedy, and S. A. El-Sharabasy, Tetrahedron, 44, 241 (1981). 3736. K. A. Krasnov, V. 1. Slesareva, E. P. Studentsov, and V. I. Slesarev, Zh. Org. Khim., 23, 1995 ( 1 987). 3737. M. Z. Girshovich, K. L. Muravich-Aleksandr, and T. N. Ragozina, Zh. Org. Khim., 23, 2454 (1987). 3738. G. W. M. Visser, R. E. Herder, F. J. J. de Kanter, J. D. M . Herscheid, J . Chem. Soc., Perkin Trans. f , 1988, 1203.

References 3739. 3740. 3741. 3742. 3743. 3744. 3745. 3746. 3747. 3748. 3749. 3750. 3751. 3752. 3753. 3754. 3755. 3756. 3757. 3758. 3759. 3760. 3761. 3762. 3763. 3764. 3765. 3766. 3767. 3768. 3769. 3770. 3771. 3772. 3773.

1279

D. Prajapati, P. Bhuyan, and J. S. Sandhu, J . Chem. Soc., Perkin Trans. I , 1988, 607. W. Dmowski and A. Hass, J . Chem. Soc., Perkin Trans. I, 1988, 1179. T. Benneche and K. Undheim, Acta Chem. Scand., Ser. B, 37, 235 (1983). 0. Kasende, G. S. D. King, and T. Zeegers-Huyskens, Bull. Soc. Chim. Belg., 97, 33 (1988). H. Yamanaka, T. Sakamoto, S. Nishimura, and M. Sagi, Chem. Pharm. Bull., 35, 31 19 (1987). T. Harayama, R. Yanada, T. Akiyama, M. Tanaka, and F. Yoneda, Biochem. Biophys. Kes. Commun., 148, 995 (1987). T. Harayama, R. Yanada, T. Akiyama, M. Tanaka, Y. Fujita, and F. Yoneda, Nucleic Acid Kes., 19, 107 (1988). R. Spitzner, M. Lesinski, M. Richter, and W. Schroth, Monatsh. Chem., 118, 485 (1987). A. M. Shestopalov, Y. A. Sharanin, V. P. Litvinov, V. Y. Mortikov, and V. N. Nesterov, Zh. Ohshch. Khim., 57, 959 (1987). H.-J. Niclas, F. Zcuner, E. Grundemann, and L. Zdch, J . Prakt. Chem., 329, 400 (1987). M. Gelbin and D. Martin, J . Prakt. Chem., 329, 753 (1987). P. I. Vainilavicius and V. Y. Sedereviciute, Khim. Geterotsikl. Soedin., 1987, 1655. P. I. Vainilavicius and V. Y. Sedereviciute, Khim. Geterotsikl. Soedin., 1987, 1520. Y. A. Sharanin, A. M. Shestopalov, V. N. Nesterov, V. P. Litvinov, V. Y. Mortikov, V. K. Promoncnkov, B. E. Shklover, and Y. T. Struchkov, Khim. Geterotsikl. Soedin., 1987, 1377. V. V. Kuz’menko, T. A. Kuz’menko, G. G. Aleksandrov, A. F. Pozharskii, and A. V. Gulevskaya, Khim. Geterotsikl. Soedin., 1987, 836. V. V. Lapachev, W. Stadlbauer, and T. Kappe, Monatsh. Chem., 119, 97 (1988). G. Y. Remennikov, L. K. Kurilenko, 1. V. Boldyrev, and V. M. Cherkasov, Khim. CeterotsikL Soedin., 1987, 1659. K. A. Krasnov, V. I. Slesarev, A. P. Zakharov, and E. G. Grigor’eva, Khim. Geterotsikl. Soedin., 1987, 1523. T. Harayama, K. Kotoji, F. Yoneda, T. Taga, K. Osaki, and T. Nagamatsu, Chem. Pharm. Bull., 32, 2056 (1984). S. B. Gashev, B. A. Korolev, L. A. Osmolovskaya, and L. D. Smirnov, Khim. Geterotsikl. Soedin., 1983, 1262. R. S. Baltrushis, Z.-I. G. Bercsnevichyus, I. M. Viagaitis, and Y. V. Gatilov, Khim. Geterotsikl. Soedin., 1983, 1267. W. E. White and M . D. Dollinger, Biochem. Pharmacol., 28, 1467 (1979). K. Hashizume, C. Toda, T. Yasui, and H. Nagano, Vitamins, 61, 611 (1987). H. Yamanaka, H. Abe, T. Sakamoto, H. Hiranuma, and A. Kamata, Chem. Pharm. Bull., 25, 1821 (1977). W. Ried and G. Beller, Liebigs Ann. Chem., 1988, 633. W. Ried and G. Beller, Liebigs Ann. Chem., 1988, 643. M. Gacek, 0. Thorstad, L. Ongstad, and K. Undheim, Chem. Scr., 13, 99 (1978-1979). G. M. Coppola, G. E. Hardtmann, and B. S. Huegi, J . Heterocycl. Chem., 11, 51 (1974). M. Dzurilla, P. Kutschy, and D. KoSEik, Collect. Czech. Chem. Commun., 52, 2260 (1987). H. Yamanaka, S. Niitsuma, M. Sakai, and T. Sakamoto, Chem. Pharm. Bull., 36, 168 (1988). H. Marley, K. J. McCullough, P. N. Preston, and S. H. B. Wright, J . Chem. Sou., Perkin Trans. I, 1988, 351. D. Prajapati and J. G. Sandhu, Synthesis, 1988, 342. T. Sakamoto, S. Nishamura, Y. Kondo, and H. Yamanaka, Synthesis, 1988,485. G. Keilen, T. Benneche, and K. Undheim, Acta Chem. Srand., Ser. B, 41, 577 (1987). H. Morrison, C. Izuno, S. Byrn, and A. McKenzie, Photochem. Photobiol., 34, 107 (1981).

1280

References

3774. R. H. Wiley, J . Polymer Sci., Polymer Chem., 25, 735 (1987). 3775. I. Z. Lulle, R. A. Paegle, I. B. Mazheika, and M. Y. Lidak, Khim. Geterotsikl. Soedin., 1983, 535. 3776. V. K. Ahluwalia, L. Nayal, and S. Bala, Zndian J . Chem., Sect. B., 27, 193 (1988); Chem. Ahstr., 109, 149462 (1988). 3777. A. Albert, R. Goldacre, and J. N. Phillips, J . Chem. Soc., 1948, 2240. 3778. N. V. Khromov-Borisov, Dokl. Akad. Nauk SSR, 180, 1129 (1968). 3779. B. Roth and J. Z . Strelitz, J. Org. Chem., 35, 2696 (1970). 3780. E. Hirai, Chem. Pharm. Bull., 14, 861 (1966). 3781. W. Pfleiderer, E. Biihler, and D. Schmidt, Chem. Ber., 101, 3794 (1968). 3782. P. Brookes and P. D. Lawley, J . Chem. Soc., 1962, 1348. 3783. T. Okano and S. Kojima, Yukugaku Zasshi, 86, 547 (1966). 3784. J. C. Gaga, J. Chem. Soc., 1949, 469. 3785. W. Pfleiderer and R. Mengel, Chem. Ber., 104, 2293 (1971). 3786. P. A. Levene, L. W. Bass, and H. S. Simms, J . Biol. Chem., 70, 229 (1926). 3787. J. J. Christensen, J. H. Rytting, and R. M. Izatt, J . Phys. Chem., 71, 2700 (1967). 3788. C. W. Whitehead and J. J. Traverso, J . Am. Chem. Soc., 82, 3971 (1960). 3789. A. Albert, personal communication. 3790. D. D. Perrin and 1. H. Pitman, J . Chem. Soc., 1965, 7071. 3791. S. F. Mason, J . Chem. Soc., 1959, 1247. 3792. E. R. Tucci, F. Takahashi, V. A. Tucci, and N. C. Li, J . Znorg. Nucl. Chem., 26, 1263 (1964). 3793. A. Albert, D. J. Brown, and G. W. H. Cheeseman, J . Chem. Soc., 1952, 1620. 3794. Y. Hirata, I. Teshima, and T. Goto, Nugoya Sangyo K a p k u Kenkyusho Kenkyu Hokoku, No. 9, p. 80 (1956); Chem. Abstr., 51, 8516 (1957). 3795. J. S. Morely and J. C. E. Simpson, J . Chem. Soc., 1949, 1014. 3796. A. Pohland, E. H. Flynn, R. G . Jones, and W. Shive, J . Am. Chem. Soc., 73, 3247 (1951). 3797. G. B. Barlin and W. Pfleiderer, Chem. Ber., 102, 4032 (1969). 3798. E. Chinoporos, N. Papathanasopoulos, and S. C. L. Fu, Chem. Chron., A, 32, No. 4, p. 35 (1967); Chem. Abstr., 68, 73591 (1968). 3799. D. D. Perrin and I. H. Pitman, Aust. J. Chem., 18, 471 (1965). 3800. S. F. Mason, J . Chem. Soc., 1958, 674. 3801. A. Albert and J. N. Phillips, J . Chem. Soc., 1956, 1294. 3802. K. Nakanishi, N. Suzuki, and F. Yamazaki, Bull. Chem. Soc. Jpn., 34, 53 (1961). 3803. Y. Sato, Nippon Kugaku Zusshi, 78, 921 (1957); Chem. Ahstr., 54, 4598 (1960). 3804. S. B. Greenbaum, J . Am. Chem. Soc., 77, 3221 (1955). 3805. D. J. Brown, unpublished data. 3806. B. A. Ivin, R. K. Glushkov, and E. G. Sochilin, Zh. Obshch. Khim., 40, 202 (1970). 3807. H. Gottschling and C. Heidelberger, J . Mol. Biol., 7, 541 (1963). 3808. S. B. Gashev, M. M. Borunov, and L. D. Smirnov, Zzc. Akad. Nuuk SSSR, Ser. Khim., 1981, 2102. 3809. H. N. Christensen, J . Biol. Chem., 160, 425 (1945). 3810. M. E. Taylor and R. J. Robinson, Talanta, 8, 518 (1961). 3811. G. M. Richardson and R. K. Cannan, Biochem. J . , 23, 68 (1929). 3812. P. J. Brignell, C. D. Johnson, A. R. Katritzky, N. Skakir, H. 0. Tarhan, and G. Walker, J . Chem. Soc. (B), 1967, 1233. 3813. A. Albert, W. L. F. Armarego, and E. Spinner, J . Chem. Soc., 1961, 2689.

References

1281

3814. E. 1. Stankevich, Y. Y. Popelis, E. E. Grinshtein, A. Y. Ozola, and G. Y. Dubur, Khim. Geterotsikl Soedin., 1970, 122. 3815. M. M. Yousif, A. A. Fadda, S. S. Elmorsey, and H. M. Hassan, Indian J . Chem. Sect. B, 26,994, (1987). 3816. T. Sakamoto, S. Nishimura, Y. Kondo, and H. Yamanaka, Heterocycles, 27, 475 (1988). 3817. M. Botta, F. de Angelis, R. Nicoletti, A. Pani, M. E. Marongiu, and P. La Colla, Tetrahedron Lett., 29, 2741 (1988). 3818. J. L. LaMattina, C. J. Mularski, and D. E. Muse, Tetrahedron, 44 3073 (1988). 3819. J. Barluenga, F. J. Gonzalez, V. Gotor, and S. Fustero, J . Chem. Soc., Perkin Trans. I , 1988, 1739. 3820. T. Benneche and K. Undheim, Chem. Scr., 20, 11 (1982). 3821. M. R. H. Elmoghayar, P. Groth, and K. Undheim, Acta Chem. Scand., Ser. B , 37, 109 (1983). 3822. M. R. H. Elmoghayar and K. Undheim, Acta Chem. Scand., Ser. B, 37, 160 (1983). 3823. T. Ishihara, Y. Okada, M. Kuroboshi, T. Shinozaki, and T. Ando, Chem. Lett., 1988, 819. 3824. B. Szaniawska, R. Bjerkvig, 0. D. Laerum, and K. Undheim, Anticuncer R e x , 6, 71 (1986). 3825. M. E. Holm-Nygaard, J. M. Dornish, R. Oftebro, and K. Undheim, Invest. New Drugs, 4,221 (1986). 3826. J. Solberg and K. Undheim, Acta Chem. Scand., Ser. B, 41, 712 (1987). 3827. G. Keilen and K. Undheim, Acta Chem. Scand., Ser. B, 42, 362 (1988). 3828. F. Rise, D. Grace, and K. Undheim, .I. Orgunomet. Chem., 338, 341 (1988). 3829. J. Sandosham, T. Benneche, B. S. Mdler, and K. Undheim, Acta Chem. Scand., Ser. B, 42,455 (19881, 3830. T. Benneche, L.-L. Gundersen, and K. Undheim, Acta Chem. Scand., Ser. B , 42, 384 (1988). 3831. J. Solberg and K. Undheim, Acta Chem. Scund., Ser. B, 43, 62 (1989). 3832. J. Arukwe, G. Keilen, and K. Undheim, Acta Chem. Scand., Ser. B, 42, 530 (1988). 3833. J. Arukwe, T. Benneche, and K. Undheim, .I. Chem. Sue., Perkin Trans. I , 1989, 255. 3834. A. H. H. Elghandour, M. M. M. Ramiz, S. A. S. Ghozlan, and M. R. H. Elmoghayar, Liehigs Ann. Chem., 1988, 983. 3835. M. Noguchi, K. Sakamoto, S. Nagata, and S. Kajigaeshi, J . Ifeterocycl. Chem., 25,205 (1988). 3836. H. Cho, A. Mizuno, K. Shima, M. Ueda, Y. Takeuchi, M. Hamaguchi, and N. Taniguchi, Heterocycles, 27, 769 (1988). 3837. T. H. Brown, R. C. Blakemore, G. J. Durant, J. C. Emmett, C. R. Ganellin, M. E. Parsons, D. A. Rawlings, and T. F. Walker, Eur. J . M e d . Chem., 23, 53 (1988). 3838. D. Briel, J. Sieler, G. Wagner, and W. Schade, Phosphorus Sulfiir, 35, 55 (1988). 3839. S. D. Pastor, H. K. Naraine, and R. Sundar, Phosphorus Suyur, 36, 11 1 (1988). 3840. D. L. Boger and Q. Dang, Tetrahedron, 44,3379 (1988). 3841. K. U. Sadek, M. A. El-Maghraby, M. A. Selim, and M. H. Elnagdi, Bull. Chem. Soc. Jpn., 61, 539 (1988). 3842. T. Nishio and Y. Omote, J . Chem. Soc., Perkin Trans. I , 1988, 957. 3843. J. Barluenga, B. Olano, S. Fustero, M.-C. Foees-Foces, and F. Hernandez-Cano, J . Chem. Soc., Chem. Cornmun., 1988, 410. 3844. J.-W. Chern, H.-Y. Lee, D. S. Wise, and L. B. Townsend, J . Org. Chem., 53, 5617 (1988). 3845. J.-W. Chern, D. S. Wise, W. Butler, and L. B. Townsend, J . Org. Chem., 53, 5622 (1988). 3846. S. Robev, Dokl. Bolg. Akad. Nauk, 40, 75 (1987). 3847. M. A. Mikhaleva, G. A. Kolesnichenko, and V. P. Mamaev, Izu. Sib. Otd. Akad. Nauk S S S R , Ser. Khim. Nauk, 1988, 109; Chem Abstr., 110, 8152 (1989). 3848. N. S. Ibrahim, M. H. Mohamed, and M. H. Elnagdi, Chem. Ind. (London),1988, 270.

1282

References

3849. S . Furuya, K. Omura, and Y. Furukawa, Chem. Pharm. Bull., 36, 1669 (1988). 3850. T. Nagdse, K. Seike, K. Shiraishi, Y. Yamada, and S. Ozaki, Chem. Lett., 1988, 1381. 3851. J. M. Dornish, K. Undheim, 0. E. Pettersen, R. Oftebro, and S . G . Laland, Anti-Cancer Drug Design, 3, 191 (1988). 3852. A. W. Thool and B. J. Ghiya, J . Indian Chem. Soc., 65, 522 (1988). 3853. F. Yoneda and M. Koga, J . Chem. Soc., Perkin Trans. 1, 1988, 1809. 3854. F. Yoneda, M. Koga, and Y . Yano, J . Chem. Soc., Perkin Trans. I, 1988, 1813. 3855. F. Yoneda and M. Koga, J . ffeterocycl. Chem., 25, 549 (1988). 3856. L. V. Ershov, N. Z. Tugusheva, and V. G. Granik, Khim. GeterotsikL Soedin., 1988, 88. 3857. M. H. Paluchowska and J. Bojarski, Arch. Pharm, (Weinheim. Ger.), 321, 343 (1988). 3858. S. K. Mitrd, B. Sanyal, S. N. Ganguly, and B. Mukherjee, J . Chem. Soc., Chem. Commun., 1989, 16. 3859. J. Davoll, J . Chem. Soc., 1960, 131. 3860. D. T. Hurst, C. Beaumont, D. T. E. Jones, D. A. Kingsley, J. D. Partridge, and T. J. Rutherford, Aust. J . Chem., 41, 1209 (1988). 3861. D. T. Hurst, A. D. Stacey, M. Nethercleft, A. Rahim, and M. R. Harnden, Aust. J . Chem., 41, 1221 (1988). 3862. H . Beyer and H. Hantschel, Chem. Ber., 95, 902 (1962). 3863. B. Koren, B. Stanovnik, and M. Tibler, J . Heterocycl. Chem., 14, 621 (1977). 3864. W. B. Cowden and N. W. Jacobsen, Aust. J . Chem., 37, 1195 (1984). 3865. A. Takamizawa and K. Tokuyama, Yakuyaku Zasshi, 79, 674 (1959). 3866. N. R. El-Rayyes, J . Heterocycl. Chem., 19, 415 (1982). 3867. K. A. Gupta, A. K. Saxena, P. C. Jain, R. C. Srimal, K. Kar, and N. Anand, Indian J . Chem., Sect. B, 22, 384 (1983). 3868. K. A. Gupta, A. K. Saxena, P. C. Jain, P. R. Dua, C. R. Prdsad, and N. Anand, Indian J . Chem., Sect. B, 22, 789 (1983). 3869. D. Sen, S. R. Bhowmik, and P. Sengupta, Indian J . Chem., 22, 388 (1983). 3870. M. Bartke and W. Pfleiderer, Pteridines, 1, 45 (1989). 3871. M. Bartke and W. Pfleiderer, Pteridines, 1 , 57 (1989). 3872. 3873. 3874. 3875.

W. Hiibsch and W. Pfleiderer, Meh. Chim. Acta, 71, 1379 (1988). J. Krechl, M. A. PCrez, F. J. Cuadrado, and J. L. Soto, Synthesis, 1988, 122. K. Kaneko, H. Katayama, T. Wakabayashi, and T. Kumonaka, Synthesis, 1988, 152.

S. M. Hussain, A. M. El-Reedy, A. M. H. Rezk, and K. A. S. El-Dien, J . Heterocycl. Chem., 24, 1605 (1987). 3876. J. Wolinski and T. Kujawa, Acta Pol. Pharm., 44, 143 (1987). 3877. W. Zhao, B. Yan, and R. Li, Yaoxue Xuehao, 22,541 (1987); Chem. Ahstr., 110, 114777 (1989). 3878. V. K. Karp, V. A. Portnyagina, V. V. Klyushin, A. V. Turov, and V. A. Kovtunenko, Ukr. Khim. Zh. (Russ. Ed.), 54, 535 (1988); Chem. Ahstr., 110, 95147 (1989). 3879. V. N. Nesterov, Y. A. Sharanin, A. M. Shestopalov, V. E. Shklover, and Y. T. Struchkov, Zh. Ory. Khim., 24, 845 (1988). 3880. P. Bayard, F. Sainte, R. Beaudegnies, and L. Ghosez, Tetrahedron Lett., 29, 3799 (1988). 3881. T. Takahashi, S.-I. Hirokami, M. Nagata, and T. Yamazaki, J. Chem. Sue., Perkin Trans. I, 1988, 2653. 3882. S. Kohra, Y. Tominaga, and A. Hosomi, J . Heterocycl. Chem., 25, 959 (1988). 3883. I. N. D. Dass and S. Dutt, Proc. Indian Acad. Sci., Sect. A , 8, 145 (1938); Chem. Ahstr., 33, 620 (1939).

References

1283

3884. G. G. Danagulyan, N. G. Balasanyan, and M. G. Zalinyan, Khim. Geterotsikl. Soedin., 1988, 563. 3885. M. Bodenteich, E. Chemelli, and H. Griengl, Monatsh. Chem., 118, 1395 (1987). 3886. Remennikov, V. M. Cherkasov, and V. V. Pirozhenko, Khim. Geterotsikl. Soedin., 1988, 562. 3887. Z. V. Belodedova, N. A. Smorygo, V. S. Mirzoyan, R. G. Melik-Orandzhanyan, E. P. Studentsov, and B. A. Ivin, Khim. Geterotsikl. Soedin., 1988, 659. 3888. V. Kvita, H. Sauter, and B. Tuck, Helu. Chim. Acta, 71, 1467 (1988). 3889. G. J. S. Doad, D. 1. Okor, F. Scheinmann, P. A. Bates, and M. B. Hursthouse, J . Chem. Soc., Perkin Trans. I, 1988, 2993. 3890. R. G. Pews, Heterocycles, 27, 1867 (1988). 3891. J. Okada, S. Morita, Y. Miwa, and S. Nakamura, Yakugaku Zasshi, 98, 1518 (1978). 3892. J. Liebscher and A. Hassoun, Synthesis, 1988, 816. 3893. A. Wada, H. Yasuda, and S. Kanatomo, Synthesis, 1988, 771. 3894. S. Kanatomo, A. Wada, M. Yomei, T. Hase, S. Nagai, S. Fukuda, M. Tanaka, and T. Sasaki, Chem. Pharm. Bull., 36, 2042 (1988). 3895. T. Kinoshita, N. Nakahata, A. Kouchi, and S. Furukawa, Chem. Pharm. Bull., 36,3887 (1988). 3896. A. Garcia-Matinez, A. Herrera, R. Martinez, E. Teso, A. Garcia, J. Osio, L. Pargdda, R. Unanue, L. R. Subramanian, and M. Hanack, J . Heterocycl. Chem., 25, 1237 (1988). 3897. T. J. Delia, B: Polenz, and M. C. Martin, J . Heterocycl. Chem., 25, 1697 (1988). 3898. S. Kumar and S. S. Chimni, Heterocycles, 27, 2523 (1988). 3899. J. Kalinowska-Torz, D. Skwarski, and M. Szymczak, Acta Pol. Pharm., 44,415 (1987); Chem. Abstr., 110, 231559 (1989). 3900. V. P. Borovik, V. A. Semikolenov, and V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk S S S K , Ser. Khim. Nauk, 1988, 9 4 Chem Abstr., 110, 212742 (1989). 3901. N. G. Pashkurov and V. S. Reznik, I z v . Akad. Nauk SSSR, Ser. Khim., 1972,422. 3902. T. Kinoshita, H. Tanaka, and S. Furukawa, Chem. Pharm. Bull., 34, 1809 (1986). 3903. P. C. Pradhan, B. K. Mishra, and G. B. Behera, Indian J . Chem., Sect. B, 27, 902 (1988). 3904. P. Pecorari, G. Vampa, A. Albasini, M. Rinaldi, M. Melegari, and M. P. Costi, Farmaco, Ed. Sci., 43, 3 11 (1988). 3905. A. Haas, M. Lieb, and B. Schwederski, Rev. Roum. Chem., 32, 1219 (1987). 3906. 1. Kulakowska, M. Geller, B. Lesyng, and K. L. Wierzchowski, Biochem. Biophys. Acta, 361, 119 (1974). 3907. D. Janietz, B. Goldmann, and W.-D. Rudorf, J . Prakt. Chem., 330, 607 (1988). 3908. R. Pucher and H. Griengl, Monutsh. Chem., 119, 953 (1988). 3909. E. Epifani, S. Florio, and G. Ingrosso, Tetrahedron, 44,5869 (1988). 3910. V. F. Sedova, G. G. Moskalenko, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1988, 654. 391 1. S. P. Tumkyavichyus and Y. P. Karmalavichyute, Khim.Geterotsikl. Soedin., 1988, 560. 3912. E. N. Dozorova, N. P. Solov’eva, and V. G. Granik, Khim. Geterotsikl. Soedin., 1988, 1109. 3913. K. G. Ghoneim, F. A. El-Telbany, M. El-Enany, and K. Youssef, Egypt. J . Pharm. Sci., 29,169 (1988); Chem. Abstr., 111, 23469 (1989). 3914. D. Sidzhakova, D. Danchev, and M. Vulcheva, Farmatsiya (Sofia),38, 5 (1988); Chem. Abstr., 111, 57668 (1989). 3915. A. Tantawy and A. Kreutzberger, Alexandria J . Pharm. Sci., 2,130 (1988); Chem. Abstr., 111, 77956 (1989). 3916. M . L. Falck-Pedersen, T. Benneche, and K. Undheim, Acta Chem. Scand., 43, 251 (1989). 3917. Y. Akcumar, B. Altural, E. Saripinar, G. Kollenz, 0. Kappe, K. Peters, E.-M. Peters, and H:G. von Schnering, J . Heterocycl. Chem., 25, 1419 (1988).

1284

References

3818. F. Oberdorfer, E. Hofmann, and W. Maier-Borst, J . Label. Compd. Rudiopharrn., 27, 137 (1989). 3919. S. R. Landor, A. Johnson, Z. T. Fomum, and A. E. Nkengfack, J . Chem. Soc., Perkin Trans. 1, 1989, 609. 3920. R. N. Butler and K. J. Fitzgerald, J . Chem. Soc., Perkin Truns. 1, 1989, 155. 3921. Y. L. Sing and L. F. Lee, J . Heterocycl. Chem., 26, 7 (1989). 3922. C. Kashima, M. Shimizu, and Y. Omote, J . Heterocycl. Chem., 26, 251 (1989). 3923. T. Nishio, M. Kato, and C. Kashima, Liebigs Ann. Chem., 1989, 611. 3924. H. Cho, Y. Takeuchi, hl. Ueda, and A. Mizuno, Tetrahedron Lett., 29, 5405 (1988). 3925. B. S. Rauckman, M. Y. Tidwell, J. V. Johnson, and B. Roth, J . Med. Chem., 32, 1927 (1989). 3926. S. E. Davis, B. S. Rauckman, J. H. Chan, and B. Roth, J . Med. Chem., 32, 1936 (1989). 3927. J. V. Johnson, R. S. Rauckman, D. P. Baccanari, and B. Roth, J . M e d . Chem., 32, 1942 (1989). 3928. B. Roth, M. Y. Tidwell, R. Ferone, D. P. Baccanari, C. W. Sigel, D. de Angelis, and L. P. Elwell, J . Med. Chem., 32, 1949 (1989). 3929. A. J. Majeed, 0. Antonsen, T. Benncche, and K. Undheim, Tetrahedron, 45, 993 (1989). 3930. S. Matsuura. H. Traub, and W. L. F. Armarego, Pteridines, 1, 73 (1989). 3931. C.-H. Kim, V. E. Marquez, D. T. Mao, D. R. Haines, and J. J. McCormack, J . M e d . Chem., 29, 1374 (1986). 3932. M. C. R. Franssen, J. D. Jansma, H. C. van der Plas, E. de Boer, and R. Wever, Bioorg. Chem., 16, 352 (1988). 3933. C. C. Winterbourne, W. B. Cowden, and H. C. Sutton, Biochem. Pharmacol., 38, 61 I (1989). 3934. N. G. Kundu, L. N. Choudhuri, and B. Das, J . Chem. Soc., Perkin Truns. 1, 1989, 1165. 3935. T. Takahashi, S.-I. Hirokami, M. Nagata, T. Yamazaki, and T. Date, J . Chem. Soc., Perkin Trans. 1, 1989, 1231. 3936. H. Uno, T. Terakawa, and H. Suzuki, Synthexs, 1989, 381. 3937. M. Nitta, T. Hamamatsu, and H. Miyano, Bull. Chem. Soc. Jpn., 61, 4473 (1988). 3938. S. V. Borodaev, 0. V. Zubkova, and S. M . Luk’yanov, Zh. Org. Khim., 24, 2330 (1988). 3939. J. Liebscher and Y. F. Kelboro, Z . Chem., 29, 170 (1989). 3940. B. M. Khutova, S. V. Klyuchko, L. P. Prikazchikova, E. A. Romanenko, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1988, 1394. 3941. C. 0. Kappe and U. G . Wagner, Heterocycles, 29, 761 (1989). 3942. C. 0. Kappe and P. Roschger, J . Heterocycl. Chem., 26, 55 (1989); C. 0. Kappe, Tetrahedron, 49, 6937 (1993). 3943. E. Epifani, S. Florio, G. Ingrosso, and F. Babudri, Tetrahedron, 45, 2075 (1989). 3944. M . Botta, M. Artico, S. Massa, and A. Gambacorta, J . Heterocycl. Chem., 26, 883 (1989). 3945. K. S. Atwal, G. C. Rovnyak, B. C. O’Reilly, and J. Schwartz, J . Org. Chem., 54, 5898 (1989). 3946. K. Jug, J . Org. Chem., 48, 1344 (1983). 3947. L. Stefaniak, J. D. Roberts, M. Witanowski, and G. A. Webb, Org. Magn. Reson., 22, 201 (1984). 3948. H. Hara and H. C. van der Plas, J . Heterocycl. Chem., 19, 1285 (1982). 3949. C. M. Adams and W. von Philipsborn, Magn. Reson. Chem., 23, 130 (1985). 3950. M. Ehsan, Pak. J . Sci. Ind. Res., 31, 15 (1988); Chem. Abstr., 109, 211000 (1988). 3951. V. P. Lezina, M. M. Kozlova, S. B. Gashev, A. V. Stepanyants, and L. D. Smirnov, Khim. Geterotsikl. Soedin., 1986, 1 1 1 1 . 3952. R. G. Pews and W. E. Puckett, J . Fluorine Chem., 42, 179 (1989). 3953. N. Guillot, Z. Janousek, and H. G. Viehe, Heterocycles, 28, 879 (1989).

References

1285

3954. M. A. Mikhaleva, G. A. Kolesnichenko, T. A. Kizner, and V. P. Mamaev, Khim Geterotsikl. Soedin., 1988, 1636. 3955. A. M. El-Reedy, S. M. Hussain, A. S. Ali, and F. Abdel-Motty, Phosphorus, Su!fur Siltcon Relat. Elem., 42, 231 (1989); Chem. Ahstr., 112, 35791 (1990). 3956. L. F. Lee and Y. L. Sing, J . Org. Chem., 55, 380 (1990). 3957. C. J. Shishoo, M. B. Devani, K. S . Jain, V. S. Bhadti, S. M. Shishoo, U. S. Pathak, S. Ananthan, and 1. S. Rathod, Indian J . Chem., Sect. B, 28, 42 (1989). 3958. V. J. Ram. Indian J . Chem., Sect. B, 28, 159 (1989). 3959. M. Debi, J . Indian Chem. Soc., 66, 418 (1989). 3960. N. S. Ibrahim, Chern. Ind. (London), 1989, 654. 3961. H. Marley, S. H. B. Wright, and P. N. Preston, J . Chern. Soc., Perkin Trans. I , 1989, 1727. 3962. S. Sen and V. Srivastava, J . Indian Chem. Soc., 66, 166 (1989). 3963. P. L. Southwick and A. S. Waggoner, Org. Prep. Proced. Int., 21. 493 (1989). 3964. S. A. Morkhade and V. N. Ingle, J . Indian Chem. SOC.,66, 37 (1989). 3965. M. Debi, J . Indian Chem. Soc., 66, 489 (1989). 3966. M. D. Ankhiwala, J . Indiun Chem. Soc., 66, 417 (1989) 3967. E. Mittag and S. Noll, Isotopenpraxis, 25, 254 (1989); Chem. Ahstr., 112, 98484 (1990). 3968. M. A. Akhmerov, V. S. Remik, and Y. S. Shvetsov, Izv. Akud. Nnuk S S S K , Ser. Khim., 1989, 975. 3969. F. Rise and K. Undheim, Acta Chem. Scand., 43, 489 (1989). 3970. J. Sandosham and K. Undheim, Acta Chem. Scand., 43, 684 (1989). 3971. W. Micklitz, B. Lippert, H. Schdlhorn, and U. Thewalt, J . Heterocycl. Chem.,26, 1499 (1989). 3972. C. 0.Usifoh, T. A. Olugbade, G. 0.Onawumi, J. 0. Oluwadiya, and J. Reisch, J . Hr.terocyc1. Chem., 26, 1069 (1989). 3973. R. A. Osisanya and J. 0. Oluwadiya, J . Heterocycl. Chem., 26, 947 (1989). 3974. M. M. El-Kerdawy, A. A. El-Emam, H. I. El-Subbagh, and E. Abushanab, J . Hefcrocycl. Chem., 26, 9 13 (1 989). 3975. 1. Murakoshi, T. Sekine, Y. Higuchi, N. Ohyama, and T. Yamada, Chem. Pharm. Bull., 37, 1984 (1989). 3976. K. Ozeki, T. Ichikawa, H. Takehara, K. Tanimura, M. Sato. and H. Yaginuma, Chem. Pharm. Bull., 37, 1780 (1989). 3977. M. Suzuki, H. Maeda, K. Kondo, H. Sugano, and K. Matsumoto, Chem. Pharm. Bull., 37, 1764 (1 989). 3978. T. Taga, N. Yamamoto, and K. Machida, Bull. Chem. Soc. Jpn., 62, 354 (1989). 3979. K. Yonemoto, I. Shibuya, and K. Honda, Bull. Chem. Soc. Jpn., 62, 1086 (1989). 3980. M. Hasegawa, Y. Endo, M. Aoyama, and K. Saigo, Bull. Chem. Soc. Jpn., 62, 1556 (1989). 3981. R. G. Melik-Ogandzhanyan, A. S. Gapoyan, V. E. Khachatryan, and V. S. Mirzoyan, Arm. Khim. Zh., 42, 530 (1989); Chem. Ahstr., 113, 40603 (1990). 3982. M. M. Litvak, Khim.-Farm. Zh., 23, 1374 (1989); Chem. Abstr., 113, 40606 (1990). 3983. S. A. Abdel-Hady, M. A. Badawy, and Y. A. Ibrahim, Sulfur Lett., 9, 101 (1989);Chem. Abstr., 113, 40602 (1990). 3984. G. Orzeszko and S. Bitny-Szlachto, Acta Pol. Pharm., 45,306 (1988); Chem. Abstr., 113,40599 (1 990). 3985. K. M. Youssef, Egypt, J . Pharm. Sci., 30, 465 (1989); Chem. Abstr., 112, 216846 (1990). 3986. M. J. Korohoda, E. Slomska, and H. Szczurek, Pol. J . Chem., 63, 163 (1989); Chem. Ahstr., 112, 235256 (1990). 3987. R. F. Evans, G. P. Savage, and G. A. Gough, Aust. J . Chem., 43, 733 (1990).

1286

References

3988. M. R. Harnden and D. T. Hurst, Aust. J . Chem., 43, 55 (1990). 3989. V. D. Sviridov, N. D. Chkanikov, I. A. Korbukh, A. F. Kolomiets, and A. V. Fokin, Izu. Akad. Nauk SSSR, Ser. Khim., 1989, 1656. 3990. S. El-Bahaie and M. G. Assy, J . Indian Chem. Soc., 66, 463 (1989). 3991. J. M. Harrowfield. B. W. Skelton, A. A. Soudi, and A. H. White, Aust. J . Chem.,42,1795 (1989). 3992. T. Mueller, M. Augustin, and H. G. Werchan, Z.Chem., 29, 281 (1989). 3993. M. Richter, A. Vogt, M. Augustin, and K. Strauss, Z . Chem., 29, 443 (1989). 3994. R. G. Pews, Heterocycles, 31, 109 (1990). 3995. K. Hirota, Y. Kitade, H. Sajiki, Y. Maki, and M. Yoga, J . Chem. Soc., Perkin Trans. I , 1990, 367. 3996. P. Schenone, L. Sansebastiano, and L. Mosti, J . Heterocycl. Chem., 27, 295 (1990). 3997. J. Barluenga, M. Tomas, A. Ballesteros, and L. A. Lopez, Tetrahedron Lett., 30,4573 (1989). 3998. T. Itoh, Y. Tomii, T. Naitoh, M. Yamamura, I. Ishikawa, N. Kawahard, Y. Mizuno, and H. Ogura, Chem. Pharm. Bull., 37, 2197 (1989). 3999. Y. Kondo, R. Watanabe, T. Sakamoto, and H. Yamanaka, Chem. Pharm. Bull., 37, 2814 (1989). 4000. A. Pinner, Ber. Dtsch. Chem. Ges., 26, 2122 (1893). 4001. H. Wamhoff and F. Korte, Synthesis, 1972, 151. 4002. D. J. Brown, in Enciclopedia della Chimica, Vol. 8 (USES Edizioni Scientifiche, Florence, Italy) 1981, p. 577. 4003. D. J. Brown, in Methodicum Chimicum, Vol. 4 (F. Korte and J. Falbe, Eds.), Georg Thieme Verlag, Stuttgart, 1980, p. 257. 4004. D. T. Hurst, Introduction to the Chemistry and Biochemistry qfthe Pyrimidines, Purines, and Pteridines, Wiley, Chichester, UK, 1980 (a) p. 19; (b) p. 104; (c) p. 157. 4005. H. Fischer and L. A. Summers, J . Heterocycl. Chem., 17, 333 (1980). 4006. P. E. Fanta and E. A. Hedman, J . Am. Chem. Soc., 78, 1434 (1956). 4007. R. Albrecht and E. Schroder, Eur. J . Med. Chem., 10, 595 (1975). 4008. S. Gronowitz and S . Liljefors, Acta Chem. Scand., Ser. B, 31, 771 (1977). 4009. H. Zaschke and R. Stolle, Z . Chem., 15, 441 (1975). 4010. A. Boller, M. Cereghetti, and H. Schemer, Z . Naturforsch., Teil B, 33, 433 (1978). 4011. S. Gronowitz and S. Liljefors, Chem. Scr., 13, 39 (1978). 4012. W. Traube and R. Schwarz, Ber. Dtsch. Chem. Ges., 32, 3163 (1899). 4013. A. Le Berre and C. Renault. Bull. Soc. Chim. Fr., 1969, 3146. 4014. E. Kobayashi and R. Sakata, Yakugaku Zasshi, 82,447 (1962). 4015. S. Yamada. T. Fujita, and J. Arita, Yakugaku Zasshi, 71, 1363 (1951) 4016. R. Sollazo, A. Vercellone, 0. Goffredo, and G. Bosisio, Farmaco, Ed. Sci., 9, 282 (1954). 4017. T. Tabuchi and G. Maemoto, Jap. Pat. 180,380 (1949); Chem. Abstr., 46, 4029 (1952). 4018. W. von Bebenburg and K. Thiele, US Pat. 3,499,898 (1970); Chem. Abstr., 72, 111498 (1970). 4019. R. Pater, J . Heterocycl. Chem., 8, 743 (1971). 4020. V. Krchdak and Z. Arnold, Collect. Czech. Chem. Commun., 39, 3327 (1974). 4021. H. Rupe and E. Knup, Helu. Chim. Acta, 10, 299 (1927). 4022. H. Rupe and A. Huber, Helu. Chim. Acta, 10, 846 (1927). 4023. D. J. Brown and T.-C. Lee, J . Chem. SOC.(C), 1970, 214. 4024. G. M. Coppola, J. D. Fraser, G. E. Hardtmann, B. S. Huegi, and F. G. Kathawala, J . Heterocycl. Chem., 16, 545 (1979). 4025. W. J. Hale and H. C. Brill, J . Am. Chem. Soc., 34, 295 (1912).

References

1287

4026. D. Reichardt and K. Schagerer, Liehigs Ann. Chem., 1982, 530. H. Zaschke, Z . Chem., 17, 63-(1977). H. W. Marson and J. P. English, US Pat. 2,675,375 (1954); Chem. Ahstr., 49, 6322 (1955). W. Franke and R. Kraft, Anyew. Chem., 67, 395 (1955). J. J. Lafferty and F. H. Case, J . Org. Chem., 32, 1591 (1967). Y. Morimoto, Yakugaku Zasshi, 82, 462 (1962). F. Effenberger, Chem. Ber., 98, 2260 (1965). F. Kunckell and L. Zumbusch, Ber. Dtsch. Chem. Ges., 35, 3164 (1902). H. Mauss and H. Andersag. Ger. Pat. 816,700 (1951); Chem. Ahstr., 47, 2778 (1953). K . Bowden and E. R. H. Jones, J . Chern. Soc., 1946, 953. W. T. Caldwell, E. C. Kornfeld, and C. K. Donnell, J . Am. Chem. Soc., 63, 2188 (1941). G . B. Bennett, R. B. Mason, L. J. Alden, and J. B. Roach, J . Med. Chem., 21, 623 (1978). H. Kristen and M. Raddatz, Z . Chem., 21, 101 (1981). A. P. Kroon and H. C. van der Plas, R e d . Traa. Chim. Pays-Bas, 92, 1020 (1973). E. J. Breaux and K . E. Zwikelmaier, J . Heterocycl Chem., 18, 183 (1981). W. R. Sherman and A. Von Esch, J . Med. Chem., 8, 25 (1965). I. K. Fel'dman and B. I. Boksiner, Biol. Aktian. Soedin., Akad. Nuuk SSSR, 1965, 79; Chem. Ahstr., 63, 18080 ( 1 965). 4043. W.-D. Rudorf and M. Augustin, J . Prukt. Chem., 320, 576 (1978). 4044. D. R. Sutherland and G. Tennant, J . Chem. Soc. (C), 1971, 2156.

4027. 4028. 4029. 4030. 4031. 4032. 4033. 4034. 4035. 4036. 4037. 4038. 4039. 4040. 4041. 4042.

4045. 4046. 4047. 4048. 4049. 4050. 4051. 4052. 4053. 4054. 4055. 4056. 4057. 4058. 4059. 4060. 4061. 4062. 4063. 4064. 4065. 4066. 4067. 4068.

Z. BudESnsky and V. M u d , Collecl. Czech. Chem. Commun., 26, 2865 (1961). R. P. Mariella and J. J. Zelko, J . Org. Chem., 25, 647 (1960). E. Longo and M . Mugnaioni. Boll. Chim. Farm., 100, 430 (1961). T. Nishiwaki, Bull. Chem. Soc. Jpn., 42, 3024 (1969). T. Nishiwaki, Bull. Chem. Soc. Jpn., 43, 937 (1970). H. G. Garg and R. A. Sharma, J . Med. Chem., 12, 1122 (1969). E. Hannig and H. Ziebandt, Phurmazie, 23, 688 (1968). H. G. Garg and R. A. Sharma, J . Med. Chem., 13, 763 (1970). F. G . Baddar, F. H. Al-Hajjar, and N. R. Al-Rayyes, J . Heterocycl. Chem., 13, 257 (1976). E. K. Dora, B. Dash, and C. S. Panda, J . Heterocycl. Chem., 20, 691 (1983). S. M. S. Chauhan and H. Junjappa, Synthesis, 1974, 880. S. M. S. Chauhan and H. Junjappa, Tetrahedron, 32, 1911 (1976). F. L. Rose and G. Swain, J . Chem. Soc., 1945, 689. G. Ito and Y. Shibanuma, Chem. Pharm. Bull., 7, 605 (1959). F. Kurzer and L. E. A. Godfrey, Anyew. Chem., 75, 1157 (1963). A. Kreutzberger and S. Leyke-Rohling, J . Heterocycl. Chem., 15, 1097 (1978). A. R. Katritzky, H. J. Salgado, A. Chermprapai, and N. K. Ponkshe, J . Chem. Soc., Perkin Truns. I , 1982, 153. A. Kreutzberger and S. Leyke-Rohling, Arzneim-Forsch, 28, 2051 (1 978). A. Kreutzberger and S. Leyke-Rohling, Arch. Pharm. (Weinheim, Ger.), 311, 884 (1978). A. Kreutzberger and B. Richter, Arch. Pharm. (Weinheim, Ger.), 315, 2 (1982). J . Schantl, Monatsh. Chem., 101, 568 (1970). T. Urbanski, B. Serafin, and J. Zylowski, J . Med. Chem., 10, 521 (1967). M. Furukawa, Y. Fujino, and S. Hayashi, Chem. Pharm. Bull., 19, 2284 (1971). A. Kreutzberger and G. Rise, J . Fluorine Chem., 14, 131 (1979).

1288 4069. 4070. 4071. 4072. 4073. 4074. 4075. 4076. 4077. 4078. 4079. 4080. 4081. 4082. 4083. 4084. 4085. 4086. 4087. 4088. 4089. 4090. 4091. 4092. 4093. 4094. 4095. 4096.

References A. Kreutzberger and G. Risse, Arch. Pharm. (Weinheim,Ger.), 313, 244 (1980). A. Kreutzberger and G. Risse, Chem.-Zty, 103, 267 (1979). W. Wendelin and A. Harler, Monutsh. Chem., 105, 563 (1974). W. Wendelin, K. Schermanz, A. Fuchsgruber, and A. Harler, Monatsh. Chem., 111, 1399 (1980). Y . H. Kim, C. M. Yoon, and N. J. Lee, Heterocycles, 16, 49 (1981). F. Kunckell and 0. Safert, Ber. Dtsch. Chem. Ges., 35, 3169 (1902). P. N. Evans, J . Prakt. Chem. [2], 46, 352 (1892). P. N. Evans, .I. Prakt. Chem. 121, 48, 489 (1893). 0. Stark, Ber. Dtsch. Chem. Ges., 42, 699 (1909). G. J. Pitt, Acta Crystallogr., 1, 168 (1948). A. Kreutzberger and U.-H. Tesch, Arch. Pharm. (Weinheim, Ger.), 310, 56 (1977). A. Kreutzberger and U.-H. Tesch, Armrim.-Forsch, 28, 235 (1978). A. NovaEek, Collect. Czech. Chem. Commun., 33, 3919 (1968). C. Kashima and A. Katoh, J . Heterocycl. Chem., 17, 913 (1980). C. Kashima, Y. Yamamoto, Y. Omote, T. Otsuka, and Y. Tsuda, Heterocycles, 4, 1387 (1976). A.-M. A. Sammour, M. M. N. El-Deen and M. Abd-El-Halim, J . Chem. UAR, 13, 7 (1970); Chem. Ahstr., 75, 5840 (1971). M. E. Brokke, US Pat. 3,250,775 (1966); Chem. Ahstr., 65, 3888 (1966). A. Kreutzberger and S. Leyke-Rohling, J . Fluorine Chem., 14, 55 (1979). S. K. Naik, R. K. Behera, and A. Nayak, Indian J . Chem., Sect. B, 21, 1124 (1982). G. Zigeuncr, H. Brunetti, H. Ziegler, and M. Bayer, Monatsh. Chem., 101, 1767 (1970). R. L. N. Harris, Aust. .I. Chem., 29, 1335 (1976). S. Inoue, A. G. Saggiomo, and E. A. NodifT, J . Ory. Chem., 26, 4504 (1961). H. W. van Meeteren and H. C . van der Plas, Recl. Trau. Chim. Pays-Bas, 86, 15 (1967). H. W. van Meeteren and H. C. van der Plas, Recl. Trau. Chim. Pays-Bas, 90, 105 (1971). H . Neunhoeffer and H.-W. Friihauf, Liehigs Ann. Chem., 758, 125 (1972). H. Andersag and K. Westphal, Ger. Pat. 670,095 (1939); Frdl., 25, 435 (1942). T. Nishino, Y . Miichi, and K. Tokuyama, Tetrahedron Lett., 1970, 4335. A. Schellenberger, H. Hanke, and G. Hiibner, Hoppe-Seyler’s Z. Physiol. Chem., 349, 517 (1968).

4097. K. A. Gupta, A. K. Saxena, and P. C. Jain, Synthesis, 1981, 905. 4098. R. 0. Roblin, J. H. Williams, P. S. Winnek, and J. P. English, J . Am. Chem. Soc., 62, 2002 (1940).

E. A. Falco, S. Du Breuil, and G. H. Hitchings, J . Am. Chem. Soc., 73, 3758 (1951). W. E. Alexander and J. G . Jeffrey, Can. Pharm. J . , Sci. Sect., 94, 45 (1961). B. Roth and G. H. Hitchings, J . Org. Chem., 26, 2770 (1961). B. Roth and E. A. Falco, G. H. Hitchings, and S. R. M. Bushby, J . Med. Pharrn. Chem., 5, 1103 (1962). 4103. Z. BudCSinsky and V. Letovsky, Cesk. Farm., 15, 432 (1966). 4104. A. A. Santilli, M. D. Rosenberg, T. S. Osdene, and S. J. Childress, J . Heterocycl. Chem., 8, 975 (1971). 4099. 4100. 4101. 4102.

4105. 4106. 4107. 4108.

D. C. Morrison and J. G. Jeffrey, Can. Pharm. J., Sci. Sect., 95, 276 (1962). L. C. Leitch, B. E. Baker, and L. Brickman, Can. J . Res., Sect. B, 25, 14 (1947). Y . P. Shvachkin and M. T. Azarova, Zh. Ohshch. Khim., 34, 407 (1964). J. D. Fissekis and B. A. Markert, J . Ory. Chem., 31, 2945 (1966).

References

1289

4109. A. Piskala and J. Gut, Collect. Czech. Chem. Commun., 28, 2376 (1963). 41 10. F. Ghmez-Contreras, T. Manzano, and P. Navarro, Heterocycles, 14, 769 (1980). 4111. J. D. Fissekis, J . W. Lehnberg, F. Sweet, and R. L. Lipnick, J . Hrrerocycl. Chem., 13, 929 ( 1 9 76). 4112. E. Phillipi and E. Spenner, Monatsh. Chem., 36, 97 (1915). 4113. H. W. Johnson, R. E. Lovins, and M. Reintjes, J . Org. Chem., 24, 1391 (1959). 4114. J. Shapira, J . Org. Chem., 27, 1918 (1962). 41 15. B. R. Baker and J. L. Kelley, J . M e d . Chem., 11, 685 (1968). 4116. J. P. Jonak, S. F. Zakrzewski, and L. H. Mead, J . Med. Chem., 14, 408 (1971). 4117. I. BaSnik and J. FarkaS, Collect. Czech. Chem. Commun., 41, 311 (1976). 4118. H. Hamamura, K. Sato, and J. G. Moffatt, J . Med. Chem., 15, 1061 (1972). 4119. A. J. Playtis and J. D. Fissekis, J . Org. Chem., 40, 2488 (1975). 4120. H. Rochling and G. Horlein, Liehigs Ann. Chem., 1974, 504. 4121. D. J. Brown, W. B. Cowden, G. W. Grigg, and D. Kavulak, Aust. J . Chem., 33, 2291 (1980). 4122. G . Y . Lesher, B. Singh, and Z. E. Mielens, J . M e d . Chem., 25, 837 (1982). 4123. R. Wintersteiger, G. Gubitz, and G. Zigeuner, Sci. Pharm., 48, 68 (1980). 4124. M. G. Biressi, M. Carissimi, and F. Ravenna, Gazz. Chim. Ital., 95, 1293 (1965). 4125. F. Sauter, P. Stanetty, and F. Fuhrmann, Monatsh. Chem., 107, 1193 (1976). 4126. L. B. Davies, 0. A. Leci, P. G. Sammes and R. A. Watt, J . Chem. Soc., Perkin Trans. I, 1978, 1293. 4127. R. L. N. Harris, J. L. Huppatz, and T. Teitei, Aust. J . Chem., 32, 669 (1979). 4128. J. S. Gillespie, S. P. Acharya, and R. E. Davis, J . Heterocycl. Chem., 9, 931 (1972). 4129. J. de Valk and H. C. van der Plas, Reel. Trau. Chim. Pays-Bas, 92, 145 (1973) 4130. J. W. Streef and H. J. den Hertog, R e d . Trau. Chim. Pays Bas, 88, 1391 (1969). 4131. J. A. Barone, J . M e d . Chem., 6, 39 (1963). 4132. H. Wamhoff and F. Korte, Chem. Ber., 100, 1324 (1967). 4133. D. S. Sanghavi, D. T. Chaudhari, and P. P. Gudadhe, Bull. H a f f i n e Inst., 9, 20 (1981). 4134. A. Marsura and C. Luu-Duc, Synthesis, 1982, 595. 4135. M. Takahashi and S.-I. Watanabe, Chem. Lett., 1213 (1979). 4136. T. L. Gilchrist, C. J. Harris, and C. W. Rees, J . Chem. Soc., Chem. Commun., 1974, 487. 4137. T. P. Culbertson, J . Heterocycl. Chem., 16, 1423 (1979). 4138. A. Sitte and H. Paul, Chem. Ber., 102, 615 (1969). 4139. H. Paul and A. Sitte, Z . Chem., 8, 336 (1968). 4140. K. R. Huffman and F. C. Schaefer, J . Org. Chem., 28, 1816 (1963). 4141. K. Sugino, K. Odo, and T. Sugido, Jap. Pat. 180,090 (1949); Chem. Ahstr., 46, 4029 (1952). 4142. S. Biniecki, B. Gutkowska, and J. Kozlowska, Acta Pol. Pharm., 19, 443 (1962). 4143. Y . Hayashi, Nagoya Shiritsu Daigaku Yakugakuhu Kenkyu Nempo, 12,42 (1964);Chem. Ahstr., 64,19605 (1966). 4144. W. Broadbent, L. A. McArdle, and F. L. Rose, J . Chem. Soc. (C), 1969, 689. 4145. F. H. S. Curd and F. L. Rose, J . Chem. Soc., 1946, 362. 4146. A. Giner-Sorolla and A. Bendich, J . Am. Chem. Soc., 80, 5744 (1958). 4147. 4148. 4149. 4150.

A. M. Triggle and D. J. Triggle, J . Med. Chem., 10, 285 (1967). M. Furukawa, Chem. Pharm. Bull., 10, 1215 (1962). P. Mamalis, J. Green, D. J. Outred, and M. Rix, J . Chem. Soc., 1962, 3915. K. A. Hyde, E. M. Acton, B. R. Baker, and L. Goodman, J . Org. Chem., 27, 1717 (1962).

1290 4151. 4152. 4153. 4154. 4155. 4156. 4157. 4158. 4159. 4160. 4161. 4162. 4163. 4164.

References B. R. Baker and J. H. Jordaan, J . Neterocycl. Chem., 3, 315 (1966). J. P. Jonak, L. H. Mead, Y. K. Ho, and S. F. Zakrzewski, J . Med. Chem., 16, 724 (1973).

M. M. Angelo, D. Ortwine, D. F. Worth, and L. M. Werbel, J . Med. Chem., 26, 1311 (1983). K. J. Rorig and H. A. Wagner, US Pat. 3.412,094 (1968); Chem. Abstr., 70, 68410 (1969). J. F. W. Keana and P. E. Eckler, J . Org. Chem., 41, 2850 (1976). B. R. Baker, B.-T. Ho, J. K. Coward, and D. V. Santi, J . Pharm. Sci., 55, 302 (1966). B. R. Baker and H. S. Shapiro, J . Phurm. Sci., 55, 308 (1966). M. Furukawa and S. Hayashi, Synthesis, 1973, 536. M. Furukawa, T. Yoshida, M. Goto, and S. Hayashi, Chem. Pharm. Bull., 21, 2594 (1973). A. P. Phillips and J. Mentha, J . Am. Chem. Soc., 76, 574 (1954). L. Almirante, A. Bianchi, and V. Zamboni, Ann. Chim. (Rome),46, 623 (1956). M. H. Maguire, R. K. Ralph, and G. Shaw, J . Chem. Soc., 1958, 2299. M. Kuchai, J. &of, and J. Vachek, Collect. Czech. Chem. Commun., 34, 331 (1969). R. Neidlein and G. Menche, Arch. Pharm. (Weinheim, Ger.), 305, 596 (1972).

4165. A. B. Boese, US Pat. 2,138,756 (1938); Chem. Abstr., 33, 2152 (1939); Ind. Eng. Chem., 32, 16 ( 1940). 4166. N. V. Khromov-Borisov and R. S. Karlinskaya, Zh. Ohshch. Khim., 26, 1728 (1956); Chem. Abstr., 51, 2809 (1957). 4167. S. I. Zav’yalov, I. A. Mikhailopulo, V. I. Gunar, and L. F. Ovechkina, Izo. Akad. Nauk SSSR, Ser. Khim., 1967, 859. 4168. 4169. 4170. 4171. 4172. 4173.

M. Nencki and N. Sieber, J . Prakt. Chem. 121, 25, 72 (1882). A. K. Bhattacharya, Indiun J . Chem., 5, 62 (1967). T. B. Johnson, J . Am. Chem. Soc., 36, 1891 (1914). Y. A. Levin, N. A. Gul’kina, and V. A. Kukhtin, Zh. Ohshch. Khim., 33, 2673 (1963). S. Senda, K. Hirota, and T. Asao, Chem. Pharm. Bull., 22, 189 (1974). B. R. Baker, M. Kawazu, and J. D. McClure, J . Pharm. Sci., 56, 1081 (1967).

4174. 4175. 4176. 4177. 4178. 4179. 4180. 4181. 4182. 4183. 4184. 4185. 4186. 4187. 4188. 4189. 4190. 4191. 4192.

J. de Valk and H. C. van der Plas, Recl. Trao. Chim. Pays-Bas, 90, 1239 (1971). L. H. Briggs and E. F. Orgias, J . Chem. Soc. (C), 1970, 1885. H. Fenner and R. Teichmann, Arch. Pharm. (Weihheim, Ger.), 311, 115 (1978). S. R. James and C. B. Reese, Tetrahedron Lett., 1975, 2915. S. Senda, K. Hirota, and 0. Otani, Yakugaku Zasshi, 94, 571 (1974). A. C. Veronese and F. d’Angeli, Ann. Chim. (Rome),60, 374 (1970). A. W. Dox and L. Yoder, J . Am. Chem. Soc., 44, 361 (1922). W. Dymek and R. Zimon, Acta Pol. Phurm., 25, 221 (1968). W. Dymek and R. Zimon, Acta Pol. Phurm., 27, 193 (1970). J. A. Hendry and R. F. Homer, J . Chem. Soc., 1952, 328. M. Robba and R. Moreau, Bull. Soc. Chim. Fr., 1960, 1648. E. Ziegler, E. Nolken, and H. Junek, Monatsh. Chem., 93, 708 (1962). H. Zaschke and H. Schubert, J . Prakt. Chem., 315, 1113 (1973). H. Schubert and H. Zaschke, J . Prakt. Chem., 312, 494 (1970). H. Zaschke, J . Prakt. Chem., 317, 617 (1975). J. P. Marquet, C. Rivalle, and E. Bisagni, Bull. SOC.Chim. Fr., 1977, 92. C. Rivalle, J. P. Marquet, and E. Bisagni, Bull. Soc. Chim. Fr., 1977, 97. E. Ziegler, A. Argyrides, and W. Steiger, Monatsh. Chem., 102, 301 (1971). T. Kappe and W. Lube, Monatsh. Chem., 102, 781.

References 4193. 4194. 4195. 4196. 4197. 4198. 4199.

1291

T. Kappe and R. H. Zadeh, Synthesis, 1975, 247. W. Steiger, A. Argyrides, and E. Ziegler, Org. Prep. Proced. Int., 4, 253 (1972). A. W. Dox and L. Yoder, J . Am. Chem. Soc., 43, 677 (1921). E. Ziegler, A. Argyrides, and W. Steiger, 2. Naturforsch., Teil B , 27, 1169 (1972). K. T. Potts and M. Sorm, J . Org. Chem., 37, 1422 (1972). D. H. Kim and A. A. Santilli, J . Med. Chem., 11, 1227 (1968). S. Basterfield, E. L. Woods, and H. N. Wright, J . Am. Chem. Soc., 48, 2371 (1926).

4200. D. E. O'Brien, F. Baiocchi, R. K. Robins, and C. C. Cheng, J . Med. Pharm. Chem., 5, 1085 (1962). 4201. R. Kotva, J. Kiepelka, A. eerny, and V. Pujman, Collect. Czech. Chem. Commun., 46, 1397 (198 I). 4202. R. Kotva, J. Kiepelka, K. Reiabek, and J. Vachek, Collect. Czech. Chem. Commun., 46, 2217 (1981). 4203. R. Zimon and A. Zejc, Acta Pol. Pharm., 37, 415 (1980). 4204. J. Kiepelka, J. BeneS, V. Pouzar, J. Vachek, and J. Holubek, Collect. Czech. Chem. Commun., 48, 304 (1983). 4205. Merck, Ger. Pat. 158,890 (1903); Frdl., 7, 664 (1902-1904). 4206. Basler Chemische Fabrik, Ger. Pat. 204,795 (1908); Frdl., 9, 998 (1908-1910). 4207. Lucuis & Briining Farbwerke, Ger. Pat. 172,979 (1906); Frdl., 8, 1104 (1905-1907). 4208. Merck, Ger. Pat. 186,456 (1907); Frdl., 8, 1070 (1905-1907). 4209. J. Tafel and A. Weinschenk, Ber. Dtsch. Chem. Ges., 33, 3383 (1900). 4210. Bayer, Ger. Pat. 165,223 (1905); Frdl., 8, 1088 (1905-1907). 4211. Merck, Ger. Pat. 175,795 (1906); Frdl., 8, 1065 (1905-1907). 4212. H. Biltz and T. Kohler, Ber. Dtsch. Chem. Ges., 56, 2482 (1923). 4213. M. A. Whiteley, J . Chem. Soc., 91, 1330 (1907). 4214. 0. Y. Magidson and I. B. Toperman, Khim.-Farm. Zh., 1, No. 8, 9 (1967); Chem. Abstr., 68, 78234 (1 968). 4215. P. Singh and L. Berlinquet, Can. J . Chem., 42, 605 (1964). 4216. A. K. Bose and S. Garratt, J . Am. Chem. Soc., 84, 1310 (1962); Tetrahedron, 19, 85 (1963). 4217. M. Frankel, I. Belsky, D. Gertner, and A. Zilkha, J . Chem. Soc. (C), 1966, 493. 4218. R. A. Jacobson, J . Am. Chem. Soc., 58, 1984 (1936). 4219. J. W. Clark-Lewis and K. Moody, Aust. J . Chem., 23, 1229 (1970). 4220. L. I. Zakharkin, A. V. Grebennikov, and A. I. L'vov, I Z L . Akud. Nuuk S S S R , Ser. Khim., 1970, 106. 4221. W. Horsch and H. Probst, Arch. Pharm. (Weinheim, Ger.), 296, 249 (1963). 4222. A. Buzas, C. Egnell, and M. Moczar, Bull. Soc. Chim. Fr., 1962, 267. 4223. Y. Otsuji, S. Wake, and E. Imoto, Tetrahedron, 26, 4293 (1970). 4224. L. T. Thorne, J . Chem. Soc., 39, 543 (1881). 4225. M. Carissimi, I. Grasso, E. Grumelli, E. Milla, and F. Ravenna, Farmaco, Ed. Sci., 17, 390 (1962). 4226. W. B. Cowden and N. W. Jacobsen, Aust. J . Chem., 35, 795 (1982). 4227. A. K. Bose and G. Mina, J . Org. Chem., 30, 812 (1965). 4228. G. Zinner and R. Vollrath, Chem. Ber., 103, 766 (1970). 4229. G . Zinner and R. Vollrath, Chem. Ber., 103, 2006 (1970). 4230. T. Nishiwaki, Chem. Pharm. Bull., 14, 1425 (1966). 4231. E. Miller, J. C. Munch, F. S. Crossley, and W. S. Hartung, J . Am. Chem. Soc., 58, 1090 (1936).

1292 4232. 4233. 4234. 4235. 4236. 4237. 4238. 4239. 4240. 4241. 4242. 4243. 4244. 4245. 4246.

References T. B. Johnson and A. J. Hill, Am. Chem. J., 45, 356 (1911). D. L. Tabern and E. H. Volwiler, J . Am. Chem. Soc., 57, 1961 (1935). F. S. Crossley, E. Miller, W. H. Hartung, and M. L. Moore, J . Org. Chem., 5, 238 (1940). K. Dolze, H. Goldharn, and H. Fiirst, Arch. Pharm. (Weinheim, Ger.), 294, 190 (1961). K. Hesse, H. Goldharn, and H. Fiirst, Arch. Pharm. (Weinheim, Ger.), 295, 598 (1962). A. Takamizawa, Vitamins, 30, 195 (1964). P. B. Russell and G . H. Hitchings, J . Am. Chem. Soc., 73, 3763 (1951). T. Nishino, M. Kiyokawa, and K. Tokuyama, Tetrahedron Lett., 1968, 4321. K.-D. Kampe, Angew. Chem., 94, 543 (1982). J. A. Barone and H. Tieckelmann, J . Org. Chem., 26, 598 (1961). R. H. Mizzoni, R. A. Lucas, R. Smith, J. Boxer, J. E. Brown, F. Goble, E. Konopka, J. Gelzer, J. Szanto, D. C. Maplesden, and G. de Stevens, J . M e d . Chem., 13, 878 (1970). S. K. Robev, Dokl. Bolg. Akad. Nauk., 33, 635 (1980). A. Takamizawa, Yakugaku Zasshi, 74, 748 (1954). P. B. Russell, G . H. Hitchings, B. H. Chase, and J. Walker, J . A m . Chem. Soc., 74, 5403 (1952). W. J. Fanshawe, V. J. Bauer, and S. R. Safir, J . Org. Chem., 30, 1278 (1965).

4247. N. V. Khromov-Borisov and I. I. Tikhideeva, Khim.-Furm. Zh., 4, No 6, 18 (1970). 4248. I. Kompis, W. Mueller, E. Boehni, R. Then, and M. Montavon, Eur. J . M e d . Chem.-Chim. Ther., 12, 531 (1977). 4249. B. P. Das and D. W. Boykin, J . Med. Chem., 17, 372 (1974). 4250. D. J. McCaustland, W. H. Burton, and C. C. Cheng, J . Heterocycl. Chem., 8, 89 (1971). 4251. P. Stenbuck, R. Baltzly, and H. M. Hood, J . Org. Chem., 28, 1983 (1963). 4252. W. Schliernann, Pharmazie, 31, 140 (1976). 4253. R. A. Swaringen, D. A. Yeowell, J. C. Wisowaty, H. A. El-Sayad, E. L. Stewart, and M. E. Darnofall, J . Org. Chem., 44, 4825 (1979). 4254. I. Kompis, R. Then, E. Boehni, G. Rey-Bellet, G. Zanetti, and M. Montavon, Eur. J . Med. Chem.-Chim. Ther., 15, 17 (1980). 4255. M. Hoffer, E. Grunberg, M. Mitrovic, and A. Brossi, J . M e d . Chem., 14, 462 (1971). 4256. E. L. Stogryn, J . Med. Chem., 16, 1399 (1973). 4257. I. Kompis and A. Wick, Helv. Chim. Actu, 60, 3025 (1977). 4258. M. Calas, A. Barbier, L. Giral, B. Balmayer, and E. Despaux, Eur. J . M e d . Chem.-Chim. Ther.. 17, 497 (1982). 4259. A. Bendich, H. Getler, and G. B. Brown, J . B i d . Chem., 177, 565 (1949). 4260. A. Lorente and J. L. Soto, An. Quim. Ser. (C), 76, 242 (1980). 4261. C. W. Whitehead and J. J. Traverso, J . Am. Chem. Soc., 77, 5872 (1955). 4262. Z. BudiSinsky, Z. Peiina, and J. Sluka, Cesk. Farm., 11, 345 (1962). 4263. A. Y. Il’chenko, V. I. Krokhtyak, and L. M. Yagupol’skii, Khim. Geterotsikl. Soedin., 1981, 1680. 4264. W. Schulze, H. Willitzer, and H. Fritzsche, Chem. Ber., 99, 3492 (1966). 4265. H. Junek, M. Mittelbach, and B. Thierrichter, Monatsh. Chem., 110, 1279 (1979). 4266. S. K . Robev, Dokl. Bolg. Akad. Nauk, 30, 719 (1977). 4267. M. F. Mincheva, Dokl. Boly. Akad. Nauk, 33, 925 (1980). 4268. S. K. Robev, Dokl. Bolg. Akad. Nauk, 34, 1677 (1981). 4269. W. Zerweck and K. Keller, US Pat. 2,211,710 (1941). 4270. B. H. Chase and J. Walker, J . Chem. Soc., 1953, 3518. 4271. E. F. Rogers, W. J. Leanza, and L. H. Sarett, J . Org. Chem., 22, 1492 (1957).

References

1293

4272. 0. Y. Magidson and V. A. Volskova, Med. Prom., 11, No. 12, 13 (1957); Chem. Ahstr., 52, 11073 (1958). 4273. R. Baltzly, L. W. Sheehan, and A. Stone, J . O r y . Chem., 26, 2353 (1961). 4274. M. Julia and F. Chastrette, Bull. Soc. Chim. Fr., 1962, 2247. 4275. B. E. Rosenkrantz, L. Citarel, G. E. Heinsohn, and E. I. Becker, J . Chem. Eny. Data, 8, 237 (1963). 4276. E. A. Falco, B. Roth, and G . H. Hitchings, J . Org. Chem., 26, 1143 (1961). 4277. B. R. Baker and J. H. Jordaan, J . Heterocycl. Chem., 2, 21 (1965). 4278. B. R. Baker and R. B. Meyer, J . Pharm. Sci., 56, 570 (1967). 4279. B. R. Baker, G. D. F. Jackson, and R. B. Meyer, J . Pharm. Sci., 56, 566 (1967). 4280. B. R. Baker and J. H. Jordaan, J . Heterocycl. Chem., 4, 31 (1967). 4281. R . W. A. Rees , S. Y . Chai, M. W. Winkley, and P. B. Russell, J . Med. Chem., 19, 723 (1976). 4282. I. I. Tikhodeeva and N. V. Khromov-Borisov, Khim.-Farm. Zh., 6, No. 4, 18 (1972). 4283. R. Evers, Z . Chem., 19, 250 (1979). 4284. W. Traube and L. Herrmann, Ber. Dtsch. Chem. Ges., 37, 2267 (1904). 4285. R. Andrisano and L. Maiola, Gazz. Chim. Ital., 83, 264 (1953). 4286. F. Bergmann, A. Kalmus, H . Ungar-Waron, and H. Kwietny-Govrin, J . Chem Soc., 1963, 3729. 4287. I.G.F., Ger. Pat. 671,787 (1939); Frdl., 25, 443 (1942). 4288. B. J. Broughton, P. Chaplen, P. Knowles, E. Lunt, S. M. Marshall, D. L. Pain, and K. R. H. Wooldridge, J . Med. Chem., 18, 1 1 17 (1975). 4289. 4290. 4291. 4292. 4293. 4294. 4295. 4296. 4297. 4298. 4299. 4300. 4301. 4302. 4303. 4304. 4305. 4306. 4307. 4308.

R. Buyle and H. G. Viehe, Tetrahedron, 25, 3453 (1969). M. Viscontini, Methods Enzymol., Sect. B, 18, 678 (1971). W. Traube and K. Gorniak, Z . Anyew. Chem., 42, 381 (1929). D. Roy, S. Ghosh, and B. C. Guha, J . Org. Chem., 25, 1909 (1960). F. Seela and U. Liipke, Chem. Ber., 110, 1462 (1977). G. Sziligyi and E. Kasztreiner, Acta Chim. Acad. Sci. Hung., 87, 177 (1975). Merck, Ger. Pat. 168,405 (1906); Frdl., 8, 1077 (1905-1907). J.-C. Muller, H. Ramuz, and H.-P. Wagner, Helu. Chim. Actu, 66, 809 (1983). M. T. Bogert and D. Davidson, J . Am. Chem. Soc., 55, 1667 (1933). Bayer, Ger. Pat. 175,415 (1906); Frdl., 8, 1150 (1905-1907). H. Biltz and W. Schmidt, Liehiys Ann. Chem., 431, 70 (1923). R. Kuhn and A. H. Cook, Ber. Dtsch. Chem. Ges., 70, 761 (1937). E. Fischer and L. Ach, Ber. Dtsch. Chem. Ges., 31, 1980 (1898). C. J. Coulson, R. E. Ford, E. Lunt, S. Marshall, D. L. Pain, I. H. Rogers, and K. R. H. Wooldridge, Eur. J . Med. Chem.-Chim. Ther., 9, 313 (1974). A. Lefebvre, J.-L. Bernier, and C. Lespagnol, J . Heterocycl Chem., 13, 167 (1976). Y. P. Shvachkin and M. T. Azarova, Zh. Ohshch. Khim., 35, 563 (1965). M. Sekiya and Y. Osaki, Yakugaku Zasshi, 86, 854 (1966). Merck, Ger. Pat. 156,384 (1904); Frdl., 7, 660 (1902-1904). Merck, Ger. Pat. 165,222 (1905); Frdl., 8, 1079 (1905-1907). Merck, Ger. Pat. 172,980 (1906); Frdl., 8, 1068 (1905-1907).

4309. T. Kishikawa and H. Yuki, Chem. Pharm. Bull., 14, 1365 (1966). 4310. A. K. Sen and C. C. Price, J . Ory. Chem., 22, 348 (1957). 4311. P. E. Gagnon, J. L. Boivin, and J. Giguere, Can. J . Chem., 29, 1028 (1951). 4312. H:G. Kazmirowski, G. Dietz, and E. Carstens, J . Prakt. Chem. 141, 19, 162 (1963).

1294 4313. 4314. 4315. 4316. 4317. 4318. 4319. 4320. 4321. 4322. 4323. 4324. 4325. 4326.

References J. S. Harper, personal communication.

S. K. Robev, Dokl. Bolg. Akad. Nauk, 32, 1235 (1979). I. Nakata and T. Ueda, Yakugaku Zusshi, 80, 1065 (1960). Y. Fujimoto and M. Teranishi, Jap. Pat, 8388 (1967); Chem. Abstr., 68, 49645 (1968). D. S. Matteson and T.-C. Cheng, J . Org. Chem., 33, 3055 (1968). S. K. Robev, Dokl. Bolg. Akad. Nauk, 33, 791 (1980). S. K. Robev, Tetrahedron Lett., 1978, 1163. S. K. Robev, Dokl. Bolg. Akad. Nauk, 32, 309 (1979). B. R. Baker and D. V. Santi, J . Pharm. Sci., 56, 380 (1967). R. M. Dodson and J. K. Seyler, J . Org. Chem., 16, 461 (1952). Merck, Ger. Pat. 166,448 (1905); Frdl., 8, 1075 (1905-1907). A. L. Vais and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1976, 1425. A. L. Vais and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1977, 674. M. A. Mikhaleva, V. V. Gulevich, 1. I. Naumenko, and V. P. Mamaev, Khim. Geterotsikl Soedin., 1979, 678. 4327. I. J. Rinkes, R e d . Trav. Chim. Pays-Bas, 46, 268 (1927).

4328. H. Weidel and E. Toithner, Monutsh. Chem., 17, 172 (1896). 4329. W. van Dam, R e d . Trav. Chim. Pays-Bas, 15, 101 (1896). 4330. J. A. McRae, A. W. Weston, and C. F. Hubbs, Can. J . Res., Sect. B, 15, 434 (1937). 4331. J. A. McRae and N. A. McGinnis, Can. J . Res., Sect. B , 18, 90 (1940). 4332. 4333. 4334. 4335. 4336. 4337. 4338. 4339. 4340. 4341. 4342. 4343. 4344. 4345. 4346. 4347. 4348. 4349. 4350. 4351. 4352. 4353. 4354. 4355. 4356.

0. S. Wolfbeis, Liebigs Ann. Chem., 1982, 182. R. W. Lamon, J . Heterocycl. Chem., 6, 37 (1969). T. Kato, H. Yamanaka, and T. Shibata, Tetrahedron, 23, 2965 (1967). T. Kato, H. Yamanaka, and T. Shibata, Chem. Phurm. Bull., 15, 921 (1967). T. Kato, H. Yamanaka, and T. Shibata, Yukuyaku Zusshi, 87, 955 (1967). M . Ohoka, S. Yanagida, and S. Komori, J . Org. Chem., 36, 3542 (1971). R. R. Schmidt, Chem. Ber., 98, 346 (1965). N. D. Venayak and B. J. Wakefield, J . Chem. Res., Synop., 200 (1983). E. Grochowski and Z . Eckstein, Heterocycles, 7, 877 (1977). H. de Koning and U. K. Pandit, R e d . Trav. Chim. Pays-Bas, 90, 874 (1971). V. M. Nesterov, S. K. Elagina, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1974, 1280. J. Liebscher, S. Anders, and H. Hartmann, Z . Chem., 18, 63 (1978). K. C. Murdock and R. B. Angier, J . Org. Chem., 27, 3317 (1962). Y. F. Shealy and C. A. O’Dell, J . Heterocycl. Chem., 13, 1041 (1976). J. Liebscher and H. Hartmann, Z . Chem., 18, 334 (1978). R. A. Mathes, J . Am. Chem. Soc., 75, 1747 (1953). M. Mittelbach and H. Junek, J . Heterocycl. Chem., 17, 1385 (1980). L. Giammaneo and F. P. Invidiata, Ann. Chim. (Rome), 60, 188 (1970). L. Giammanco and F. P. Invidiata, Ann. Chim. (Rome), 61, 36 (1971). J. M. McCall and R. E. TenBrink, Synthesis, 1978, 673. J . M. McCall, D. Kloosterman, and B. V. Kamdar, J . Org. Chem., 44, 1562 (1979). J. M. McCall, B. V. Kamdar, and D. Kloosterman, Synthesis, 1980, 123. T. Haga and R. Majima, Ber. Dtsch. Chem. Ges., 36, 333 (1903). C. Harries and T. Haga, Ber. Dtsch. Chem. Ges., 32, 1191 (1899). R. F. Evans, Aust. J . Chem., 20, 1643 (1967).

References 4357. 4358. 4359. 4360. 4361. 4362. 4363. 4364. 4365. 4366. 4367. 4368. 4369. 4370. 4371. 4372. 4373. 4374. 4375. 4376. 4377. 4378. 4379. 4380. 4381. 4382. 4383. 4384. 4385. 4386. 4387. 4388. 4389. 4390. 4391. 4392. 4393. 4394. 4395. 4396.

1295

G. Shaw and G. Sugowdz, J . Chem. Soc., 1954, 665. D. J. Brown and W. B. Cowden, Aust. J . Chem., 35, 1203 (1982). T. Kato and M. Kondo, Chem. Pharm. Bull., 24, 356 (1976). D. J. Brown, W. B. Cowden, and L. Strekowski, Aust. J . Chem., 35, 1209 (1982). H. Goncalves and M. Bon, C. R. Acad. Sci., Ser. C , 280, 141 (1975); Chem. Ahstr., 82, 170824 ( I 975). Z. BudtSinsky, F. Roubinek, and E. Svitek, Collect. Czech. Chem. Commun., 30, 3730 (1965). C. W. Whitehead, C. A. Whitesitt, and A. R. Thompson, J . Org. Chem., 39, 587 (1974). Y. Fujimoto, Jap. Pat. 4260 (1967); Chem. Abstr., 68, 29717 (1968). A. A. Aroyan, M. A. Kaldrikyan, and R. G. Melik-Ogandzhanyan, Arm. Khim.Zh., 20, 61 (1967); Chem. Ahstr., 67, 100101 (1967). A. A. Aroyan and M. A. Kaldrikyan, Sin. Geterosikl. Soedin., Akad. Nauk Arm. SSR, Inst. Tonkoi Org. Khim., 1966, No. 7, 30; Chem. Abstr., 68, 114538 (1968). Bayer, Ger. Pat. 168,407 (1906); Frdl., 8, 1095 (1905-1907). W. R. Boon, H. C. Carrington, N. Greenhalgh, and C. H. Vasey, J . Chem. Soc., 1954, 3263. A. Einhorn, Ger. Pat. 168,553 (1906); Frdl., 8, 1109 (1905-1907). Bayer, Ger. Pat. 163,136 (1905); Chem. Zentr., 1905, 11, 1141. Anilin-Fabrikation, Ger. Pat. 167,332 (1905); Frdl., 8, 1 1 18 (1905-1907). H. J. Morsman, Efelu. Chim. Actrr, 18, 1254 (1935). J. T. Bornwater, Rec. Trati. Chim.Pays-Bas, 35, 124 (1915). A. Einhorn, Ger. Pat. 225,457 (1910); Frdl., 10, 1151 (1910-1912). A. Einhorn, Ger. Pat. 227,321 (1910); Frdl., 10, 1152 (1910-1912). W. Traube, Ger. Pat. 171,992 (1906); Frdl., 8, 1097 (1905-1907). W. Traube, Ger. Pat. 172,885 (1906); Frdl., 8, 1099 (1905-1907). W. Traube, Ger. Pat. 172,886 (1906); Frdl., 8, 1099 (1905-1907). W. Trdube, Ger. Pat. 179,946 (1906); Frdl., 8, 1100 (1905-1907). Bayer, Ger. Pal. 183,628 (1907); Frdl., 8, 1096 (1905-1907). H. Meyer, Liehiys Ann. Chem., 1979, 1291. W. F. Keir and H. C. S. Wood, J . Chem. Soc., Perkin Trans. I , 1976, 1847. H. Hoberg and J. Barluenga-Mur, Synthesis, 1970, 363. T. Kato, H. Yamanaka, S. Konno, and H. Shimomura, Yakugaku Zasshi,90, 606 (1970). G. Thomas, S. Braeuer, H. Furst, and P. Held, E. Ger. Pat. 71,767 (1970); Chem. Abstr., 73, 87936 (1970). A. Y. Tikhonov and L. B. Volodarskii, Tetrahedron Lett., 1975, 2721. G. de Stevens, H. M. Blatter, and R. W. J. Carney, Angew. Chem., 78, 125 (1966). G. de Stevens, A. Halarnandaris, P. Wenk, R. A. Mull, and E. Schlitter, Arch. Biochem. Biophys., 83, 141 (1959). A. W. Lutz and S. H. Trotto, J . Heterocycl. Chem., 9, 513 (1972). A. W. Lutz and S. H. Trotto, J . Heterocycl. Chem., 9, 729 (1972). C. C. Cheng and L. R. Lewis, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 63. M . E. Peel, Chem. Ind. (London), 1960, 1112. G. Bianchetti, P. Dalla-Croce, and D. Pocar, Gazz. Chim. Ital., 94, 606 (1964). T. Okano, S. Goya, and T. Takahashi, Yakugaku Zasshi,88, 11 12 (1968). F. Eiden and B. S. Nagar, Arch. Pharm. (Weinheim, Ger.),297, 367 (1964). H. Bredereck, F. Effenberger, and H. J. Treiber, Chem. Ber., 96, 1505 (1963).

1296

References

4397. 4398. 4399. 4400. 4401. 4402. 4403. 4404. 4405. 4406. 4407. 4408 4409 4410

B. Staakun and H. Stephen, J . Chem. Soc., 1956, 4708. 0. Hromatka, US Pat. 2,235,638 (1941); Chem. Ahstr., 35, 4041 (1941). P. R. Levy and H. Stephen, J . Chem. Soc., 1956, 985. H. Stephen and B. Staskum, J . Chem. Sor., 1956, 980. H. M. Wuest and M. Hoffer, US Pat. 2,271,503 (1941); Chem Abstr., 36, 3632 (1942). R. R. Crenshaw and R. A. Partyka, J . Heterocycl. Chem., 7, 871 (1970). W. H. Davies and H. A. Piggott, J . Chem. Sou., 1945, 347.

441 1 4412 4413 4414

W. H. Davies, A. W. Johnson, and H. A. Piggott, J . Chem. Soc., 1945, 352. M. A. Perez and J. L. Soto, J . Weterocycl. Chem., 19, 177 (1982). S. Skotsch and E. Breitmaier, Chem. Ber., 111, 2003 (1978). M. Hedayatullah and G. Motavaze, Bull. Soc. Chim. Fr., 1975, 2089. G. Drafahl and H. Hanschmann, J . Prakt. Chem. 141, 23, 324 (1964). G. Tsatsaronis and F. ElTenberger, Chem. Ber., 94, 2876 (1961). H. Bredereck, R. Gompper, H. G . Schuh, and G. Theilig, in Newer Methods off'reparutiw Organic Chemistry, Vol. 3 (W. Foerst, Ed.), Academic Press, New York, 1964, p. 268. S. A. Lang and E. Cohen, J . Med. Chem., 18, 623 (1975). J. A. Hyatt and J. S. Swenton. J . Org. Chem., 37, 3216 (1972). T. Hirota, T. Koyama, C. Basho, T. Nanba, K. Sasaki, and M. Yamato, Chem. Pharm. Bull., 25, 3056 (1977). T. Koyamd, T. Hirota, C. Basho, Y. Watanabe, Y. Kitauchi, Y. Satoh, S. Ohmori, and M. Yamato, Chem. Pharm. Bull., 24, 1459 (1976).

4415 A. J. Appelquist, US Pat. 2,517,824 (1950); Chem. Zentr., 1951, 11, 2393. 4416 E. J. Modest, S. Chatterjee, and H. K. Protopapa, J . Org. Chem., 30, 1837 (1965). 4417 E. J. Modest, S. Chatterjee, G. E. Foley, and S. Farber, Actu Uhio Int. Contra Cancrum, 20, 112 (1 964). 4418 V. M. Cherkasov, N. A. Kapran, and V. N. Zavatskii, Ukr. Khim. Zh., 35, 1057 (1969); Chem. Abstr., 72, 43596 (1970). 4419 A. Etienne, A. Le Berre, G. Lonchambon, J. Roques, and B. Lemmens, C. R . Acad. Sci., Ser. C, 285, 33 (1977). 4420 V. P. Mamaev and Z . D. Dubovenko, Khim. Geterotsikl. Soedin., 6, 541 (1970). 442 1 G. Barnikov and H. Ebeling, Z. Chem., 14, 404 (1974). 4422 T. Sasaki and A. Kojima, J . Chem. Soc. (C), 1971, 3056. 4423 J. Goerdeler and D. Wieland, Chem. Ber., 100, 47 (1967). 4424 M. Kulka, Can. J . Chem., 58, 2044 (1980). 4425 S. Yanagida, M. Yokoe, M. Ohoka, and S. Komori, Bull. Chem. Soc. Jpn., 44, 2182 (1971). 4426 M. Reich, Monatsh. Chem., 25, 966 (1 904). 4427 J. Bourguignon, J.-M. Boucly, J.-C. Clinet, and G. Queguiner, C. R. Acad. Sci., Ser. C, 1975, 1019. 4428 A. Kreutzberger and D. Abel, Arch. Pharm. (Weinheim, Ger.), 302, 362 (1969). 4429. T. Koyama, T. Hirota, C. Bashou, T. Nanba, S. Ohmori, and M. Yamato, Chem. Pharm. Bull., 25, 1923 (1977). 4430. D. P. Hansell, Chem. Ind. (London), 1959, 884. 4431. T. Koyama, M. Toda, T. Hirota, Y. Katsuse, and M. Yarnato, Yukugaku Zasshi, 90, 11 (1970). 4432. T. Koyama, Y. Katsuse, M. Toda, T. Hirota, and M. Yamato, Yakugaku Zusshi, 90, 1207 (1970). 4433. T. Koyama, T. Hirota, Y Shinohara, S. Matsumoto, S. Ohmori, and M. Yamato, Chem. Pharm. Bull., 23, 2029 (1975).

References

1297

4434. A. G . Bayer, Ber. Dtsch. Chem. Ges., 2, 319 (1869). 4435. 4436. 4437. 4438. 4439. 4440. 4441. 4442. 4443. 4444. 4445. 4446.

E. Grigat and R. Putter, Angew. Chem., 77, 913 (1965). A. Weddige, J . Prakt. Chem. [2], 33, 76 (1886). R. Otto and K. Voigt, J . Prakt. Chem. 121, 36, 78 (1887). E. von Meyer, J . Prakt. Chem. [2], 37, 396 (1888). J. Troeger, J . Prakt. Chem. [2], 37,407 (1888). E. von Meyer, J . Prakt. Chem. 121, 38, 584 (1888). E. von Meyer, J . Prakt. Chem. [2], 39, 188 (1889). E. Grigat, R. Putter, and E. Muhlbauer, Chem. Ber., 98, 3777 (1965). G . Herfeldt, J . Prakt. Chem. [2], 53, 246 (1895). N. Tscherwen-Iwanoff, J . Prukt. Chem. [2], 44, 160 (1891). N. Tscherwen-Iwanoff, J . Prakt. Chem. 121, 46, 142 (1892). E. von Meyer, J . Prukt. Chem. [2], 52, 81 (1895).

4447. L. S. Meriwether, U.S. Pat. 3,113,945 (1963); Chem. Ahstr., 60, 5519 (1964); Chem. Zentr., 137, 3-2472 (1966). 4448. S. Pasynkiewicz, W. Kuran, and A. Zbierzchowska, Liehigs Ann. Chem., 1975, 636. 4449. J. H. Forsberg, T. M. Balasubramanian, and V. T. Spaziano, J . Chem. Soc., Chem. Cornmun., 1976, 1060. 4450. H.-J. Kabbe, Liehigs Ann. Chem., 704, 144 (1967). 4451. H. Weidinger and H. J. Sturm, Liehiys Ann. Chem., 716, I43 (1968). 4452. 4453. 4454. 4455. 4456. 4457. 4458. 4459. 4460. 4461. 4462. 4463. 4464. 4465. 4466. 4467. 4468. 4469. 4470.

B. Corain, M. Basato, and H.-F. Klein, Angew. Chem., 93, 1034 (1981). K. Burger, F. Hein, U. Wassmuth, and H. Krist, Synthesis, 1981, 904. B. Corain, C. Crotti, A. Del Pra, F. Filira, and G. Zanotti, Inorg. Chem., 20, 2044 (1981). E. Grigat and R. Putter, Chem. Ber., 100, 1385 (1967). A. G. Davies and R. J. Puddephatt, Tetrahedron Lett., 1967, 2265. H. Wittman, P. Beutel, and E. Ziegler, Monutsh. Chem., 100, 1362 (1969). E. Dyer, T. E. Majewski, T. J. Nycz, and J. D. Travis, .I. Heterocycl. Chem., 9, 955 (1972). L. Capuano and R. Zander, Chem. Ber., 106, 3670 (1973). P. Biginelli, Gazz. Chim. Ital., 23, 360 (1893). E. E. Liepin’sh, E. L. Khanina, and G. Y. Dubur, Khim. Geterotsikl. Soedin., 1981, 524. H. Bredereck, R. Gompper, H. G. Schuh, and G. Theilig, Anyew. Chem., 71, 753 (1959). H. Bredereck, R. Gompper, and G. Morlock, Anyew. Chem., 68, 151 (1956). W. Ziegenbein and W. Franke, Angew. Chem., 71, 628 (1959). M. A. Volodina, A. P. Terent’ev, L. G . Roshchupkina, and V. G. Mishina, Zh. Obshch. Khim., 34, 469 (1964). M. H. Elnagdi, S. M. Fahmy, E. A. A. Hafez, M. R. H. Elmoghayar, and S. A. M. Amer, J . Heterocycl. Chem., 16, 1109 (1979). E. Barnatek, J. A. Elvidge, T. Stensrud, and N. A. Zaidi, Acta Chem. Scand., 22, 2048 (1968). J. S. Davis, J. A. Elvidge, and A. B. Foster, J . Chem. Soc., 3638 (1962). T. Koyama, T. Hirota, M. Toda, K. Iwai, M. Minami, and M. Yamato, Yukugaku Zasshi, 89, 1334 (1969). T. Koyama, T. Hirota, M. Yamato, and S. Kohki, Yakugaku Zasshi, 93, 1536 (1973).

4471. T. Koyama, T. Hirota, M. Yamato, and S. Kohki, Yukugaku Zasshi, 93, 1481 (1973). 4472. T. Koyama, M. Toda, T. Hirota, M. Hashimoto, and M. Yamato, Yakuguku Zasshi, 89, 1688 (1 969). 4473. T. Koyama, T. Hirota, T. Matsumura, and M. Yamato, Yakugaku Zasshi, 92, 1233 (1972).

1298

References

4474. S. Yanagida and S. Komori, Syn:hesis, 1973, 189. 4475. S. Yanagida, T. Fujita, M. Ohoka, I. Katagiri, and S. Komori, Bull. Chem. Soc. Jpn., 46, 292 (1973). 4476. S. Yanagida, M. Ohoka, and S. Komori, J . Org. Chem., 34, 4127 (1969). 4477. M. Ohoka, S. Yanagida, K. Sugahara, T. Fujita, M. Okahara, and S. Komori, Bull. Chem. Soc. Jpn., 46, 1275 (1973). 4478. F. Krohnke, E. Schmidt, and W. Zecher, Chem. Ber., 97, 1163 (1964). 4479. H.-J. Teuber, G. Schutz, and W. Kern, Chem. Ber., 108, 383 (1975). 4480. T. Ajello, Gazz. Chim. Ital., 70, 504 (1940). 4481. T. Ajello, Gazz. Chim. Ital., 69, 460 (1939). 4482. T. Ajello, Gazz. Chim. Ital., 72, 325 (1942). 4483. S. S. Washburne, W. R. Peterson, and D. A. Berman, J . Org. Chem., 37, 1738 (1972). 4484. S. Capuano and L. Giammanco, Gazz. Chim. It& 86, 119 (1956). 4485. S. Capuano and L. Giammanco, Gazz. Chim. Ital., 86, 126 (1956). 4486. S. Capuano and L. Giammanco, Gazz. Chim. Ital., 86, 109 (1956). 4487. C. Venturello and R. D’Aloisio, Tetrahedron Lett., 1982, 2895. 4488. J. F. Freeman, E. G. Duthie, M. J. OHare, and J. F. Hansen, J . Org. Chem., 37, 2756 (1972). 4489. I. Adachi, Chem. Pharm. Bull., 17, 2209 (1969). 4490. M. Ridi, S. Mangiavacchi, and G. Franchi, Boll. Chim. Farm., 106,664 (1967); Chem. Abstr., 68, 114537 (1968). 4491. Z. Machon, Rocz. Chem., 42, 2091 (1968). 4492. M. P. Zhdanova, E. A. Zvezdina, and G. N. Dorofeenko, Khim. Geterotsikl. Soedin., 1975,277. 4493. J. W. Streef and H. J. den Hertog, Reel. Trau. Chim. Pays-Bas, 85, 803 (1966) 4494. R. D. Chambers, M. Clark, J. R. Maslakiewicz, and W. K. R. Musgrave, Tetrahedron Lett., 1973, 2405. 4495. R. D. Chambers, M. Clark, J. R. Maslakiewicz, W. K. R. Musgrave, and P. G. Urben, J . Chem. Soc., Perkin Trans. 1, 1974, 1513. 4496. R. D. Chambers, J. A. H. MacBride, and W. K. R. Musgrave, J . Chem. Sue. (C), 1971, 3384. 4497. T. Aiello, S. Giambrone, and L. Giammanco, Atti Accad, Sci. Lett. Arti Palermo, Parte I, 26, 321 (1967). 4498. F. Lahmani, N. Ivanoff, and M. Magat, C. R. Acud. Sci., Ser. C, 1966, 1005. 4499. N. A. Kapran, V. G. Lukamanov, L. M. Yagupol’skii, and V. M. Cherkasov, Khirn. Geterotsikl. Soedin., 1977, 122. 4500. F. C. Schaefer and G. A. Peters, J . Am. Chem. Soc., 81, 1470 (1959). 4501. A. Kreutzberger and M. U. Uzbek, Chem.-Ztg, 96, 111 (1972). 4502. A. Kreutzberger and D. Wiedemann, Liebigs Ann. Chem., 1977, 537. 4503. D. R. Osborne and R. Levine, J . Org. Chem., 28, 2933 (1963). 4504. L. S. Cook and B. J. Wakefield, Tetrahedron Lett., 1979, 1241. 4505. L. S. Cook, G. Prudhoe, N. D. Venayak, and B. J. Wakefield, J . Chem. Rex, Synop. 113, Minipr. 1357 (1982). 4506. R. M. Anker and A. H. Cook, J . Chem. Soc., 1941, 323. 4507. K. Yanagiya, M. Yasumoto, and M. Kurabayashi, Bull. Chem. Soc. Jpn., 46, 2809 (1973). 4508. D. J. Anderson and A. Hassner, J . Chem Soc., Chem. Cornmun., 1974, 45. 4509. G. Kleineberg and E. Ziegler, Monatsh. Chem., 94, 502 (1963). 4510. G. Kleineberg and E. Ziegler, Monutsh. Chem., 96, 1352 (1965). 4511. R. N. Warrener and E. N. Cain, Tetrahedron Lett., 1966, 3231.

References

1299

4512. Y. Yamamoto and Y. Azuma, Heterocycles, 6, 1817 (1977). 4513. V. I. Gunar, I. A. Mikhailopulo, L. F. Ovechkina, and S. I. Zav’yalov, Khim. Geterotsikl. Soedin., 1967, 48; Chem. Abstr., 67, 54097 (1967). 4514. F. Eiden and B. S. Nagar, Naturwissenschaften, 50,403 (1963). 4515. V. Sprio, Ric. Sci.,Parte 2, Sez. B, 34, 585 (1964). 4516. R. R. Schmidt, Chem. Ber., 98, 334 (1965). 4517. G. Stagno-D’Alcontras, G. Lo-Vecchio, M. Crisafulli, and M. Gattuso, Gazz. Chim.Ital., 97, 997 (1967). 4518. T. Kato and Y. Yamamoto, Chem. Pharm. Bull., 15, 1334 (1967). 4519. I. Shibuya and M. Kurabayashi, Heterocycles, 2, 253 (1974). 4520. L. Giammanco, Atti Accad. Sci.,Lett. Arti Palermo, Parte I , 27,469 (1966-1967); Chem. Abstr., 71, 49884 (1969). 4521. A. Takamizawa and K. Hirai, J . Org. Chem., 30, 2290 (1965). 4522. C. J. Cavallito, C. M. Martini, and F. J. Nachod, J . Am. Chem. SOC.,73, 2544 (1951). 4523. I. Shibuya and M. Kurabayashi, Bull. Chem. Soc. Jpn., 42, 2382 (1969). 4524. I. Shibuya and M. Kurabayashi, Bull. Chem. Soc. Jpn., 46, 3902 (1973). 4525. M. Hubert-Habart, K. Takagi, and R. Royer, Bull. Soc. Chim.Fr., 1967, 356. 4526. S. Ueda, Y. Hayashi, and R. Oda, Tetrahedron Lett., 1969, 4967. 4527. P. Eitner, Ber. Dtsch. Chem. Ges., 25, 461 (1892). 4528. M . Hubert-Habart, K. Takagi, A. Cheutin, R. Royer, and M.-L. Desvoye, Bull. Soc. Chim.Fr., 1966, 1587. 4529. K. Tagaki. M. Hubert-Habart, and R. Royer, C. R . Acad. Sci., 260, 5302 (1965). 4530. K. Takagi and M. Hubert-Habart, Bull. Chim.Ther., 1970, 264. 4531. M. Hubert-Habart, C. Pene, G. Bastien, and R. Royer, Chim. Ther., 1973, 314. 4532. K. Takagi and T. Ueda, Chem. Pharm. Bull., 23, 2427 (1975). 4533. C. Pene, M. Hubert-Habart, and R. Royer, Eur. J . Med. Chem.-Chim. Ther., 10, 340 (1975). 4534. M. Hubert-Habart, G. Menichi, K. Takagi, A. Cheutin, M.-L. Desvoye, and R. Royer, Bull. Chim. Ther., 1968, 280. 4535. H. Wamhoff and C. von Waldow, Chem. Ber., 107, 2265 (1974). 4536. H. Wamhoff and C. von Waldow, Chem. Ber., 110, 1730 (1977). 4537. F. Sauter, P. Stanetty, and E. Schrom, Arch. Pharm. (Weinheim,Ger.), 310, 337 (1977). 4538. W. J. Irwin and D. G . Wibberley, J . Chem. Soc., Chem. Commun., 1968, 878. 4539. W. J. Irwin and D. G. Wibberley, J . Chem. Soc. (C), 1971, 3237. 4540. D. H. Kim and A. A. Santilli, Tetrahedron Lett., 1972, 2301. 4541. W. Pfleiderer, personal communication. 4542. A. Schlieper, Liebiys Ann. Chem., 55, 251 (1845). 4543. H. Biltz and M. Heyn, Liehiys Ann. Chem., 413, 60 (1917). 4544. A. M. Mian and R. T. Walker, J . Chem. Soc. (C), 1968, 2577. 4545. E. Dyer, G. C. Emmett, D. M. Nycz, and D. B. Smith, J . Heterocycl. Chem., 10, 1043 (1973). 4546. J. Altman and D. Ben-Ishai, J . Heterocycl. Chem., 5,679 (1968). 4547. J. A. Montgomery, K. Hewson, S. J. Clayton, and H. J. Thomas, J . Ory. Chem., 31,2202 (1966). 4548. E. Falch and T. Natvig, Acta Chem. Scand., 24, 1423 (1970). 4549. K. Eistetter and W. Pfleiderer, Chem. Ber., 106, 1389 (1973). 4550. W. L. F. Armarego and P. A. Reece, Tetrahedron Lett., 1975, 423. 4551. T. Novinson, P. Dea, and T. Okabe, J . Org. Chem., 41, 385 (1976). 4552. D. R. Sutherland and G. Tennant, J . Chem. Soc., Chem. Commun., 1969, 1070.

1300

References

4553. Y. Hirata, K. Iwashita, and K. Teshima, Nagoya Sanyyo Kagaku Kenkyujho Kenkyu Hokoku, No. 9, 83 (1957); Chem. Abstr., 51, 12074 (1957). 4554. T. Higashino, E. Hayashi, H. Matsuda, and T. Katori, Heterocycles, 15, 483 (1981). 4555. G. R. Revankar, R. K. Robins, and R. L. Tolman, J . O r y . Chem., 39, 1256 (1974). 4556. D. H. Kim and A. A. Santilli, Chem. Ind. (London),1969, 458. 4557. J . H. Dewar and G. Shaw, J . Chem. Soc., 1965, 1642. 4558. K . Gewald, J . Prakt. Chem. [4], 32, 26 (1966). 4559. R. Hull and R. Farrand, J . Chem. Soc., 1963, 6028. 4560. E. C. Taylor, S. F. Martin, Y. Maki, and G. P. Beardsley, J . Org. Chem., 38, 2238 (1973). 4561. H. Gehlenand and B. Simon, Arch. Pharm. (Weinheim, Ger.), 303, 511 (1970). 4562. Y. F. Shealy and C. A. O’Dell, J . Org. Chem., 29, 2135 (1964). 4563. V. P. Mamaev, M. A. Mikhaleva, and A. 1. Shadrina, Khim. Geterotsikl. Soedin., 1988, 371. 4564. G. Menichi, C. Pene, M. Hubert-Habart, N. Platzer, A. Cheutin, and R. Royer, Bull. Chim. Ther., 1970, 422. 4565. T. Okabe, E. Taniguchi, and K . Maekawa, Bull. Chem. Soc. J p n . , 47, 2813 (1974). 4566. W. Lowe, Liehigs Ann. Chem., 1977, 1050. 4567. C. Pene and M. Hubert-Habart, J . Heterocycl. Chem., 17, 329 (1980). 4568. M. Hubert-Habart and R. Royer, Bull. Chim. Ther., 1972, 1. 4569. M.-C. Dubroeucq, F. Rocquet, and F. Weiss, Tetrahedron Lett., 1977, 4401. 4570. K. Takagi and M. Hubert-Habart, Eur. J . Med. Chem.-Chim. Ther., 9, 14 (1974). 4571. K. Takagi and M. Hubert-Habart, Eur. J . Med. Chem.-Chim. Ther., 9, 681 (1974). 4572. C. Pene, G. Menichi, h4. Hubert-Habart, A. Cheutin, and R. Royer, Bull. Chim. Ther., 1970, 111. 4573. H. Wamhoff and F. Korte, Chem. Ber., 101, 772 (1968). 4574. G. Herbertz, H. Wdmhoff, and F. Korte, Z . Naturforsch., Teil B, 23, 312 (1968). 4575. H. Schulte, Chem. Ber., 87, 820 (1954). 4576. H. C. Scarborough, J . Ory. Chem., 29, 219 (1964). 4577. D. J. Brown, Fused Pyrimidines Part 3: Pteridines, Wiley, New York, 1988, p. 37. 4578. A. Albert, J . Chem. Soc., 1955, 2690. 4579. J. Clark and G. Neath, J . Chem. Soc. (C), 1966, 1112. 4580. V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl. Soedin., 6, 691 (1970). 4581. E. F. Schroeder and R. M. Dodson, J . Am. Chem. Soc., 84, 1904 (1962). 4582. H. W. Heine, R. H. Weese, R. A. Cooper, and A. J. Durbetaki, J . Org. Chem., 32,2708 (1967). 4583. D. J. Brown and J. S. Harper, in Pteridine Chemistry, (W. Pfleiderer and E. C. Taylor, Eds.), Pergamon, Oxford, 1964, p. 219. 4584. A. Dlugosz, H. C. van der Plas, and A. van Veldhuizen, J . Heterocycl. Chem., 19, 373 (1982). 4585. W. Huckel and C. M. Salinger. Ber. Dtsch. Chem. Ges., 77, 810 (1944). 4586. A. T. Amos and G. G. Hall, Mol. Phys., 4, 25 (1961). 4587. H. F. Hameka and A. M. Liquori, Mol. Phys., 1, 9 (1958). 4588. D. W. Davies, Trans. Faraday Sac., 51, 449 (1955). 4589. P. J. Wheatley, Acta Crystallogr., 13, 80 (1960). 4590. H. Kim and H. F. Hameka, J . Am. Chem. Soc., 85, 1398 (1963). 4591. C. A. Coulson, J . Chem. Soc., 1963, 5893. 4592. J. R. de la Vega, J . Am. Chem. Soc., 85, 3504 (1963). 4593. J. Tjebbes, Acta Chem. Scand., 16, 916 (1962). 4594. R. D. Brown and B. A. W. Coller, Theor. Chim. Acta, 7, 259 (1967).

References

1301

4595. M. N. Adamov and I. F. Tupitsyn, Vestn. Leningr. Uniu., 17, No. 16: Ser. F i s i Khim., No. 3,47 (1 962); Chem. Ahstr., 59, 735 I (1 963). 4596. W. Woinicki, J. Dolewski, K . Jankowski, J. Karwowski, and S. Kwiatkowski, Bull. Acad. Pol. Sci., Ser. Sci. Math. Astron. Phys., 12, 655 (1964). 4597. S . Kwiatkowski and B. Zurawski, Bull. Acad. Pol. Sci., Ser. Sci. Math. Astron. Phys., 13. 487 (1965). 4598. J. S. Kwiatkowski and B. Zurawski, Acta Phys. Pol., 32, 893 (1967). 4599. 4600. 4601. 4602.

S. F. Mason, J . Chem. Soc., 1959, 1240. M. A. El-Sayed, J . Chem. Phys., 36, 552 (1962). J. W. Dodd, F. J . Hopton, and N. S. Hush, Proc. Chem. Soc., 1962, 61. J. D. Simmons and K. K. Innes, J . Mol. Spectrosc., 13, 435 (1964).

4603. G. Favini and M. Simonetta, Atti Accad. Naz. Lincei, C1. Sci. Fis. Mat. Nut., Rend., 28, 57 (1960); Chem. Abstr., 55, 105 (1961). 4604. H. C. Borresen, Acta Chem. Scand., 17, 921 (1963). 4605. K. Jankowski, Bull. Acad. Pol. Sci.,Ser. Sci. Muth. Astron. Phys., 11, 621 (1963). 4606. R. C. Lord, A. L. Marston, and F. A. Miller, Spectrochim. Acta, 9, 113 (1957). 4607. R. Foglizzo and A. Novak, J . Chim. Phys., 64, 1484 (1967). 4608. R. Foglizzo and A. Novak, Spectrochim. Acta, Part A , 26, 2281 (1970). 4609. V. I. Bliznyukov and V. A. Gain, Trudy Khar’kou. Farm. Inst.; No. I , 26 (1957); Chem. Ahstr., 55, 12031 (1961). 4610. D. B. Cunliffe-Jones, Spectrochim. Actu, 21, 747 (1965). 4611. 4612. 4613. 4614. 4615. 4616. 4617. 4618. 4619. 4620. 4621. 4622. 4623. 4624. 4625. 4626. 4627. 4628. 4629. 4630. 4631.

G. S. Reddy, R. T. Hobgood, and J. H. Goldstein, J . Am. Chem. Soc., 84, 336 (1962). S. Gronowitz and R. A. Hoffman, Ark. Kemi, 16,459 (1960). C. J. Turner and G. W. H. Cheeseman, Org. Mayn. Reson., 8, 357 (1976). J. Riand, M.-T. Chcnon, and N. Lumbroso-Bader, Tetrahedron Lett., 1974, 3123. J. Riand, M.-T. Chenon, and N. Lumhroso-Badcr, Org. Mugn. Reson., 9, 572 (1977). J. Riand, M.-T. Chenon, and N. Lumbroso-Bader, J . Am. Chem. Soc., 99, 6838 (1977). J. Riand, C. Coupry, and M.-T. Chenon, .1. Chem. Soc., Perkin Trans. 2, 1981, 783. R. J. Pugmire and D. M. Grant, J . Am. Chem. Soc., 90, 697 (1968). V. M. S. Gil and A. J. L. Pinto, Mol. Phys., 19, 573 (1970). F. J. Weigert, J. Husar, and J. D. Roberts, J . Org. Chem., 38, 1313 (1973). M. Witanowski, L. Stefaniak, and H. Januszewski, Tetrahedron, 27, 3129 (1971). H. Saito, Y. Tanaka, and S. Nagata, J . Am. Chem. Soc., 95, 324 (1973). W. McFarlane and C. J. Turner, Bull. Soc. Chim. Belg., 87, 271 (1978). W. Stadeli and W. von Philipsborn, Org. Magn. Reson., 15, 106 (1981). J. Momigny, J. Urhain, and H. Wankenne, Bull. Soc. R. Sci. Liege, 34, 337 (1965). J. M. Rice, G. 0. Dudek, and M. Barber, J . Am. Chem. Soc., 87, 4569 (1965). S. M. McElvain and M. A. Goese, J . Am. Chem. Soc., 65, 2227 (1943). S. M. McElvain and M. A. Goese, J . Am. Chem. Soc., 65, 2226 (1943). J. E. Fildes, personal communication (1960). H. C. van der Plas and H. Jongejan, Tetrahedron Lett., 1967, 4385. E. A. Oostveen and H. C. van der Plas, Reel. Trau. Chim. Pays-Bas, 95, 104 (1976).

4632. W. Kurtz, Chem. Ber., 108, 3415 (1975). 4633. F. Roeterdink and H. C. van der Plas, J . Chem. Soc., Perkin Trans. 1, 1976, 1202. 4634. S. Veeraraghavan, D. Bhattacharjee, and F. D. Popp, J , Heterocycl. Chem., 18, 443 (1981). 4635. W. P. K. Girke, Chem. Ber., 112, l(1979).

1302 4636. 4637. 4638. 4639.

References J . Haginima and Y. Higuchi, Yakuyaku Zasshi, 94, 12 (1974).

Y. Asahina and E. Kuroda, Ber. Dtsch. Chem. Ges., 47, 1815 (1914). A. Maggiolo and P. B. Russell, J . Chem. Soc., 1951, 3297. E. A. Oostveen, H. C. van der Plas, and H. Jongejan, Kecl. Trau. Chim. Pays-Bas, 95, 209 (1976). 4640. E. A. Oostvecn and H. C. van der Plas, Reel. Truu. Chim. Pays-Bas, 93, 233 (1974). 4641. J. Taylor and D. G. Wibberley, J . Chem. Soc. (C), 1968, 2693. 4642. T. D. Heyes and J. C. Roberts, J . Chem. Soc., 1951, 328. 4643. W. K. Detweiler and E. D. Amstutz, J . Am. Chem. Soc., 73, 5451 (1951). 4644. M. Ochiai and K. Morita, Tetrahedron Lett., 1967, 2349. 4645. C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, J . Chem. Soc., Perkin Trans. 1, 1981, 489. 4646. M. Conrad and H. Reinbach. Ber. Dtsch. Chem. Ges., 34, 1339 (1901). 4647. A. I. Dyachkov, B. A. Ivin, N. A. Smorygo, and E. G. Sochilin, Zh. Ory. Khim., 12, 1 1 15 (1976). 4648. D. E. O’Brien, L. T. Weinstock, and C. C. Cheng, J . fieterocycl. Chem., 7, 99 (1970). 4649. B. A. Ivin, A. I. D’yachkov, I. M. Vishnyakov, N. A. Smorygo, and E. G. Sochilin, Zh. Ory. Khim., 11, 1337 (1975). 4650. G . M. Blackburn, R . G. Fenwick, and M. H. Thompson, Tetrahedron Lett., 1972, 589. 4651. C. W. Whitehead and C. A. Whitesitt, J . Ory. Chem., 39, 591 (1974). 4652. J. Clark and P. N. T. Murdoch, J . Chem. Soc. ( C ) , 1969, 1883. 4653. E. Ochiai, Yakuyaku Zasshi, 60, 164 ( I 940); Chem. Abstr., 34, 5449 (1 940). 4654. T. Sakamoto and H. Yamanaka, Heterocycles, 15, 583 (1981). 4655. K.-I. Tanji, T. Sakamoto, and H. Yamanaka, Chem. Pharm. Bull., 30, 1865 (1982). 4656. T. Sakamoto, Y. Kondo, and H. Yamanaka, Chem. Pharm. Bull., 30,2417 (1982). 4657. H. Yamanaka, S. Ogawa, and S. Konno, Chem. Pharm. Bull., 28, 1526 (1980). 4658. L. S. German, V. R. Polishchuk, and G. Y. Bekker, Khim. Geterotsikl. Soedin., 1974, 1433. 4659. J. F. Wolfe and T. P. Murray, J . Chem. Soc., Chem. Commun., 1970, 336. 4660. T. P. Murray, J. V. Hay, D. E. Portlock, and J. F. Wolfe, J . Org. Chem., 39, 595 (1974). 4661. C. E. Loader and C. J. Timmons, J . Chem. Soc. (C), 1967, 1343. 4662. M. Korach and W. Bergmann, J . Org. Chem., 14, 11 18 (1949). 4663. E. Ochiai, K. Tunoda, I. Nakayama, and G. Masuda, Yakuyaku Zasshi, 59,462; Supplement, p. 228 (1939); Chem. Zentr., 1941, I , 1907; Chem. Abstr., 34, 101 (1940). 4664. J.-L. Fourrey and P. Jouin, Tetrahedron Lett., 1976, 3201. 4665. B. R. Baker and J. H. Jordaan, J . Heterocycl. Chem., 3, 319 (1966). 4666. K. Suzuki, H. Fukawa, T. Okugawa, and M. Sekiya, Chem. Pharm. Bull., 24, 607 (1976). 4667. B. R. Baker and N. M. J. Vermeulen, J . M e d . Chem., 13, 82 (1970). 4668. R. R. Schmidt, D. Schwille, and H. Wolfe, Chem. Ber., 103, 2760 (1970). 4669. G. E. Wright, L. Bauer, and C. L. Bell, J . Weterocycl. Chem., 3, 440 (1966). 4670. A. Pompon, J . Chim. Phys., 72, 505 (1975). 4671. W. C. J. Ross, J . Chem. Soc., 1948, 1128. 4672. D. M. Brown and W. C. J. Ross, J . Chem. Soc., 1948, 1715. 4673. D. M. Brown and G. A. R. Kon, J . Chem. Soc., 1948, 2147. 4674. 0. Stark and M. Bogemann, Ber. Dtsch. Chem. Ges., 43, 1126 (1910). 4675. I. Saikawa, Yakugaku Zasshi, 84, 121 (1964). 4676. J. H. Lister and G . M. Timmis, J . Chem. Soc., 1960, 1113. 4677. E. C. Taylor and E. E. Garcia, J . Ory. Chem., 30, 655 (1965). 4678. E. Profft and H. Raddatz, J . Prakt. Chem. [4], 12, 206 (1961).

References

1303

H. Bredereck. G. Simchen, and P. Speh, Liebigs Ann. Chem., 737, 46 (1970). F. I. Carroll and A. Philip, Org. Prep. Proced., 2, 223 (1970). 0. Buckendorff, Liebigs Ann. Chem., 385, 314 (191 I). H. Bredereck and W. Jentzsch, Chem. Ber., 93, 2410 (1968). T. Sakamoto, T. Sakasai, and H. Yamanaka. Chem. Pharm. Bull., 29,2485 (1961). T. Sakamoto, K.-I. Tanji, and H. Yamanaka, Chem. Pharm. Bull., 30, 610 (1982). B. R. Baker and W. Rzeszotarski, J . Med. Chem., 10, 1109 (1967). A. Brossi, E. Grunberg, M. Hoffer, and S. Teitel, J . Med. Chem., 14, 58 (1971). H. Biere and R. Russe, Tetrahedron, 30, 3513 (1974). E. Oehiai, M. Ishikawa, and Z.-R. Sai, Yakugaku Zasshi, 65, 72 (1945). T. Kubota, Bull. Chem. Soc. Jpn., 35, 946 (1962). T. Kubota and H. Watanabe, Bull. Chem. Soc. Jpn., 36, 1093 (1963). H. Yamanaka, S. Ogawa, and T. Sakamoto, Heterocycles, 16, 573 (1981). H. Yamanaka, T. Sakamoto, and S. Niitsuma, Heterocycles, 31, 923 (1990). R. A. Clarke, B. Graham, and B. E. Christensen, J . Am. Chem. Soc., 70, 1088 (1948). V. F. Sedova, A. S. Lisitsyn, and V. P. Mamaev, Khim.Geterotsikl. Soedin., 1978, 1392. P. Martigny and H. Lund. Acta Chem. Scund., Ser. B, 33, 575 (1979). V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl, Soedin., 1969, 1089. A. G. Ismail and D. G. Wibberley, J . Chem. Soc. C, 1968, 2706. K. Tanaka, T. Sugawa, R. Nakamori, Y. Sanno, and Y. Ando, Yukuyuku Zusshi, 75, 770 (1955). 4699. R. H. Springer, W. J. Haggerty, and C. C. Cheng, J . Heterocycl. Chem., 2, 49 (1965).

4679. 4680. 4681. 4682. 4683. 4684. 4685. 4686. 4687. 4688. 4689. 4690. 4691. 4692. 4693. 4694. 4695. 4696. 4697. 4698.

4700. V. M. Cherkasov, L. P. Prikazchikova, B. M. Chutova, I. F. Vladimirtsev, and I. V. Boldyrev, Khim. Geterotsikl. Soedin., 1973, 1132. 4701. L. P. Prikazchikova, B. M. Khutova, and E. A. Romanenko, Khim. Geterotsikl. Soedin., 1977, 1256. 4702. B. M. Khutova, S. V. Klyuchko, L. P. Prikazchikova, and V. M . Cherkasov, Khim.Geterotsikl. Soedin., 1982, 687. 4703. Y. P. Shvachkin and M. K. Berestenko, Zh. Obshch. Khim., 34, 3506 (1964). 4704. S. B. Gashev, V. P. Lezina, and L. D. Smirnov, Khim. Geterotsikl Soedin., 1980, 681. 4705. G. Zigeuner, A. Frank, H. Dujmovits, and W. Adam, Monatsh. Chem., 101, 1415 (1970). 4706. G . Zigeuner, W. Adam, A. Frank, and H. Reuther, Monatsh. Chem., 101, 1403 (1970). 4707. D. E. OBrien, R. H. Springer, and C. C. Cheng, J . Heterocycl. Chem., 3, 115 (1966). 4708. V. D. Lyashenko, M. S. Kolesova, and K. L. Aleksandr, Zh. Obshch. Khim., 34, 2752 (1964). 4709. R. C. Elderfield and J. R. Wood, J . Ory. Chem., 26, 3042 (1961). 4710. B. M. Lynch and L. Poon, Can. J . Chem., 45, 1431 (1967). 471 1. D. Adams, M. Dosanjh, and D. T. Hurst, Heterocycles, 14, 1989 (1980). 4712. D. T. Hurst and M. L. Wong, J . Chem. Soc., Perkin Trans. I , 1977, 1985. 4713. K. Breuker and H. C . van der Plas, J . Org. Chem., 44,4677 (1979). 4714. J. Breuker and H. C. van der Plas, Reel. Trau. Chim.Pays-Bas, 102, 367 (1983). 4715. S. K. Roy, K. S. Rao, G . S. Reddi, and M. Sachdeva, Indian J . Chem., Sect. B, 16, 907 (1978). 4716. K. Takemoto, J . Macromol. Sci., Rev. Macromol. Chem., 5, 29 (1970). 4717. R. S. Sagitullin, A. N. Kost, and G. G. Danagulyan, Tetrahedron Lett., 1978, 4135. 4718. L. B. Davies, P. G. Sammes, and R. A. Watt, J . Chem. Soc.. Chem. Commun., 1977, 663. 4719. G . Zigeuner, R. Hopmann, C. Knopp, and A. Fuchsgruber, Monatsh. Chem., 101, 1829 (1970). 4720. H. Wamhoff and K. Wald, Chem. Ber., 110, 1716 (1977).

1304

References

4721. G. B. Barlin and D. J. Brown, in Topics in Heterocyclic Chemistry (R. N. Castle, Ed.), Wiley, New York, 1969, p. 122. 4722. L. M. Stempel, G. B. Brown, and J. J. Fox, Am. Chem. Soc., 145th Meeting (New York, 1963), p. 14-0. 4723. C. D. Johnson, A. R. Katritzky, M. Kingsland, and E. F. V. Scriven, J . Chem. Sue. B, 1971, I . 4724. V. Papesch and R. M. Dodson, J . Org. Chem., 28, 1329 (1963). 4725. H. Zondler, H. S. Forrest, and J. M. Logowski, J . Heterocycl. Chem., 4, 124 (1967). 4726. 4727. 4728. 4729. 4730. 4731. 4732. 4733. 4734. 4735. 4736. 4737. 4738. 4739. 4740. 4741. 4742. 4743. 4744. 4745. 4746. 4747. 4748.

A. R. Katritzky, R. G. Shepherd, and A. J. Waring, Reel. Trau. Chim. Pays-Bas, 81,443 (1962). B. R. Baker and D. V. Santi, J . Pharm. Sci., 54, 1252 (1965). B. W. Harris, J. L. Singleton, and M. D. Coburn, J . Heterocycl. Chem., 10, 167 (1973). C. Kaiser and A. Burger, J . Ory. Chem., 24, 113 (1959). C. von Vogel, Liebigs Ann. Chem., 315, 259 (1901). R. Bartling, Liehiys Ann. Chem., 339, 37 (1905). E. W. Bousquet and R. Adams, J . Am. Chem. Soc., 52, 224 (1930). A. E. Pierce and M. M. Rising, J . Am. Chem. Soc., 58, 1361 (1936). N. V. Khromov-Borisov, Zh. Obshch. Khim., 22, 1680 (1952). J. W. Clark-Lewis, G. L. Aldous, and M. J. Thompson, Aust. J . Chem., 29, 2219 (1976). J. C. Jamoulle, C. L. Lapiere, and J. Bourdais, Ann. Pharm. Fr., 37, 331 (1979). N. Okuda, Y. Fukuda, I. Kuniyoshi, and H. Shinoda, Yakugaku Zasshi, 82, 1043 (1962). J. Borjarski and W. Kahl, Rocz. Chem., 38, 1305 (1964). B. R. Baker and T. J. Schwan, J . Med. Chem., 9, 73 (1966). V. M. Cherkasov and L. K. Kurilenko, Khim. Geterotsikl. Soedin., 1970, 1432. F. Yoneda, Y. Sakuma, and K. Shinozuka, J . Chem. Soc., Perkin Trans. 1, 1978, 348. C. Temple, A. G. Laseter, J. D. Rose, and J. A. Montgomery, J . Heterocycl. Chem., 7, 1195 (1970). M. D. Potter and T. Henshall, J . Chem. Soc., 1956, 2000. T. Neilson and H. C. S. Wood, J . Chem. Soc., 1962, 44. W. Pfleiderer and H. Fink, Chem. Ber., 96, 2964 (1963). J. H. Lister and G. M. Timmis, J. Chem. Soc., 1960, 327. J. M. Marsico and L. Goldman, J . Org. Chem., 30, 3597 (1965). A. S. Jones, A. M. Mian, and R. T. Walker, J . Chem. Soc. C , 1966, 692.

4749. L. N. Roitshtein, K. L. Muravich-Aleksandr, and A. V. El’tsov, Zh. Obshch. Khim., 39, 2125 (1969). 4750. 4751. 4752. 4753. 4754. 4755. 4756. 4757. 4758.

J. Mirza, W. Pfleiderer, A. D. Brewer, A. Stuart, and H. C. S. Wood, J . Chem. Soc. C , 1970,437. R. M. Cresswell, T. Neilson, and H. C. S. Wood, J . Chem. Soc., 1961, 476. J. Clark, W. Kernick, and A. J. Layton, J . Chem. Soc., 1964, 3215. R. Hull, J . Chem. Soc., 1958, 2746. J. Clark and F. S. Yates, J . Chem. Soc. C , 1971, 2278. J. Clark, P. N. T. Murdoch, and D. L. Roberts, J . Chem. Soc. (C), 1969, 1408. D. Autenreith, H. Schmid, K. Harzer, M. Ott, and W. Pfleiderer, Anyew Chem., 83,970 (1970). Y. Sakuma, T. Nagamatsu, and F. Yoneda, J . Chem. Soc., Chem. Commun., 1975, 977. Z. D. Dubovenko and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1980, 1278.

4759. 4760. 4761. 4762.

W. W. Hartman and 0. E. Sheppard, Ory. Synth., Collect. Vol., 2, 617 (1943). H. W. van Meeteren and H. C. van der Plas, Reel. Trau. Chim. Pays-Bas, 87, 1089 (1968). J. I. De Craw, V. H. Brown, R. L. Kisliuk, and Y. Gaumont, J . Med. Chem., 14, 866 (1971). A. Albert and J. Clark, J . Chem. Soc., 1964, 1666.

References 4763. 4764. 4765. 4766. 4767. 4768. 4769. 4770. 4771. 4772. 4773. 4774. 4775. 4776. 4777.

1305

A. Albert, Angew. Chem., 79, 913 (1967). F. Yoneda and T. Nagamatsu, Chem. Pharm. Bull., 23, 1885 (1975). Y. Sakuma, S . Matsumoto, T. Nagamatsu, and F. Yoneda, Chem. Phurm. Bull., 24,338 (1976). F. Yoneda, Y. Sakuma, and K. Shinozuka, J . Chem. Soc., Chem. Commun., 1977, 681. H. U. Blank and J. J. Fox, J. Am. Chem. Soc., 90, 7175 (1968). H. U. Blank, I. Wempen, and J. J. Fox, J. Org. Chem., 35, 1131 (1970). V. N. Charushin and H. C. van der Plas, J . Org. Chem., 48, 2667 (1938). J. Clark, M. Curphey, and I. W. Southon, J . Chem. Soc., Perkin Trans. I , 1974, 1611. J. Clark, J . Heterocycl. Chem., Suppl. Issue, 3, S-79 (1976). J. C. Jamoulle, C. L. Lapiere, R. Bassleer, E. Heinen, Z. Selak, F. de Paermentier, M. P. Lhoest-Gauthier, A. Lepoint, and A. M. Renard, Ann. Pharm. Fr., 38, 217 (1980). C. C. Cheng and B. Roth, Prog. Med. Chem., 8, 61 (1971). A. Hantzsch and P. C. C. Isherwood, Ber. Dtsch. Chem. Ges., 42, 986 (1909). W. Traube, H. Ohlendorf, and H. Zander, Ber. Dtsch. Chem. Ges., 53, 1477 (1920). R. P. Royer, personal communication (1950). H. Schmid, M. Schranner, and W. Pfleiderer, Chem. Ber., 106, 1952 (1973).

4778. N. S. Drozdov and V. P. Krylov, Nauchn.-Dokl. Vyssh.Shk., Khim. Khim. Tekhnol.,No. 2,342 (1958); Chem. Abstr., 52, 201x6 (1958). 4779. S. Kuwada, T. Masuda, T. Kishi, and M. Asao, Chem. Pharm. Bull., 8, 798 (1960). 4780. L. V. Alekseeva and Z. V. Pushkareva, Zh. Ohshch. Khim., 33, 1693 (1963). 4781. T. S. Osdene, A. A. Santilli, L. E. McCardle, and M. E. Rosenthale, J . M e d . Chem., 10, 165 (1967). 4782. D. Roy, S. Ghosh, and B. C. Guha, J . Indiun Chem. Soc., 36, 651 (1959). 4783. E. Kalatzis, J . Chem. Soe. B, 1967, 273. 4784. F. Bergel, S. S. Brown, C. L. Leese, G. M. Timmis, and R. Wade, J . Chem. Soc., 1963, 846. 4785. H. Goldner, G. Dietz, and E. Carstens, Naturwissenschafen, 51, 137 (1964). 4786. J. A. Montgomery and H. J. Thomas, J . Org. Chem., 28, 2304 (1963). 4787. C. J. Thoman, J. M. Tien, J.-P. Anselme, and I. M. Hunsberger, Org. Prep. Proced., 1, 137 (1969). 4788. F. Yoncda and S. Matsumoto, Chem. Pharm. Bull., 22, 1652 (1974). 4789. F. Yoneda, K. Shinozuka, Y. Sakuma, and K. Senga, Heterocycles, 6, 1179 (1977). 4790. A. Albert, J . Chem. Sou. ( B ) ,1966, 427. 4791. A. Hantzsch and R. Robison, Ber. Dtsch. Chem. Ges., 43, 45 (1910). 4792. J. Lifschitz and L. Kritzmann, Ber. Dtsch. Chem. Ges., 50, 1719 (1917). 4793. S. Prakash and S. Dutt, Proc. N a t l . Acad. Sci., India, 8, 29 (1938); Chem. Ahstr., 33, 621 (1939). 4794. I. R. Gambhir and R. P. Singh, Proc. Indian Acad. Sci., Sect. A , 23,330 (1946);Chem. Abstr., 40, 6423 (1946). 4795. I. N. D. Dass and S. Dutt, Proc. Natl. Acad. Sci., [ndia, 9, 93 (1939); Chem. Ahstr., 35, 1033 (1941). 4796. E. RuiiEka and K. LyEka, Collect. Czech. Chem. Commun., 27, 1790 (1962). 4797. B. G. Gowenlock and Q. R. Liittke, Q. Reu. Chem. Soc., 12, 321 (1958). 4798. C. Valenzuela-Calahorro, R. Galisteo-Tirado, and J. de D. Lopez-Gonzalez, An. Quim.,73, 1129 (1977). 4799. C. Valenzuela-Calahorro, R. Galisteo-Tirado, and J. de D. Lopez-Gonzalez, An. Quim.,74. 412 (1978). 4800. C. Valenzuela-Calahorro, R. Galisteo-Tirado, and J. de D. Lopez-Gonzalez, An. Quim.,74, 1386 (1978).

1306

References

4801. C. Valenzuela-Calahorro, R. Galisteo-Tirado, and J. de D. Lopez-Gonzalez, An. Quim., 74, 1392 (1978). 4802. M. Tsuchiya, Nippon Kagaku Kaishi, 1978, 827. 4803. M. Tsuchiya, Nippon Kagaku Kaishi, 1979, 597. 4804. B. R. Baker, J. P. Joseph, and J. H. Williams, J . Org. Chem., 19, 1793 (1954). 4805. D. Sen and P. Sengupta, J . Indian Chem. Soc., 50, 260 (1973). 4806. F. Yoneda and Y. Sakuma, Heterocycles, 6, 25 (1977). 4807. T. Sugimoto, K. Shibata, S. Matsuura, and T. Nagatsu, Bull. Chem. Soc. Jpn., 52,2933 (1979). 4808. W. Pfleiderer, J. W. Bunting, D. D. Perrin, and G. Nubel, 99, 3503 (1966). 4809. E. C. Taylor, C. W. Jefford, and C. C. Cheng, J . Am. Chem. Soc., 83, 1261 (1961). 4810. W. Pfleiderer and F. E. Kempter, Angew. Chem., 79, 234 (1967). 4811. D. J. Brown, Fused Pyrimidines Part 3: Pteridines, Wiley, New York, 1988, p. 108. 4812. I. J. Pachter and P. E. Nemeth, J . Org. Chem., 28, 1187 (1963). 4813. R. L. N. Harris and W. Pfleiderer, Liebigs Ann. Chem., 1981, 1457. 4814. G. M. Timmis, Nature (London), 164, 139 (1949). 4815. G. M. Timmis, 1. Cooke, and R. G. W. Spickett, in Chemistry and Biology ofPurines (G. E. W. Wolstenholme and C. M. OConnor, Eds.), Churchill, London, 1957, p. 134. 4816. 4817. 4818. 4819. 4820.

E. C. Taylor and E. E. Garcia, J . Am. Chem. Soc., 86, 4720 (1964). E. C. Taylor and E. E. Garcia, J . Am. Chem. Soc., 86, 4721 (1964). H. Goldner, G. Dietz, and E. Carstens, Z . Chem., 4, 454 (1964). H. Goldner, G. Dietz, and E. Carstens, Tetrahedron Lett., 1965, 2701. W. Pfleiderer and F. E. Kempter, Angew. Chem., 79, 234 (1967).

4821. F. Yoneda, T. Matsumura, and K. Senga, J . Chem. Soc., Chem. Commun., 1972, 606. 4822. 4823. 4824. 4825. 4826.

K. Gorlitzer and D. Buss, Arch. Pharm. (Weinheim, Ger.), 314, 949 (1981). 0. Kiihling, Ber. Dtsch. Chem. Ges., 24, 4140 (1891). 0. Kiihling, Ber. Dtsch. Chem. Ges., 31, 1972 (1898). W. Pfleiderer and G. Niible, Chem. Ber., 93, 1406 (1960). J. Hampshire, P. Hebborn, A. M. Triggle, and S. Vickers, J . Med. Chem., 8, 745 (1965).

4827. 4828. 4829. 4830. 4831. 4832.

D. E. O’Brien, J. D. Westover, R. K. Robins, and C. C. Cheng, J . Med. Chem., 8, 182 (1965). E. F. Elslager and D. F. Worth, J . Med. Chem., 6, 444 (1963). T.-T. Chang, S. Lou, S.-C. Cheng, C.-A. Chi, and P.-C. Chen, Acta Chim. Sinica, 30, 88 (1964). A. B. Sen and R. N. Kapoor, J . Zndiun Chem. Soc., 50, 486 (1973). D. Sen and P. Sengupta, Indian J . Chem., 13, 549 (1975). S. S. Chatterjee, D. R. Garrison, R. Kaprove, J. F. Moran, A. M. Triggle, D. J. Triggle, and A. Wayne, J . Med. Chem., 14, 499 (1971). D. Sen and S. D. Chaudhuri, J . Indian Chem. Soc., 47, 369 (1970). S. S. Chatterjee, J. F. Moran, D. J. Triggle, and A. Wayne, J . Med. Chem., 14, 1244 (1971). S. S. Chatterjee, S. Ludwig, J. F. Moran, D. J. Triggle, and A. Wayne, J . Med. Chem., 14, 1237 ( I 971). F. Yoneda, M. Higuchi, K. Mori, K. Senga, Y. Kanemori, K. Shimizu, and S. Nishigaki, Chem. Pharm. Bull., 26, 2905 (1978). G. M. Timmis, D. G. I. Felton, H. 0.Collier, and P. L. Huskinson, J . Pharm. Pharmacol., 9,46 (1957). T. B. Johnson and D. B. Jones, Am. Chem. J . , 40, 538 (1908). M. T. Bogert and D. Davidson, Proc. Natl. Acad. Sci. U S A , 18, 215 (1932).

4833. 4834. 4835. 4836. 4837. 4838. 4839.

References

1307

4840. M. Israel, H. N. Schlein, C. L. Maddock, S. Farber, and E. J. Modest, J . Pharm. Sci., 55, 568 (1966). 4841. E. D. Day and W. A. Mosher, J . B i d . Chem., 197, 227 (1952). 4842. E. D. Day and W. A. Mosher, J . Franklin Inst., 255, 455 (1953). 4843. H. Steudel, Hoppe-Seyler’s Z . Physiol. Chem., 42, 165 (1904). 4844. T. B. Johnson and S. H. Clapp, J . Biol. Chem., 5 , 163 (1908). 4845. G. Hunter, Biochem. J., 30, 745 (1936). 4846. D. T. Hurst, A. D. Stacey, and D. K. Weerasinghe, Heterocycles, 14, 1753 (1980). 4847. E. A. Falco, G. H. Hitchings, and P. B. Russell, J . Am. Chem. Soc., 71, 362 (1949). 4848. R. Behrend, Liebigs Ann. Chem., 245, 213 (1888). 4849. T. B. Johnson, 0. Baudisch, and A. Hoffrnann, Ber. Dtsch. Chem. Ges., 64, 2629 (1931). 4850. E. F. Elslager, D. B. Capps, D. H. Kurtz, L. M. Werbel, and D. F. Worth, J . M e d . Chem., 6,646 (1 963). 4851. E. F. Elslager, US Pat. 3,083,195 (1963); Chem. Abstr., 59, 10077 (1963). 4852. G. Pellizzari and C. Cantoni, Gazz. Chim. Ital., 41 (I), 21 (1911). 4853. G. E. Wright and N. C. Brown, J . Med. Chem., 20, 1181 (1977). 4854. G. E. Wright and N. C. Brown, J . Med. Chem., 17, 1277 (1974). 4855. J. Weinstock and R. L. Dunoff, J . Med. Chem., 11, 565 (1968). 4856. J. I. De Craw, V. H. Brown, M. Cory, P. Tsakotellis, R. L. Kisliuk, and Y. Gaumont, J . M e d . Chem., 14, 206 (1971). 4857. G . W. Kenner, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1944, 652. 4858. R. Andrisano and G. Modena, Boll. Sedute Accad. Gioenia Sci. Nat. Catania 141, 2, 1 (1952). 4859. H. C. Koppel, D. E. O’Brien, and R. K. Robins, J . Am. Chem. Soc., 81, 3046 (1959). 4860. G . W. Kenner, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1948,957. 4861. Kyowa Fermentation Industry, Fr. Pat. 1,415,224 (1965); Chem. Abstr., 64, 51 15 (1966). 4862. W. Pfleiderer and H.-U. Blank, Angew. Chem., 78, 679 (1966). 4863. M. Higuchi and F. Yoneda, Heterocycles, 6, 1901 (1977). 4864. F. Yoneda, M . Ichiba, K . Ogiwara, and S. Nishigaki, J . Chem. Soc., Chem. Commun., 1971,23. 4865. J. 1. De Craw, V. H. Brown, W. T. Colwell, and N. E. Morrison, J . M e d . Chem., 17, 144 (1974). 4866. S. Goya, T. Takahashi, and T. Okano, Yakugaku Zasshi, 86, 952 (1966). 4867. L. Strekowski and J. Langer, Rocz. Chem., 51, 959 (1977). 4868. V. P. Mamaev and 0.A. Zagulyaeva, Khim. Geterotsikl. Soedin., Sb. I, 1967,354; Chem. Ahslr., 70, 87723 (1969). 4869. V. P. Sedova, V. I. Marnatyuk, V. A. Sarnsonov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1977, 678. 4870. 2 . BudESinsky and F. Roubinek, Collect. Czech. Chem. Commun., 29, 2341 (1964). 4871. J. Brock, Z . Chem., 8, 143 (1968). 4872. B. R. Baker and B.-T. Ho, J . Pharm. Sci., 54, 1261 (1965). 4873. M. G. Katnel’son, V. B. Del’nik, and L. M. Semikolennykh, Med. Prom. SSSR, 20, 17 (1966); Chem. Ahstr., 65 18579 (1966). 4874. F. R. Gerns, A. Perrotta, and G. H. Hitchings, J . M e d . Chem., 9, 108 (1966). 4875. J. P. Geerts and H. C . van der Plas, J . Org. Chem., 43, 2682 (1978). 4876. V. I. Slesarev, B. A. Ivin, N. A. Srnorygo, and E. G. Sochilin, Puti Sin. Izyskaniya Protivoopukholevykh Prep., 1968, 279; Chem. Abstr., 75, 35927 (1971). 4877. V. I. Slesarev, B. A. Ivin, N. A. Srnorygo, and E. G . Sochilin, Zh. Obshch. Khim., 40, 1593 (1 970).

1308

References

4878. S. Nishigaki, Y. Kanemori, J. Sato, and K. Senga, Chem. Pharm. Bull., 26, 3237 (1978). 4879. D. S. Sanghavi, D. T. Chaudhari, and P. P. Gudadhe, Bull. Huffkine Inst., 8, 95 (1980). 4880. A. Aroyan and R. G. Melik-Organdzhanyan, Arm. Khim. Zh., 20, 314 (1967); Chem Ahstr., 68, 29669 (1968). 4881. D. H. Kim and A. A. Santilli, J . Med. Chem., 12, 3121 (1969). 4882. C. A. H. Rasmussen and H. C. van der Plas, Recl. Trao. Chim.Pays-Bas, 97, 288 (1978). 4883. A. Attar, H. Wamhoff, and F. Korte, Chem. Ber., 106, 3524 (1973). 4884. H. Wolfers, U. Kraatz, and F. Korte, Heterocycles, 3, 187 (1975). 4885. D. H. Kim and A. A. Santilli, J . Heterocycl. Chem., 8, 715 (1971). 4886. J. de Valk and H. C. van der Plas, Reel. Trau. Chim. Pays-Bas, 92, 471 (1973). 4887. M. Zimmermann, S. African Pat. 68/00,102 (1968); Chem. Abstr., 71, 30491 (1969). 4888. A. C. Scotese, A. A. Santilli, and G. L. Nelson, J . Med. Chem., 18, 852 (1975). 4889. S. Ruhemann and A. S. Hemmy, Ber. Dtsch. Chem. Ges., 30, 2022 (1897). 4890. G. M. Coppola, G. E. Hardtmann, and B. S. Huegi, J . Heterocycl. Chem., 17, 1479 (1980): 4891. D. E. Heitmeier, E. E. Spinner, and A. P. Gray, J . Ory. Chem., 26, 4419 (1961). 4892. S.-H. Chang, J. Y. Koo, and Y. H. Kim, Daehan IIwuhak Kwoejee, 18, 210 (1974). 4893. A. Y. Tikhonov, V. F. Sedova, L. B. Volodarskii, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1981, 526. 4894. Z. Arnold, Collect. Czech. Chem. Commun., 24, 4048 (1 959). 4895. H. H. Bosshard, R. Mory, M. Schmid, and H. Zollinger, Helo. Chim. Acta, 42, 1653 (1959). 4896. J. Zemlieka, J. Smrt, and F. Sorm, Tetrahedron Lett., 1962, 397. 4897. J. 2emliEka and F. Sorm, Collect. Czech. Chem Commun., 30, 2052 (1965). 4898. C. A. H. Rasmussen and H. C. van der Plas, Tetrahedron Lett., 1978, 3841. 4899. C. A. H. Rasmussen and H. C. van der Plas, Recl. Trau. Chim. Pays-Bas, 96, 101 (1977). 4900. D. A. de Bie, H. C. van der Plas, and B. Geurtsen, J . Chem. Soc., Perkin Trans. f, 1974, 1363. 4901. A. P. Kroon and H. C. van der Plas, Reel. Trao. Chim. Pays-Bas, 93, 227 (1974). 4902. F. E. Anderson, US Pat. 2,696,488 (1954); Chem. Ahstr., 49, 15981 (1955). 4903. A. P. Kroon and H. C. van der Plas, Reel. Truv.Chim. Pays-Bas, 93, 11 1 (1974). 4904. J. de Valk and H. C. van der Plas, Reel. Trau. Chim. Pays-Bas, 91, 1414 (1972). 4905. J. de Valk, H. C. van der Plas, and J. W. A. de Bode, Reel. Trau. Chim.Pays-Bas, 92,442 (1973). 4906. K. Rhode and H. Nahme, Ger. Pat. 738,497 (1943); Chem. Zentr., 1943 (II), 21 8 0 Chem. Abstr., 38, 4273 (1944). 4907. H. Kast, Ber. Dtsch. Chem. Ges., 45, 3124 (1912). 4908. C. G. Allison, R. D. Chambers, Y. A. Cheburkov, J. A. H. MacBride, and W. K. R. Musgrdve, J . Chem. SOC.,Chem. Commun., 1969, 1200. 4909. T. B. Johnson and J. C. Ambelang, J . Am. Chem. Soc., 60, 2941 (1938). 4910. J . Filip and J. Morivek, Chem. Znd. (London),1960, 260. 4911. T. J. Krees and S. M. Constantino, J . Heterocycl. Chem., 10, 409 (1973). 4912. B. A. Otter, E. A. Falco, and J. J. Fox, J . Org. Chem., 34, 2636 (1969). 4913. W. Wierenga, H. I. Skulnick, R. L. Dow, and C. G. Chidester, Heterocycles, 16, 563 (1981). 4914. T. Seita, M. Kinoshita, and M. Imoto, Bull. Chem Soc. Jpn., 46, 1572 (1973). 4915. J. Kiepelka, V. Pouzar, J. Schlanger, J. Holubek, J. Korbl, F. Jantik, and R. Kotva, Collect. Czech. Chem. Commun., 48, 1212 (1983). 4916. M. Sako, M. Suzuki, M. Tdnabe, and Y. Maki, J . Chem. Soc., Perkin Trans. 1, 1981, 3114. 4917. F.Yoneda, K. Shinozuka, K. Hiromatsu, R. Matsushita, Y. Sakuma, and M. Hamana, Chem. Pharm. Bull., 28, 3576 (1980).

References

1309

4918 J. P. Geerts, H. C. van der Plas, and A. van Veldhuizen, Org. Magn. Reson., 7, 86 (1975). 4919. N. M. Bui, R. Gillet, and A. Dumont, Int. J . A p p l . Radiat. Isot., 16, 337 (1965). 4920. C. N. M. Bakkcr, E. M. Kaspersen, A. van Langevclde, and E. K. J. Pauwels, Int. J . Appl. Radiat. Isor., 31, 513 (1980). 4921. 1. V. Vigalok, Y. A. Fedotov, and L. S . Afonskaya, Khim. Geterotsikl. Soedin., 1974, 552. 4922. A. M. Clover, Can. Pat. 245,806 (1924); Chem. Abstr., 19, 657 (1925). 4923. J. V. Backcs, R. W. West, and M. A. Whiteley, J . Chem. Soc., 119, 359 (1921). 4924. E. Schmidt, A. Aschcrl, and W. von Knilling, Ber. Dtsch. Chem. Ges., 59, 1876 (1926). 4925. H. J. Tormey, Sci. Stud., St. Bonauenture Uniu., 23, 21 (1965-1966); Chem Abstr., 67, 90753 ( 1 967). 4926. F. B. Slezak and H. A. McElravy, J . Org. Chem., 24, 1333 (1959). 4927. 0. Baudisch and D. Davidson, Ber. Dtsch. Chem. Ges., 58, 1680 (1925). 4928. W. Joncs, Hoppe-Seyler’s Z . Physiol. Chem., 29, 20 (1900). 4929. R. Duschinsky, T. Gabriel, W. Tautz, A. Nussbaum, M. Hoffer, E. Grunberg, J. H. Burchenal, and J. J. Fox, J . M e d . Chem., 10, 47 (1967). 4930. 0. S. Tee and S . Banerjee, J . Chem. Soc., Chem. Commun., 1972, 1032. 4931. S . Banerjee and 0. S. Tee, J . Chem. Soc., Chem. Commun., 1974, 535. 4932. W. E. Cohn, Biochem. J . , 64, 28P (1956). 4933. D. Barszcz, Z. Tramer, and D. Shugar, Actu Biochem. Pol., 10, 9 (1963). 4934. K. Senga, Chem. Phurm. Bull., 19, 2643 (1971). 4935. S. H. Chang, B.-S. Hahn, I. K. Kim, and S. H. Oh, Daehan Hwahak Hwoejee, 10, 5 1 (1966). 4936. B. Y. Karcle, S. V. Kalnin’, I. P. Grinberga, and 0. Y. Neiland, Khim. Geterotsikl. Soedin., 1973, 553. 4937. R. S. Karlinskaya and N. V. Khromov-Borisov, Zh. Ohshch. Khim., 32, 1847 (1962). 4938. A. P. Phillips and A. Maggiolo, .I. Am. Chem. Soc., 74, 3922 (1952). 4939. Y. P. Shvachkin and M. K. Bcrestenko, Zh. Obshch. Khim., 33, 3132 (1963). 4940. D. A. Lyttlc and H. G. Petering, .I. Am. Chem. Soc., 80, 6459 (1958). 4941. E. G. Sochilin and T. A. Chumak, Zh. Obshch. Khim., 40, 2273 (1970). 4942. J. Tulecki and E. Musial, Diss. Phurm. Pharmucol., 23, 41 (1971). 4943. D. S. Sanghavi, D. T. Chaudhari, and P. P. Gudadhe, Bull. Huffkine Inst., 9, 51 (1981). 4944. J. N. Singh and A. B. Lal, J . Indian Chem. Soc., 43, 308 (1966). 4945. K. L. Nagpal and M. M. Dhar, Tetrahedron, 23, 1297 (1967). 4946. Z. Ledochowski, A. Wolski, A. Ledochowski, and H. Trzeciak, Rocz. Chem., 37, 1083 (1963). 4947. Z . Ledochowski, A. Wolski, H. Trzeciak, and A. Ledochowski, Rocz. Chem., 41, 215 (1967). 4948. L. 0. Ross, W. W. Lee, M. G. M. Schelstraete. L. Goodman, and B. R. Baker, J . Org. Chem., 26, 3021 (1961). 4949. J. Filip and J. FarkaS, Collect. Czech. Chem. Commun., 32, 462 (1967). 4950. M. Chadwick, J. Hampshire, P. Hebborn, A. M. Triggle, and D. J. Triggle, J . Med. Chem., 9, 874 (1966). 4951. H. Segal and C. G. Skinner, J . Org. Chem., 27, 199 (1962). 4952. J. A. Montgomery, A. L. Fikes, and T. P. Johnston, J . Org. Chem., 27, 4080 (1962). 4953. E. Ochiai and Z . Ichikawa, Yukugaku Zasshi, 58, 632; Supplement, p. 168 (1938). 4954. J. P. H. Verheyden and J. G. Mopdtt, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S . Tipson, Eds.), Wiley, New York, 1968, p. 414. 4955. T. B. Johnson and A. J. Hill, Am. Chem. J., 48, 296 (1912). 4956. E. Reimann. Liebigs Ann. Chem., 1975, 1252.

1310 4957. 4958. 4959. 4960. 4961. 4962. 4963. 4964. 4965. 4966. 4967. 4968. 4969. 4970. 4971. 4972. 4973. 4974. 4975. 4976.

References M. P. Mertes, S. E. Saheb, and D. Miller, J . Med. Chem., 9, 876 (1966). M. P. Mcrtes and S. E. Saheb, J . Pharm. Sci., 52, 508 (1963). C. Heidelberger, D. Parsons, and D. C. Remy, J . Am. Chem. Soc., 84, 3597 (1962). C. Heidelberger, D. G . Parsons, and D. C. Remy, J . M e d . Chem., 7, 1 (1964). A. Haas and W. Hinsch, Chem. Ber., 105, 1768 (1972). M. P. Mertcs and S. E. Saheb, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 112. V. S. Gupta and F. M. Huennekens, Biochemistry, 6, 2168 (1967). A. Albert and F. Reich, J . Chem. Soc., 1961, 127. J. FarkaS and F. Sorm, Collect. Czech. Chem. Commun., 31, 1413 (1966). M. Sprinzl, J. FarkaS, and F. Sorm, Collect. Czech. Chem. Commun., 32, 1649 (1967). B. R. Baker, D. V. Santi, J. K. Coward, H. S. Shapiro, and J. H. Jordaan, J . Heterocycl. Chem., 3, 425 (1966). Y. Nitta, T. Miyamoto, T. Nebashi, and F. Yoneda, Chem. Pharm. Bull., 13, 901 (1965). H. Aft and B. E. Christensen, J . Org. Chem., 27, 2170 (1962). D. Ghosh, J . Med. Chem., 9, 423 (1966). N. G. Pashkurov and V. S. Reznik, Khim. Geterotsikl. Soedin., 1967, 1087. C. T. Goralski and G. A. Burk, J . Org. Chrm., 47, 3094 (1977). A. Haas and W. Hinsch, Chem. Ber., 104, 1855 (1971). K. T. Potts and J. Kane, J . Ory. Chem., 38, 3087 (1973). L. S. German, V. R. Polishchuk, M. N. Preobrazhenskaya, S. Y. Mel’nik, and L. M. Kirshchenya, Khim. Geterotsikl, Soedin., 1974, 859. P. H. Stahl, R. Barchet, and K. W. M e n , Arzneim-Forsch., 18, 1214 (1968).

4977. S. Fabrissin, M. de Nardo, C. Nisi, L. Morasca, E. Dolfini, and G. Franchi, J . Med. Chem., 19, 639 (1976). 4978. E. Hayashi, N. Shimada, and Y. Matsuoka, Yakugaku Zasshi, 99, 114 (1979). 4979. S. Rossi, F. L. Piselli, 0. Pirola, S. Bertani, and N. Passerini, Farmaco, Ed. Sci., 18,499 (1963). 4980. D. J. Brown and R. F. Evans, J . Chem. Soc., 1962, 527. 4981. D. Shapiro, J . Am. Chem. Soc., 73, 3526 (1951). 4982. T. W. Thompson, J . Chem. Soc., Chem. Commun., 1968, 532. 4983. A. Albert and G. Catterall, J . Chem. Soc. ( C ) , 1967, 1533. 4984. C. K. Banks, J . Am. Chem. Soc., 66, 1127 (1944). 4985. A. Maggiolo and A. P. Phillips, J . Org. Chem., 16, 376 (1951). 4986. H. Ackermann, Hell;. Chim. Acta, 49, 454 (1966). 4987. R. G. Shepherd and J. L. Fedrick, Adv. HeterocycL Chem., 4, 145 (1965). 4988. V. P. Mamaev, 0. A. Zagulyaeva, S. M. Shein, and A. I. Shvets, Reakts. Sposobn. Org. Soedin., 2, 61 (1965); Chem. Abstr., 65, 10461 (1966). 4989. S. M. Shein, V. P. Mamaev, 0. A. Zagulyaeva, and A. I. Shvets, Reakts. Sposobn. Org. Soedin., 2, 65 (1965); Chem. Abstr., 65, 10461 (1966). 4990. V. P. Mamaev and 0. A. Zagulyaeva, Zh. Org. Khim., 8, 583 (1972). 4991. V. P. Mamaev, 0. A. Zagulyaeva, and S. M. Shein, Khim. Geterotsikl. Soedin., 1973, 723. 4992. S. G. Smith and I. D. R. Stevens, J . Chem. Educ., 38, 574 (1961). 4993. 4994. 4995. 4996.

T. Kauffmann, R. Niirnberg, and R. Wirthwein, Chem. Ber., 102, 1161 (1969). H. C. van der Plas and A. Koudijs, Rec. Trav. Chim. Pays-Bas, 92, 71 1 (1973). N. B. Chapman and H. Taylor, J . Chem. Soc., 1961, 1908. T. P. Johnston and A. Gallagher, J . Org. Chem., 28, 1305 (1963).

References

131 1

4997. H. Grube and H. Suhr, Chem. Ber., 102, 1570 (1969). 4998. L. N. Yakhontov, M. S. Sokolova, N. I. Koretskaya, K. A. Chkhikvadze, 0.Y. Magidson, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., 1969, 145. 4999. V. K. Karp, V. A. Portnyagina, and I. S. Barkova, Khim. Ceterotsikl. Soedin., 1977, 1252. 5000. .A. M. Buzueva, Khim. Geterotsikl. Soedin., 1968, 157. 5001. R. Andrisano, Boll. Sci. Fac. Chim. Ind. Bologna, 5, 45 (1944-1947); Chem. Abstr., 44, 3904 (1 950). 5002. C. K. Banks, J . A m . Chem. Soc., 66, 1131 (1944). 5003. M. Yanai, S. Takeda, T. Baba, and K. Kitagawa, Yakuguku Zasshi, 94, 1503 (1974). 5004. D. Ghosh and M. Mukherjee, J . Med. Chem., 10, 974 (1967). 5005. M. A. Mikhaleva, I. I. Naumenko, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1979, 821. 5006. P. Roy-Burman, D. Roy, and D. Sen, Naturwissenschafen, 47, 515 (1960). 5007. P. Roy-Burman, D. Sen, and B. C. Guha, Naturwissenschaften, 48, 737 (1961). 5008. P. Roy-Burman and D. Sen, Naturwissenschaften, 49, 494 (1962). 5009. F. Declerck, R. Degroote, J. de Lannoy, R. Nasielski-Hinkens, and J. Nasielski, Bull. Soc. Chim. Belg., 74, 119 (1965). 5010. S . Nishigaki, K . Senga, K. Ogiwara, and F. Yoneda, Chem. Pharm. Bull., 18, 997 (1970). 5011. A. Goldberg, Bull. Soc. Chim. Fr., 1951, 895. 5012. J . Wojciechowski, Rocz. Chem., 41, 1047 (1967). 5013. J. G. Pomomis, D. T. North, and R. G. Zaylskie, J . Med. Chem., 13, 989 (1970). 5014. D. Sen and P. K. Dutta, J . Indian Chem. Soc., 52, 774 (1975). 5015. R. G . R. Bacon and S. D. Hamilton, J. Chem. Soc., Perkin Trans. I , 1972, 1970. 5016. M. Polonovski and H. Jereme, C. R . Acad. Sci., 230, 392 (1950). 5017. J. Clark and A. J. Layton, J . Chem. Soc., 1959, 3411. 5018. J. Clark and T. Ramsden, J . Chem. Soc. (C), 1971, 675. 5019. J. Clark and W. Pendergast, J . Chem. Soc. (C), 1969, 1751. 5020. R. G. Ramage and G . Trappe, J . Chem. Soc., 1952, 4410. 5021. D. E. O’Brien, F. Baiocchi, R. K. Robins, and C. C. Cheng, J . Ory. Chem., 27, 1104 (1962). 5022. A. Stuart, H. C. S. Wood, and D. Duncan, J . Chem. Soc. (C), 1966, 285. 5023. Y. P. Shvachkin and M. K. Berestenko, Zh. Ohshch. Khim., 32, 1712 (1962). 5024. Y. P. Shvachkin and M. K. Berestenko, Zh. Ohshch. Khim., 33, 2842 (1963). 5025. V. P. Shvaehkin, M. K. Berestenko, and V. K. Lapuk, Vestn. Mosk. Uniu., Ser. 2, Khim., 17, N o 3, 74 (1962); Chem. Abstr., 58, 4564 (1963). 5026. J. Clark and F. S. Yates, J . Chem SOC.(C), 1971, 2475. 5027. W. Pfleiderer, Chem. Ber., 107, 785 (1974). 5028. N. Theobald and W. Pfleiderer, Chem. Ber., 111, 3385 (1978). 5029. D. J. Brown and M. N. Paddon-Row, J . Chem. Soc. (C), 1967, 1856. 5030. H. H. Lin and C. C. Price, J . Org. Chem., 26, 108 (1961). 5031. C. L. Leese and G. M. Timmis, J . Chem. Soc., 1958,4107. 5032. R. Hull, J . Chem. Soc., 1958, 4069. 5033. M. Ikehara and E. Ohtsuka, Chem. Pharm. Bull., 9 , 2 7 (1961). 5034. J. H. Lister, J . Chem. Soc., 1960, 3394. 5035. E. Kraas, E. Stark, F.-S. Tjoeng, E. Breitmaier, and G. Jung, Chem. Ber., 108, 1111 (1975). 5036. L. D. Protsenko and Y. I. Bogodist, Ukr. Khim. Zh., 32, 867 (1966); Chem. Abstr., 66, 2531 (1967). 5037. Y. 1. Bogodist, U k r . Khim. Zh., 32, 1091 (1966); Chem. Abstr., 66, 37870 (1967).

1312

References

5038. Y. I. Bogodist and L. D. Protsenko, Ukr. Khim. Zh., 32, 1094 (1966); Chem. Ahstr., 66,94988 (1 967). 5039. G. Konrad and W. Pfleiderer, Chem. Ber., 103, 735 (1970). 5040. C. Temple, C. L. Kussner, and J. A. Montgomery, J . Med. Pharm. Chem., 5, 866 (1962). 5041. H. J. Schaeffer and R. D. Weimar, J . Org. Chem., 2.5, 774 (1960). 5042. J. A. Montgomery and C. Temple, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorhach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 47. 5043. H. J. Schaeffer and C. F. Schwender, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 6. 5044. M. Y. Lidak, Y. Y. Shluke, B. V. Zarinya, and S. E. Poritere, Khim. Geterotsikl. Soedin., 1971, 262. 5045. M. Y. Lidak, Y. Y. Shluke, S. E. Poritere, and Y. P. Shvachkin, Khim. Geterotsikl. Soedin., 1971, 427. 5046. H. Nagano, S. h u e , A. G. Saggiomo, and E. A. Nodiff, J . M e d . Chem., 7, 215 (1964). 5047. T. Masuda, T. Kishi, M. Asai, and S. Kuwada Chem. Pharm. Bull., 7, 361, 366 (1959). 5048. F. Yoneda, Y. Sakuma, M. Ichiba, and K. Shinomura, J . Am. Chem. Soc., 98, 830 (1976). 5049. E. C. Taylor and H. M. Loux, J . Am. Chem. Soc., 81, 2474 (1959). 5050. K. Senga, K. Shimazu, S. Nishigaki, and F. Yoneda, Heterocycles, 6 , 1361 (1977). 5051. S. Nishigaki, J. Sato, K . Shimazu, K. Furukawa, K. Senga, and F. Yoneda, Chem. Phurm. Bull., 28, 142 (1980). 5052. S. Senda and K. Hirota, Chem. Pharm. Bull., 22, 2921 (1974). 5053. A. B. Sen and 0. P. Madan, J . Indian Chem. Soc., 37, 617 (1960). 5054. S. Hoffmann, %. Chem., 8, 147 (1968). 5055. T. B. Johnson and E. H. Hemingway, J . Am. Chem. Soc., 37, 378 (1915). 5056. E. Prom and L. Sitter, Arch. Pharm. (Weinheim, Ger.), 296, 151 (1963). 5057. Y.-F. Chi and Y.-L. T'ien, J . Am. Chem. Soc., 55, 4185 (1933). 5058. M. Pesson and S. Chabassier, C. R . Acad. Sci., Ser. C, 279, 413 (1974). 5059. H. C. Koppel. R. H. Springer, R. K. Robins, and C. C. Cheng, in Nucleic Acid Chemistry, Part 1 (L. B. Townsend and R. S. Tipson, Eds.), Wiley, New York, 1978, p. 53. 5060. 1. Y. Ulane and M. Y. Lidak, Khim. Geterotsikl. Soedin., 1971, 527. 5061. H.-Y. Guo, Z.-L. Yu, S.-M. Su, R.-M. Lian, and Z.-P. Zhang, Yaouxue Xuehao, 18, 185 (1983). 5062. M. Pesson, M. Antoine, S. Chabassier, P. Girard, and D. Richer, C. R. Acad. Sci., Ser. C, 278, 717 (1974). 5063. M. Pesson, P. de Lajudie, M. Antoine, S. Chabassier, D. Richer, and P. Girard, C. R . Acad. Sci., Ser. C, 278, 1169 (1974). 5064. Y. I. Bogodist and L. D. Protsenko, Ukr. Khim. Zh., 36, 1142 (1970); Chem. Abstr., 74, 125614 (1971). 5065. H. Diringcr, T. A. Khwaja, and C. Heidelherger, J . M e d . Chem., 13, 151 (1970). 5066. G. B. Barlin and W. V. Brown, J . Chem. Soc. (B), 1967, 648. 5067. M. Avramoff, J . Med. Chem., 11, 1106 (1968).

C. Temple, B. H. Smith, and J. A. Montgomery, J . Org. Chem., 33, 530 (1967). R. W. Morrison and V. L. Styles, J . Ory. Chem., 47, 674 (1982). M. Ganguly and D. Sen, Indian J . Chem., 1, 364 (1963). I. V. Boldyrev, 0. M. Polumbrik, L. N. Markovskii, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1980, 1545. 5072. J . A. Hyatt and J. S. Swenton, J . Heterocycl. Chem., 9, 409 (1972). 5073. T. L. Chan and J. Miller, Aust. J . Chem., 20, 1595 (1967). 5068. 5069. 5070. 5071.

References 5074. 5075. 5076. 5077.

1313

R. Daniels, L. T. Grady, and L. Bauer, J . Am. Chem. Soc., 87, 1531 (1965). D. H. Kim and A. A. Santilli, J . Heterocycl. Chem., 12, 477 (1975). W. Pfleiderer and R. Lohrmann, Chem. Ber., 95, 738 (1962). M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 33, 210 (1968).

A. W. Dox, J . A m Chem. Soc., 53, 2741 (1931). B. Ohta and H. Kawasaki, Yakugaku Zasshi, 71, 1420 (1951); Chem. Abstr., 46, 8095 (1952). F. H. S. Curd, M. I . Davis, E. Hoggarth, and F. L. Rose, J . Chem. Soc., 1947, 783. D. Ghosh and M. Mukherjee, J . M e d . Chem., 11, 1237 (1968). D. Sen and P. K. Dutta, J . Indian Chem. Soc., 53, 913 (1976). D. Lockhart and E. E. Turner, J . Chem. Soc., 1937, 424. A. Albert and S. Matsuura, J . Chem. Soc., 1961, 5131. E. Warmington, J . Prukt. Chem. 121, 47, 201 (1893). E. C. Taylor and E. A. Garcia, J . Ory. Chem., 29, 2121 (1964). S. Kukolja and Z. Cvetnic, Croat. Chem. Acta, 34, 115 (1962). A. P. Kroon, H. C. van der Plas, and G. van Garderen, Recl. Trav. Chim. Pays-Bas, 93, 325 (1974). 5089. H. C. Koppel, R. H. Springer, R. K. Robins, and C. C. Cheng, J . M e d . Pharm. Chem., 5, 639 (1 962). 5090. I. K. Fel’dman and G . M. Kheifets, Zh. Ohshch. Khim., 31, 755 (1961); Chem. Ahstr., 55, 23544 (1961). 5091. P. A. van Zwieten and H. 0. Huisman, Recl. Trav. Chim.Pays-Bus, 81, 554 (1962).

5078. 5079. 5080. 5081. 5082. 5083. 5084. 5085. 5086. 5087. 5088.

5092. F. Kaimierczak and K. Golankiewicz, Pol. J . Chem., 54, 2357 (1980).

F. Yoneda, K. Tsukuda, M . Kawazoe, and A. Sone, J . Heterocycl. Chem., 18, 1329 (1981). D. J. Brown and P. W. Ford, J . Chem. Soc. (C), 1969, 2720. W. P. Trompen and H. 0. Huisman, Recl. Trac. Chim.Pays-Bas, 85, 177 (1966). B. R. Baker, G . J. Lourens, and J. H. Jordaan, J . Heterocycl. Chem., 4, 39 (1967). V. A. Portnyagina and V. K. Karp, Ukr. Khim. Zh., 31, 83 (1965); Chem. Ahstr., 62, 14665 (1965). 5098. G . H. Singhal, P. M. Thomas, and I . C. Popoff, J . Heterocycl. Chem., 5, 411 (1968). 5099. J. A. Montgomery and K. Hewson, J . Org. Chem., 30, 1528 (1965). 5100. Y.-F. Chi and T.-Y. Ho, Trans. Sci. Soc. Chinu, 8, 69 (1934); Chem. Abstr., 29, 472 (1935). 5101. Y.-F. Chi, Y.-S. Kao, and Y.-T. Huang, J . Am. Chem Soc., 58, 773 (1936). 5102. 0. A. Zagulyaeva and V. P. Mamaev, Izu. Akad. Nauk SSSR, Ser. Khim.,1965, 2087. 5103. Y. P. Shvachkin and M . K. Berestenko, Vestn. Mosk. Uniti., Khim., 18, N o . 1, 74 (1963); Chem. Ahstr., 59, 2811 (1963). 5104. Y. P. Shvachkin, L. A. Syrtsova, M. K. Berestenko, and M. A. Prokof‘ev, Zh. Obshch. Khim., 32, 2060 (1962). 5105. V. V. Lepachev, 0. A. Zagulyaeva, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1977, 395. 5106. J. A. Montgomery and A. G. Laseter, J . Heterocycl. Chem., 9, 1077 (1972). 5107. C. J. Drayton, W. T. Flowers, and R. N. Haszeldine, J . Chem. Soc. (C), 1971, 2750. 5108. B. A. Arbuzov and B. P. Lugovkin, Z h . Ohshch. Khim., 22, 1199 (1952). 5109. T. Itoh, H. Ogura, N. Kawahara, and K. A. Watanabe, Heterocycles, 14, 159 (1980). 5110. H. W. van Meeteren and H. C. van der Plas, Red. Trav. Chim. Pays-Bas, 86, 567 (1967). 5111. H. W. van Meeteren and H. C. van der Plas, Tetrahedron Lett., 1966, 4517. 51 12. V. I . Gunar, 1. A. Mikhailopulo, and S. I. Zav’yalov, Izc. Akad. Nauk SSSR, Ser. Khim., 1966. 1496.

5093. 5094. 5095. 5096. 5097.

1314

References

51 13. R. D. Youssefyeh and M. Weisz, Tetrahedron Lett., 1973, 4317. 51 14. A. Kowalewski, L. Strekowski, M. Szajda, K. Walenciak, and D. J. Brown, Aust. J . Chem.,34, 2629 (1981). 5115. A. P. Phillips, J . Am. Chem. Soc., 75, 4092 (1953). 5116. T. K. Fukuhara and D. W. Visser, J . Am. Chem. Soc., 77,2393 (1955). 5117. M. Roberts and D. W. Visser, J . Am. Chem. Soc., 74, 668 (1952). 51 18. A. Paul and D. Sen, Indian J . Chem., 1 , 9 8 (1963). 5119. A. Paul and D. Sen, Indian J . Chem., 2, 212 (1964). 5120. T. J. Schwan and H. Tieckelmann, J . Org. Chem., 29, 941 (1964). 5121. S. Senda and K. Hirota, J . Chem. Soc., Chem. Commun., 1974,483. 5122. S. Senda, K. Hirota, K. Banno, T. Asao, J. Haruta, and Y. Yamada, Heterocycles, 3, 1128 (1975). 5123. E. C. Taylor, W. W. Paudler, and C. K. Cain, J . Org. Chem., 20, 264 (1955). 5124. M. Busch and F. Keyser, Biochem. Z . , 293, 16 (1937). 5125. Y. 0. Gabel and S. B. Babich, Trudy. Inst. Khim. Khar'koo. Gosudarst. Univ., 5, 21 (1940); Chem. Abstr., 37, 6649 (1943). 5126. Y. 0. Gabel and A. L. Gerschuns, Trudy. Inst. Khim. Khar'kov. Gosudart. Univ., 5, 29 (1940); Chem. Abstr., 37, 6649 (1943). 5127. G. K. Hughes, A. K. Macbeth, and S. W. Pennycuick, J . Chem. Soc., 1934, 769. 5128. G. K. Hughes and A. K. Macbeth, J . Chem. Soc., 1938, 1622. 5129. V. Voorhees and G. S. Skinner, J . Am. Chem. Soc., 47, 1124 (1925). 5130. P. A. Levene and F. B. La Forge, Ber. Dtsch. Chem. Ges., 45, 608 (1912). 5131. H. G. Bray, H. J. Lake, and W. V. Thorpe, Biochem. J., 48,400 (1951). 5132. B. Roth and J. F. Bunnett, J . Am. Chem. Soc., 87, 340 (1965). 5133. W. T. Caldwell and A. N. Sayin, J . Am. Chem. Soc., 74, 4314 (1952). 5134. E. Mulder, Ber. Dtsch. Chem. Ges., 12, 2309 (1879). 5135. T. Yoshikawa, Yakugaku Zasshi, 76, 776 (1956). 5136. A. N. Frolov, A. V. El'tsov, and 0. V. Kul'bitskaya, Khim. Geterotsikl. Soedin., 1974, 1645. 5137. L. Strekowski, Pol. J . Chem., 52, 1579 (1978). 5138. T. V. Rajkumar and S. B. Binkley, J . M e d . Chem., 6, 550 (1963). 5139. T. Kauffmann, B. Greving, R. Kriegesmann, A. Mitschker, and A. Woltermann, Chem. Ber., 111, 1330 (1978). 5140. H. Erlenmeyer and H. D. Furger, Helv. Chim. Acta, 26, 366 (1943). 5141. H. Erlenmeyer and H. D. Furger, H e h . Chim. Acta, 30, 585 (1947). 5142. H. D. Furger, Helv. Chim. Acta, 33, 1689 (1950). 5143. S. Senda, K. Hirota, and J. Notani, Chem. Pharm. Bull., 22, 1179 (1974). 5144. 0.A. Zagulyaeva and V. P. Mamaev, Izv. Sih;Otd. Akad, Nauk SSSR,Ser. Khim. Nauk, No. 5, 115 (1967); Chem. Ahstr., 69, 67314 (1968). 5145. A. Schellenberger and K. Winter, Hoppe-Seyler's Z . Physiol. Chem., 322, 173 (1960). 5146. M. Horiuchi and Y. Sawa, Yakugaku Zashi, 77, 493 (1957). 5147. R. R. Williams, J . Am. Chem. Soc., 57, 229 (1935). 5148. R. R. Williams, R. E. Waterman, J. C. Keresztesy, and E. R. Buchnan, J . Am. Chem. Soc., 57, 536 (1935). 5149. V. P. Shvachkin and L. A. Syrtsova, Vestn. Mosk. Univ., Ser. ZI, Khim., 16, No. 6, 75 (1961); Chem. Ahstr., 57, 8577 (1962). 5150. Y. P. Shvachkin, L. A. Syrtsova, and V. L. Savel'ev, Vestn. Mosk. Unio., Ser. 11, Khim., 17, No. 1, 73 (1962); Chem. Ahstr., 58, 4565 (1963).

References

1315

5151. Y. P. Shvachkin, M. A. Novikova, M. B. Reznikova, and N. S. Padyukova, Zh. Ohshch. Khim., 33, 4022 (1963). 5152. Y. P. Shvachkin and I. K. Shprunka, Vest. Mosk. Unic., Ser. II, Khim., 19, No. 6, 72 (1964); Chem. Ahstr., 62, 6481 (1965). 5153. Y. P. Shvachkin and I. K. Shprunka, Zh. Ohshch. Khim., 35, 2251 (1965). 5154. T. Kato, N. Katagiri, A. Wagai, and Y. Katagiri, Heterocycles, 16, 387 (1981). 5155. W. Schulz and H. Willitzer, Chem. Ber., 100, 3460 (1967). 5156. R. B. Trattner, G. B. Elion, G. H. Hitchings, and D. M. Sharefkin, J . Org. Chem., 29, 2674 (1 964). 5157. K. Sirakawa, Yakugaku Zasshi, 80, 956 (1960). 5158. G. Pellizari and C. Roncagliolo, Gazz. Chim. Ital., 31(I), 513 (1901). 5159. J. Thiele and R. Bihan, Liebigs Ann. Chem., 302, 299 (1898). 5160. G. H. Hitchings, P. B. Russell, and N. Whittaker, J . Chem. Soc., 1956, 1019. 5161. N. A. Poddubnaya and G. I. Lavrenova, Vestn. Mosk. Uniu., Ser. I t , Khim., 18, No. 5, 65 (1963); Chem. Ahstr., 60, 1750 (1964). 5162. V. SkariL, B. GaSpert, and D. Skarit, Croat. Chem. A m , 36, 87 (1964). 5163. R. 0. Hurst and A. Kuksis, Can. J . Biochem. Physiol., 36, 931 (1958); Chem. Ahstr., 52, 20329 (1958). 5164. A. S . Jones, A. M. Mian, and R. T. Walker, J . Chem. Soc. (C), 1966, 1784. 5165. T. L. V. Ulbricht, J . Chem. Soc., 1961, 3345. 5166. R. J. Cushley, I. Wernpen, and J. J. Fox, J . Am. Chem. Soc., 90, 709 (1968). 5167. C. W. Noel1 and C. C. Cheng. J . Heterocycl. Chem., 3, 5 (1966). 5168. N. Ueda, T. Kawabata, and K. Takernoto, J . Heterocycl. Chem., 8, 827 (1971). 5169. M . PrystaS, Collect. Czech. Chem. Commun., 32, 4260 (1967). 5170. W. J. Kriyzosiak, J. Biernat, J. Ciesioika, P. Gornicki, and M. Wiewiorowski, Tetrahedron Lett., 1979, 2647. 5171. A. R. Katritzky and A. J. Waring, Chem. Ind. (London), 1962, 695. 5172. A. R. Katritzky and J. M. Lagowski, Ado. Heterocycl. Chem., 1, 311, 339 (1963). 5173. J. Elguero, C. Marzin, A. R. Katritzky, and P. Linda, Ado. Heterocycl. Chem., Suppl. I , 1976, 71. 5174. Y. Inoue, N . Furutachi, and K. Nakanishi, J . Org. Chem., 31, 175 (1966). 5175. S. Furberg, and J. Solbakk, Acta Chem. Scund., 24, 3230 (1970). 5176. E. Mootz, D. Mootz, and G. A. Jeffrey, Actu Cryst., 19, 691 (1965). 5177. B. M. Craven, personally distributed review (ca. 1966). 5178. G. A. Jeffrey and Y. Kinoshita, Actu Cryst., 16, 20 (1963). 5179. W. Bolton, Actu Cryst., 16, 166 (1963). 5180. G . A. Jeffrey, S. Chose, and J. 0. Warwicker, Acta Cryst., 14, 881 (1961). 5181. B. M. Craven, Acta Cryst., 17, 282 (1964). 5182. G. S . Parry, Aura Cryst., 7, 313 (1954). 5183. S. Swaminathan, B. M. Craven, and R. K. McMullan, Act0 Cryst., Sect. B, 41, 113 (1985). 5184. C. Singh, Acta Cryst., 13, 1036 (1960); 19, 759 (1965). 5185. L. E. Alexander and D. T. Pitman, Actu Cryst., 9, 501 (1956). 5186. W. Bolton, Acta Cryst., 19, 1051 (1965). 5187. W. Bolton, Acta Cryst., 16, 950 (1963). 5188. B. M. Craven, S . Martinez-Carrera, and G. A. Jeffrey, Acta Cryst., 17, 891 (1964). 5189. B. M. Craven and Y. Mascarenhas, Acta Cryst., 17, 407 (1964).

1316

References

5190. 5191. 5192. 5193. 5194.

B. M. Craven and W. J. Takei, Acta Cryst., 17, 415 (1964). H. Gillier, C. R. Acad. Sci., 257, 427 (1963). H. Gillier, Bull. Soc. Chim. Fr., 1965, 2373, 2385. J. Silverman and N. F. Yannoni, Acta Cryst., 18, 756 (1965). F. Bertinotti, M. Bonamico, A. Braibanti, F. Coppola, and G. Giacomello, Ann. Chim. (Rome),

5195. 5196. 5197. 5198. 5199. 5200. 5201. 5202. 5203. 5204. 5205. 5206. 5207. 5208.

J. Berthou, C. Cavelier, C. Marek, B. Rtrat, and C. Rerat, C. R . Acud. Sci.,255, 1632 (1962).

49, 825 (1959). J. Berthou, B. Rerat, and C. Rerat, Acta Cryst., 18, 768 (1965).

R. F. Bryan and K.-I. Tomita, Nature (London), 192, 812 (1961). R. F. Bryan and K.-I. Tomita, Acta Cryst., 15, 1174 (1962). H. M. Sobell and K.-I. Tomita, Acta Cryst., 17, 122 (1964). K. Hoogsteen, Acta Cryst., 16, 28 (1963). S. Chose, G. A. Jeffrey, B. M. Craven, and J. 0. Warwicker, Acta Cryst., 13, 1034 (1960). C. A. Dekker, Annu. Rev. Biochem., 29, 453 (1960). 0. Jardetzky, P. Pappas, and N. G. Wade, J . Am. Chem. Soc., 85, 1657 (1963). J. P. Kokko, J. H. Coldstein, and L. Mandell, J . Am. Chem. SOC.,83, 2909 (1961). J. P. Kokko, L. Mandell, and J. H. Goldstein, J . Am. Chem. Soc., 84, 1042 (1962). A. R. Katritzky and R. A. Y . Jones, Chem. lnd. (London), 1961, 722. E. Wittenburg, Chem. Ber., 99, 2391 (1966). K. Berens and D. Shugar, Acta Biochim. Pol., 10, 25 (1963). 5209. D. Cook, Can. J . Chem., 44, 335 (1966). 5210. B. W. Roberts, J. B. Lambert, and J. D. Roberts, J . Am. Chem. Soc., 87, 5439 (1965). 5211. H. T. Miles, R. B. Bradley, and E. D. Becker, Science, 142, 1569 (1963). 5212. T. L. V. Ulbricht, J . Chem. Soc., 1965, 6134. 5213. A. R. Katritzky, F. D. Popp, and A. J. Waring, J . Chem. Soc. ( B ) , 1966, 565. 5214. Y. M. Boyachuk, M. V. Volkenstein, G. M. Kheifets, and N. V. Khromov-Borisov, Khim. Geterotsikl. Soedin., 1967, 338. 5215. G. M. Kheifets, N. V. Khromov-Borisov, A. I. Koltsov, and M. V. Volkenstein, Tetrahedron, 23, 1197 (1967). 5216. M. Berndt, M. Ingwer, and J. S. Kwiatkowski, J . Mol. Struct., 19, 247 (1973). 5217. M. Draminski and B. Fiszer, Rocz. Chem., 45, 211 (1971). 5218. R. L. Lipnick and J. D. Fissekis, J . Org. Chem., 44, 1627 (1979). 5219. J. A. Glasel, Ory. M a p . Reson., 1, 481 (1969). 5220. F. Mihai and R. Nutiu, Rev. Roum. Chim., 13, 39 (1968). 5221. Z. Simon, F. Mihai, and R. Nu+, Rev. Roum. Chim., 13, 147 (1968). 5222. R. Nutiu and Z. Simon, Rev. Roum. Chim., 14, 311 (1969). 5223. R. Nutiu, L. Kurunczi, and 2. Simon, Rev. Roum. Chim., 14, 1435 (1969). 5224. D. Shugar and K. Szczepaniak, lnt. J . Quantum Chem., 20, 573 (1981). 5225. A. R. Katritzky, M. Kingsland, and 0. S. Tee, J . Chem. Soc., Chem. Commun., 1968, 289; J . Chem. Soc. ( B ) , 1968, 1484. 5226. T. Nishiwaki, Tetrahedron, 23, 2657 (1967). 5227. S. Schiebye, J. Kristensen, and S . - 0 . Lawesson, Tetrahedron, 35, 1339 (1979). 5228. A. G. Beaman and R. K. Robins, J . Am. Chem. Soc., 83, 4038 (1961). 5229. I. Wempen, N. Miller, E. A. Falco, and J. J. Fox, J . Med. Chem., 11, 144 (1968). 5230. B. Dash, E. K. Dora, and C. S. Panda, Heterocycles, 19, 2093 (1982). 5231. Y. Mizuno, M. Ikehara, and K. A. Watanabe, Chem. Phurm. Bull., 10, 647 (1962).

References

1317

5232. K. Golankiewicz and J. Langer, Rocz. Chem., 50, 1805 (1976). 5233. S. Scheibye, B. S. Pedersen, and S. 0. Lawesson, Bull. Soc. Chim. Bely., 87, 229 (1978). 5234. H. C. Carrigton, J . Chem. Soc., 1944, 124. 5235. H. R. Henze and P. E. Smith, J . Am. Chem. Soc., 65, 1090 (1943). 5236. A. Pinner, Ber. Dtsch. Chem. Ges., 18, 759 (1x85). 5237. A. NoviEek, D. Hesoun, and J. Gut, Collect. Czech. Chem. Commun., 30, 1890 (1965). 5238. J. Gubin, N. Durant, R. Nasielski-Hinkens, and R. Promel, Bull. Soc. Chim. Belg., 82, 371 (1973). 5239. L. Birkofer, P. Richter, and A. Ritter, Chem. Ber., 93, 2804 (1960). 5240. L. Birkofer, H. P. Kuhlthau, and A. Ritter, Chem. Bey., 93, 2810 (1960). 5241. J. C. Nnadi and S. Y. Wang, J . Am. Chem. Soc., 92, 4421 (1970). 5242. L. Strekowski, Rocz. Chem., 47, 1645 (1973). 5243. E. Wittenburg, Angew. Chem., 77, 1043 (1965). 5244. L. Birkofer and A. Ritter, Angew. Chem., 77, 414 (1965). 5245. R. Funakoshi, M. Irk, and T. Ukita, Chem. Pharm. Bull., 9, 406 (1961). 5246. K. 0. Ellis, T. J. Schwan, F. L. Wessels, and N. J. Miles, J . Phurm. Sci., 69, 1194 (1980). 5247. Y. S. Shvetsov, A. N. Shirshov, and V. S. Reznik, Izv. Akad. Nuuk SSSR, Ser. Khim., 1977,884. 5248. G . Tsatsaronis and D. Grekou-Lazana, Bull. Soc. Chim. Fr., 1980, 11, 559. 5249. A. Pinner, Ber. Dtsch. Chem. Ges., 23, 3820 (1890). 5250. S. I. Zav’yalov, V. 1. Gunar, and L. F. Oveehkina, Izu. Akud. Nauk SSSR, Ser. Khim., 1972, 210. 5251. S. I. Zav’yalov, V. 1. Gunar, Z . A. Martirosyan, and L. F. Ovechkina, Izo. Akad. Nuuk S S S R , Ser. Khim., 1972, 2530. 5252. A. S. Mikhailov, N. G. Pashkurov, and V. S . Reznik, Izu. Akud. Nuuk SSSR, Ser. Khim., 1981, 155. 5253. V . B. Ivanov, V. S. Reznik, and Y. Y. Efremov, Izv. Akad. Nauk S S S R , Ser. Khim., 1982, 217. 5254. S. Hillers, R. A. Zhuk, and Y. G. Nashatyr, Khim. Geterotsikl. Soedin., 1968, 557. 5255. T. Kanno and M. Kawazu, Chem. Phurm. Bull., 22, 2836 (1974). 5256. C. Runti and A. Colautti, Pror.. f n t . Conyr. Chemother., 5, 307 (1967); Chem. Ahstr., 70, 20019 (1969). 5257. A. J. H. Nollet, G. J. Koomen, W. 4607.

F.A. Grose, and U. K. Pandit, Tetrahedron Lett., 1969,

5258. J. FarkaS and F. Sorm, Collect. Czech. Chem. Commun., 28, 1620 (1963). 5259. J. Evans and T. B. Johnson, J . Am. Chem. Soc., 52, 4993 (1930). 5260. W. Szer and D. Shugar, Actu Biuchim. Pol., 7, 491 (1960). 5261. E. A. Falco and J. J. Fox, J . Med. Chem., 1 1 , 148 (1968). 5262. J. F. Codington, R. J. Cushley, and J. J. Fox, J . Org. Chem., 33, 466 (1968). 5263. N. Yamaoka, B. A. Otter, and J. J. Fox, J . Med. Chem., 11, 55 (1968). 5264. Z. A. Martirosyan, V. I. Gunar, and S. I. Zav’yalov, Izo. Akad. Nauk SSSR, Ser. Khim., 1969, 2339. 5265. L. Strqkowski, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 21, 257 (1973). 5266. T. Kunieda and B. Witkop, J . Am. Chem. Soc., 93, 3478 (1971). 5267. J. Herzig, Hoppe-Seyler’s Z . Physiol. Chem., 117, 13 (1921). 5268. P. Gold-Aubert and E. Gysin, Helu. Chim. Acta, 44, 105 (1961). 5269. M. Conrad and M. Guthzeit, Ber. Dtsch. Chem. Ges., 14, 1643 (1881). 5270. J. A. Vida, Tetrahedron Lett., 1972, 3921.

1318

References

5271. J. Bojarski. W. Kahl. and M. Melzacka. Rocz. Chem., 36, 1259 (1962); Chem. Ahstr., 59, 5158 ( 1963). 5272. J. Bojarski and W. Kahl. Rocz. Chem., 37, 589 (1963); Chem. Abstr., 59, 8746 (1963). 5273. W. Kahl and M. Melzacka. Rocz. Chem., 37, 591 (1963); Chem. Ahstr., 59, 8746 (1963). 5274. J. Bojarski and W. Kahl. Rocz. Chem., 38, 1493 (1964); Chem. Ahstr., 62, 9127 (1965). 5275. J. Bojarski, W. Kahl, and M. Melzacka, Rocz. Chem., 39, 875 (1965); Chem. Ahstr., 64, 5088 (1966). 5276. J. Bojarski, W. Kahl, and M. Melzacka, Rocz. Chem., 40, 1465 (1966); Chem. Ahstr., 67, 11470 (1967). 5277. W. Kahl and Z. Chytros-Majchrowicz, Rocz. Chem., 40, 1905 (1966); Chem. Abstr., 67, 11469 (1967). 5278. J. Bojarski and W. Kahl, Rocz. Chem., 41, 311 (1967); Chem. Abstr., 67, 54093 (1967). 5279. J. P. Scannell, A. M. Cresfield, and F. W. Allen, Biochim. Biophys. Acta, 32, 406 (1959). 5280. T. B. Johnson and J. H. Derby, Am. Chem. J . , 40, 444 (1908). 5281. U. Sanyal and S. K. Chakraborti, Synth. Commun., 12, 1047 (1982). 5282. T. Kametani, K. Kigasawa, M. Hiiragi, K. Wakisaka, 0. Kusama, H. Sugi, and K. Kawasaki, Heterocycles, 6, 529 (1977). 5283. A. J. H. Nollet and U. K. Pandit, Tetrahedron Lett., 1969, 4605. 5284. T. Itoh and W. Pfleiderer, Chem. Ber., 109, 3228 (1976). 5285. P. D. Lawley and P. Brookes, Biochem. J., 89, 127 (1963). 5286. J. A. Vida, Synth. Commun., 3, 105 (1973). 5287. E. A. Arutyunyan, V. I. Gunar, E. P. Gracheva, and S. I. Zav’yalov, Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 445. 5288. E. A. Arutyunyan, V. I. Gunar, and S. I. Zav’yalov, Izv. Akad. Nauk SSSR, Ser. Khim., 1969, 2857. 5289. L. Helgeland and S. Laland, Biochim. Biophys. Acta, 87, 353 (1964). 5290. V. P. Mamaev and E. A. Gracheva, Khim. Geterotsikl. Soedin., 1968, 516. 5291. H. Gysin and A. Margot, Agr. Food Chem., 6, 900 (1958). 5292. S. Y. Wang et al., in Photochemistry and Photobiology of Nucleic Acids, Vols. 1, 2 (S. Y. Wang, Ed.), Academic Press, New York, 1976. 5293. A. M. Moore, Can. J . Chem., 36, 281 (1958). 5294. F. F. Heyroth and J. R. Loofbourow, J . Am. Chem. Soc., 53, 3441 (1931). 5295. R. L. Sinsheimer and R. Hastings, Science, 110, 525 (1949). 5296. S. Y. Wang, J . Am. Chem. Soc., 80, 6199 (1958). 5297. A. M. Moore and C. H. Thompson, Science, 122, 594 (1955). 5298. A. M . Moore and C. H. Thompson, Can. J . Chem., 35, 163 (1957). 5299. H. Gattner and E. Fahr, Liehigs Ann. Chem., 670, 84 (1963). 5300. G. Scholes, J. F. Ward, and J. J. Weiss, Science, 133, 2016 (1961). 5301. S. Y. Wang, Photochem. Photobiol., 1, 135 (1962). 5302. I. Pietrzykowska and D. Shugar, Acta Biochim. Pol., 17, 361 (1970). 5303. (a) S. Y. Wang, J. C. Nnadi, and D. Greenfeld, J . Chem. Soc., Chem. Commun., 1968, 1162; (b) S. Y. Wang and J. C. Nnadi, J . Chem. Soc., Chem. Commun., 1968, 1160. 5304. D. Elad and I. Rosenthal, J . Chem. Soc., Chem. Commun., 1968, 879. 5305. D. Shugar and K. L. Wierzchowski, Posfepy. Biochem., Suppl., 4, 243 (1958). 5306. B. Ekert and R. Monier, Nature (London),184, BA 58 (1959). 5307. S. Y. Wang, Nature (London), 184, BA 61 (1959).

References

1319

5308. S. Y. Wang, in Excited States in Organic Chemistry and Biochemistry (B. Pullmam and N. Goldblum, Eds.), Reidel, Dordrecht, 1977, p. 39. 5309. J. Cadet, L . 3 Kan, and S. Y. Wang, J . Am. Chem. Soc., 100, 6715 (1978). 5310. G. J. Fisher and H. E. Johns, in Photochemistry and Photobiology of Nucleic Acids, Vol. 1 (S. Y. Wang, Ed.), Academic Press, New York, 1976: (a) p. 169, (b) p. 225, (c) p. 252. 5311. W. E. Cohn, N. J. Leonard, and S. Y. Wang, Photochem. Photobiol., 19, 89 (1974). 5312. R. Alcantara and S. Y. Wang, Photochem. Photobiol., 4, 473 (1965). 5313. S. Y. Wang and R. Alcantara, Photochem. Photobiol., 4, 477 (1965). 5314. M. Danield and A. Crimson, Nature (London),197, 484 (1963). 5315. D. Barszcz and D. Shugar, Acta Biochim. Pol., 8, 455 (1961). 53 16. C. Nofre. P. Bobillier. M . Chabre. and A. Cier, Bull. Soc. Chim. Fr., 1965, 2820. 5317. B. S. Hahn and S. Y. Wang, Biochem. Biophys. Res. Commun., 54, 1224 (1973). 5318. H.-S. Ryang and S. Y. Wang, J . Am. Chem. Soc., 100, 1302 (1978). 5319. G. Scholes, J. J. Weiss, and C. M. Wheeler, Nature (London),178, 157 (1956). 5320. J. Cadet and R. Teoule, Biochim. Biophys. Acta, 238, 8 (1971). 5321. R. Teoule and J. Cadet, J . Chem. Soc., Chem. Cornmun., 1971, 1269. 5322. L. W. Bass, J . Am. Chem. Soc., 46, 190 (1924). 5323. S. Y . Wang, Photochem. Photobiol., 3, 395 (1964). 5324. S. Y. Wang, Fed. Proc., Fed. Am. Soc. Exp. Biol., 24, S-71 (1965). 5325. A. J. Varghese and S. Y. Wang, Nature (London),213, 909 (1967). 5326. A. J. Varghese and S. Y. Wang, Science, 156, 955 (1967). 5327. S. Y. Wang, M. A. Patrick, A. J. Varghese, and C. L. Rupert, Proc. Natl. Acad. Sci. U S A ,57, 465 (1967). 5328. K. L. Wierzchowski, Postepy Biochem., 13, 127 (1967). 5329. R. Beukers, J. Ylstra, and W. Berends, Reel. Trau. Chim. Pays-Bas, 77, 729 (1958). 5330. R. Beukers and W. Berends, Biochim. Biophys. Actu, 41, 550 (1960). 5331. R. Beukers and W. Berends, Biochirn. Biophys. Acta, 49, 181 (1961). 5332. S. Y. Wang, Nature (London), 188, 844 (1960). 5333. S. Y. Wang, Nature (London), 190, 690 (1961). 5334. A. W. Wacker, H. Dellweg, and E. Lodemann, Angew. Chem., 73, 64 (1961). 5335. D. L. Wulff and G. Fraenkel, Biochim. Biophys. Acta, 51, 332 (1961). 5336. S. Y. Wang, Nature (London),200, 879 (1963). 5337. A. W. Wacker, Proyr. Nucleic Acid Res., 1, 369 (1963).

5338. G. M. Blackburn and R. J. H. Davies, J . Chem. Soc., Chem. Commun., 215 (1965);J . Chem. Soc. (C), 1966, 2230. 5339. R. Anet, Tetrahedron Lett., 1965, 3713. 5340. D. P. Hollis and S. Y. Wang, J . Org. Chem., 32, 1620 (1967). 5341. C. Fenselau, S. Y. Wang, and P. Brown, Tetrahedron, 26, 5923 (1970). 5342. I. von Wilucki, H. Matthaus, and C. H. Krauch, Photochem. Photobiol., 6,497 (1967). 5343. T. Kunieda and B. Witkop, J . Am. Chem. Soc., 93, 3493 (1971). 5344. H. Ishihara, Photochem. Photobiol., 2, 455 (1963). 5345. A. Wacker, J . Chim. Phys., 58, 1041 (1961). 5346. A. Wacker, D. Weinblum, D. Triger, and 2. H. Moustafa, J . Mol. Biol., 3, 790 (1961). 5347. K. C. Smith, Photochem. Photohiol,, 2, 503 (1963). 5348. A. Rorsch, R. Beukers, R . Ijlstra, and W. Berends, R e d . Tral;. Chim. Pays-Bas, 77, 423 (1958).

1320 5349. 5350. 5351. 5352. 5353. 5354. 5355. 5356. 5357.

References E. Adman, M. P. Gordon, and L. H. Jensen, J . Chem. Soc., Chem. Commun., 1968, 1019. J. Fendler and G. Bogan, Photochem. Photobiol., 20, 323 (1974). I. H. Brown and H. E. Johns, Photochem. Photohiol., 8, 273 (1968). D. Elad, I. Rosenthal, and S. Sasson, .I. Chem. Soc. (C),1971, 2053. E. Fahr, R. Pastille, and H.Mager1, 2. Naturforsch., Teil B, 28, 454 (1973). H. Taguchi and S. Y. Wang, J . Org. Chem., 42, 3321 (1977). G. Furst, E. Fahr, and H. Wieser, Z . Naturforsch., Teil B, 22, 354 (1967). E. Stepien, R. Lisewski, and K. L. Wierzchowski, Actu Biochim. Pol., 20, 313 (1973). J. C. Nnadi and S. Y. Wang, Tetrahedron Lett., 1969, 221 1.

5358. J. Konnert, J. W. Gibson, I. L. Karle, M. N. Khattak, and S. Y. Wang, Nature (London),227, 953 (1970). 5359. H. Morrison, A. Feeley, and R. Kleopfer, J . Chem. Soc., Chem. Commun., 1968, 358. 5360. H. Morrison and R. Kleopfer, J . Am. Chem. Soc., 90, 5037 (1968). 5361. N. Camerman, D. Weinblum, and S. C. Nyberg, J . Am. Chem. Soc., 91, 982 (1969). 5362. R. Lisewski and K. L. Wierzchowski, Mol. Photochem., 3, 231 (1971). 5363. R. Kleopfer and H. Morrison, J . Am. Chem. Sue., 94, 255 (1972). 5364. B. H. Jennings, S. C. Pastra, and J. L. Wellington, Photochem. Photohiol., 11, 215 (1970). 5365. G . J. Fisher and H. E. Johns, Photochem. Photobid., 11, 429 (1970). 5366. G. M. Blackburn and R. I. H. Davies, J . Chem. Soc. (C),1966, 1342. 5367. J. R. Einstein, J. L. Hosszu, J. W. Longworth, R. 0.Rahn, and C. W. Wei, J . Chem. Soc., Chem. Commun., 1967, 1063. 5368. R. Lisewski and K. L. Wierzchowski, Photochem. Photobiol., 11, 327 (1970). 5369. M. N. Khattak and S. Y. Wang, Tetrahedron, 28, 945 (1972). 5370. A. Smietanowska and D. Shugar, Bull. Acad. Pol. Sci.,Cl. 2, 9, 375 (1961); Chem. Ahstr., 56, 11982 (1962). 5371. J. G. Otten, C. S. Yeh, S. Byrn, and H. Morrison, J . Am. Chem. Soc., 99, 6353 (1977); D. W. Whillans and H. E. Johns, Photochem. Photobiol., 9, 323 (1969). 5372. G. I. Birnbaum, S. M. Dunston, and A. G. Szabo, Tetrahedron Lett., 1971, 947. 5373. J. L. Flippen, 1. L. Karle, and S. Y. Wang, Science, 169, 1084 (1970). 5374. S. Y. Wang, J . Am. Chem. Soc., 93, 2768 (1971). 5375. K. Golankiewicz, M. Szajda, and E. Wyrzykiewicz, Pol. J . Chem., 53, 529 (1979). 5376. K.-H. Pfoertner, Helu. Chim. Actu, 58, 865 (1975). 5377. B. Czochralska, D. Shugar, S. K. Arora, R. B. Bates, and R. S. Cutler, J . Am. Chem. Soc., 99, 2583 (1977). 5378. A. J. Varghese and S. Y. Wang, Biochem. Biophys. Res. Commun., 33, 102 (1968). 5379. I. L. Karle, S. Y. Wang, and A. J. Varghese, Science, 164, 183 (1969). 5380. M. N. Khattak and S. Y. Wang, Science, 163, 1341 (1969). 5381. D. F. Rhoades and S. Y. Wang, Biochemistry, 9, 4416 (1970). 5382. S. Y. Wang and D. F. Rhoades, J . Am. Chem. Soc., 93, 2554 (1971). 5383. S. Y. Wang and A. J. Varghese, Biochem. Biophys. Res. Commun., 29, 543 (1967). 5384. J. L. Flippen, R. D. Gilardi, I. L. Karle, D. F. Rhoades, and S. Y. Wang, J . Am. Chem. Soc., 93, 2556 (1971). 5385. H. Ishihara and S. Y. Wang, Biochemistry, 5, 2303, 2307 (1966). 5386. S. Sasson and S. Y. Wang, Photochem. Photohiol., 26, 357 (1977). 5387. S. Y. Wang, in Photochemistry and Photobiology of Nucleic Acids, Vol. 1 (S. Y. Wang, Ed.), Academic Press, New York, 1976: (a) p 295; (b) p. 326.

References

1321

S. C. Shim and K. H. Chae, Photochem. Photobiol., 30, 349 (1979). T. Itoh, H. Ogura, N. Kawahara, and K. A. Watanabe, Heterocycles, 12, 1175 (1979). J. S. Swcnton, J. A. Hyatt, J. M. Lisy, and J. Clardy, J . Am. Chem. Soc., 96, 4885 (1974). G. Sziligyi, H. Wamhoff, and P. Sohar, Chem. Ber., 107, 1265 (1974). 5392. A. Albert and J. J. McCormack, J. Chem. Soc., 1965, 6930. 5393. A. Albert and J. J. McCormack, J . Chem. Soc. (C), 1968, 63. 5394. S. M. Sax, P. J. Migliori, and R. H. Baughman, Anal. Biochem., 3, 150 (1962). 5395. M. Freifelder, A. 0. Geiszler, and G. R. Stone, J . Org. Chem., 26, 203 (1961). 5396. A. Ascoli, Moppe-Seyler’s Z. Physiol. Chem., 31, 161 (1900). 5397. T. B. Osborn and I. F. Harris, Hoppe-Seyler’s Z . Physiol. Chem., 36, 85 (1902). 5398. A. Kossel and H. Steudel, Iioppe-Seyler’s Z. Physiol. Chem., 37, 245 (1902). 5399. P. A. Levene, fioppe-Seyler’s Z . Physiol. Chem., 38, 80 ( I 903). 5400. A. J. Varghese and S. Y. Wang, Science, 160, 186 (1968). 5401. F. Simon and M. Meneghini, Arq. Inst. B i d , Sao Puulo, 30, 69 (1963). 5402. K. Hirota, K. A. Watanabe, and J. J. Fox, J . Heterocycl. Chem., 14, 537 (1977). 5403. W. Snipes and W. Bernhard, Radiut. Res., 33, 162 (1968); Chem. Ahstr., 68, 44735 (1968). 5404. J. P. Ferris and P. C. Joshi, J . Org. Chem., 44, 2133 (1979). 5405. M. H. Pfdltz and 0. Baudisch, J . Am. Chem. Soc., 45, 2972 (1923). 5406. L. W. Bass and 0. Baudisch, J . Am. Chem. Soc., 46, 181 (1924). 5407. G. Harris and R. Parsons, Chem. Ind. (London), 1956, 1312. 5408. E. B. Brown and T. B. Johnson, J . Am. Chem. Soc., 45, 2702 (1923). 5409. R. Fosse, A. Hieulle, and L. W. Bass, C. R . Acad. Sci., 178, 811 (1924). 5410. F. Lingens and H. Schneider-Bernlohr, Angew. Chem., 76, 378 (1964). 5411. D. H. Hayes and F. Hayes-Baron, J . Chem. Soc. (C), 1967, 1528. 5412. S. Fujita and S. Steenken, J . Am. Chem. Soc., 103, 2540 (1981). 5413. S. Lewin, J . Chem. Soc., 1964, 792. 5414. H. Steudel, lioppe-Seyler’s Z . Physiol. Chem., 32, 241 (1901). 5415. J. W. Littlefield and D. B. Dunn, Nature (London), 181, 254 (1958). 5416. J. W. Littlefield and D. B. Dunn, Biochem. J., 70, 642 (1958). 5417. T. B. Johnson, J . Biol. Chem., 4, 407 (1908). 5418. 0. Baudisch and D. Davidson, J . Biol. Chem., 64,233 (1925). 5419. 0. Baudisch and L. W. Bass, J . Am. Chem. Soc., 46, 184 (1924). 5420. J. Cadet, J. Ulrich, and R. Teoule, Tetrahedron, 31, 2057 (1975). 5421. H. Hatsu and S. Iida, Tetrahedron Lett., 1969, 1031. 5422. F. Freeman, C. 0. Fuselier, C. R. Armstead, C. E. Dalton, P. A. Davidson, E. M. Karchesfski, D. E. Krochman, M. N. Johnson, and N. K. Jones, J . Am. Chem. Soc., 103, 1154 (1981). 5423. H. H. Harkins and T. B. Johnson, J . Am. Chem. Soc., 51, 1237 (1929). 5424. A. Kossel and H. Steudel, Hoppe-Seyler’s Z . Physiol. Chem., 37, 177 (1902). 5425. A. Kossel and H. Steudel, Hoppe-Seyler’s Z . Physiol. Chem., 37, 377 (1902). 5426. A. Kossel and H. Steudel, Hoppe-Seyler’s Z. Physiol. Chem., 38, 49 (1903). 5427. F. Kutscher, Hoppe-Seyler’s Z . Physiol. Chem., 38, 170 (1903). 5428. H. L. Wheeler and T. B. Johnson, Am. Chem. J., 29, 505 (1903). 5429. F. Cramer and H. Seidel, Biochim. Biophys. Acta, 72, 157 (1963). 5430. T. J. Delia, M. J. Olsen, and G. B. Brown, J . Org. Chem., 30, 2766 (1965). 5431. H. Schuster, J . Mol. Bid., 3, 447 (1961).

5388. 5389. 5390. 5391.

1322 5432. 5433. 5434. 5435. 5436. 5437. 5438. 5439. 5440. 5441. 5442. 5443. 5444. 5445.

References D. M. Brown and P. Schell, J . Mol. Biol., 3, 709 (1961). D. M. Brown and M. J . E. Hewlins, J . Chem. Soc. (C), 1968, 1922. D. E. Bergstrom and N. J. Leonard, Biochemistry, 11, 1 (1972). D. E. Bergstrom, I. Inoue, and N. J. Leonard, J . Org. Chem., 37, 3902 (1972). H. Ritthausen and U. Kreusler, J . Prakt. Chem. 121, 2, 333 (1870). H. Ritthausen, Ber. Dtsch. Chem. Ges., 9, 301 (1876). H. Ritthausen, J . Prakt. Chem. 121, 24, 202 (1881). H. Ritthausen, Ber. Dtsch. Chem. Ges., 29, 2108 (1896). E. Schulze and G. Trier, Hoppe-Seyler’s Z . Physiol. Chem., 70, 143 (1911). T. B. Johnson, J . Am. Chem. Soc., 36, 337 (1914). T. B. Johnson and C. 0. Johns, J . Am. Chem. Soc., 36, 545 (1914). P. A. Levene, J . Biol. Chem., 18, 305 (1914). R. E. Bowman and J. Davoll, Chem. Ind. (London),1956, 138. 1. A. Clark, W. B. Cowden, N. H. Hunt, L. E. Maxwell, and E. J. Mackie, Br. J . Haematol., 57, 479 (1984).

5446. H. J. Fisher and T. B. Johnson, J . Am. Chem. Soc., 54, 2038 (1932). 5447. J. Mager, G. Glaser, A. Razin, G. Izdk, S. Bien, and M. Noam, Biochem. Biophys. Res. Commun., 20, 235 (1 965). 5448. T. B. Johnson and R. D. Coghill, J . Am. Chem. Soc., 47, 2838 (1925). 5449. E. Vischer, S. Zamenhof, and E. Chargaff, J . B i d . Chem., 177, 429 (1949). 5450. R. D. Hotchkiss, J . Biol. Chem., 175, 315 (1948). 5451. G. R. Wyatt, Nature (London), 166, 237 (1950). 5452. G. R. Wyatt, Biochem. J., 48, 581 (1951). 5453. G. R. Wyatt, Biochem. J., 48, 584 (1951). 5454. G. Brawerman and E. Chargaff, J . Am. Chem. Soc., 73, 4052 (1951). 5455. G. R. Wyatt, E x p . Cell Res., Suppl., 2, 201 (1952). 5456. G. R. Wyatt and S. S. Cohen, Nature (London),170, 1072 (1952). 5457. G. R. Wyatt and S. S. Cohen, Biochem. J., 55, 774 (1953). 5458. J. L. Nichols and B. G. Lane, Biochim. Biophys. Acta, 119, 649 (1966). 5459. R. Gmelin, Hoppe-Seyler’s Z . Physiol. Chem., 316, 164 (1959). 5460. R. Gmelin, Acta Chem. Scand., 15, 1188 (1961). 5461. A. Kjaer, A. Knudsen, and P. Olesen-Larsen, Acta Chem. Scand., 15, 1193 (1961). 5462. F. Tanaka, S. Takeuchi, N. Tanaka, H. Yonehara, H. Umezawa, and Y. Sumiki, J . Antibiot., Ser. A , 14, 161 (1961). 5463. F. Tanaka, N. Tanaka, H. Yonehara, and H. Umezawa, J . Antihiot., Ser. A, 15, 191 (1962). 5464. C. C. Cheng, Prog. Med. Chem., 6, 67 (1969). 5465. T. Kanzaki, E. Higashide, H. Yamamoto, M. Shibata, K. Nakazawa, H. Iwasaki, T. Takewaka, and A. Miyake, J . Antibiot., Ser. A , 15, 93 (1962). 5466. J. J. Fox and K. A. Watanabe, Tetruhedron Lett., 1966, 897. 5467. J. J. Fox, Y. Kuwada, K. A. Watanabe, T. Ueda, and E. B. Whipple, Antimicrob. Agents Chemother., 1964, 518; Chem. Abstr., 63, 3477 (1965). 5468. J. J. Fox, Y. Kuwada, and K. A. Watanabe, Tetrahedron Lett., 1968, 6029. 5469. K. A. Watanabe, M. P. Kotick, and J. J. Fox, Chem. Pharm. Bull., 17, 416 (1969). 5470. K. A. Watanabe, E. A. Falco, and J. I. Fox, J . Am. Chem. Soc., 94, 3272 (1972). 5471. S. Takeuchi, K. Hirayama, K. Ueda, H. Sakai, and H. Yonehara, J . Antibiot., Ser. A , 11, 1 (1958).

References

1323

5472. H. Yonehara, S. Takeuchi, N. Otaka, T. Endo, and Y. Sumiki, J . Antihiof.,Ser. A, 16, 195 (1963). 5473. N. Otaka, S. Takeuchi, T. Endo, and H. Yonehara, Tetrahedron Lett., 1965, 1405, 1411. 5474. S. Onuma, Y. Nawata, and Y. Saito, Bull. Chem. Soc. Jpn., 39, 1091 (1966). 5475. K. A. Watanabe, I. Wempen, and J. J. Fox, Chem. Pharm. Bull., 18, 2368 (1970). 5476. C. de Boer, E. L. Caron, and J. W. Hinman, J . Am. Chem. SOC., 75, 499 (1953). 5477. J. W. Hinman, E. L. Caron, and C. de Boer, J . Am. Chem. Soc., 75, 5864 (1953). 5478. T. H. Haskell, A. Ryder, R. P. Frohardt, S. A. Fusari, Z. L. Jakubowski, and Q. R. Bartz, J . Am. Chem. Soc., 80, 743 (1958). 5479. C. L. Stevens, R. J. Gasser, T. K. Mukherjee, and T. H. Haskell, J . Am. Chem. Soc., 78, 6212 (1956). 5480. T. H. Haskell, J . Am. Chem. Soc., 80, 743 (1958). 5481. C. L. Stevens, K. Nagarajan, and T. H. Haskell, J . Ory. Chem., 27, 2991 (1962). 5482. J. J. Fox, C. Lopez, and K. A. Watanabe, in Medicinal Chemistry Adljances (F. G. de las Heras and S. Vega, Eds.), Pergamon Press, Oxford, 1981, p. 27. 5483. S. P. Owen, A. Dietz, and G. W. Camiener, Antimicroh. Agents Chemother., 1962, 772. 5484. A. D. Argoudelis and R. R. Herr, Antimicrob. Agents Chernother., 1962, 780. 5485. H. C. J. Ottenheijm, R. M. J. Liskamp, P. Helquist, J. W. Lauher, and M. S. Shekhani, J . Am. Chem. Soc., 103, 1720 (1981). 5486. H. C. J. Ottenheijm and R. M. J. Liskamp, Tetrahedron Lett., 1978, 2437. 5487. H. C. J. Ottenheijm, R. M. J. Liskamp, and M. J. Tijhuis, Tetrahedron Left., 1979, 387. 5488. P. Helquist and M. S. Shekhani, J . Am. Chem. Soc., 101, 1057 (1979). 5489. C.-C. L. Lin and R. J. Dubois, J . Med. Chem., 20, 337 (1977). 5490. C. K. Lee and R. Vince, J . M e d . Chem., 21, 176 (1978). 5491. S. Kanatomo, S. Nagai, T. Hase, K. Ohki, C. Nomura, and E. Okezaki, Chem. Pharm. Bull., 31, 135 (1983). 5492. J. Golenser, J. Miller, D. T. Spira, T. Navok, and M. Chevion, Blood, 61, 507 (1983). 5493. S. I. Zav’yalov, I. A. Mikhailopulo, and V. I. Gunar, Izu. Akad. Nauk S S S R ,Ser, Khim., 1965, 1887. 5494. J. S. Evans, E. A. Musser, G. D. Mengel, K. R. Forsblad, and J. H. Hunter, Proc. Soc. E x p . Biol. Med., 106, 350 (1961). 5495. H. Nakatani, M. Nishikawa, and E. Mizuta, Ynkugaku Zasshi, 84, 1051 (1964). 5496. H. Nakatani, Yakugaku Zasshi, 84, 1057 (1964). 5497. K. Inagaki, J. Shirai, K. Okamoto, K. Suzuki, and Y. Kidani, Nagoya Shiritsu Daigaku Yakugakuhu Kenkyu Nernpo, 26, 11 (1978). 5498. D. R. Sargent and C. G. Skinner, J . Med. Chem., 15, 1196 (1972). 5499. R. 0. Marshall, L. M. Hall, and P. P. Cohen, Biochim. Biophys. Acta, 17, 279 (1955). 5500. P. Reichard, L. H. Smith, and G. Hanshoff, Acta Chem. Scand., 9, 1010 (1955). 5501. M. E. Jones, L. Spector, and F. Lipmann, J . Am. Chem. SOC.,77, 819 (1955). 5502. J. M. Lowenstein and P. P. Cohen, J . Am. Chem. Soc., 76, 5571 (1954). 5503. J. M. Lowenstein and P. P. Cohen, J . B i d . Chem., 220, 57 (1956). 5504. I. Lieberman and A. Kornberg. J . Biol. Chem., 207, 911 (1954). 5505. C. S. Miller, J. T. Gordon, and E. L. Engelhardt, J . Am. Chem. Soc., 75, 6086 (1953). 5506. I . Lieberman and A. Kornberg, Biochirn. Biophys. Acta, 12, 223 (1953). 5507. R. A. Yaks and A. B. Pardee, J . B i d . Chem., 221, 743 (1956). 5508. A. Kornberg, 1. Lieberman, and E. S. Simms, J . Am. Chem. Soc., 76,2027 (1954);J . Biol. Chem., 215, 389 (1955).

1324

References

5509. I. Lieberman, A. Kornberg, and E. S. Simms, J . Am. Chem. Soc., 76,2844 (1954);J . Biol. Chem., 215, 403 (1955). 5510. I. Lieberman, J . Am. Chem. Soc., 77, 2661 (1955). 5511. E. Fischer and J. von Mering, Ther. Gyw., 44,97 (1903); Ther. Monatsh., 17,208 (1903); Chem. Zentr., 1903, I, 1155. 5512. S. C. Harvey, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G. Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 349. 5513. H. A. Shonle, J . Am. Chem. Soc., 56, 2490 (1934). 5514. I. G. F., Br. Pat., 401,693 (1933); Chem. Abstr., 28, 2850 (1934). 5515. 2. B u d t h s k y and M. Protiva, Synthetische Arzneimittel, Akademie-Verlag, Berlin, 1961, p. 238K 5516. A. M. Chesney, T. A. Clawson, and B. Webster, Bull. Johns Hopkins Hosp., 43,261 (1928);Biol. Abstr., 4, 140 (1930). 5517. D. Marine, E. J. Baumann, A. W. Spence, and A. Cipra, Proc. Soc. E x p . B i d . Med., 29, 772 (1932). 5518. J. B. MacKenzie, C. G. MacKenzie, and E. V. McCollum, Science, 94, 518 (1941). 5519. C. P. Richter and K. H. Clisby, Proc. Soc. E x p . Bid. Med., 48, 684 (1941). 5520. T. H. Kennedy, Nature (London), 150, 233 (1942). 5521. E. B. Astwood, J . Pharmacol. E x p . Ther., 78, 79 (1943). 5522. E. B. Astwood J . Am. Med. Assoc., 122, 78 (1943). 5523. E. B. Astwood, J . Clin. Endocrinol., 4, 229 (1944). 5524. J. Thomas (Ed.), Prescription Products Guide, 18th ed., Australian Pharmaceutical Publishing Co., Melbourne, 1989, p. 1586. 5525. R. C. Haynes and F. Murad, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G . Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 1397. 5526. R. Handley and A. S. R. Stewart, Lancet, 1952, I, 742. 5527. I. P. Baumel, B. B. Gallagher, J. Di Micco, and H. Goico, J . Pharmacol. Exp. Ther., 186, 305 (1973). 5528. T. W. Rall and L. S. Scheifer, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G. Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 448. 5529. P. Calabresi and R. E. Parks, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G. Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 1249. 5530. T. Y. Shen, H. M. Lewis, and W. V. Ruyle, J . Ory. Chem., 30, 835 (1965). 5531. W. K. Roberts and C. A. Dekker, in Synthetic Procedurs in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 296. 5532. W. K. Roberts, and C. A. Dekker, J . Ory. Chem., 32, 816 (1967). 5533. J. J. Fox, N. Miller, and I. Wempen, J . Med. Chem., 9, 101 (1966). 5534. H. P. M. Fromageot and C. B. Reese, Tetrahedron Lett., 1966, 3499. 5535. R. J. Rutman, A. Cantarow, and K. E. Paschkis, Cancer Res., 14, 119 (1954). 5536. K. C. Leibman and C. Heidelberger, Fed. Proc., Am. Soc. E x p . Biol., 14, 243 (1955). 5537. S. S. Yemul, H. B. Kagan, and R. Setton, Tetrahedron Lett., 21, 277 (1980). 5538. C. C. Cheng and B. Roth, Proy. Med. Chem., 7, 285 (1970). 5539. C . E. Hoffmann, J. W. McGahen, and P. B. Sweetser, Nature (London),202, 577 (1964). 5540. H. L. Pease and J. F. Deye, Anal. Methods Pestic., Plant Growth Reyul., Food Addit., 5, 335 ( I 967). 5541. P. Koech, Liebigs Ann. Chem., 315, 246 (1901). 5542. E. S. Hill, J . Biol. Chem., 85, 713 (1929).

References 5543. 5544. 5545. 5546. 5547. 5548. 5549. 5550. 5551. 5552. 5553. 5554. 5555. 5556. 5557. 5558. 5559. 5560. 5561. 5562. 5563. 5564. 5565. 5566. 5567. 5568. 5569. 5570. 5571. 5572. 5573. 5574. 5575. 5576. 5577. 5578. 5579. 5580. 5581. 5582. 5583. 5584. 5585.

1325

B. M. Visinski and G . Dryhurst, Anal. Chim. Acta, 81, 273 (1976). S. Kato and G . Dryhurst, J . Electroanal. Chem., 79, 391 (1977). J. L. Owens and G. Dryhurst, J . Electround. Chem., 80, 171 (1977). S. Kato and G. Dryhurst, J . Electroanal. Chem., 80, 181 (1977). H. Kinoshita, S. D. Christian, and G . Dryhurst, J . ElectroanaL Chem., 85, 377 (1977). V. Brabec, S. D. Christian, and G. Dryhurst, J . Electroanal. Chem., 85, 389 (1977). G. Brugnatelli, G. Eiz. Chim. Storia Natur. Pauia [decade seconda], 1, 117 (1818); Ann. Chim. Phys. 127, 8, 201 (1 8 18). X. Hardy, Ann. Chim. Phys. [4]. 2, 372 (1864). S. M. McElvain, J . A m . Chem. Soc., 57, 1303 (1935). E. Biilmann and N. Berg, Ber. Dtsch. Chem. Ges., 63, 2188 (1930). J. H. Speer and T. C. Dabovich, Ory. Synth., 21, 5 (1941). H. M. Barnes and S. M. McElvain, J . Am. Chem. Soc., 59, 2348 (1937). A. Schlieper, Liebigs Ann. Chem., 56, 1 (1845).

D. J. van Prooye, Reel. Trav. Chim.Pays-Bas, 34, 326 (1915). W. Gregory, Liebigs Ann. Chem., 87, 125 (1853). G. vom Rath, Ann. Phys. Chem. Leipzig, 110, 93 (1860). W. Heintz, Ann. Phys. Chem. Leipziy, 111, 436 (1860). R. Otto, Liebigs Ann. Chem., Suppl., 4,256 (1866). A. S. Wheeler, J . Am. Chem. Soc., 32, 809 (1910). M. T. Bogert, J . Am. Chem. Soc., 32, 809 (1910). E. C. Franklin, J . Am. Chem. Soc., 32, 1362 (1910). R. A. Gortner, J . Am. Chem. Soc., 33, 85 (1911). B. Pullman, Acta Cryst., 17, 1074 (1964). H. Biltz, M. Heyn, and M. Bergius, Liebigs Ann. Chem., 413, 68 (1916). W. Herold, Z . Electrochem., 39, 566 (1933). J. W. Patterson, A. Lazarow, and S. Levey, J . Biol. Chem., 177, 187 (1949). H. Kwart and I. M. Sarasohn, J . Am. Chem. Soc., 83, 909 (1961). 0. Kiihling, Ber. Dtsch. Chem. Ges., 24, 2363 (1891). R. Mohlau and H . Litter, J . Prakt. Chem. 121, 73, 472 (1906). J. W. Clark-Lewis and J. A. Edgar, J . Chem. Soc., 1965, 5551. J. W. Clark-Lewis and J. A. Edgar, J . Chem. Sdc., 1965, 5556. 0. Bromberg, Ber. Dtsch. Chem. Ges., 30, 131 (1897). E. C. Taylor and R. W. Morrison, J . Am. Chem. Soc., 87, 1976 (1965). L. Heinisch, W. Ozegowski, and M. Miihlstidt, Chem. Ber., 98, 3095 (1965). A. W. Dox and A. Thomas, J . Am. Chem. Soc., 45, 1811 (1923). A. C. Cope and S. M. McElvain, J . Am. Chem. Soc., 54, 4319 (1932). H. Limpricht and W. Wuth, Liebigs Ann. Chem., 108, 41 (1858). M . A. Whiteley and W. V. Thorpe, in Thorpe’s Dictionary of Applied Chemistry, 4th ed., Vol. 1, Longmans Green, London, 1937, p. 243. W. N. Hartley, J . Chem. Soc., 87, 1796 (1905). M. M . Richter, Ber. Dtsch. Chem Ges., 44, 2155 (1911). J. M. Retinger, J . Am. Chem. SOC., 39, 1059 (1917). E. Biilmann and J. Bentzon, Ber. Dzsch. Chem. Ges., 51, 522 (1918). D. Nightingale, J . Am. Chem. Soc., 59, 806 (1937).

1326

References

5586. N. M. Winslow, J . Am. Chem. Soc., 61, 2089 (1939). 5587. R. Moubasher and A. M. Othman,J. Am. Chem. Soc., 72, 2667 (1950). 5588. J. Liebig, Liehiys Ann. Chem., 121, 80 (1852). 5589. J. A. Russell, Annu. Rev. Biochem., 14, 309 (1945). 5590. F. D. W. Lukens, Physiol. Rev., 28, 304 (1948). 5591. I. Kadota, J . Lab. Clin.Med., 35, 568 (1950). 5592. I. Kadota and 0. Midorikawa, J . Lab. Clin.Med., 38, 671 (1951). 5593. C. R. Morgan and A. Lazarow, Diabetes, 14, 669 (1965). 5594. I. A. Clark and N. H. Hunt, Infect. Immun., 39, 1 (1983). 5595. E. Biilmann and H. Lund, Ann. Chim. Phys. [9], 19, 137 (1923). 5596. E. S. Hill and L. Michaelis, Science, 78, 485 (1933). 5597. M. A. Whiteley, in Thorp’s Dictionary of Applied Chemistry, 4th ed., Longmans Green, London, 1937, Vol. 1, p. 248. 5598. X. Prout, Ann. Chim. Phys. [2], 11, 48 (1819). 5599. D. Davidson, J . Am. Chem. Soc., 58, 1821 (1936). 5600. R. Mohlau and H. Litter, J . Prakt. Chem. [2], 73, 449 (1906). 5601. R. Mohlau, Ber. Dtsch. Chem. Ges., 37, 2686 (1904). 5602. E. Fischer, Ber. Dtsch. Chem. Ges., 30, 2226 (1897). 5603. S. Y. Mel’nik, A. A. Bakhmedova, T. P. Nedorezova, G. I. Vornovitskaya, N. N. Preobrazhenskaya, E. A. Avetisyan, L. S. German, V. R. Polishchuk, E. V. Chekunava, et al., Bioorg. Khim., 7, 1047 (1981); Chem. Abstr., 95, 151089 (1981). 5604. J. M. McCall and R. E. Ten-Brink, Synthesis, 1975, 443. 5605. S. H. Chang, 1. K. Kim, and B.-S. Hahn, Daehan Hwahak Hwoejee, 9, 75 (1965). 5606. H. Aspelund, Acta Acad. Aho., Math. Phy., 28, No. 5, 14 pp. (1968); Chem. Abstr., 70, 106469 (1969). 5607. S. I. Zav’yalov and G. V. Pokhvisneva, IZG. Akad. Nauk SSSR, Ser. Khim., 1973, 655. 5608. V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1979, 827. 5609. H. Aspelund, Acta Acud. Aha., Math. Phys., 26, No. 9, 20 pp. (1967); Chem. Ahstr., 68, 29671 (1968). 5610. T. Kato, N. Oda, and I. Ito, Chem. Pharm. Bull., 25, 491 (1977). 5611. Y. Kurasawa, K. Nagahara, and A. Takada, Chem. Pharm. Bull., 27, 2143 (1979). 5612. K. Ikeda and Y. Mizuno, Chem. Pharm. Bull., 19, 564 (1971). 5613. P. A. Levene, J . Biol. Chem., 63, 653 (1925). 5614. J. A. Barone, E. Peters, and H. Tieckelmann, J . Ory. Chem., 24, 198 (1959). 5615. F. F. Ebetino and E. D. Amstutz, J . Med. Chem., 7, 389 (1964). 5616. S. Senda and K. Hirota, Yakugaku Zasshi, 91, 1367 (1971). 5617. L. Nordholm and L. Dalgaard, Arch. Pharm. Chem., Sci. Ed., 11, 1 (1983). 5618. K. C. Murdock and R. B. Angier, J . Am. Chem. Soc., 84, 3758 (1962). 5619. N. E. Britikova, E. I. Metel’kova, K. A. Chkhikvadze, and 0. Y. Magidson, Khim. Geterotsikl, Soedin., 1967, 1089. 5620. T. J. Kress, J . Org. Chem., 44,2081 (1979). 5621. R. Brossmer, Angew. Chem., 79, 691 (1967). 5622. 5623. 5624. 5625.

A. Stuart, T. Paterson, B. Roth, and E. Aig, J . Med. Chem., 26, 667 (1983). D. E. Bergstrom and K. F. Rash, J . Org. Chem., 44, 1414 (1979). J. H. Lister, J . Chem. Soc., 1960, 899. B. Bobranski and E. Wagner, Rocz. Chem., 38, 237 (1964).

References

1327

5626. E. P. Gracheva, Z. S. Volkova, V. I. Gunar, E. A. Arutyunyan, and S. I. Zav’yalov, Izo. Akad. Nauk SSSR, Ser. Khim., 1970, 420. 5627. H. Yamanaka, Chem. Pharm. Bull., 7, 505 (1959). 5628. R. Bouche, J . Pharm. Sci., 63, 1633 (1974). 5629. V. F. Sedova and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1978, 1397. 5630. C. Janion and D. Shugar, Biochem. Biophys. Res. Cornmun., 18, 617 (1965). 5631. D. J. Brown and B. T. England, Aust. J . Chem., 23, 625 (1970). 5632. B. S. Thyagarajan, Adu. Heterocycl. Chem., 8, 143 (1967). 5633. G . T. Rogers, R. S. Shadbolt, and T. L. V. Ulbricht, J . Chem. Soc. (C), 1969, 209. 5634. L. Strekowski, Pol. J . Chem., 52, 283 (1978). 5635. E. S. Spinner and J. C. B. White, Chem. Ind. (London), 1967, 1784. 5636. K. B. Wiberg, T. M. Shryne, and R . R . Kintner, J . Am. Chem. Soc., 79, 3160 (1957). 5637. T.-C. Lee, Ph.D. thesis, Australian National University, Canberra, 1968. 5638. T. Ueda and H. Nishino J . Am. Chem. Soc., 90, 1678 (1968). 5639. J. Pliml and M. PrystaS, Adti. Heterocycl. Chem., 8, 115 (1967). 5640. G. Tsatsaronis and T. Soulis, Bull. Soc. Chim. Fr., 1973, 3397. 5641. G. E. Hilbert and T. B. Johnson, J . Am. Chem. Soc., 52,4489 (1930). 5642. G . A. Howard, B. Lythgoe, and A. R . Todd, J . Chem. Soc., 1947, 1052. 5643. D. W. Visser, I. Goodman, and K. Dittmer, J . Am. Chem. Soc., 70, 1926 (1948). 5644. J. J. Fox and I. Goodman, J . Am. Chem. Soc., 73, 3256 (1951). 5645. G . E. Hilbert and E. F. Jansen, J . Am. Chem. Soc., 58, 60 (1936). 5646. M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 29, 131 (1964). 5647. M. PrystaS and F. Sorm, Collect. Czech. Chem. Cornmun., 29, 2956 (1964). 5648. M . PrystaS and F. Sorrn, Collect. Czech. Chem. Cornmun., 30, 2960 (1965). 5649. T. L. V. Ulbricht and G. T. Rogers, J . Chem. Soc., 1965, 6125. 5650. T. L. V. Ulbricht and G. T. Rogers J . Chem. Soc., 1965, 6130. 5651. D. Thacker and T. L. V. Ulbricht, J . Chem. Soc. (C), 1968, 333. 5652. M. PrystaS and F. Sorm, Collect. Czech. Chem. Commun., 34, 331 (1969). 5653. T. Ueda and H. Ohtsuka, Chem. Pharm. Bull., 21, 1530 (1973). 5654. E. Wittenburg, Chem. Ber., 101, 1095 (1968). 5655. F. Kaimierczak, J. Langer, and K. Golankiewicz, Rocz. Chem., 47, 1943 (1973). 5656. R. A. Zhuk, A. E. Berzinya, L. A. Sherin’, L. T. Kaulinya, and S. A. Giller, Khim. Geterotsikl. Soedin., 1977, 1258. 5657. M. Yasumoto, A. Moriyama, N. Unemi, S. Hashimoto, and T. Suzue, J . Med. Chem., 20, 1592 (1977). 5658. T. Nishitani, T. Iwasaki, Y. Mushika, I. Inoue, and M. Miyoshi, Chem. Pharm. Bull., 28, 1137 (1980). 5659. G. Tsatsaronis and T. Soulis, Prakt. Panelkniou Chem. Synedriou, 4th, 1, 64 (1970); Chem. Ahstr., 85, 78077 (1976). 5660. N. E. Alexandrou and T. P. Soulis, Tetrahedron Lett., 1972, 1417. 5661. G. Tsatsaronis, T. Soulis, and D. Graikou-Lazana, Chim. Chron., 9, 37 (1980). 5662. R. A. F. Deeleman and H. C. Van der Plas, Reel. Trau. Chim. Pays-Bas, 92, 317 (1973). 5663. T. Takahashi, %-I. Hirokami, K. Kato, and M. Nagata, J . Chem. Soc., 48, 2914 (1983). 5664. T. Nishio, A. Kato, C. Kashirna, and Y. Omote, J . Chem. Soc., Perkin Trans. 1, 1980, 607. 5665. G. I. Podzigun, N. G. Pashkurov, V. S. Reznik, and B. E. Ivanov, I z v . Akad. Nauk SSSR, Ser. Khim., 1980, 2564.

1328

References

J. H. Boothc and C. 0. Wilson, J . Am. Chem. Soc., 68, 448 (1946). Y.-F. Chi and Y.-L. T'ien, J . Am. Chem. Soc., 55, 4181 (1933). G. Zigcuner, H. Hamberger, and R. Ecker, Monatsh. Chem., 101, 881 (1970). M. Sano, Chem. Pharm. Bull., 10, 320 (1962). B. Stanovnik and M. TiSler, Bull. Sci., Conseil Acad. R S F Yugoslauie,9, 2 (1964) Chem. Abstr., 62, 420 (1965). 5671. E. C. Taylor and A. E. Martin, J . Am. Chem. Sac., 74, 6295 (1952). 5672. C. D. Hurd and B. Ruddner, J . Am. Chem. Soc., 73, 5157 (1951). 5673. J. Stantk and J. Sidlo, Chem. Lisly, 47, 471 (1953). 5674. J. Clark, R. K. Grantham, and J. Lydiate, J . Chem. Soc. (C),1968, 1122. 5675. L. 0. Ross, L. Goodman, and B. R. Baker, J . Am. Chem. Soc., 81, 3108 (1959). 5676. G. H. Hitchings and P. B. Russell, J . Chem. Soc., 1949, 2454. 5677. H. Segal, C. Hedgcoth, and C. G. Skinner, J . Med. Pharm. Chem., 5, 871 (1962). 5678. B. Capon and N. B. Chapman, J . Chem. Soc., 1957, 600. 5679. S.-C. J. Fu, E. Chinoporos, and H. Terzian, J . Org. Chem., 30, 1916 (1965). 5680. P. Hassanaly, H. Dou, and M. Ludwikow, Bull. Soc. Chim. Belg., 91, 661 (1982). 5681. Y.-F. Chi, J . Am. Chem. Soc., 58, 1150 (1936). 5682. S. Inoue, Chem. Pharm. Bull., 6, 352 (1958). 5683. T. Itoh, M. Honma, and H. Ogura, Chem. Pharm. Bull., 24, 1390 (1976). 5684. W. Klosa and K. Schwarz, J . Heterocycl. Chem., 19, 1165 (1982). 5666. 5667. 5668. 5669. 5670.

5685. H. Voigt, D. Heydenhauss, F. Hofmann, and G. Jaenecke, Z . Chem., 14,472 (1974). 5686. D. J. Brown and L. G. Stephanson, Aust. J . Chem., 29, 1031 (1976). 5687. D. J. Brown, G . W. Grigg, Y. Iwai, K. N. McAndrew, T. Nagamatsu, and R. van Heeswyck, Aust. J . Chem., 32, 2713 (1979). 5688. S. Rajappa and R. Sreenivasan, Indian J . Chem., 9, 761 (1971). 5689. N. G. Pashkurov and V. S. Reznik, Dokl. Akad. Nauk SSSR, 171, 874 (1967). 5690. N. G. Pashkurov and V. S. Reznik, Khim. Geterotsikl. Soedin., 1968, 918. 5691. R. S. Klein, M.-I. Lim, S.Y.-K. Tam, and J. J. Fox, J . Org. Chem., 43, 2536 (1978). 5692. A. W. Spassov and Z. D. Raikov, Z . Chem., 11, 260 (1971). 5693. J. van Eyk and H. Veldstra, Phytochemistry, 5, 457 (1966). 5694. W. E. Fidler and H. C. S. Wood, J . Chem. Soc., 1957, 3980. 5695. G. I. Podzigun, N. G. Pashkurov, V. S. Reznik, and B. E. Ivanov, lzu. Akud. Nauk SSSR, Ser. Khim., 1980, 2346. 5696. W. H. Miller, R. 0. Roblin, and E. B. Atswood, J . Am. Chem. Soc., 67, 2201 (1945). 5697. T. B. Johnson, Proc. Natl. Acad. Sci. U S A , 25, 448 (1939). 5698. I. P. Khullar and U. Agarwala, Aust. J . Chem., 27, 1877 (1974). 5699. I. P. Khullar and U. Agarwala, Aust. J . Chem., 28, 1529 (1975). 5700. T. Nagamachi, P. F. Torrence, J. A. Waters, and 9. Witkop, J . Chem. Soc., Chem. Commun., 1972, 1025. 5701. Y.-F. Jen and Y.-Y. Wang, Acta Pharm. Sinica, 10, 298 (1963). 5702. S. Hoffmann, H. Schubert, and K. Nitsche, Z.Chem., 12, 21 (1972). 5703. F. H. S . Curd and F. L. Rose, J . Chem. Soc., 1946, 343. 5704. F. H. S. Curd, M. I. Davis, E. C. Owen, F. L. Rose, and G. A. P. Tuey, J . Chem. Sue., 1946,370. 5705. T. Matsukawa and S. Sirakawa, Yakugaku Zasshi, 71, 943 (1951); Chem. Abstr., 46, 8122 (1952). 5706. F. H. S. Curd, M. I. Davis, and F. L. Rose, J . Chem. Soc., 1946, 351.

References 5707. 5708. 5709. 5710. 571 1. 5712. 5713. 5714. 5715. 5716.

1329

A. Myles and J. J. Fox, J . Med. Chem., 11, 143 (1968). R. Paegle, M. Plata, and M. Lidaks, Khim. Geterotsikl. Soedin., 1969, 558. S. Hoffmann, H.-C. Schmidt, and H. Schubert, Z . Chem., 15,270 (1975). S. Hoffmann and H.-C. Schmidt, Z . Chem., 15, 306 (1975). J. R. Barrio, J . D. Bryant, and G. E. Keyser, J . Med. Chem., 23, 572 (1980). I. Nabih and H. Zoorob, J . Pharm. Sci., 61, 967 (1972). T. Sawayama, R. Yamamoto, H. Kinugasa, and H. Nishimura, Heterocycles, 8, 299 (1977). W. E. Barnett and R. F. Koebel, Tetrahedron Lett., 1971, 2867. K. Golankiewicz, M. Szajda, and E. Wyrzykiewicz, Pol. J . Chem., 54, 363 (1980). T. Nishio and Y. Omote, J . Chem. Sor., Perkin Trans. I , 1982, 2149.

5717. C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, Chem. Pharm. Bull., 30, 1942 (1982). 5718. 5719. 5720. 5721.

R. G. Dickinson and N. W. Jacobsen, Anal. Chem., 41, 1324 (1969). A. Maggiolo, J . Am. Chem. Soc., 1951, 5815. P. Dubs and R. Stussi, Hell;. Chim. Aeta, 59, 1307 (1976). R. J. Badger, D. J. Brown, and N. V. Khromov-Borisov, Aust. J . Chem., 25, 2275 (1972)

5722. I. H. Pitman, E. Shefter, and M. A. Ziscr, J . Am. Chem. Soc., 92, 3414 (1970) 5723. 5724. 5725. 5726. 5727. 5728. 5729. 5730. 5731. 5732. 5733.

I. H. Pitman and M. A. Ziser, J . Pharm. Sci., 59, 1295 (1970). I. H. Pitman, M. J. Cho, and G . S. Rork, J . Am. Chem. Soc., 96, 1840 (1974). G. S. Rork and I. H. Pitman, J . Am. Chem. Soc., 96, 4654 (1974). I. K. Fel’dman and D. I . Biskupskaya, Sintez Prirodn., ikh Analogou i Fraymentou, Akad. Nauk SSR, Otd. Ohshch. i Tekhn. Khim., 1965, 266; Chem. Abstr., 65, 3953 (1966). M. Semonsky and A. Cerny. Chem. Listy, 45, 156 (1951); Chem. Abstr., 46, 1556 (1952). D. J. Brown, P. W. Ford, and M. N. Paddon-Row, J . Chem. Soe. (C), 1968, 1452. R. A. Abramovitch, R. B. Rogers, and G. M. Singer, .I. Ory. Chem., 40, 41 (1975). A. B. Patel and H. D. Brown, Nature (London), 214, 402 (1967). S. 1. Zav’yalov and L. F. Ovechkina, Izu. Akad. Nauk S S S R , Ser. Khim., 1976, 2819. K. Klemm, W. Prusse, and U. Kruger, Arzneim.-Forsch., 27, 1895 (1977). F. Yoneda, S. Matsumoto, Y. Sakuma, and S. Fukasawa, J . Chem. Soc., Perkin Trans. 1, 1975, 1908.

5734. S. Minami, T. Shono, and J.-I. Matsumoto, Chem. Pharm. Bull., 19, 1482 (1971). 5735. B. Singh and G. V. Lesher, J . Heterocycl. Chem., 19, 1581 (1982). 5736. H . L. Friedman and A. V. Tolstoouhov, US Pat. 2,500,283 (1950); Chem. Abstr., 44, 5399 (1950). 5737. I. A. Kaye and I. C. Kogon, Reel. Trau. Chim. Pays-Bus, 71, 309 (1952). 5738. S. Nishigaki, K. Senga, K. Ogiwara, and F. Yoneda, Tetrahedron Lett., 1969, 539. 5739. K. Sirakawa, Yakuyaku Zasshi, 79, 1487 (1959). 5740. S. Senda, A. Suzui. and M. Honda, Chem. Pharm. Bull., 6,487 (1958). 5741. M. D. Fenn and J. H. Lister, Aust. J . Chem., 33, 1611 (1980). 5742. T. Iwatsu, Yakuyaku Zasshi, 72, 366 (1952); Chem. Abstr., 47, 2179 (1953). 5743. B. R. Baker and J. Novotny, J . Heterocycl. Chem., 4, 23 (1967). 5744. H. J. Roth, K. Jager, and R. Brandes, Arch. Pharm. (Weinheim, Ger.), 298, 885 (1965). 5745. H. J. Roth and R. Brandes, Arch. Pharm. (Weinheim Ger.), 299, 612 (1966). 5746. J. Haginiwa, Y. Higuchi, and Y. Yamamoto, Yakuyaku Zasshi, 95, 8 (1975). 5747. D. V. Santi, C. F. Brewer, and D. Farber, J . Heterocycl. Chem., 7, 903 (1970). 5748. N. C. Brown J. Gambino, and G . E. Wright, J . Med. Chem., 20, 1186 (1977).

1330

References

5749. R. N. Jones, J . Am. Chem. SOC.,67, 2127 (1945). 5750. A. Albert, Q. Rev. Chem. SOC., 6, 197 (1952). 5751. A. Albert and H. Taguchi, J . Chem Soc., Perkin Trans. 2, 1973, 1101. 5752. A. Angeli, Gazz. Chim. I d , 24, 11, 366 (1894). 5753. Y. Sakuma and F. Yoneda, Heterocycles, 6, 1911 (1977). 5754. S. Romani, P. Schonholzer, and W. Klotzer, J . Heterocycl. Chem., 16, 293 (1979). 5755. Z. Swistun and H. C. van der Plas, J . Heterocycl. Chem., 18, 1639 (1981). 5756. F. E. Kempter, H. Rokos, and W. Pfleiderer, Angew. Chem., 79, 233 (1967). 5757. J. Baddiley, G . W. Kenner, B. Lythgoe, and A. R. Todd, J . Chem. Soc., 1944, 657. 5758. L. T. Weinstock, B. F. Grabowski, and C. C. Cheng, J . Med. Chem., 13, 995 (1970). 5759. V. M. Cherkasov and L. K. Kurilenko, Khim. Geterotsikl, Soedin., 1970, 1579. 5760. A. Albert, J . Chem. Soc., Perkin Trans. I, 1981, 2974. 5761. K. A. Watanabe and J. J. Fox, Angew. Chem., 78, 589 (1966). 5762. J. M . McCall, R. E. TenBrink, M. E. Royer, and H. KO, J . Heterocycl. Chem., 15, 1529 (1978). 5763. G. Tennant and C. W. Yacomeni, J . Chem. Soc., Chem. Commun., 1975, 819. 5764. K. Sirakawa, Yakugaku Znsshi, 79, 903 (1959). 5765. K. Sirakawa, Yakugaku Zasshi, 79, 899 (1959). 5766. T. Koyama, T. Hirota, M. Yamato, and N. Ohta, Yakugaku Zasshi, 93, 330 (1973). 5767. N. Acton, A. Brossi, D. E. Davidson, and T. R. Sweeney, Heterocycles, 14, 471 (1980). 5768. K. Takatori and M. Ueda, Yakugaku Zasshi, 71, 1373 (1951); Chem. Ahstr., 46, 8052 (1952). 5769. G. B. Elion, E. Burgi, and G. H. Hitchings. J . Am. Chem. Soc., 73, 5235 (1951). 5770. W. T. Caldwell, J . Am. Chem. Sue., 73, 2357 (1951). 5771. A. Colautti, V. Maurichi, and F. Rubessa, Farmaco, Ed. Sci., 26, 710 (1971). 5772. R. D. Youssefyeh and A. Kalmus, J . Heterocycl. Chem., 8, 747 (1971). 5773. V. M. Cherkasov, I. F. Vladimirtsev, and I. V. Boldyrev, Khim. Geterotsikl. Soedin., 1976, 536. 5774. H. Bredereck, E. Siegel, and B. Fohlisch, Chem. Ber., 95, 403 (1962). 5775. H. Fiirst and 1. Ebert, Chem. Ber., 93, 99 (1960). 5776. J. R. Piper and T. P. Johnston, J . Org. Chem., 30, 1247 (1965). 5777. P. A. Petyunin and Z . G. Kalugina, Zh. Obshch. Khim., 34, 1255 (1964). 5778. L. A. Gutorov and E. S. Golovchinskaya, Khim.-Farm. Zh., 1, 28 (1967); Chem. Ahstr., 67, 82193 (1967). 5779. F. Bergmann, M. Tamari, and H. Ungar-Waron, J . Chem. Soc., 1964, 565. 5780. T. Uno, K. Machida, K. Hanai, and M. Ueda, Chem. Pharm. Bull., 11, 704 (1963). 5781. R. Dahlbom and T. Ekstrand, Sven. Kem. Tidskr., 55, 122 (1943); Chem. Zentr., 1943,II, 1188. 5782. J. P. English, D. Chappell, P. H. Bell, and R. 0. Roblin, J . Am. Chem. Soc., 64, 2516 (1942). 5783. M. J. Kalm, J . Org. Chem., 26, 3026 (1961). 5784. Y. Nitta, K. Okui, K. Ito, and M. Togo, Chem. Pharm. Bull., 13, 568 (1965). 5785. F. Craveri and G. Zoni, Farmaco, Ed. Sci., 17, 573 (1962). 5786. E. P. Lira, J . Heterocycl. Chem., 9, 713 (1972). 5787. K. Okui, K. Ito, M. Koizumi, K. Fukumoto, and T. Kametani, J . Heterocycl. Chem., 9, 1283 (1972). 5788. T. R. Bosin, R. N. Hanson, J. V. Rodricks, R. A. Simpson, and H. Rapoport, J . Org. Chem., 38, 1591 (1973). 5789. T. Koyama, T. Hirota, M. Ikeda, T. Satoh, A. Iwadoh, and S. Ohmori, Chem. Pharm. Bull., 23, 917 (1975). 5790. S. Nishigaki, K. Ogiwara, and F. Yoneda, J . Heterocycl. Chem., 8, 183 (1971).

References

1331

5791. W. Pfleiderer and H. Rokos, in Chemistry and Biology of Pteridines (K. Iwai, M. Akino, M. Goto, and Y. Iwanami, Eds.), International Academic Printing Co., Tokyo, 1970, p. 113. 5792. F. Yoneda, M . Higuchi, and T. Nagamatsu, J. Am. Chem. Soc., 96, 5607 (1974). 5793. G. H. Rogul'chenko, I. A. Mazur, and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1975, 93. 5794. J. Bodeker and K. Courault, J . Prakt. Chem., 322, 336 (1980). 5795. S. K. Chakraborti and B. K. De, J . Indian Chem. Soc., SO, 137 (1973). 5796. G. T. Rogers and T. L. V. Ulbricht, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 15. 5797. W. Pfleiderer and H.-U. Blank, Angew. Chem., 80, 534 (1968). 5798. M. Higuchi, T. Nagamura, and F. Yoneda, Heterocycles, 4, 977 (1976). 5799. F. Yoneda and M. Higuchi. J . Chem. Soc., Perkin Trans. I , 1977, 1336. 5800. K. Senga, K. Shimizu, and S. Nishigaki, Chem. Pharm. Bull., 25, 495 (1977). 5801. C. Temple, R. L. McKee, and J. A. Montgomery, J . Org. Chem., 28, 2257 (1963). 5802. W. Pfleiderer and F. Reisser. Chem. Ber., 95, 1621 (1962). 5803. R. B. Angier J . Org. Chem., 28, 1398 (1963). 5804. W. Traube and W. Nithack, Ber. Dtsch. Chem. Ges., 39, 227 (1906). 5805. C. Temple and J. A. Montgomery, J . Org. Chem., 28, 3038 (1963). 5806. S. Ban, K. Sirawawa, and M. Yoneda, Yakugaku Zasshi, 73, 601 (1953). 5807. M. Claesen and H. Vanderhaeghe, Bull. Soc. Chim. Belg., 68, 47 (1959). 5808. C. L. McLeod, J . Res. Nut. Bur. Stand., Sect. A, 66, 65 (1962). 5809. K. Miura, M. Ikeda, T. Oohashi, Y. Igarashi, and I. Okada, Chem. Pharm. Bull., 13,529 (1965). 5810. P. A. Crooks and B. Robinson, Chem. Ind. (London), 1967, 547. 5811. M. F. Marshalkin, V. A. Azimov, L. F. Linberg, and L. N. Yakhontov, Khim. Geterotsikl. Soedin., 1978, 1124. 5812. B. Jenko, B. Stanovnik, and M. TiSler, Synthesis, 1976, 833. 5813. A. W. Spassov and 2. Raikov, Z . Chem., 11,422 (1971). 5814. F. Yoneda and T. Nagamatsu, Synthesis, 1973, 300. 5815. F. Yoneda, T. Nagamatsu, and M. Ichiba, J. Heterocycl. Chem., 11, 83 (1974). 5816. Y. Iwanami and T. Seki, Bull. Chem. Soc. Jpn., 45,2829 (1972). 5817. M. E. C. Biffin, D. J. Brown, and T. Sugimoto, in Chemistry and Biology ofl'teridines (K. Iwai, M. Akino, M. Goto, and Y. Iwanami, Eds.), International Academic Printing Co., Tokyo, 1970, p. 71. 5818. D. J. Brown and J. R. Kershaw, J . Chem. Soc., Perkin Trans. I , 1972, 2316. 5819. L. Vio and M. G. Mamolo, Farmaco, Ed. Sci., 38, 255 (1983). 5820. Y. Haraoka, A. Sugihara, and M. Ito, Jap. Pat. 10,052 (1965); Chem. Abstr., 63, 5659 (1965). 5821. Y. Moromoto, Yakugaku Zasshi, 82, 465 (1962). 5822. I. J. Pachter, J . Org. Chem., 28, 1191 (1963). 5823. D. J. Brown, Fused Pyrimidines Part 3: Pteridines, Wiley, New York, 1988, p. 135. 5824. W. Pfleiderer, Liebigs Ann. Chem., 1974, 2030. 5825. M. Viscontini and A. Bobst, Helu. Chim. Acta, 49, 1815 (1966). 5826. W. Pfleiderer and M. Rukwied, Chem. Ber., 94, 118 (1961). 5827. 0. Baudisch and D. Davidson, J . Biol. Chem., 71, 497 (1927). 5828. R. Behrend and G. Offe, Liebigs Ann. Chem., 353, 267 (1907). 5829. C. W. Noell and C. C. Cheng, J . Med. Chem., 11, 63 (1968). 5830. A. A. Krapacheva, N. V. Sazonov, and S. I. Sergievskaya, Zh. Obshch. Khim., 32,3796 (1962). 5831. H. C. van der Plas, S. Baloniak, and H. Jongejan, J . Heterocycl. Chem., 20, 415 (1983).

1332

References

5832. C. Biilow, Err. Dtsch. Chem. Ges., 42,4429 (1909). 5833. C. Temple, C. J. Kussner, and J. A. Montgomery, J . Org. Chem., 31, 2210 (1966). 5834. C. Temple, W. C. Coburn, M. C. Thorpe, and J. A. Montgomery, J . Org. Chem., 30, 2395 (1965). 5835. N. P. Buu-Hoi, R. Rips, and C. Derappe, J . M e d . Chem., 7, 364 (1964). 5836. G . Auzou and R. Rips, J . Heterocycl. Chem., 18, 835 (1981). 5837. L. 0. Ross, L. Goodman, and B. R. Baker, J . Org. Chem., 25, 1950 (1960). 5838. P. P. T. Sah and T. F. Woo, Recl. Trau. Chim. Pays-Bas, 58, 1013 (1939). 5839. E. C. Taylor and F. Sowinski, J . Am. Chem. Soc., 90,1374 (1968). 5840. F. Yoneda, S. Matsumoto, and M. Higuchi, J . Chem. Soc., Chem. Commun., 1975, 146. 5841. F. Yoneda, M. Higuchi, and S. Matsumoto, J . Chem. Soc., Perkin Trans. I , 1977, 1754. 5842. W. Broadbent, G. W. Miller, and F. L. Rose, J . Chem. Sac., 1965, 3369. 5843. D. J. Brown, W. C. Dunlap, G. W. Grigg, L. Danckwerts, and T. Nagamatsu, Aust. J . Chem., 31, 397 (1978). 5844. G . Auzou, M. Desiles, and R Rips, Eur. J . M e d . Chem.-Chim. Ther., 16, 345 (1981). 5845. A. S. Jones and J. H. Warren, Tetrahedron, 26, 791 (1970). 5846. F. J. Moore and E. S. Gatewood, J . Am. Chem. Soc., 45, 135 (1923). 5847. B. Hepner and S . Frenkenberg, Helu. Chim. Acta, 15, 533 (1932). 5848. N. B. Galstukhova, M. N. Shchukina, and Z. Buesinsky, Khim. Geterotsikl. Soedin., Sh. I , 1967, 364; Chem. Ahsir., 70, 87717 (1969). 5849. K. T. Potts and J. Kane, J . Org. Chem., 39, 3783 (1974). 5850. G . N. Vassilev, N. H. Spassovska, and A. V. Spassov, C. R . Acad. Bulg. Sci., 33, 849 (1980). 5851. W. V. Curran and R. B. Angier, personal communication. 5852. I. G . Farbenindustrie, Fr. Pat. 753,178 (1933); Chem. Ahstr., 28, 781 (1934). 5853. M. Angelo, D. Ortwine, D. Worth, L. M. Werbel, and J. W. McCall, .I. Med. Chem., 26, 1258 (1983). 5854. V. P. Mamaev and V. P. Krivopalov, Khim. Geterotsikl. Soedin., Akad. Nauk Latv. SSR, 1966, 145; Chem. Ahstr., 65, 710 (1966). 5855. R. Clarkson and A. R. Martin, Nature (London), 192, 523 (1961). 5856. W. Schulze and H. Willitzer, J . Prakt. Chem. [4], 33, 50 (1966). 5857. R. R. Williams and J. K. Cline, J . Am. Chem. Soc., 58, 1504 (1936). 5858. J. H. Lister, Fused Pyrimidines Part 2 Purines, Wiley, New York, 1971. 5859. A. Katoh, M. Sagane, Y. Omote, and C. Kashima, Synthesis, 1983, 409. 5860. F. Roeterdink and H. C. van der Plas, R e d . Trau. Chim. Pays-Bus, 96, 156 (1977). 5861. T. Sugimoto and S. Matsuurd, Bull. Chem. Soc. Jpp., 48, 725, 1679 (1975). 5862. A. E. Tschitschibabin and R. A. Konowalowa, Ber. Dtsch. Chem. Ges., 58, 1712 (1925). 5863. A. E. Tschitschibabin and A. W. Kirssanow, Ber. Dtsch. Chem. Ges., 61, 1223 (1928). 5864. D. J. Brown, in Mechanisms of Molecular Migrations, Vol. 1 (B. S . Thyagardjan, Ed.), Wiley, New York, 1968, p. 209. 5865. B. Rathke, Ber. Dtsch. Chem. Ges., 21, 867 (1888). 5866. 0. Dimroth, Liehigs Ann. Chem., 364, 183 (1909). 5867. M. Wahren, Z.Chem., 9, 241 (1969). 5868. D. J. Brown and N. W. Jacobsen, Tetrahedron Lett., 1960, No. 25, 17. 5869. R. B. Angier and W. V. Curran, J . Am. Chem. Soc., 81, 5650 (1959). 5870. D. D. Perrin, J . Chem. Soc., 1963, 1284. 5871. R. B. Angier, in Pteridine Chemistry (W. Pfleiderer and E. C. Taylor, Eds.), Pergamon Press, Oxford, 1964, p. 232.

References

1333

5872. D. J. Brown and K. Ienaga, Heterocycles, 3, 283 ( 1 975). 5873. T.-L. Su, K. A. Watanabe, and J. J. Fox, Tetrahedron, 38, 1405 (1982). 5874. E. A. Bell, Biochim. Biophys. Acta, 47, 602 (1961). 5875. E. Nowacki and J. Przybylska, Bull. Acud. Pol. Sci., Ser. Sci. Biol., 9,279 (1961); Chem. Abstr., 56, 1725 (1962). 5876. E. A. Bell and R. G. Foster, Nature (London), 194, 91 (1962). 5877. A. Watanabe, Yakuyaku Zasshi, 59, 500 (and Supplemenl, p. 133) (1939). 5878. R. Abderhalden, Klin. Wochenschr., 18, 171 (1939); Chem. Ahstr., 33, 4643 (1939). 5879. W. H. G. Richards, Adu. Pharmacol. Chemother., 8, 121 (1970). 5880. G. H. Hitchings et al., Inhibition ofFolate Melabolism in Chemotherapy, Vol. 64 of Handhook of Experimental Pharmacology, Springer-Verlag, Berlin, 1983. 5881. WHO Scientific Group, World Health Oryanization Tech. Rep. Ser., 1967, No. 375. 5882. S. R. M. Bushby and G. H. Hitchings, Br. J . Pharmacol., 33, 72 (1968). 5883. E. F. Elslager, L. M. Werbel, A. Curry, N. Headen, and J. Johnson, J . M e d . Chem., 17, 75 (1 974). 5884. A. Brossi, P. N . Sharma, K. Takahashi, J. F. Chiang, I. L. Karle, and G. Seibert, Helu. Chim. Acta, 66, 795 (1983). 5885. M. Calas, C. Pages, A. Barbier, L. Gird, and E. Despaux, Eur. J . Med. Chern.-Chim. Ther., 18, 97 (1983). 5886. B. Roth and C. C. Cheng, Proy. Med. Chem., 19, 269 (1982). 5887. R. E. Lux, Antibiot. Chemuther., 4, 971 (1954).

M. L. Clarke, Vet. Kec., 74, 845 (1962). G. H. Hitchings and J. J. Burchall, Adu. Enzymol., 27, 417 (1965). E. Ochiai, Aromatic Amine Oxides, Elsevier, New York, 1967. A. R. Katritzky and J. M. Lagowski, Chemistry of Heterocyclic N-Oxides, Academic Press, London, 1971. 5892. A. R. Katritzky, G . H. Millet, R. H. M. Noor, and F. S. Yates, J . Ory. Chem., 43, 3957 (1978). 5893. T. Sakamoto, S. Niitsuma, M. Mizugaki, and H. Yamanaka, Chem. Phurm. Bull., 27, 2653 (1 979). 5894. R . Peereboom, H. C. van der Plas, and A. Koudijs, Recl. Trau. Chim. Pays-Bas, 93,58 (1974). 5895. G . Rey-Belle1 and R . Reiner, Helc. Chim. Acta, 53, 945 (1970). 5896. J. J. Ursprung and W. C. Anthony, Fr. Pat. 1,513,739 (1968);Chem. Ahstr., 70, 115172 (1969). 5897. W. C. Anthony, Ger. Pat. (Offen) 2,114,887 (1971); Chem. Abstr., 76, 34284 (1972). 5898. K. Kasuga, M. Hirobe, and T. Okamoto, Chem. Pharm. Bull., 22, 1814 (1974). 5899. Y. Kobayashi, 1. Kumadaki, H. Sato, Y. Sekine, and T. Hara, Chem. Phurm. Bull., 22, 2097 (1974). 5900. S. R. Safir, J. J. Hlavka, and J. H. Williams, J . Ory. Chem., 18, 106 (1953). 5901. L. Simet, D. B. Reisner, B. J. Ludwig, F. Diirsch, and F. M. Berger, J . Med. Chem., 13, 1067 (1970). 5902. R . M . Khachatryan, S. A. Vartanyan, and T. R . Akopyan, Arm. Khim. Zh., 27, 1037 (1974); Chem. Abstr., 82, 156210 (1975). 5903. J . T. Chou, W. T. Beck, T. Khwaja, K. W. Mayer, and E. J. Lien, J . Pharm. Sci., 66,1556 (1977). 5904. S. Ahmed, R . Lofthouse, and G. Shaw, J . Chem. Soc., Chem. Commun., 1974,959;J . Chem. Soc., Perkin Trans. 1, 1976, 1969. 5905. F. Roeterdink and H. C. van der Plas, Tetrahedron Lett., 1976, 3337. 5906. H. Otomasu, H. Takahashi, and M. Ogata, Chem. Pharm. Bull., 12, 714 (1964). 5907. T. Kubota, K. Nishikida, H. Miyazaki, K. Iwatani and Y. Oishi, J . Am. Chem. Soc., 90, 5080 (1968).

5888. 5889. 5890. 5891.

1334

References

R. 0. Loutfy and R. 0. Loutfy, Can. J . Chem., 54, 1454 (1976). H. Miyazaki, T. Kubota, and M. Yamakawa, Bull. Chem. Soc. Jpn, 45, 780 (1972). J. P. Maier, J.-F. Muller, and T. Kubota, Helu. Chim.Acta, 58, 1634 (1975). G. V. Kulkami, A. Ray, and C. C. Patel, Proc. Indian Acad. Sci., Sect. A , 86, 273 (1977). F. Escudero, 0. Mo , a n d M. Yaiiez, J . Chem. Soc., Perkin Trans. 2, 1983, 1735. Y. Goto, T. Niiya, N. Honjo, T. Sakamoto, H. Yoshizawa, H. Yamanaka, and T. Kubota, Chem. Pharm. Bull., 30, 1126 (1982). 5914. A. G. Moritz and D. B. Paul, Aust. J . Chem., 22, 1305 (1969). 5915. D. J. Elias, A. G. Moritz, and D. B. Paul, Aust. J . Chem., 25, 427 (1972). 5916. W. W. Paudler and S. A. Humphrey, Org. M a p . Reson., 3, 217 (1971). 5917. L. Stefaniak, Spectrochim. Acta, Part A , 32, 345 (1976). 5918. N. Kulevsky and R. G. Severson, Spectrochim. Acta, Sect. A , 26,2227 (1970); J . Phys. Chem., 75, 2504 (1971). 5919. T. Kubota and H. Miyazaki, Chem. Pharm. Bull., 9, 948 (1961). 5920. W. E. Oberhiinsli, Helo. Chim. Acta, 53, 1787 (1970). 5921. W. B. Cowden, N. W. Jacobsen, and H. Stunzi, Aust. J . Chem., 35, 1251 (1982). 5922. J. Streith, C. Leibovici, and P. Martz, Bull. Soc. Chim. Fr., 1971, 4152. 5923. J. M. McCall and R . E. Ten-Brink, Synthesis, 1975, 335. 5924. T.-C. Lee, G. Stohrer, M. N. Teller, A. Myles, and G. B. Brown, Biochemistry, 10,4463 (1971). 5925. J.-C. Muller and H. Ramuz, Helo. Chim.Acta, 65, 1445 (1982). 5926. J. Streith and P. Martz, Tetrahedron Lett., 1969, 4899. 5927. F. Bellamy, P. Martz, and J. Streith, Tetrahedron Lett., 1974, 3189. 5928. F. Roeterdink, H. C. van der Plas, and A. Koudijs, Recl. Trau. Chim.Pays-Bas, 94, 16 (1975). 5929. M’. V. Jovanovich, Heterocycles, 22, 1115 (1 984). 5930. J. M. McCall, J. W. Aiken, C. G. Chidester, D. W. D u Charme, and M. G. Wendling, J . Med. Chem., 26, 1791 (1983). 5931. T. Kato, H. Yamanaka, T. Adachi, and H. Hirdnuma, J . Org. Chem., 32, 3788 (1967). 5932. R. E. Banks, R. N. Haszeldine, and J. M. Robinson, J . Chem. Soc., Perkin Trans. 1, 1976, 1226. 5933. V. F. Sedova and V. P. Mamaev, Zh. Org. Khim., 13, 2220 (1977). 5934. H. Yamanaka, S. Niitsuma, Y. Bannai, and T. Sakamoto, Chem. Pharm. Bull., 23,2591 (1975). 5935. R. A. Abramovitch and D. A. Abramovitch, J . Chem. Soc., Chem. Cornmun., 1979, 956. 5936. H. C. van der Plas, M. C. Vollering, H. Jongejan, and B. Juurdeeg, Recl. Trau. Chim. Pays-Bas, 93, 225 (1974). 5937. M. A. Khan and B. M. Lynch, Can. J . Chem., 49, 3566 (1971).

5908. 5909. 5910. 5911. 5912. 5913.

5938. 5939. 5940. 5941. 5942. 5943. 5944. 5945. 5946. 5947. 5948. 5949.

K. A. Gupta, A. K. Saxena, and P. C. Jian, Indian J . Chem., Sect. B, 21, 228 (1982). T. J. Schwan, J . Heterocycl. Chem., 14, 695 (1977). P. F. Juby and T. W. Hudyma, J . Med. Chem., 10, 954 (1967). W. Pfleiderer, L. Grozinger, and F. Sagi, Chem. Ber., 99, 3524 (1966). S. Senda, K. Hirota, and J. Notani, Chem. Pharm. Bull., 20, 1389 (1972). V. P. Shvachkin, M. K. Berestenko, and G. P. Mishin, Zh. Obshch. Khim., 34, 1687 (1964). M. M. El-Kerdawy, A. A. Abou-Ouf, and Y. M. Abou-Zeid, J . Pharm. Sci. LIAR, 9, 1 (1968). V. H. Bono, C. C. Cheng, E. Frei, and M. G. Kelly, Cancer Res., 24, 513 (1964). R. Kotva, J. Vachek, and J. Kfepelka, Collect. Czech. Chem. Commun., 48, 299 (1983). E. L. Khanina and G. Y. Dubur, Khim. Geterotsikl. Soedin., 1982, 525. R. A. Clarke and B. E. Christensen, J . Am. Chem. Soc., 70, 1818 (1948). D. G. Crosby and R. V. Berthold, J . Med. Chem., 6, 334 (1963).

References

1335

5950. W. Hepworth and T. W. Thompson, Br. Pat. 1,121,922 (1968, 1969); Chem. Abstr., 69, 77274 (1968); 75, 151831 (1971). 5951. J. Okada, K. Nakano, H. Miyake, and S. Yasufuku, Chem. Pharm. Bull., 30, 91 (1982). 5952. P. Roy-Burman and D. Sen, Biochem. Phurmacol., 13, 1437 (1964). 5953. F. Yoneda, Y. Sakuma, T. Nagamatsu, and S. Mizumoto, J . Chem. Soc., Perkin Trans. I , 1976, 2398. 5954. Y. Kimura, T. Miyamoto, J.-I. Matsumoto, and S. Minarni, Chem. Pharm. Bull., 24, 2637 (1 976). 5955. H. Bredereck, F. Effenberger, and W. Resemann, Angew. Chem., 74, 253 (1962). 5956. 5957. 5958. 5959. 5960. 5961. 5962. 5963. 5964. 5965. 5966. 5967.

T. Sakamoto, K.-I. Tanji, and H. Yamanaka, Chem. Pharm. Bull., 30, 1033 (1982). V. V. Lapachev, 0.A. Zagulyaeva, and V. P. Mamaev, Khim.Geterotsikl. Soedin., 1975, 1136. T. S. Safonova and L. A. Myshkina, Zh. Ohshch. Khim., 34, 1682 (1964). H. Pazdro; Diss. Pharm. Pharmacol., 18, 359 (1966); Chem. Ahstr., 66, 18691 (1967). B. Radziszewski, Ber. Dtsch. Chem. Ges., 18, 355 (1885). E. H. Keiser and L. McMaster, Am. Chem. J . , 49, 81 (1913). L. McMaster and F. B. Langreck, J . Am. Chem. Soc., 39, 103 (1917). J. C. Ambelang and T. B. Johnson, .I. Am. Chem. Soc., 63, 1289 (1941). R. Niess and H. Eilingsfeld, Liebigs Ann. Chem., 1974, 2019. A. J. Kirby and T. G. Mujahid, Tetrahedron Lett., 1978, 4081. T. B. Johnson and A. Litzinger, J . Am. Chem. Soc., 57, 1139 (1935). S. C. Bennur, V. B. Jigajinni, and V. V. Badiger, Rev. Roum. Chim., 21, 757 (1976).

5968. S. Robev, Dokl. Bolg. Akad. Nauk, 31, 865 (1978). 5969. R. Schenck and H. Finken, Liebigs Ann. Chem., 462, 267 (1928). 5970. F. Sauter, P. Stanetty, and A. Mesbah, J . Chem. Res., Synop. 186, Minipr. 2001 (1977). 5971. Y. Kobayashi, T. Kutsuma, and K. Morinaga, Chem. Pharm. Bull., 19, 2106 (1971). 5972. F. Georgescu, E. I. Georgescu, F. Chiralev, and I. Zugravescu, Rev. Roum. Chim., 27, 635 (1982); Chem. Ahstr., 98, 107240 (1983). 5973. M. Sekiya and M. Imaida, Jap. Pat. 172,524 (1946) 172,540 (1946), 172,541 (1946); Chem. Ahstr., 43, 7051 (1949). 5974. H. Gysling and G . Schwarzenbach, Helv. Chim.Acta, 32, 1484 (1949). 5975. T. B. Johnson and N. Shepard, Am. Chem. J., 46, 345 (1911). 5976. R. H. Wiley, A. B. Canon, and K. F. Hussung, J . Med. Chem., 6, 333 (1963). 5977. M. Ridi and P. Papini, Gazz. Chim.Ztal., 76, 376 (1946). 5978. T. Nishino, M. Kiyokawa, Y. Miichi, and K. Tokuyama, Bull. Chem. Soc. Jpn., 46,253 (1973). 5979. T. B. Johnson and L. A. Mikeska, J . Am. Chem. Soc., 42, 2349 (1920). 5980. F. Johnson, K. M . R. Pillai, A. P. Grollman, L. Tseng, and M. Takeshita, J . Med. Chem., 27, 954 (1984). 5981. A. A. Santilli, D. H. Kim, R. A. Fieber, and S. V. Wanser, J . Pharm. Sci., 63, 449 (1974). 5982. R. Brossmer and D. Ziegler, Angew. Chem., 79, 322 (1967). 5983. K.-Y. Zee-Cheng and C. C. Cheng, J . Org. Chem., 33, 892 (1968). 5984. B. R. Baker, B.-T. Ho, and G. B. Chheda, J . Heterocycl, Chem., 1, 88 (1964). 5985. T. Sasaki and M. Ando, Bull. Chem. Soc. Jpn., 41, 2960 (1968). 5986. T. B. Johnson, J . Am. Chem. Soc., 51, 1274 (1929). 5987. L. P. Prikazchikova, B. M. Khutova, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1974, 1146. 5988. H. Yamanaka and T. Sakarnoto, Kagaku no Ryoiki Zokan, 9, 249 (1979).

1336

References

5989. L. P. Zalukaev and V. L. Trostyanetskaya, Khim. Geterotsikl. Soedin., 1971, 836. 5990. 5991. 5992. 5993. 5994. 5995. 5996. 5997. 5998. 5999. 6000.

B. Roth, J . M e d . Chem., 12, 227 (1969). E. A. Oostveen and H. C. van der Plas, Recl. Trav. Chim. Pays-Bas, 98, 441 (1979). L. FarkaS, J. Keuler, and H. Wamhoff, Chem. Ber., 113, 2566 (1980). Y. P. Shvachkin, M. K. Berestenko, and L. Tung-Hai, Khim. Geterotsikl. Soedin., Akad. Nauk Latu. S S R , 1965, 626; Chem. Ahstr., 64, 801 (1966). E. C. Taylor and R. W. Morrison, Angew. Chem., 77, 859 (1965). H. L. Wheeler and H. F. Merriam, J . Am. Chem. Soc., 23, 283 (1901). C. Grundmann, Fortschr. Chem. Forsch., 7, 62 (1966). C. Grundmann and J. M. Dean, J . Org. Chem., 30, 2809 (1965). A. Albert, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 2 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1973: (a) p. 1; (b) p. 47. A. Albert, in Physical Methods in Heterocyclic Chemistry (A. R. Katritzky, Ed.), Academic Press, New York: (a) Vol. 1 (1963), p. 1; (b) Vol. 3 (1971), p. 1. K. Kamala, P. J. Rao, and K. K. Reddy, Synth. Commun., 19, 2621 (1989).

6001. A. H. H. Elghandour, M. M. M. Ramiz, and M. H. Elnagdi, Synthesis, 1989, 775. 6002. K. Hirota, H. Sajiki, Y. Maki, H. Inoue, and T. Ueda, J . Chem. Soc., Chem. Commun., 1989, 1659. 6003. J. Bomelburg, G. Heppke, and A. Ranft, Z . Naturforsch., Teil B, 44, 1127 (1989). 6004. J. Zheng and K. Undheim, Acta Chem. Scand., 43, 816 (1989). 6005. I. K. Korobeinicheva, V. F. Sedova, S. B. Gashev, L. D. Smirnov, 0. V. Yagodina, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1989, 1094. 6006. N. G. Kundu, G. Das, C. P. Spears, A. Majumdar, and S.-I. Kang, J . Med. Chem., 33, 1975 (1990). 6007. B. Altural, Y. Akcamur, E. Saripinar, I. Yildirim, and G. Kollenz, Monatsh. Chem., 120, 1015 (1989). 6008. J . Liebscher, A. Hassoun, and J. Fabian, Monatsh. Chem., 120, 749 (1989). 6009. V. J. Ram, J . Prukt. Chem., 331, 957 (1989). 6010. F. Zeuner and H.-J. Niclas, J . Prakt. Chem., 331, 324 (1989). 6011. S. A. El-Sharabsy, S. M. Abdel-Gawad, and S. M. Hussain, J . Prakt. Chem., 331, 207 (1989). 6012. F. Zeuner and H.-J. Niclas, J . Prakt. Chem., 331, 121 (1989). 6013. G. G. Moskalenko, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1989, 1100. 6014. 0 . V. Yagodina, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1989, 1088. 601 5. E. L. Khanina, R. M. Zolotoyabko, D. K. Mutsenietse, and G . Y. Dubur, Khirn. Geterotsikl. Soedin., 1989, 1076. 6016. G. G. Moskalenko, V. F. Sedova, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1989, 962. 6017. S. B. Gashev, L. V. Gol'tsova, L. D. Smirnov, and V. P. Lezina, Khim. Geterotsikl. Soedin., 1989, 636. 6018. B. E. Mandrichenko, 1. A. Mazur, G. 1. Tkachenko, I. A. Yudina, A. V. Karpenko, and P. N. Steblyuk, Farm. Zh. (Kiev), 1990, 56; Chem. Ahstr., 114, 42700 (1991). 6019. H. Li, Z. Zhang, Y. Mai, and K. Huang, Zhongguo Yiyao Gongye Zazhi, 21, 3 (1990); Chem. Ahstr., 114, 23912 (1991). 6020. F. V. Sharipova, L. A. Baltina, Y. G. Kuvatov, Y. A. Murinov, and G. A. Tolstikov, Radiokhimiya, 32, 33 (1990); Chem. Ahstr., 113, 191283 (1990). 6021. K. Takagi, A. Bajnati, and M. Hubert-Habart, Heterocycles, 31, 1105 (1990). 6022. S. El-Bahaie, M. G. Assy, and A. Kadry, Collect. Czech. Chem. Commun., 55, 1049 (1990). 6023. P. Molina and M. J. Vilaplana, Synthesis, 1990, 474.

References

1337

6024. A. Garcia-Martinez, A. Herrara-Fernandez, R. Martinez-Alvarez, M. C. Silva-Lasada, D. Molero-Vilchez, L. R . Subramanian, and M. Hanack, Synthesis, 1990, 881. 6025. M. Legraverend, H. Boumchita, and E. Bisagni, Synthesis, 1990, 587. 6026. J. Liebscher, A. Hassoun, H. van der Plas, and C. Stam, J . Heterocycl, Chem., 27, 1441 (1990). 6027. Y. Tominaga, Y. Matsuoka, Y. Oniyama, Y. Urchimura, H. Kominya, M. Hirayama, S. Kohra, and A. Hosomi, J . Heterocycl. Chem., 27, 647 (1990). 6028. R. L. Wydra, E. S. Patterson, and L. Strekowski, J . Heterocycl. Chem., 27, 803 (1990). 6029. V. A. Dorokhov, M. F. Gordeev, A. V. Komkov, and V. S. Bogdanov, Izu. Akad. Nauk S S S R , Ser. Khim., 1990, 145. 6030. S. N. Mazumdar and M. P. Mahajan, Tetrahedron Lett., 31,4215 (1990). 6031. M. Doise, F. Dennin, D. Blondeau, and H. Sliwa, Tetrahedron Lett., 31, 1155 (1990). 6032. K. Hirota, H. Sajiki, P.-Z. Ni, Y. Kitadi, and Y. Maki, Tetrahedron, 46, 3431 (1990). 6033. L. Strekowski, M. J. Harden, W. B. Grubb, S. E. Patterson, A. Czarny, M. J. Mokrosz, M. T. Cegla, and R. L. Wydra, J . Heterocycl Chem., 27, 1393 (1990). 6034. I. I. Nechayuk, N. V. Shibaeva, S. V. Borodaev, I. A. Pyshchev, and S. M. Lukyanov, Khim. Geterotsikl. Soedin., 1990, 134. 6035. E. N. Dozorova, S. I. Grizik, and V. G. Granik, Khim. Geterotsikl. Soedin., 1990, 81. 6036. V. G. Kartsev, 2. G. Aliev, G. N. Voronina, and L. Atovmyan, Khim. Geterotsikl. Soedin., 1990, 515. 6037. J. H. Chan and B. Roth, J . Med. Chem., 34, 550 (1991). 6038. A. D. Shutalev, L. A. Ignatova, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., 1990, 133. 6039. (a) K. Ienaga and W. Pfleiderer, Liebigs Ann. Chem., 1872 (1979);(b) K. Ienaga, T. Hasegawa, D. J. Brown, and W. Pfleiderer, J . Chem. Soc., Perkin Trans. I, 1988, 593. 6040. H. R . Rosenberg, Chemistry and Physiology of h e Vitamins, Interscience, New York, 1942, pp. 99-150. 6041. B. C. P. Jansen and W. F. Doneth, Chem. Werkbl.,23,201 (1926); Chem. Abstr., 20,2005 (1926). 6042. B. C. P. Jansen and W. F. Doneth, Geneeskd. Tijdschr. Ned.-lndie, 66,810 (1927);Chem. Ahstr., 21, 2150 (1927) 6043. D. E. Danford and H. N. Munro, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G. Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 1560. 6044. G. L. Mandell and M. E. Sande, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G . Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 1106. 6045. I. M. Rollo, in The Pharmacological Basis of Therapeutics, 6th ed. (A. G. Gilman, L. S. Goodman, and A. Gilman, Eds.), Macmillan, New York, 1980, p. 1038. 6046. K. Maeda, H. Kosaka, G. Yagishita, and H. Umezawa. .I. Antihiot., Ser. A , 9, 82 (1956). 6047. D. J. Brown and G. W. Grigg, Med. Res. Rev.,2, 193 (1982). 6048. T. E. Allen, D. J. Brown, W. B. Cowden, G. W. Grigg, H. K. Hart, J. A. Lamberton, and A. Lane, J . Antihiot., 37, 376 (1984). 6049. F. Himmelsbach, B. S. Schulz, T. Trichtinger, R. Charubala, and W. Pfleiderer, Tetrahedron, 40, 59 (1984). 6050. H. Yamanaka, T. Sakamoto, and S. Niitsuma, Heterocycles, 31, 923 (1990). 6051. G. Zvilehovsky and M . David, J . Org. Chem., 48 575 (1983). 6052. A. TomaiiE, M. TiSler, and B. Stanovnik, Tetrahedron, 37, 1787 (1981). 6053. T. Sakamoto, H. Yoshikawa, H. Yamanaka, Y. Goto, T. Niiya, and N. Honjo, Heterocycles, 17, 73 (1982). 6054. W. W. Paudler and M. V. Javanovic, Heterocycles, 19, 93 (1982). 6055. L. Stefaniak, M. Witanowski, and G. H. Webb, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 29, 489 (1981).

1338

References

6056. D. W. Boykin, P. Balakrishnan, and A. L. Baumstark, J . Heterocycl. Chem., 22, 981 (1985). 6057. V. p. Lezina, M. M. Kozlova, S. B. Gashev, L. V. Gol’tsova, A. V. Stepanyants, and L. D. Smirnov, Khim. Geterotsikl, Soedin., 1987, 1369. 6058. M. V. Jovanovich, Spectrochim. Acta, Part A , 41, 1135 (1985). 6059. M. V. Jovanovic, Heterocycles, 22, 1195 (1984). 6060. W. W. Paudler and M. V. Jovanovic, J . Org. Chem., 48, 1064 (1983). 6061. V. M. Campese, Drugs, 22, 257; (1981), Chem. Abstr., 95, 214623 (1981). 6062. V. H. Price, J . Am. Acad. Dermatol., 16, 749 (1987). 6063. M. J. de Geeter, J. M. McCall, and D. L. Teagarden, US Pat. 4,393,065 (1983); Chem. Abstr., 99, 157105 (1983). 6064. H. Yagihara, Y. Morishima, K. Osabe, Y. Goto, and K. Masamoto, Jap. Pat 01,180,805 (1989); Chem. Abstr., 112, 50609 (1990). 6065. J. A. May and A. C. Sartorelli, J . Med. Chem., 21, 1333 (1978). 6066. V. F. Sedova, T. Y. Mustafina, V. P. Krivopalov, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1983, 102. 6067. K. Minn, Synlett, 1991, 115; Chem. Abstr., 115, 8710 (1991). 6068. Y. Liang, H. Long, K. Li, Y. Lou, X. Yang, F. Xiao, and Z. Zheng, Zhongguo Yiyao Gongye Zazhi, 21, 388 (1990); Chem. Abstr., 114, 143339 (1991). 6069. M. Radojkovic-Velickovic and M. Misic-Vukovic, J . Serb. Chem. Soc., 54, 563 (1989); Chem. Abstr., 114, 101859 (1991). 6070. M . M. El-Kerdawy, H. M. Eisa, A. A. El-Emam, M. A. Massound, and M. N. Nasr, Arch. Pharrnacol. Res., 13, 142 (1990); Chem. Abstr., 114, 101905 (1991). 6071. A. Wada, J. Yamamoto, Y. Hamaoka, K. Ohki, S. Nagai, and S. Kanatomo, J . Heterocycl. Chem., 27, 1831 (1990). 6072. I. Ibnusaud, E. J. P. Malar, and N. Sundaram, Tetrahedron Lett., 31, 7357 (1990). 6073. A. Naim and P. B. Shevlin, Synth. Commun., 20, 3439 (1990). 6074. T. Benneche, G. Keilen, G. Hagelin, R. Oftebro, and K. Undheim, Acta Chem. Scand., 45, I77 ( 1 99 1). 6075. D. T. Hurst, S. Atcha, and K. L. Marshall, Aust. J . Chem., 44, 129 (1991). 6076. N. Ple, A. Turck, E. Fiquet, and G. Queguiner, J . Heterocycl. Chem., 28, 283 (1991). 6077. A. Wada, K. Ohki, S. Nagai, and S. Kanatomo, J . Heterocycl. Chem., 28, 509 (1991). 6078. A. Albert, Heterocyclic Chemistry, 2nd ed. (Athlone Press, London, 1968). 6079. S. F. Mason, in Physical Methods in Heterocyclic Chetnistry, Vol. 2 (A. R. Katritzky, Ed.), Academic Press, New York, 1963, p. 1. 6080. W. L. F. Armarego, in Physical Methods in Heterocyclic Chemistry, Vol. 3 (A. R. Katritzky, Ed.), Academic Press, New York, 1971, p. 67. 6081. D. J. Brown, in Comprehensive Heterocyclic Chemistry, Vol. 3 (A. J. Boulton and A. McKillop, Eds, Pergamon Press, Oxford, 1984) p. 57. 6082. A. Albert and E. P. Serjeant, The Determination oflonization Constants, 3rd ed. (Chapman and Hall, London, 1984). 6083. D. D. Perrin, Dissociation Constants of Oryanic Bases in Aqueous Solution and Supplemenl, Butterworths, London, 1965, 1972. 6084. G. Kortum, W. Vogel, and K. Andrussow, Pure Appl. Chem., 1, 189 (1960). 6085. E. P. Serjeant and B. Dempsey, Ionization Constants of Organic Acids in Aqueous Solution, Pergamon Press, Oxford, 1979. 6086. J. Clark and D. D. Perrin, Q. Rev. Chem. Soc., 18, 295 (1964). 6087. G. B. Barlin and D. D. Perrin, Q. Reo. Chem. Soc., 20, 75 (1966).

References

1339

6088. D. D. Perrin, B. Dempsey, and E. P. Serjeant, pK, Predictionfor Organic Acids and Bases, Chapman and Hall, London, 1981. 6089. S. F. Mason, Chem. Soc. Spec. Puhl., 1955, No. 3, 139. 6090. S. F. Mason, J . Chem. Soc., 1959, 1253. 6091. A. Albert and E. Spinner, J . Chem. Soc., 1960, 1221. 6092. E. Spinner, J . Chem. Soc., 1960, 1226. 6093. E. Spinner, J . Chem. Soc., 1960, 1232. 6094. E. Spinner, J . Chem. Soc., 1960, 1237. 6095. T. Nishiwaki, Tetrahedron. 23, 1153 (1967). 6096. A. Costopanagiotis and H. Budzikiewicz, Monatsh. Chem., 96, 1800 (1965). 6097. H.-F. Griitzmacher and W. Arnold, Tetrahedron Lett., 1966, 1365. 6098. H. Ichikawa and M. Ogata, J . Am. Chem. Soc., 95, 806 (1973). 6099. S. F. Mason, J . Chem. Soc., 1958, 3619. 6100. S. F. Mason, J . Chem. Soc., 1959, 1281. 6101. Q. N. Porter, Mass Spectrometry ofHeterocyclic Compounds, 2nd ed., Wiley, New York, 1985, p. 721ff. 6102. F. Milani-Nejad and H. D. Stidham, Spectrochim. Actu, Part A , 31, 1433 (1975). 6103. J. H. Betnon, R. M. Caprioli, and T. Ast, Org. Mass Spectrom., 6, 273 (1972). 6104. K. Undheim and G . Hvistendahl, Actu Chem. Scand., 25, 3227 (1971). 6105. T. Kato, H. Yamanaka, H. Abe, S. Sasaki, and H. Ichikawa, Org. Mass Spectrom., 9, 981 (1974). 6106. J. Hitzke and J. Guion, Org. Mass Spectrom., 11, 20 (1976). 6107. L. Y. Ivanovskaya, M. 1. Gorfinkel, V. F. Sedova, and Z. D. Dubovenko, Ory. M a s s Spectrum., 7, 91 1 (1973). 6108. J. Ulrich, R. Teoule, R. Massot, and A. Cornu, Ory. Muss Spectrom., 2, 1183 (1969). 6109. E. White, V. P. M. Krueger, and J. A. McCloskey, J . Org. Chem., 37, 431 (1972). 6110. C. Fenselau and S. Y. Wang, Tetrahedron, 25, 2853 (1969). 6111. R. W. Reiser, Org. Mass Spectrom., 2, 467 (1969). 6112. J. Clark, Z. Munawar, and A. W. Timms, J . Chem. Soc., Perkin Trans. 2, 1972, 233. 6113. E. C. Alexander and R. J. Jackson, J . Org. Chem., 40, 1500 (1975). 6114. J. G. Liehr, C. L. Weise, P. F. Crain, G. H. Milne, D. S. Wise, L. B. Townsend, and J. A. McCloskey, J . Heterocycl. Chem., 16, 1263 (1979). 6115. E. Wyrzykiewicz, M. Stobiecki, and K. Golankiewicz, Org. Muss Spectrorn., 14, 405 (1979). 6116. G . B. Barlin and D. D. Perrin, in Techniques of Chemistry, Vol. 4, Part 1, 2nd ed. (K. W. Bentely and G. W. Kirby, Eds.), Wiley, New York, 1972, p. 611. 6117. R. J. Mattson and C. P. Sloan, J . Ory. Chem., 55, 3410 (1990). 6118. M. Matsui, K. Kamiya, K. Shibata, and H. Muramatsu, J . Org. Chem., 55, 1396 (1990). 61 19. H. Yamanaka and S. Ohba, Heterocycles, 31, 895 (1990). 6120. T. Sakakibara, T. Kume, and K. Shimohara, Heterocycles, 31, 459 (1990). 6121. K. Takagi, A. Bajnati, and M. Hubert-Habart, J . Heterocycl Chem., 27, 1847 (1990). 6122. K. Takagi, A. Bajnati, and M. Hubert-Habart, Bull. Soc. Chim. Fr., 127, 660 (1990). 6123. I. I. Gerus, S. I. Vdovenko, M . G. Gorbunova, and V. P. Kukhar, Khim. Geterotsikl. Soedin., 1991, 502. 6124. A. Turck, N. Ple, L. Mojovic, and Q. Queguiner, J . Heterocycl. Chem., 27, 1377 (1990). 6125. D. Peters, A,-B. Hornfeldt, and S. Gronowitz, J . Heterocycl. Chem., 27, 2165 (1990). 6126. N. G . Kundu, B. Das, and A. Majumdar, Synthesis, 1990, 243.

1340

References

6127. N. C. Mathur and H. Shechter, Tetrahedron Lett., 31, 6965 (1990). 6128. E. Grimaux, C. R . Acad. Sci., 87, 752 (1878); 88, 85 (1879); [ J . Chem. Soc., Abstr., 36, 375,460, respectively (1879)l. 6129. G. Vasilev, Dokl. Bolg. Akud. Nauk. 43, 57 (1990); Chem. Ahstr., 115, 49603 (1991). 6130. M. Botta, F. dc Angelis, F. Corelli, M. Menichincheri, R. Nicoletti, M. E. Maronqiu. A. Pani, and P. La Colla, Arch. Phurm. (Weinheim,Ger.), 324, 203 1991. 6131. M. D. Ankhiwala, J . Indian. Chem. Sue., 67, 848 (1990). 6132. M.-C. Sacquet, M.-C. Fargeau-Bellassoued, and B. Graffe, J . Heterocycl. Chem., 28, 667 (199 1). 6133. L. Strekowski, R. L. Wydra, L. Janda, and D. B. Harden, J . Org. Chem., 56, 5610 (1991). 6134. R. Radinov, K. Chanev, and M. Haimova, J . Org. Chem., 56, 4793 (1991). 6135. M. B. Mitchell and P. J. Wallbank, Tetrahedron Lett., 32, 2273 (1991). 6136. G. de Nanteuil, Tetrahedron Lett., 32, 2467 (1991). 6137. K. Seki, N. Kanazashi, and K. Ohkurd, Heterocycles, 32, 229 (1991). 6138. J. Nasielski, A. Standaert, and R. Nasielski-Hinkens, Synth. Commun., 21, 901 (1991). 6139. M. T. Cocco, C. Congiu, V. Ornnia, and A. Maccioni, Synthesis, 1991, 529. 6140. I. V. Vendernikova, Y. I. Ryabukhin, M. I. Khaitin, and Y. N. Sinkina, Bull. Soc. Chim. Belg., 100, 487 (1991). 6141. U. Hees, M. Lederrnann, and M. Regitz, Synlett, 1990, 401. 6142. V. P. Borovic, N. A. Yazykov, and V. P. Mamacv, Sib. Khim. Zh., 87(1991); Chem. Ahstr., 115, 183224 (1991). 6143. Y. Tominaga, S. Ohno, S. Kohra, H. Fujito, and H. Mazurne, J . Heterocycl. Chem., 28, 1039 (1 991). 6144. A. Pinner, Ber. Dtsch. Chem. Ges., 17, 2519 (1884). 6145. 0. Widman, J . Prakt. Chem. [2], 38, 185 (1888). 6146. A. Skita, Ber. Dtsch. Chem. Ges. A, 59, 158 (1926). 6147. J. Colrnan and A. Albert, Ber. Dtsch. Chem. Ges. A , 59, 7 (1926). 6148. K . Hosch, Ber. Dtsch. Chem. Ges., 54, Sonderheft (1921). 6149. H. Pringsheirn, H. Leuchs, F. Hahn, and W. Lange, Z . Angew. Chem., 39, 61 (1926). 6150. W. Hempel, Z . Angew. Chem., 29, I, 189 (1916). 6151. H. B. Vickery, Biogr. Mem., Nut. Acad. Sci., 27, 83 (1952). 6152. T. B. Johnson, J . Ind. Eng. Chem., 10, 305 (1918). 6153. P. Jacobson, in Meyer und Jacobson: Lehruhuch der Organischen Chemie, Vol. 2, Part 3 (H. Kuh and F. Richter, Eds.), de Gruyter, Berlin, 1920, p. 1172. 6154. T. B. Johnson and D. A. Hahn, Chem. Rev., 13, 193 (1933). 6155. T. B. Johnson, in Organic Chemistry, Vol. 2 (H. Gilrnan, Ed.), Wiley, New York, 1983, p. 948. 6156. B. Lythgoe, Q. Rev., Chem. Soc., 3, 181 (1949). 61 57. G. W. Kenner, in Thorp’s Dictionary of Applied Chemistry, Vol. 10,4th ed. Longrnans Green, London, 1950, p. 137. 6158. D. 3. Brown. Rev. Pure A p p l . Chem., 3, 115 (1953). 6159. R. E. Wiley, in Organic Chemistry, 2nd ed. Vol. 4 (H. Gilrnan, Ed.), Wiley, New York, 1953-1958, p. 864. 6160. A. Bendich, in Nucleic Acids, Vol. 1 (E. Chargaff and J.N. Davidson, Eds.), Academic Press, New York, 1955, p. 81. 6161. G. W. Kenner and A. R. Todd, in Heterocyclic Compounds, Vol. 6 (R. C. Elderfield Ed.), Wiley, New York, 1957, p. 234.

References

1341

6162. G. R. Ramage and J. K. Landquist, in Chemistry of Carbon Compounds, Vol. 4h (E. H. Rodd, Ed.), Elsevier, Amsterdam, 1959, p. 1257. 6163. D. J . Brown, T. J. Batterham, W. B. Cowden, R. F. Evans, M. D. Fenn, and S . F. Mason, The Pyrimidines, Wiley, New York, 1962; Supplement I (1970); Supplement I I (1985). 6164. R. T. Walker, in Rodd's Chemistry of Carbon Compunds, 2nd ed. Vol. 4iJ (M. F. Ansell, Ed.), Elsevier, Amsterdam, 1989, p. 155. 6165. D. J . Brown, Nist. Rec. Aust. Sci., 8, 63 (1990). 6166. IUPAC, Nomenclature of Organic Chemistry, Section A-F and H (J. Rigaudy and S. P. Klesney, Eds.), Pergamon Press, Oxford, 1979, pp. xix, 559. 6167. W. Bergmann and R. J. Feeney, J . Am. Chem. Soc., 72, 2809 (1950); J . Org. Chem., 16, 981 ( 1951). 6168. N. Suryaprakash, R. Ugolini, and P. Diehl, Magn. Reson. Chem., 29, 1024 (1991). 6169. T. Iwaoka, M. Sato, and C. Kaneko, J . Chem. Soc., Chem. Commun., 1991, 1241. 6170. J. T. Gupton, J. E. Gall, S. W. Riesinger, S. Q. Smith, K. M. Bevirt, J. A. Sikorski, M. L. Dahl, and Z. Arnold, J . Heterocycl. Chem., 28, 1281 (1991). 6171. T. Benneche, G. Kelien, J. Solberg, R. Ofterbro, and K. Undheim, Acta Chem. Scund., 45, 731 (1991). 6172. K. Ohkura, K. Matsuda, and K.-I. Seki, Heterocycles, 32, 1371 (1991). 6173. V. J. Ram, N. Haque, P. Y. Guru, and A. Shoeb, Indiun .I. Chem., Sect. B, 30, 962 (1991). 6174. S. Kambe, K. Saito, H. Kishi, A. Sakurai, and H. Midorikawa, Synthesis, 1979, 287. 6175. A. L. Weis and H. C . van der Plas, Heterocycles, 24, 1433 (1986). 6176. M. N. Glukhovtsev, B. Y. Simkin, V. I. Minkin, and 1. A. Yudilevich, Zh. Strukt. Khim.,23,23 (1982); Chem. Ahstr., 97, 71645 (1982). 6177. A. L. Weis and F. Frolow, Heterocycles, 19, 493 (1982). 6178. A. L. Weis and F. Frolow, J . Chem. Soc., Chem. Commun., 1982, 89. 6179. T. Eicher and G. Franke, Liehigs Ann. Chem., 1981, 1337. 6180. A. L. Weis and F. Frolow, J . Org. Chem., 49, 3635 (1984). 6181. A. L. Weis, unpublished data quoted in ref. 6175. 6182. V. P. Mamaev and A. I. Shchadrina, USSR Pat. 569,571 (1977);Chem. Abstr., 88,89702 (1978). 6183. M. Yogo, K. Hirota, and S. Senda, J . Chem. Soc., Perkin Trans. I , 1982, 473. 6184. A. R. Butler and I. Hussain, J . Chem. Soc., Perkin Trans. 2, 1980, 229. 6185. H. H. Hatt, G. D. Liehtenwalter, and G. H. Riessen, Aust. J . Chem., 23, 561 (1970). 6186. L. Birkofer and I. Storch, Chem. Ber., 86, 529 (1953). 6187. J. Mirek and T. A. Holak, Chem. Scripfa, 22, 133 (1983). 6188. R. Onoda, K. Sugimoto, R. Toyosawa, T. Sato, and M. Anhai, Akita Daiguku Kyoikuya K e n k y u Kiyo, Shizen Kagaku, 1982, 15; Chem. Abstr., 99, 53695 (1983). 6189. R. Zimmermann, Angew. Chem., 75, 1025 (1963). 6190. T. J. Delia, Fused Pyrimidines Part 4: Miscellaneous Fused Pyrimidines, Wiley, New York, 1992. 6191. W. L. F. Armarego, Fused Pyrimidines Part 1: Quinazolines, Wiley, New York, 1967. 6192. M. F. Gordeev, A. V. Komkov, and V. A. Dorokhov, Khim. Geterotsikl, Soedin., 1990, 1286. 6193. T. A. Kizner, M. A. Mikhaleva, and E. S. Serebryakova, Khim. Geterotsikl. Soedin., 1990, 801. 6194. M. A. Mikhaleva, T. A. Kizner, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1990, 804. 6195. G. G. Danagulyan, L. G. Saakyan, and M. G. Zalinyan, Khirn.Geterotsikl. Soedin., 1990, 850. 6196. G. Y. Remennikov, I . A. Dyachenko, V. V. Pirozhenko, and V. M. Cherkasov, Khim. Geterotsikl. Soedin., 1990, 849.

1342

References

6197. J. F. Wolfe, J. A. Campbell, and T. D. Greenwood, 1 . Pharm. Sci., 80, 705 (1991). 6198. R. Kumar, E. E. Knaus, L. I. Wiebe, T. M. Allen, and M. L. Tempest, Eur. J . Med. Chem., 26, 557 (1991). 6199. H. Kropf and W. Niirnberg, J . Chem. R e x , Synop. 146, Minipr. 664 (1991). 6200. S. E. Zayed, M. A. Hassan, F. M. Manhi, and I. A. Hussin, Arch, Pharm. ( Weinheim, Ger.), 322, 841 (1989). 6201. A. Diugosz, Arch. Pharm. (Weinheim. Ger.),322, 599 (1989). 6202. V. Kvita and A, Schweizer, Arch. Pharm. (Weinheim, Ger.), 322, 153 (1989). 6203. N. M. Smirnova, N. M. Cherdantseva, 0. A. Burova, V. M. Nesterov, and T. S. Safonova, Khim. Geterotsikl. Soedin., 1990, 971. 6204. S.-I. Hirokami, T. Takahashi, K. Kurosawa, M. Nagata, and T. Yamazaki, J . Org. Chem., 50, 166 (1985). 6205. C. J. Shishoo, M. B. Davani, K. S. Jain, S. R. Jain, V. S. Bhadti, S. Anathan, and P. D. Anvekar, Indian J . Chem., Sect. B, 29, 674 (1990); Chem. Abstr., 113, 231306 (1990). 6206. M. R. Mahmoud, A. Y. Soliman, and H. M. Bakeer, Indian J . Chem., Sect. B, 29, 830 (1990); Chem. Ahstr., 114, 23918 (1991). 6207. J. A. Barone, H. Tieckelmann, R. Guthrie, and J. F. Holland, J . Org. Chem., 25, 211 (1960). 6208. Z. BudbSinsky and V. Musil, Collect. Czech. Chem. Commun., 24, 4022 (1959). 6209. K. Sirakawa, Yakugaku Zasshi, 79, 1482 (1959). 6210. H.-D. Stachel, Chem. Ber., 95, 2172 (1962). 6211. A. J . Vazakas and W. W. Bennetts, J . Med. Chem., 7, 342 (1964). 6212. D. J. Collins, J . Chem. Soc., 1963, 1337. 6213. E. Kober and R. Ratz, J . Org. Chem., 27, 2509 (1962). 6214. S. Kajihara, T: Hirata, and A. Odaka, Nippon Kagaku Zasshi, 87, 884 (1966). 6215. 3 . Clark, 1. Gelling, and G. Neath, J . Chem. Soc., Chem Commun., 1967, 859. 6216. A. M. Triggle and D. J. Triggle, J . Pharm. Sci., 54, 795 (1965). 6217. J. L. Hilton, T. J. Monaco, D. E. Moreland, and W. A. Gentner, Weeds, 12, 129 (1964). 6218. J. N. Singh and A. B. Lal, J . Indian Chem. Soc., 40, 195 (1963). 6219. R. Daniels, L. T. Grady, and L. Bauer, J . Org. Chem., 27, 4710 (1962). 6220. T. Matsukawa and S. Yurugi, in Ret'iew of Japanese Literuture on Beriberi and Thiamine (N. Shimazono and E. Katsura, Eds.), University of Kyoto, Japan, pp. 81, 104. 6221. D. J. Brown, Proc. R. Aust. Chem. Inst., 33, 57 (1966). 6222. G . L'Abble, Ind. Chim. Belg., 36, 3 (1971). 6223. G. Menichi, M. Hubert-Habart, and R. Royer, Eur. J . Med Chem.-Chim. Ther., 9, 11 (1974). 6224. K. Takagi and M. Hubert-Habart, Bull. Soc. Chim. Fr., 1977, 369. 6225. R . D. Youssefyeh and A. Kalmus. J . Heterocycl. Chem., 8, 33 (1971). 6226. L. Giammanco, Atti Accad. Sci. Lett. Arti Palermo, Parte I [4], 27, 449 (1968). 6227. H. C. van der Plas, P. Smit, and A. Koudijs, Tetrahedron Lett., 1968, 9. 6228. J. W. Streef and H. J. den Hertog, Tetrahedron Lett., 1968, 5945. 6229. D. M. Brown and M. G . Burdon, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 399 6230. 0.A. Zagulyaeva, E. A. Travintseva, and V. P. Mamaev, Izu. Sib. Otd. Akad. Nauk S S S R ,Ser. Khim. Nuuk, 1975, 119. 6231. S. I. Zav'yalov, L. F. Ovechkina, and V. I. Gunar, Izu. Akud. Nauk SSSR, Ser, Khim., 1976, 2821. 6232. A. A. Aroyan, R. G. Mclik-Organdzhanyan, B. T. Garibdzanyan, and G. M. Stepanyan, Arm. Khim. Zh., 21, 868 (1968), Chem. Abstr., 71, 13083 (1969).

References 6233. 6234. 6235. 6236. 6237. 6238. 6239. 6240. 6241. 6242. 6243. 6244. 6245.

1343

R. A. Zhuk, J. Eiduss, and S. Hillers, Khim. GeterotsikL Soedin., 1968, 1111. C. O’Murchu, Chimiu, 29, 508 ( I 975). T. Koyama, M. Toda, T. Hirota, and M. Yamato, Yakugaku Zasshi, 90, 8 (1970). J. A. Montgomery, H. J. Thomas, and K. Hewson, J . Med. Chem., 15, 1189 (1972). C. Temple, C. L. Kussner, and J. A. Montgomery, J . Org. Chem., 33, 2086 (1968). G. L. Anderson and A. D. Broom, J . Org. Chem., 42,4159 (1977). J. B. Hynes, R. F. Gratz, and W. T. Ashton, J . Med. Chem., 15, 1332 (1972). D. H. Kim and A. A. Santilli, J . Org. Chem., 35, 1680 (1970). J. A. Montgomery and K. Hewson, in Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1 (W. W. Zorbach and R. S. Tipson, Eds.), Wiley, New York, 1968, p. 31. J. Clark and M. Curphey, J . Chem. Soc., Perkin Trans. I , 1977, 1855. A. P. Martinez, W. T. Lee, and L. Goodman, J . M e d . Chem., 11, 384 (1968). L. A. Ignatova, A. E. Gekhman, and B. V. Unkovskii, Khim. Geterotsikl Soedin., 1976, 561. N. V. Sazonov and A. A. Kropacheva, Khim. Geterotsikl Soedin., 1970, 710.

6246. S. Gabriel, Ber. Dtsch. Chem. Ges., 38, 630 (1905). 6247. A. W. Schwarz and G. J. F. Chittendon, Origin L f e , Proc. I S S O L Meet., 2nd 1977, 205; Chem. Ahstr., 90, 67950 (1979). 6248. A. W. Schwarz and G. J. F. Chittendon, Bio-Systems, 9, 87 (1977); Chem. Ahstr., 87, 195709 (1 977). 6249. R. D. Hotchkiss and T. B. Johnson, J . Am. Chem. Soc., 58, 525 (1936). 6250. E. Fischer and H. Leuchs, Ber. Dtsch. Chem. Ces., 35, 3787 (1902). 6251. D. Keglevik and A. Kornhauser, Croat. Chem. Acta, 31, 47 (1959). 6252. H. G. Henning, H. Haber, and A. Knoll, Z.Chern., 22, 58 (1982). 6253. W. Traube, Ber. Dtsch. Chem. Ges., 27, 277 (1894). 6254. W. Traube and H. Lorenz, Ber. Dtsch. Chem. Ges., 32, 3156 (1899). 6255. R. Lantzsch and D. Ark, Synthesis, 1977, 756. 6256. R. A. Mathes, F. D. Stewart, and F. Swedish, J . Am. Chem. Suc., 70, 1452 (1948). 6257. N. W. Gabel and S. B. Binkley, J . Ory. Chem., 23, 643 (1958). 6258. V. M. Rodionov and 0. S. Urbanskaya, Zh. Obshch. Khim., 18, 2023 (1948); Chem. Ahstr., 43, 3793 (1949). 6259. W. Ried and D. Piechaczek, Liebigs Ann. Chem., 696, 97 (1966). 6260. A. L. J. Beckwith and R. J. Hickman, J . Chem. Soc. (C), 1968, 2756. 6261. H. Burrows and C. A. Kaine, J . Chem. Soc., 91, 269 (1907). 6262. H. Rohnert, Chem. Ber., 89, 2239 (1956). 6263. A. Einhorn, Liehiys Ann. Chem., 343, 207 (1905). 6264. A. Einhorn, Liebigs Ann. Chem., 343, 272 (1905). 6265. H. Meyer, Liebigs Ann. Chem., 1980, 673. 6266. V. M. Rodionov and V. K. Zvorykina, Izu. Akad. Nauk S S S R , Odt. Khim. Nauk, 1948, 330; Chem. Ahstr., 43, 235 (1949). 6267. K. Folkers, H. J. Harwood, and T. B. Johnson, J . Am. Chem. Soc., 54, 3751 (1932). 6268. K. Folkers and T. B. Johnson, J . Am. Chem. Soc., 55, 3784 (1933). 6269. A. Ehsan and X. Karimullah, Pak. J . Sci. Ind. Rex, 10, 83 (1967); Chem. Ahstr., 68, 78231 (1968). 6270. T. George, R. Tahilramandi, and D. V. Mehta, Synthesis, 1975, 405. 6271. V. N. Konyukhov, G. S. Sakovich, L. V. Krupnova, and Z. V. Pushkareva, Zh. Org. Khim., 1, 1487 (1965).

1344

References

6772. E. Bullock, R. A. Carter, R. M. Cochrane, B. Gregory, and D. C. Shields, Can. J . Chem., 55,895 (1977). 6273. L. Y. Ivanovskaya, Z. D. Dubovenko, and V. P. Mamaev, Izu. Sib. Otd. Akad. Nauk S S S R ,Ser. Khim. Nuuk, 1969, 132; Chem. Ahstr., 72, 66892 (1970). 6274. J. Svetlik, V. HanuS, and J. Bella, J . Chem. Res., Synop. 4, Minipr. 101 (1991). 6275. E. L. Khanina, M. B. Andaburskaya, G. Duburs, and R. M. Zolotoyabko, Latc. P S R Zinat. Akud. Vestnis, Kim. Ser., 197 (1978); Chem. Abstr., 89, 43319 (1978). 6276. G. Y. Dubur and E. L. Khanina, Khim. Geterotsikl. Soedin., 1976, 220. 6277. T. Kato, T. Chiba, and M. Sasaki, Yukugaku Zusshi, 101, 182 (1981). 6278. H. A. Rutter and L. 0. Gustafson, J . Franklin Inst., 258, 413 (1954). 6279. K. S. Atwal, G. C. Rovnyak, S. D. Kimball, D. M. Floyd, S. Moreland, B. N. Swanson, J. Gougoutas, J. Schwartz, K. M. Smillie, and M. F. Malley, J . M e d . Chem., 33, 2629 (1990). 6280. H. Cho, M. Ueda, K. Shima, A. Mizuno, M. Hayashimatsu, Y. Ohnaka, Y. Takeuchi, M. Hamaguchi, and nine others, J . Med. Chem., 32, 2399 (1989). 6281. H. Yagihara, Y. Goto, K. Masarnoto, Y. Morishima, and H. Osabe, Jap. Kokai Tokkyo Koho, J P 63,198,669 (1988), 63,198,670 (1988); Chem. Ahstr., 110, 75557, 75558 (1989). 6282. D. N. Dhar and K. S. K. Murthy, Synthesis, 1986, 437. 6283. F. Hollywood, H. Suschitzky, and R. Hull, Synthesis, 1982, 662. 6284. H. Hagemann and K. Le., Angew. Chem., 84, 1062, 1063 (1972). 6285. A. M. Buzueva, Khim. Geterotsikl. Soedin., 1969, 345; Chem. Abstr., 71, 30439 (1969). 6286. J. Molina-Molina, J. P. Abad-Lonenzo, and J. A. Lopez-Sastre, An. Quim., Ser. ( C ) , 78, 250 (1982); Chem. Ahstr., 97, 145217 (1982). 6287. F. J. Lopez-Aparicio, J. A. Lopez-Sastre, J. Molina-Molina, and F. J. Lopez-Herrera, An. Quim., Ser. (C), 77, 147 (1981); Chem. Ahstr., 97, 72696 (1982). 6288. J. Ashby and D. Grifiths, J . Chem. Soc., Perkin Trans. I , 1975, 657. 6289. L. A. Clauss, H. J. Friedrich, and H. Jensen, Liebigs Ann. Chem., 1974, 561. 6290. L. A. Lazukina, V. 1. Gortbatenko, L. F. Lur’e, and V. P. Kukhar, Z h . Org. Khim., 13, 290 ( I 977). 6291. R. Nast, K. Ley, and U. Eholzer, Ger. Pat. 1,248,056 (1967); Chem. Ahstr., 68, 87305 (1968). 6292. C. Kashirna, M. Shirnizu, A. Katoh, and Y. Omote, J . Chem. Soc., Perkin Trans. I , 1983, 1799. 6293. J . Barluenga, M. Tornis, S. Fustero, and V. Gotor, Synthesis, 1979, 346. 6294. V. Gornez-Aranda, J. Barluenga, V. Gotor, and S. Fustero, Synthesis, 1974, 720. 6295. S. Hoffmann and W. Schultze, DDR Pat. 48617 (1966); Chem. Abstr., 66, 28793 (1967). 6296. S. Hoffrnann and E. Miihle, Z . Chem., 9, 66 (1969). 6297. D. Lloyd and H. McNab, J . Chem. Soc., Perkin Trans. 1, 1976, 1784. 6298. A. L. Weis and V. Rosenbach, Tetrahedron Lett., 1981, 1453. 6299. M . Mittclbach and H. Junek, Z . Naturforsch., Teil B, 34, 1580 (1979). 6300. K. Findcisen and K. Wagner, Synthesis, 1978, 40. 6301. P. J. Garratt, S. N. Thorn, and R. Wrigglesworth, Tetruhedron Lett., 32, 691 (1991). 6302. G. W. Crosbie, in The Nucleic Acids, Vol. 3 (E. Chargaff and J. N. Davidson, Eds.), Academic Press, New York, 1960, p. 323. 6303. E. F. Silversmith, J . Org. Chem., 27, 4090 (1962). 6304. A. Takamizawa and K. Hirai, Jap. Pat. 14950 (1967); Chem. Ahstr., 68, 105219 (1968). 6305. A. Takamizawa and K. Hirai, Jap. Pat. 14951 (1967); Chem. Ahstr., 68, 105223 (1968). 6306. T. Takeshirna, T. Imamoto, M. Yokoyama, K. Yamamoto, and M. Akano, J . Org. Chem., 33, 2877 (1 968). 6307. G. Zigeuner, T. Strallhofcr, F. Wede, and W. B. Lintschinger, Monatsh. Chem., 106, 1469 ( 1 975).

References 6308. 6309. 6310. 6311. 6312. 6313. 6314. 6315. 6316. 6317. 6318. 6319. 6320. 6321. 6322. 6323. 6324. 6325. 6326. 6327. 6328. 6329. 6330. 6331. 6332. 6333. 6334. 6335. 6336. 6337. 6338. 6339. 6340. 6341. 6342. 6343. 6344. 6345. 6346. 6347. 6348.

1345

J. Goerdeler, C. Lindner, and F. Zander, Chem. Ber., 114, 536 (1981). P. L. Southwick, A. S.Wagman, and A. S. Waggoner, Org. Prep. Proced. fnt., 23,713 (1991). F. I . Luknitskii, D. D. Taube, and B. A. Vovsi, Zh. Org. Khim., 5, 1844 (1969). F. I. Luknitskii, D. D. Taube, and B. A. Vovsi, Zh. Org. Khim., 5, 1851 (1969). F. I. Luknitskii, USSR Pat. 275,069 (1970); Chem. Abstr., 73, 131025 (1970). D. Borman, Chem. Ber., 107, 270 (1974). T. Okawara, K. Nakayama, and M. Furukawa, Chem. Lett., 1982, 1791. T. Okawara, K. Nakayama, and M. Furukawa, Chem. Pharm. Bull., 31, 507 (1983). M. D. Nair and P. A. Malik, Indian J . Chem., 5, 603 (1967). B. A. Tertov and Y. G. Bogaehev, Khim. Geterotsikl. Soedin., 1981, 119; Chem. Ahstr., 94, 208798 (1981). W. Ried and R. Schweitzer, Synthesis, 1976, 475. A. de la Hoz, C. Pardo, and J. Elguero, Tetruhedron Lett., 26, 3869 (1985). A. Padwa and L. Gehrlein, J . Am. Chem. Soc., 94, 4933 (1972). N. S. Narasimhan, H. Heimgartner, H.-J. Hansen, and H. Schmid, Hell;. Chim. Acta, 56, 1351 (1973). Y. Ito, Y. Inuhushi, and T. Saegusa, Synth. Commun., 4, 289 (1974). R. F. Evans, in Modern Methods in Organic Chemistry (C. J. Timmons, Ed.), van Nostrand, London, 1969, Chap. I . K. Eckardt, W. Ihn, D. Tresselt, and D. Krebs, Int. Con$ Chem. Biotechnol. B i d . Act. N u t . Prod., Proc. I s / , 3, 236 (1981); Chem. Ahstr., 97, 92674 (1982). J. T. Madison and R. W. Holley, Biochem. Biophys. Rex Commun., 18, 153 (1965). R. A. Jacobson and J. Bonncr, Biochem. Biophys. Res. Commun., 33, 716 (1968). P. Sabatier, in Nohel Lectures: Chemistry 1901-1921, Elsevier, Amsterdam, 1966, p. 22 1 [reprint of 19 12 Nobel Prize lecture]. D. C. Burke, J . Org. Chem., 20, 643 (1955). D. M. Brown, B. D. Parihar, C. B. Reese, and A. R. Todd, J. Chem. Soc., 1958, 3035. F. J. Di Carlo, A. S. Schulz, and A. M. Kent, J . Bid. Chem., 199, 333 (1952). C. Mannich and G. Heilner, Ber. Dtsch. Chem. Ges., 55, 365 (1922). R. F. Evans, Ret.. Pure A p p l . Chem., 15, 23 (1965). R. F. Evans, unpublished results. R. F. Evans and R. G. Hoare, unpublished results. 0. A. Zagulaeva, L. V. Skorokhodova, and V. P. Mamaev, Izti. Sib. Odt. Akad. Nauk S S S K , Ser. Khim. Nauk, 1976, 92; Chem. Ahstr., 87, 6063 (1977). Y. Kondo and B. Witkop, J . Am. Chem. Soc., 90, 764 (1968). V. SkariC and J. Matulik-Adamik, Helv. Chim. Acta, 63, 2179 (1980). R. F. Dietrich, T. Sakurai, and G . L. Kenyon, J . Org. Chem., 44,1894 (1979). M. J. Robins and M. MacCoss, J . Am. Chem. Soc., 99, 4654 (1977). M. MacCoss, F. S.Ezra, M. J. Robins, and S.S. Danyluk, J . Am. Chem. Soc., 99, 7495 (1977). V. Skaric and J. Matulic-Adamii, ffelu. Chim. Acta, 66, 687 (1983). V. Skarii-, B. GaSpert, and M. Hohnjec, J . Chem. Soc. (C), 1970, 2444. V. Skarii., B. GaSpert, M. Hohnjec, and G. Lacan, J . Chem. Soc., Perkin Trans. I , 1974, 267. J. A. Kelley, M. M. Abhasi, and J. A. Beisler, Anal. Biochem., 103, 203 (1980). J. S. Pizey, Synthetic Reagents, Vol. 2, Wiley, New York, 1974, p. 234ff. J. Buchi, H. Braunschweiger, M. Kird, and H. Lauener, Helc. Chim. Acta, 49, 2337 (1966). H. Fiirst and J. Hendel, D D R Pat. 59,788 (1968); Chem. Abstr., 70, 28935 (1969). H. Fiirst and J. Hendel, DDR Pat. 59,789 (1968); Chem. Abstr., 70, 28939 (1969).

1346

References

6349. V. Skarii., B. GaSpert, and I. Jerkunica, Croat. Chem. Acts, 38, 1 (1966). 6350. C. Kashima, M. Shimizu, A. Katoh, and Y. Omote, Tetrahedron Lett., 24, 209 (1983). 6351. D. Elad and I. Rosenthal, J . Chem. Soc., Chem. Commun., 1968, 879. 6352. R. F. Evans and K. N. Mewett, unpublished results. 6353. P. Cerutti, Y. Kondo, W. R. Landis, and B. Witkop, J . Am. Chem. Soc., 90, 771 (1968). 6354. A. L. Weis, F. Frolow, and R. Vishkautsan, J . Urg. Chem., 51, 4623 (1986). 6355. C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, J . Chem. Soc., Perkin Trans. 1,1981, 1622. 6356. K. H. Dudley, I. J. Davis, D. K. Kim, and F. T. Ross, 1.Org. Chem., 35, 147 (1970). 6357. M. Rautio, Acta Chem. Scand., Ser. B, 33, 770 (1979). 6358. M. Rautio, Ann. Acad. Sci. Fenn., Ser. A2, 1976, 178; Chem. Abstr., 85, 177350 (1976). 6359. M. Rautio, Ventron Alembic, 27, 1 (1982); Chem. Abstr., 97, 216044 (1982). 6360. M. Rautio, Farm. Aikak., 84, 143 (1975); Chem. Abstr., 86, 16627 (1977). 6361. M. Rautio, Farm. Aikak., 84, 155 (1975); Chem. Abstr., 86, 16628 (1977). 6362. C. J . Squire and K. E. H. Warren, Br. Pat. 1,597,796 (1981); Chem. Abstr., 96, 20115 (1982). 6363. S. J. Hannon, N. G. Kundu, P. J. Hertzberg, R. S. Bhatt, and C. Heidelberger, Tetrahedron Lett., 21, 1105 (1980). 6364. N. G. Kundu, S. Sikdar, R. P. Hertzberg, S. A. Schmitz, and S. G. Khatri, J . Chem. Soc., Perkin Trans. I , 1985, 1295. 6365. E. Sato and Y. Kanaoka, Chem. Pharm. Bull., 22, 799 (1974). 6366. B. C. Hui, Ventron Alembic, 20, 1 (1980); Chem. Abstr., 94, 174242 (1981). 6367. M. Rautio and E. Rahkamaa, Org. M a p . Reson., 15, 53 (1981). 6368. C. Ghosh, D. G. Schmidt, and B. C. Pal, J . Org. Chern., 49, 5256 (1984). 6369. B. Czochralska, M. Wrona, and D. Shugar, Top. Curr. Chem., 130, 133 (1986). 6370. J. E. O’Reilly and P. J. Elving, J . Am. Chem. Soc., 93, 1871 (1971). 6371. B. Janik and P. J. Elving, Chem. Rev., 68, 295 (1968). 6372. P. J. Elving, S. J. Pace, and I. E. O’Reilly, J . Am. Chem. Soc., 95, 647 (1973). 6373. H. Lund, Adv. Heterocycl. Chem., 12, 213 (1970). 6374. H. Lund, in Organic Electrochemistry (M. M. Blaizer, Ed.), Marcel Dekker, New York, 1973, p. 563. 6375. H. Lund, in Organic Electrochemistry, 2nd edn (M. M. Blaizer and H. Lund, Eds.), Marcel Dekker, New York, 1983, p. 533. 6376. H. Lund and I. Tabakovic, Adv. Heterocycl. Chem., 36, 235 (1984). 6377. B. Czochralska, M. Wrona, and D. Shugar, Bioelectrochem. Bioenerg., 1, 40 (1974). 6378. B. Czochralska and H. Sierakowski, Proc. 8th Sundbjerg Meet., 1979, p. 45; quoted in ref. 6369. 6379. M. Wrona, J. Giziewicz, and D. Shugar, Nucleic Acids Res., 2, 2209 (1975). 6380. M. Wrona, Bioelectrochem. Bioenerg., 6, 243 (1979). 6381. M. Wrona, Bioelectrochem. Bioenerg., 10, 169 (1983). 6382. M. Wrona and B. Czochralska, J . Electroanal. Chem. Interfar. Electrochem., 48, 433 (1973). 6383. M. Wrona, B. Czochralska, and D. Shugar, J . Electroanal, Chem. Interfac. Electrochem, 68, 355 (1976). 6384. V. P. Mamaev, Biol. Akt. Soedin., Akad. Nauk SSSR, 1965,38; Chem. Abstr., 63, 18081 (1965). 6385. W. P. Seebode and C. H. Vasey, Br. Pat. 919,703 (1963); Chem. Abstr., 59, 7539 (1963). 6386. G. Dryhurst, Electrochemistry of Biological Molecules, Academic Press, New York, 1977, p. 186& 6387. A. W. Dox, 1.Am. Chem. Soc., 53, 1559 (1931).

References

1347

6388. J. L. Longridge and T. W. Thompson, J . Chem. Soc. (C), 1970, 1658. 6389. N. C. Deno, H. J. Peterson, and G. S. Saines, Chem. Rev., 60, 7 (1960). 6390. J.-P. Sommadossi, D. A. Gewirtz, R. P. Diasio, C. Aubert, J.-P. Cano, and I. D. Goldman, J . B i d . Chem., 257, 8171 (1982). 6391. I. Muiznieks, Latu. P S R Zinat. Akad. Vestis, 1980, 145; Chem. Abstr., 93, 110317 (1980). 6392. R. Schaefer and A. C. Schwarz, Arch. Microbiol., 124, 111 (1980); Chem. Ahstr., 92, 124634 (1980). 6393. K. Wallenfels and H. Schiily, Liehigs Ann. Chem., 621, 178 (1959). 6394. D. Gani and D. W. Young, J . Chem. Soc., Perkin Trans. 1, 1985, 1355. 6395. T. W. Kensler, N. Han, and D. A. Cooney, Anal. Biochem., 111, 49 (1981). 6396. D. Leonov, J. Salomon, S. Sasson, and D. Elad, Photochem. PhotobioL, 17, 465 (1973). 6397. B. J. Swanson, J. C. Kutzer, and T. H. Koch, J . Am. Chem. Soc., 103, 1274 (1981). 6398. B. J. Swanson, Diss. Abstr. Int. B, 42, 4432 (1982); Chem. Abstr., 97, 92069 (1982). 6399. A. E. Reeve and T. R. Hopkins, Photochem. Photohiol., 30, 677 (1979). 6400. D. Gani, P. B. Hitchcock, and D. W. Young, J . Chem. Soc., Perkin Trans. I , 1985, 1363. 6401. H. Bredereck, R . Gompper, and H. Herlinger, Angew. Chem., 70, 571 (1958). 6402. A. L. Vais and V. P. Mamaev, I z u . Sib. Otd. Akad. Nauk S S S R , Ser. Khim. Nauk, 1975, 148; Chem. Ahstr., 84, 121764 (1976). 6403. R. E. van der Stoel and H. C. van der Plas, R e d . Trau. Chim. Pays-Bas, 97: 116 (1978). 6404. R. E. van der Stoel, H. C. van der Plas, H. Jongejan, and L. Hoeve, R e d . Trau. Chim. Pays-Bas, 99, 234 (1980). 6405. 6406. 6407. 6408. 6409. 6410. 6411. 6412. 6413. 6414. 6415. 6416. 6417. 6418. 6419. 6420. 6421. 6422. 6423. 6424. 6425.

R. E. van der Stoel and H. C. van der Plas, J . Chem. Soc., Perkin Trans. I , 1979, 1228. R . E. van der Stoel and H. C. van der Plas, J . Chem. Soc., Perkin Trans. 1, 1979, 2393. R. F. Evans and G. Cohn, unpublished results. T. J. Kress and E. F. Szymanski, US Pat. 4,252,955 (1981); Chem. Ahstr., 94, 192368 (1981). L. Strekowski, D. Harden, and R. A. Watson, Synthesis, 1988, 70. R. F. Evans and R. H. Carroll, unpublished results. L. Strekowski and R. A. Watson, J . Org. Chem., 51, 3226 (1986). A. L. Weis and G. Kaminas, unpublished results, cited in ref. 6175. G. E. Hardtmann and H. Ott, US Pat 3,829,422 (1974); Chem. Ahstr., 81, 136172 (1974). G. E. Hardtmann and F. G. Kathawala, Ger. Offen. 2,056,407 (1971); Chem. Abstr., 75, 88635 (1971). J. G. Wilson, P i p . Cell Res., 2, 297 (1989). G. E. Hardtmann and F. G. Kathawala, Ger. Offen, 2,056,406; Chem. Ahstr., 75,63813 (1971). A. Katoh, T. Nishio, and C. Kashima, Heterocycles, 26, 2223 (1987). T. J. Delia and M. Baumann, J . Heterocycl. Chem., 28, 1553 (1991). A. Garcia-Martinez, A. Herrera-Fernandez, F. Moreno-Jimenez, A. Garcia-Fraile, L. R. Subramanian, and M. Hanack, J . Org. Chem., 57, 1627 (1992). N. Bischofberger, Tetrahedron Lett., 30, 1621 (1989). T:L. Su and K. A. Watanabe, J . Heterocycl. Chem., 19, 1261 (1982). H. P. M. Thiellier, G. J. Koomen, and U. K. Pandit, Tetrahedron, 33, 1493 (1977). U. K. Pandit, Heterocycles, 8, 609 (1977). K. Takakusaki, N. Kakimoto, Y. Takeuchi, and S. Tomoda, Tetrahedron Lett., 24, 1707 (1983). J. E. Cadet, L. Voituriez, A. Grand, F. E. Hruska, P. Vigny, and L.-S. Kan, Biochemie,67,277 (1985).

1348 6426. 6427. 6428. 6429. 6430. 6431. 6432. 6433. 6434. 6435. 6436. 6437. 6438. 6439. 6440. 6441. 6442. 6443. 6444. 6445. 6446. 6447. 6448. 6449. 6450. 6451. 6452. 6453. 6454. 6455. 6456. 6457. 6458. 6459. 6460. 6461. 6462. 6463.

References J. Moan and M. J. Peak, J . Photochem. Photobiol., B , 4, 21 (1989). H. J. Niggli and P. A. Cerutti, Biochem. Biophys. Res. Commun., 105, 1215 (1982). J. E. Cadet, Tetrahedron Lett., 1976, 4275. S. C. Shim and S. H. Lee, Photochem. Photobiol., 29, 1035 (1979). H. Taguchi, B.-S. Hahn, and S. Y. Wang, J . Org. Chem., 42, 4127 (1977). D. Sen and C. H. J. Wells, Pestic. Sci., 12, 339 (1981); Chem. Abstr., 95, 187187 (1981). T. Kunieda, T. Takahashi, and M. Hirobe, Tetrahedron Lett., 24, 5107 (1983). C. Kaneko and N. Shimomura, Tetrahedron Lett., 23, 2571 (1982). V. V. Kaminski, R. N. Comber, A. J. Wexler, and J. S. Swenton, J . Org. Chem., 48,2337 (1983). I . Saito, K. Shimozono, and T. Matsuura, J . Am. Chem. Soc., 102, 3948 (1980). I . Saito, K. Shimozono, S. Miyazaki, T. Matsuurd, F. Fukuyama, and Y. Katsube, Tetrahedron Lett., 21, 2317 (1980). C. Shih, E. R. Fritzen, and J. S. Swenton, J . Org. Chem., 45, 4462 (1980). V. V. Kaminski, J. S. Swenton, and C. E. Cottrell, Tetrahedron Lett., 23, 4207 (1982). G. Szilagyi and H. Wamhofi, Angew. Chem., 95, 156 (Supplement, p. 120) (1983). D. Kanna, H. Straub, J. E. Hearst, and H. Rapoport, J . Am. Chem. Soc., 104, 6754 (1982). S. C. Shim and Y. Z. Kim, Photochem. Photobiol., 38, 265 (1983). S. C. Shim, J. S. Koh, and H. K. Shim, Phofoochem. Photobiol., 38, 369 (1983). S. C. Shim and Y. Z. Kim, Bull. Korean Chem. Soc., 4,95 (1983); Chem. Abstr., 99,2389 (1983). K.-Y. Akiba, A. Sakaguchi, and Y. Yamamoto, Tetrahedron Lett., 27, 5651 (1986). H. Morrison, C. Bernasconi, and G. Paudey, Photochem. Phntohiol, 38, 23 (1983). Y. Yamamoto, A. Sakaguchi, H. Yoshida, and K.-Y. Akiba, Heterocycles, 23, 207 (1985). J. A. Zoltewicz and L. S . Helmick, J . Am. Chem. Soc., 94, 682 (1972). H. C. van der Plas, V. N. Charushin, and B. van Veldhuizen, J . Org. Chem., 48, 1354 (1983). P. P. Onys’ko, Y. G . Gololobov, G. Y. Remennikov, and V. M. Cherkasov, Khim.Ceterotsikl. Soedin., 1980, 124. P. P. Onys’ko, Y. G. Gololobov, G. Y. Remennikov, and V. M. Cherkasov, Zh. Ohshch. Khim., 50, 1230 (1980). H. C. van der Plas, Ace. Chem. Res., 11, 462 (1978). G. Illuminati and F. Stegel, Adv. Neterocycl. Chem., 34, 305 (1983). M. S. Brouwer, H . C. van der Plas, and A. van Veldhuizen, Reel. Truu. Chim. Pays-Bus, 97, 110 (1978). K. Hirota, H. Sajiki, Y. Kitade, and Y. Maki, J . Chem. Soc., Perkin Trans. 1, 1990, 123. H. C. van der Plas, Heterocycles, 9, 33 (1978). G. M. Blackburn, V. C. Solan, D. M. Brown, and P. F. Coe, J . Chem. Soc., Chem. Cornmun., 1976, 724. P. J. Atkins, D. J. Palling, N. L. Poon, and C. D. Hall, J . Chem. Soc., Perkin Trans. 2, 1982, 1107. D. J. Palling, P. M. Schalke, P. J. Atkins, and C. D. Hall, J . Chem. Soc., Perkin Trans. 2,1981, 113. J. H. Priest, J. E. Scheffler, and E. G. Sander, J . Heterocycl. Chem., 17, 29 (1980). E. G. Sander, J. H. Priest, and J. E. Schemer, Biochem. Biophys. Res. Commun., 89, 1341 (1979). K . Hirota, Y. Kitade, K. Shimada, S. Senda, and Y. Maki, J . Chem. Soc., Perkin Trans. 1,1983, 1293. K. Hirota, Y. Yamada, T. Asao, and S. Senda, J . Chem. Soc., Perkin Trans. I , 1982, 277. I. Saito, H. Sugiyama, S. Ito, N. Furukawa, and T. Matsuura, J . Am. Chem. Soc., 103, 1598 (1981).

References

1349

6464. P. R. Perrier and S. R. Byrn, J . Org. Chem., 47, 4671 (1982). 6465. H. M. Schwarz, M. MacCoss, and S. S. Danyluk, J . Am. Chem. Soc., 105, 5901 (1983). 6466. Y. Kita, Kagaku to K o y y o (Osaka), 56, 159 (1982); Chem. Ahstr., 97, 67943 (1982). 6467. 6468. 6469. 6470. 6471. 6472. 6473. 6474. 6475. 6476. 6477. 6478. 6479. 6480. 6481. 6482. 6483. 6484. 6485. 6486.

G. Illuminati and F. Stegel, Tetrahedron Lett., 1968, 4169. E. Fahr and P. Fecher, Z.Naturforsch., Sect. B, 36, 226 (1981). R. 0. Rahn and H. G. Sellin, Photochem. Photobiol., 30, 317 (1979). J. G. Burr, C. Gilligan, and W. A. Summers, Photochem. Photohiol., 24, 483 (1976). N. Numao, T. Hamada, and 0. Yonemitsu, Tetrahedron Lett., 1977, 1661. A. J. Varghese, Photophysioloyy, 7, 207 (1972). H. A. Lozeron, M. P. Gordon, T. Gabriel, E. Tautz, and R. Duschinsky, Biochemistry, 3, 1844 ( 1 964). A. W. Wacker, A. Kornhauser, and L. Triger, Z. Naturfixsch., Teil B, 20, 1043 (1965). F.-T. Liu and N. C. Yang, Biochemistry, 17, 4877 (1978). E. Fahr, R. Kleber, and E. Boebinger, Z.Naturjbrsch., Teil B, 21, 219 (1966). K. I. Ekpenyong, R. B. Meyer, and M. D. Shetlar, Tetrahedron Lett., 1978, 1619. M. D. Shetlar, Photochem. Photohiol., 32, 587 (1980). M. D. Shetlar, Photochem. Photohiol., 29, 253 (1979). M. D. Shetlar, 7etrahedron Lett., 1975, 477. M. D. Shetlar, Photochem. Photohiol., 24, 315 (1976). J.-L. Fourrey and P. Jouin, Tetrahedron Lett., 1973, 3225. J.-L. Fourrey and J. Moron, Tetrahedron Lett., 1976, 301. J.-L. Fourrey, Tetrahedron Lett., 1976, 297. M. D. Shctlar, J . Chem. Soc., Chem. Commun., 1975, 653. T. Nishio, K. Katahira, and Y. Omote, Chem. Lett., 1982, 1675.

6487. R. Cathcart, E. A. Schwiers, R. L. Saul, and B. N. Ames, Proc. Nutl. Acad. Sci. U S A , 81, 5633 ( 1 984). 6488. M. Berger, J . Cadet, and J. Ulrich, Can. J . Chem., 63, 6 (1985). 6489. T. Harayama, R. Yanada, M. Tanaka, T. Taga, K. Machida, F. Yoneda, and J . Cadet, J . Chem. Soc., Perkin Trans. 1, 1988, 2555 and references cited therein. 6490. K. Frenkel, M. S. Goldstein, N. J. Duker, and G. W. Teebor, Biochemistry, 20, 750 (1981). 6491. S. Iida and H. Hayatsu, Biochim. Biophys. Acta, 228, 1 (1971). 6492. L. I. Simandi, M. Jaky, F. Freeman, C. D. Fuselier, and E. M. Karchefski, Inorg. Chim. Actu, 31, 1157 (1978). 6493. S. Iida and H. Hayatsu, Biochim. Biophys. Actu, 213, 1 (1970). 6494. J. Cadet and R. Teoule, Bull. Soc. Chim.Fr., 1974, 1565. 6495. P. Howgate, A. S. Jones, and J. R. Tittensor, J . Chem. Soc. ( C ) , 1968, 275. 6496. L. R. Subbaraman, J. Subbaraman, and E. J. Buhrman, J . Org. Chem., 38, 1499 (1973). 6497. C.-H. Chang, H. Ford, and E. J. Behrman, Inorg. Chim. Actu, 55, 77 (1981). 6498. T. J. Kristenmacher, L. J. Marzillic, and M. Rossi, Bioinory. Chem., 6, 347 (1976). 6499. T. Itahara, Y . Fujii, and M. Tada, J . Org. Chem., 53, 3421 (1988). 6500. H:S. Ryang and S. Y. Wang, J . Ory. Chem., 44, 1191 (1979). Ryang, S. Y. Wang, and J. L. Flippen-Anderson, J . Org. Chem., 44,3736 6501. E. P. Burrows, H.-S. (1979). 6502. M. J. Robins, M. MacCoss, S. R. Naik, and G. Ramani, J. Am. Chem. Soc., 98, 7381 (1976). 6503. T. Itahard and S. Koga, Chem. Lett., 1991, 85. 6504. T. Itahara and A. Nashino, Chem. Lett., 1991, 2203.

1350

References

6505. T. Harayama, R. Yanada, K. Iio, and F. Yoneda, Yakugaku Zusshi, 106, 1064 (1986). 6506. T. Harayama, R. Yanada, T. Taga, K. Machida, and F. Yoneda, Chem. Pharm. Bull., 34,4961 (1986). 6507. T. Harayama, R. Yanada, T. Taga, K. Machida, and F. Yoneda, J . Heterocycl. Chem., 23,283 (1986). 6508. R. W. Murray and R. Jeyaraman, J . Ory. Chem., 50, 2847 (1985). 6509. T. Takai, T. Yarnada, and T. Mukaiyarna, Chem. Lett., 1990, 1657. 6510. R. Kurnar, L. I. Wiebe, E. E. Knaus, and T. T. Nakashirna, J . Heterocycl. Chem., 28, 1467 (199 1). 6511. J. F. Ward, J . Chem. Educ., 58, 135 (1981). 6512. A. A. Shaw, L. Voituriez, J. Cadet, S. Gregoli, and C. R. Symons, J . Chem. Soc., Perkin Trans. 2, 1988, 1303. 6513. T.-J. Yu, R. G. Sutherland, and R. E. Verrall, Cun. J . Chem., 58, 1909 (1980). 6514. J. R. McKee, C. L. Christman, W. D. O’Brien, and S. Y. Wang, Biochemistry, 16, 4651 (1977). 6515. H. Ide, N . Otsuki, %-I. Nishimoto, and T. Kagiya, J . Chem. Soc., Perkin Trans. 2, 1985, 1387. 6516. J. Cadet, C. R. Acad. Sci., Ser. D, 283, 725 (1976). 6517. M. N. Schuchmann and C. von Sonntag, J . Chem. Soc., Perkin Trans. 2, 1983, 1525. 6518. D. K. Hazrd and S. Steenken, J . Am. Chem. Soc., 105, 4380 (1983). 6519. R. Ducolornb, J. Cadet, and R. Ttoule, Bull. Soc. Chim. Fr., Part 2, 1979, 7 6520. J. Cadet and R. TCoule, Bull. Soc. Chim. Fr., 1975, 879. 6521. J. Cadet and R. Teoule, J . Chrornatogr., 115, 191 (1975). 6522. M. Polverelli, M. Beeger, and J. Cadet, Nucleosides Nucleotides, 10, 563 (1991). 6523. S. V. Jovanovic and M. G. Simic, J . Am. Chem. Sue., 108, 5968 (1986). 6524. H. M. Novais and S. Steenken, J . Am. Chem. Soc., 108, 1 (1986). 6525. S. Steenken and V. Jagannadham, J . Am. Chem. Soc., 107, 6818 (1985). 6526. S. Korninami, S. Rokushika, and H. Hatano, Radiut. Res., 72, 89 (1977); Chem. Ahstr., 87, 179990 (1977). 6527. S. Rustgai and P. Riesz, Int. J . Radiat. B i d . Relat. Stud. Phys. Chem. Med., 33, 21 (1978); Chem. Abstr., 89, 54936 (1978). 6528. J. Cadet, M. Berger, M. Guttin-Lombard, and M. J. Bobenreith, Tetruhedron. 35,2743 (1979). 6529. F. E. Hruska, M. Berger, J. Cadet, and M. Remin, Can. J . Chem., 63, 15 (1985). 6530. T. Wada, H. Ide, S.-I. Nishimoto, and T. Kagiya, Chem. Lett., 1982, 1041. 6531. T. Kagiya, C. Komuro, K. Sakano, and S.-I. Nishimoto, Chem. Lett., 1983, 365. 6532. 6533. 6534. 6535. 6536. 6537. 6538. 6539. 6540. 6541.

T. Kagiya, R. Kimura, C. Komuro, K. Sakano, and S.-I. Nishirnoto, Chem Lett., 1983, 1471. K. M. Idriss-Ali and G. Scholes, J . Radiut. Res., 20, 146 (1979); Chem. Ahstr., 91, 170930 (1979). S.-I. Nishimoto, H. Ide, K. Nakarnichi, N . Otsuki, and T. Kagiya, Chem. Lett., 1983, 1441. S.-I. Nishirnoto, H. Ide, N. Otsuki, K. Nakamichi, and T. Kagiya, J . Chem. SOC.,Perkin Trans. 2, 1985, 1127. E. L. Mead, R. G. Sutherland, and R. E. Verrall, Can. J . Chem., 53, 2394 (1975). C. M . Sehgal and S. Y. Wang, J . Am. Chem. Soc., 103, 6606 (1981). T.-J. Yu, R. G. Sutherland, and R. E. Verrall, Can. J . Chem., 65, 1162 (1987). R. S. Davidson, in Chemistry with UItrasuund (T. J. Mason, Ed.), Elsevier, London, 1990, p. 102. B. Ohtani, H. Nagasaki, S.-I. Nishimoto, K. Sakano, and T. Kagiya, Can. J . Chem., 64, 2297 (1986). L. P. Candeias and S. Steenken, J . Am. Chem. Soc., 114, 699 (1992).

References

1351

6542. J. Cadet, L. Voituriez, F. E. Hruska, L.-S. Kan, F. A. A. M. de Leeuw, and C. Altona, Can. J . Chem., 63, 2861 (1985). 6543. R. B. Setlow, Science, 153, 379 (1966). 6544. D. L. Mitchell, D. E. Brash, and R . S. Nairn, Nucleic Acids R e x , 18, 963 (1990). 6545. W. A. Franklin and W. A. Haseltine, Proc. Natl. Acud. Sci. U S A , 81, 3821 (1984). 6546. T. Matsunaga, K. Hieda, and 0. Nikaido, Photochem. Photobiol., 54, 403 (1991). 6547. T. Douki, L. Voituriez, and J. Cadet, Photochern. Photohiol., 53, 293 (1991). 6548. P. Clivio, J.-L. Fourrey, J. Gasche, and A. Favre, Tetrahedron Lett., 33, 1615 (1992). 6549. P. Clivio, A. Favre, C. Fontaine, J.-L. Fourrey, J. Gasche, E. Guittet, and P. Laugia, Tetrahedron, 48, 1605 (1992). 6550. J. Cadet and P. Vigny, Bioorg. Photochem., I , 1 (1990). 6551. E. C. Taylor, T. H. Schrader, and L. D. Walensky, Tetrahedron, 48, 19 (1992). 6552. H. Hayatsu, Y. Wataya, and K. Kai, J . Am. Chem. Soc., 92, 724 (1970). 6553. E. G. Sander and C. L. Deyrup, Arch. Biochem. Biophys., 150, 600 (1972). 6554. F. A. Sedor, D. G. Jacobson, and E. G. Sander, Bioorg. Chem., 3, 221 (1974). 6555. I. H. Pitman and N. B. Jain, Aust. J . Chem., 32, 545 (1979). 6556. N. B. Jain, B. Lee, K. B. Mertes, and I. H. Pitman, Acta Crystallogr., Sect. B, 34, 927 (1978). 6557. H. Hayatsu, Y. Wataya, K. Kai, and S. Iida, Biochemistry, 9, 2858 (1970). 6558. R. Shapiro, R. E. Servis, and M. Welcher, J . Am. Chem. Soc., 92, 422 (1970). 6559. E. D. Sverdlov, G. S. Monastyrskaya, N. S. Tarabakina, and E. 1. Budivskii, F E B S Lett., 62, 212 (1976). 6560. 6561. 6562. 6563. 6564. 6565. 6566. 6567. 6568. 6569. 6570. 6571. 6572. 6573. 6574. 6575. 6576.

H. Taguchi and S. Y. Wang, J . Ory. Chem., 42, 2028 (1977). C. L. Barnes and S. W. Hawkinson, Acta Cryst., Sect. B, 38, 1907 (1982). H. Hayatsu, Pure Appl. Chem., 50, 1063 (1978). H. Hayatsu, J . Mol. Biol., 115, 19 (1977). M. Shiragami, I . Kudo, S. Iida, and H. Hayatsu, Chem. Phurm. Bull., 23, 3027 (1975). A. Itadani, M. Shiragami, R. Kawada, Y. Wataya, and H. Hayatsu, J . Chem. Soc., Perkin Trans. 1, 1981, 1287. K. C. Smith and R. T. Aplin, Biochemistry, 5, 2125 (1966). K. C. Smith, Biochem. Biophys. Res. Cornmun., 39, 101 1 (1970). N.-C. C. Yang, R. Okazaki, and F.-T. Liu, J . Chem. Soc., Chem. Commun., 1974, 462. B. C. Pal, J . Am. Chem. Soc., 100, 5170(1978), F. A. Sander, D. G . Jacobson, and E. G. Sander, Bioorg. Chem., 3, 154 (1974). S. Kumar and S. S. Chimni, Indian J . Chem., Sect. B, 28, 107 (1989). F. A. Sedor and E. G. Sander, Biochem. Biophys. Res. Commun., 50, 329 (1973). B. Bannister and F. Kagan, J . Am. Chem. Soc., 82, 3363 (1960). R. N. Barnes, R. D. Chambers, R. D. Hercliffe, and W. K. R. Musgrave, J . Chem. Soc., Perkin Trans. I , 1981, 2059. D. Snikere, A. Lazdins, A. Veinbergs, S. Hillers, I. L. Knunyants, and L. Germains, USSR Pat. 397,004 (1977); Chem. Ahstr., 87, 168089 (1977). S. Stavber and M. Zupan, J . Chem. Soc., Chem. Commun., 1983, 563; Tetrahedron, 46, 3093 ( 1990).

6577. G. W. M. Visser, S. Boele, B. W. van Halteren, G . H. J. N. Knops, J. D. M. Herscheid, G. A. Brinkman, and A. Hoekstra, J . Org. Chem., 51, 1466 (1986). 6578. R. F. Evans and G. P. Savage, Ausr. J . Chem., 45, 463 (1992). 6579. T. Kinoshita, T. Okunaka, T. Ohwada, H. Kawanaka, and S. Furukawa, J . Heterocycl. Chem., 28, 1901 (1991).

1352

References

6580. H. Hayatsu, T. Chikuma, and K. Negishi, J . Org. Chem., 40, 3862 (1975). 6581. F. A. Sedor, D. G. Jacobson, and E. G. Sander, J . Am. Chem. Soc., 97, 5572 (1975). G. S. Rork and I. H. Pitman, J . Am. Chem. Soc., 97, 5559 (1975). G. S. Rork and I. H. Pitman, J . Am. Chem. Soc., 97, 5566 (1975). D. G. Jacobson, F. A. Scdor, and E. G. Sander, Bioorg. Chem., 4, 72 (1975). J.-H. Lin, P. R. Le Breton, and L. L. Shipman, J . Phys. Chem., 84, 431 (1980). W. A. Summers, C. Enwall, T. G. Burr, and R. L. Letsinger, Photochem. Photobiol., 17, 295 (1973). 6587. G. W. M. Visser, R. E. Herder, P. Noordhuis, 0.Zwaagstra, and J. D. M. Herscheid, J . Chem. Soc., Perkin Trans. I , 1988, 2547. 6588. A. Haas and D. Kortmann, Chem. Ber., 114, 1176 (1981). 6589. E. N. Vine, D. Young, W. H. Vine, and W. Wolf, Int. J . A p p l . Radial. Isotop., 30, 401 (1979); Chem. Abstr., 91, 211361 (1979). 6590. P. D. Schuman, P. Tarrant, and D. A. Warner, Can. Pat. 985,681 (1976); Chem Abstr., 85, 46738 (1976). 6591. J. Nakamura, T. Takeuchi, K. Sakuma, and H. Tomioka, Jap. Kokai Tokkyo Koho 144,583 (1978); Chem. Abstr., 91, 20536 (1979). 6592. R. Anderson and P. D. Schuman, US Pat. 3,954,759 (1976); Chem. Abstr., 85, 46744 (1976). 6593. T. Takahara, Jap. Kokai Tokkyo Koho 135,990 (1978); Chem. Abstr., 90, 152230 (1979). 6594. I. Kumadaki, M. Nakazawa, and Y. Kobayashi, Tetrahedron Lett., 24, 1055 (1983). 6595. 0. Miyashita, H. Shimadzu, K. Matsumura, and N. Hashimoto, Ger. Pat. Offen. 2,714,392 (1978); Chem. Abstr., 88, 152655 (1978). 6596. 0. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Jap. Kokai Tokkyo Koho 103,480 (1978); Chem Abstr., 90, 72226 (1979). 6597. 0. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Jap. Kokai Tokkyo Koho 118,480 (1977); Chem. Abstr., 88, 105397 (1978). 6598. 0. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Jap. Kokai Tokkyo Koho 63,090 (1979); Chem. Abstr., 91, 21 I435 (1979). 6599. B. Schwarz, D. Cech, A. Holy, and J. Skoda, Collect. Czech. Chem. Cornmun., 45, 3217 (1980). 6600. D. Cech and A. Holy, Collect. Czech. Chem. Cornmun., 41, 3335 (1976). 6601. 0.Miyashita, T. Kasahara, K. Matsumura. H. Shimadzu, M . Takamoto, and N. Hashimoto, Chem. Pharm. Bull., 30, 2333 (1982). 6602. 0. S. Tee and M. Paventi, J . Org. Chem., 46, 4172 (1981). 6603. 0. S. Tee and M. Paventi. J . Org. Chem., 45, 2072 (1980). 6604. 0. S. Tee and S. Banerjee, Can. J . Chem., 57, 626 (1979). 6605. C. N. M . Bakker and F. M. Kaspersen, R e d . Trau. Chim. Pays-Bas, 100, 267 (1981). 6606. R. Teoule, B. Fouque, and J. Cadet, Nucleic Acids R e x , 2, 487 (1975). 6607. J. Cadet, R. Ducolomb, and R. Teoule, Tetrahedron, 33, 1603 (1977). 6608. J. Elguero, P. Goya, A. Martinez, and I . Rozas, Chem. Ber., 122, 919 (1989). 6609. S. A. Stekhova, V. V. Lapachev, and V. P. Mamaev, Khim. Geterotsikl. Soedin., 1990, 75. 6610. V. V. Lapachev, M. A. Fedotov, V. P. Mamaev, L. P. Prikazchikova, V. M. Khutova, and V. M. Cherkasov, Zh. Org. Khim., 22, 2185 (1986). 6611. V. V. Lapachev, 0. A. Zagulyaeva, 0. P. Petrenko, S. F. Bichkov, V. I. Mamatyuk, and V. P. Mamaev, Tetrahedron, 41, 4897 (1985). 6612. A. Y. Denisov, V. P. Krivopalov, V. I. Mamatyuk, and V. P. Mamaev, Mayn. Reson. Chem., 26, 42 (1988). 6613. W. E. Hull, M. Kiinstlinger, and E. Breitmaier, Anyew. Chem., 92, 957 (1980).

6582. 6583. 6584. 6585. 6586.

References

1353

6614. G. E. Wright, J . Heterocycl. Chem., 20, 1037 (1983). 6615. V. V. Lapachev, I. Y. Mainagashev, S. A. Stekhova, M. A. Fedotov, V. P. Krivopalov, and V. P. Mamaev, Zh. Org. Khim., 23, 565 (1987). 6616. G . B. Barlin and M. D. Fenn, unpublished results. 6617. G . B Barlin and M. D. Fenn, Heterocycles, 24, 1301 (1986). 6618. P. C. Lauterbur, J. Chem. Phys., 43, 360 (1965). 6619. G . W. H. Cheeseman, C. J. Turner, and D. J. Brown, Ory. Magn. Reson., 12, 212 (1979). 6620. A. V. Ivashchenko, 0. N. Garicheva, L. V. Shmelev, and Y. S. Ryabokobylko, Khim. Geterotsikl. Soedin., 1980, 11 14. 6621. T. Kitagawa, T. Miura, and H. Taniyama, J . Biochem. (Tokyo),81, 1759 (1977). 6622. T. Shiba, S. Nomoto, T. Teshima, and T. Wakamiya, Tetrahedron Lett., 1976, 3907; T. Shiba, S. Nomoto, and T. Wakamiya, Experientia, 32, 1109 (1976). 6623. A. W. Hofmann, Ber. Dtsch. Chem. Ges., 21, 2332 (1888). 6624. S. R. Aspinall, J . Am. Chem. Soc., 62, 2160 (1940). 6625. G . S. Skinner and R. R. Wunz, J . Am. Chem. SOC.,73, 3814 (1951). 6626. W. E. Rader, C. M. Momroe, and R. R. Whetstone, Science, 115, 124 (1952). 6627. S. A. Ballard and R. R. Whetstone, US Pat. 2,658,895 (1953); Chem. Ahstr., 48, 12184 (1954). 6628. D. 0. Spry and H. S. Aaron, J . Org. Chem., 31, 3838 (1967). 6629. K. G. Phillips, US Pat. 3,041,338 (1962); Chem. Ahstr., 57, 13773 (1962). 6630. R. Gras, A. Schott, and E. Wolf, Ger. Pat. Offen. 2,751,805 (1979); Chem. Ahstr., 91, 92430 (1979). 6631. H. Baganz and L. Domaschke, Angew. Chem., 75, 1025 (1963). 6632. H. Baganz, L. Domaschke, J. Fock, and S. Rabe, Chem. Ber., 95, 1832 (1962). 6633. H. Baganz, S. Rabe, and J. Repplinger, Chem. Ber., 98, 2572 (1965). 6634. H. Baganz and L. Domaschke, Arch. Pharm. (Weinheim, Ger.), 295, 758 (1962). 6635. H. Baganz and S. Rabe, Chem. Ber., 98, 3652 (1965). 6636. G. M. J. Slusarczuk and M. M. Joullie, J . Org. Chem., 36, 37 (1971). 6637. H. Baganz and L. Domaschke, Chem. B w . , 95, 1840 (1962). 6638. S. Saba, A. Brescia, and M. K. Kaloustian, Tetrahedron Lett., 32, 5031 (1991). 6639. H. Mikolajewska and A. Kotelko, Actn Pol. Pharm., 22, 219 (1965); Chem. Ahstr., 63, 17891 (1965). 6640. J. J. McBride and E. J. Miller, Fr. Pat. 1,415,468 (1965); Chem. Ahstr., 64, 5111 (1966). 6641. H. Giescke, J. Hocker, and R. Rerten, Ger. Pat. Offen. 2,748,976 (1979); Chem. Ahstr., 91, 57012 (1979). 6642. Drew Chemical Corp., Br. Pat. 986,057 (1965); Chem. Abstr., 63, 1793 (1965). 6643. A. L. Langis and C. A. Pilkington, US Pat. 3,126,381 (1964); Chem. Abstr., 60, 14517 (1964). 6644. R. N. Butler, J. D. Thornton, and C . B. ORegan, J . Chem. Soc., Perkin Trans. I , 1983, 2197. 6645. I. Perillo and S . Lamdan, J . Heterocycl. Chem., 10, 915 (1973). 6646. A. M. Reverdito, L. Orelli, M. Dalmaso, I. Perillo, and B. M. Fernbndez, J . Heterocycl. Chem., 28, 273 (1991). 6647. M. Seefelder and W. Jentzsch, Ger. Pat. 1,189,998 (1965); Chem. Abstr., 63, 610 (1965). 6648. W. Jentzsch and M. Seefelder, Chem. Ber., 98, 1342 (1965). 6649. J. A. Faust, L. S. Yee, and M. Sahyun, J . Ory. Chem., 26, 4044 (1961). 6650. P. T. Charlton, G. K. Maliphant, P. Oxley, and D. A. Peak, J . Chem. Soc., 1951, 485. 6651. V. B. Piskov and V. M. Kasperovich, Zh. Org. Khim., 14, 820 (1978). 6652. Pfizer Corp., Br. Pat. 877,306 (1961); Chem. Abstr., 58, 2458 (1963).

1354

References

6653. J. A. Faust and M. Sahyun, US Pat. 3,042,674 (1962); Chem. Ahstr., 57, 16568 (1962). 6654. Parke Davis Co., Br. Pat. 948,897 (1964); Chem Ahstr., 60, 10690 (1964). 6655. J. L. Archibald, A. C. White, and R. M. Black, Br. Pat. 1,428,389 (1976); Chem. Abstr., 85, 46737 (1976). 6656. D. Nardi, E. Massardni, G. Motta, A. Leonardi, M. J. Magistretti, and I. Setnikar, Farmaco, Ed. Sci., 34, 789 (1979); Chem. Ahstr., 92, 76401 (1980). 6657. D. G. Neilson, I. A. Khan, and R. S. Whitehead, J . Chem. Soc. (C), 1968, 1853. 6658. Y . Ito, Y. Inubushi, M. Zenbayashi, S. Tomita, and T. Saegusa, J . Am. Chem. Soc., 95, 4447 (1973). 6659. A. P. N. Franchimont and H. Friedmann, Reel. Trau. Chim. Pays-Bas, 26, 218 (1907). 6660. E. Fischer and H. Koch, Liehiys Ann. Chem., 232, 222 (1886). 6661. J. Barlwenga, H. Cuervo, B. Olano, S. Fustero, and V. Gotor, Synthesis, 1986, 469. 6662. A. Hanssen, Ber. Dtsch. Chem. Ges., 20, 781 (1887). 6663. R. Merten, Belg. Pat. 611,643 (1962); Chem. Abstr., 57, 16573 (1962). 6664. H. Timmler, Ger. Pat. 1,126,392 (1962); Chem. Abstr., 57, 9859 (1962). 6665. E. M. Wilson, Tetrahedron, 21, 2561 (1965). 6666. K. B. Bradbury, N. C. Hancox, and H. H. Hatt, J . Chem. Soc., 1947, 1394. 6667. R. L. Wayland, US Pat. 3,158,501 (1964); Chem. Abstr., 62, 4158 (1965). 6668. Chemische Werke Huels A.-G., Belg. Pat. 631,698 (1963); Chem. Abstr., 6 i , 1876 (1964). 6669. R. Schneider, Swiss Pat. 357,400 (1961); Chem. Abstr., 57, 839 (1962). 6670. Sun Chemical Corp., Br. Pat. 931,560 (1963); Chem. Ahstr., 60, 1772 (1964). 6671. B. J. Barker, J. Rosenfarb, and J. A. Caruso, Angew. Chem., 91, 560 (1979). 6672. T. Mukhopadhyay and D. Seebach, Helti. Chim. Acta, 65, 385 (1982). 6673. W. E. Martin and M. F. Farona, J . Organomet. Chem., 206, 393 (1981). 6674. R. Merten and G. Muller, Anyew. Chem., 74, 866 (1962). 6675. F. B. Zienty, J . Am. Chem. Soc., 68, 1388 (1946). 6676. A. F. McKay and W. G. Hatton, J . Am. Chem. SOC.,78, 1618 (1956). 6677. G. Rigatti, F. d’Angeli, A. C. Veronese, G. Boccalon, and C . Toniolo, Gazz. Chim. Ital., 99, 1000 (1969). 6678. 6679. 6680. 6681. 6682. 6683. 6684. 6685. 6686. 6687. 6688.

6689. 6690. 6691.

A. Kosasayama, T. Konno, K. Higashi, and F. Ishikawa, Chem. Pharm. Bull., 27, 841 (1979). G. Assef, J. Kister, and J. Metzger, Bull. Soc. Chim. Fr., Sect. 2, 1979, 165. C.-D. Li, S. L. Mella, and A. C. Sartorelli, J . Med. Chem., 24, 1089 (1981). S. D. Ziman, J . Org. Chem., 41, 3253 (1976). W. Broda and E. V. Dehmlon, Liehigs Ann. Chem., 1983, 1839. T. J. Batterham, N M R Spectra ofSimple Heterocycles, Wiley, New York, 1973. A. J. Boulton and A. McKillop, in Comprehensive Heterocyclic Chemistry, Vol. 2 (A. R. Katritzky and C. W. Rees, Eds.), Pergamon Press, Oxford, 1984, p. 9ff. I. Hermecz, Ado. Heterocycl. Chem., 42, 83 (1987). H. Oediger, F. MBller, and K. Eiter, Synthesis, 1972, 591. H. Oediger and F. Moller, Angew. Chem., 79, 53 (1967). W. S. Saari, M. B. Freedman, J. R. Huff, S. W. King, A. W. Raab, S. J. Bergstrand, E. L. Engelhardt, A. Scriabine, G . Morgan, A. Morris, J. M. Stavorski, R. M. Noll, and D. E. Duggan, J . Med. Chem., 21, 1283 (1978). R. N. Johnson and H. M. Woodburn, J . Org. Chem., 27, 3958 (1962). M. J. Hurwitz and H. Aschkenasy, Belg. Pat. 637,380 (1964); Chem. Ahstr., 62, 7892 (1965). B. Adcock, A. Lawson, and D. H. Miles, J . Chem. Soc., 1961, 5120.

References

1355

H. Yamamoto and K. Maruoka, J . Am. Chem. Soc., 103, 4186 (1981). B. L. Booth, K. 0. Jibodu, and M. F. Proenca, J . Chem. Sac., Chem. Commun., 1980, 1151. M. Sahyun and J. A. Faust, US Pat. 3,009,915 (1962); Chem. Ahstr., 56, 15521 (1962). Pfizer Corp., Belg. Pat. 658,987 (1965); Chem. Absfr., 64, 8192 (1966). R. J. Pugmire and D. M. Grant, J . Am. Chem. Soc., 90,4232 (1968). G. Remaud, J. Kjellberg, N. G . Johansson, and J. Chattapadhyaya, Tetrahedron, 43, 365 (1987). 6698. M . Schindler, J . Am. Chem. Soc., 110, 6623 (1988). 6699. P. K. Glasoe and F. A. Long, J . Phys. Chem., 64, 188 (1960). 6700. D. V. Griffith and S. P. Swetnam, J . Chem. Soc., Chem. Commun., 1981, 1224. 6701. J. Riand, J . Chem. Sac., Chem. Commun., 1983, 105. 6702. R . L. Benoit and M. Frechette, Can. J . Chem., 64, 2348 (1986). 6703. S. V. Shorshnev, S. E. Esipov, and A. I. Chernyshev, Khim. Geterotsikl. Soedin., 1988, 1532. 6704. E. V. Dhemlow, personal communication. 6705. J. S. Warner, J . Org. Chem., 28, 1642 (1963). 6706. D. J. Brown and R. F. Evans, J . Chem. Soc., 1962, 4039. 6707. C. Grundmann and A. Kreutzberger, J . Am. Chem. Soc., 77,6559 (1955). 6708. A. L. Weis, F. Frolow, and R . Vishkautsan, J . Heterocycl. Chern., 23, 705 (1986). 6709. H. Uno, Y. Matsushima, T. Tasaka, and H. Susuki, Bull. Chem. Soc. Jpn., 63, 293 (1990). 6710. H. Yagihara, Y. Goto, K. Masamoto, Y. Morishima, and H. Osabe, Jap. Kokai Tokkyo Koho J P 63,196,572 (1988); Chem. Abstr., 110, 23909 (1989). 671 I . W. Wendelin, A. Harler, and A. Fuchsgruber, Monafsh. Chern., 107, 141 (1976). 6712. T. Suzuki and K. Mitsuhashi, Seikei Daigaku Kogakuhu Koyuku Kohoku, 22, 1579 (1976); Chem. Abstr., 86, 139916 (1977). 6713. G.-D. Zhu, J.-H. Huang, and C.-S. Chi, J . Fluorine Chem., 43, 319 (1989). 6714. Wellcome Foundation, Neth. Pat. Appl. 6,510,117 (1966); Chem. Ahstr., 65, 3791 (1966). 6715. D. Korbonits, E. Tobias-Hija, and P. Kolonits, Chem. Ber., 124, 1199 (1991). 6716. H. Gnichtel and B. P. Gau, Liehigs Ann. Chem., 1982, 2223. 6717. F. Aradi and A. Foldesi, M a y n . Reson. Chem., 25, 892 (1987). 6718. F. Aradi and A. Foldesi, Magn. Resan. Chem., 27, 249 (1989). 6719. F. Aradi and A. Foldesi, Mugn. Reson. Chem., 27, 592 (1989). 6720. F. Aradi, M a p . Reson. Chem., 28, 246 (1990). 6721. W. H. Gmeiner and C. D. Poulter, J . Am. Chem. Soc., 110, 7640 (1988). 6722. A. F. Abramov, Zh. Ory. Khim., 17, 346 (1988). 6723. D. B. Davies, M. MacCross, and S. S. Danyluk, J . Chem. Sac., Chem. Commun., 1984, 536. 6724. D. B. Davies, P. Rajani, M. MacCross, and S. S. Danyluk, Magn. Reson. Chem., 23, 72 (1985). 6725. D. B. Davies, P. Rajani, and H. Sadikot, J . Chem. Soc., Perkin Trans. 2, 1985, 279. 6726. P. C. Kline and A. S. Serianni, Magn. Reson. Chem., 26, 120 (1988). 6727. J. Rebek, B. Askew, M. Killoran, D. Nemeth, and F.-T. Lin, J . Am. Chem. Soc., 109, 2426 (1987). 6728. N. A. Naulet and D. B. Le Botlan, Nouu. J . Chim., 8, 741 (1984); Chem. Abstr., 103, 160785 (1985). 6729. B. T. Golding and I. K. Nassereddin, J . Chem. Soc., Perkin Trans. 1, 1985, 2011. 6730. F. A. L. Anet and M. Kopelevich, J . Chem. Soc., Chem. Commun., 1987, 595. 6731. V. K. Madan, A. D. Taneja, and V. P. Kudesia, J . Indian Chem. Soc., 68, 471 (1991). 6732. E. Kleinpeter, W. Schroth, and K. Pihlaja, Magn. Reson. Chem., 29, 223 (1991).

6692. 6693. 6694. 6695. 6696. 6697.

1356

References

6733.J. Clark and G. Varvounis, J. Chem. Soc., Perkin Trans. 1, 1984, 1475. 6734.C. H. J. Wells, Org. Magn. Reson., 20, 274 (1982). 6735.K.-Y. Akiba, M. Ohsugi, H. Iwasaki, and K. Ohkata, J . Am. Chem. Soc., 110, 5576 (1988). 6736.B. M . Fung, R. V. Sigh, and M. M. Alcock, J . Am. Chem. Soc., 106, 7301 (1984). 6737.S. Crddock, P. B. Liescheski, D. W. H. Rankin, and H. E. Robertson, J . Am. Chem. Soc., 110, 2758 (1988). 6738.C. F. Bigge, J.-P. Wu, and J. R. Drummond, Tetrahedron Lett., 32, 7659 (1991). 6739.A. Talab, C. Cave, A. Yebga, S. Menager, C. F. Combet, and 0. Lafont, J . Pharm. Belg., 46, 293 (1991);Chem. Abstr., 116, 106216 (1992). 6740.M.Sako, R. Totani, K. Hirota, and Y. Maki, Chem. Pharm. Bull., 40, 235 (1992). 6741.P. Demange, A. Bateman, J. K. Macleod, A. Dell, and M. A. Abdullah, Tetrahedron Lett., 31, 7611 (1990). 6742.D. Tome and N. Naulet, Int. J . Pept. Protein Rex, 17,501(1981);Chem. Ahstr., 95,2134(1981). 6743.Y. Kitamoto and H. Maeda, J . Biochem. (Tokyo), 87, 1519 (1980);Chem. Abstr., 93, 63876 (1980). 6744.P. M.Hardy and D. J. Samworth, J . Chem. Soc., Perkin Trans. I , 1977, 1954. 6745.C. Klein, G. Schulz, and W. Steglich, Liebigs Ann. Chem., 1983, 1623. 6746.G. Stideler, Liebigs Ann. Chem., 111, 277 (1859). 6747.E.Mulder, Liebigs Ann. Chem., 168, 228 (1873). 6748.S . Ruhemann, J . Chem. Soc., 83, 374 (1903). 6749.S. Ruhemann and E. R. Watson, J . Chem. Soc., 85, 456 (1904). 6750.T.S. Patterson and A. McMillan, J . Chem. Soc., 119, 269 (1921). 6751.E.Matter, Helo. Chim. Acta, 30, Ill4 (1947). 6752.V. E. Haury, US Pat. 2,516,626(1950);Chem. Abstr., 45, 673 (1951). 6753.S. Kajiyama, T. Koyayashi, and K . Yoshizue, Ger. Pat. Offen. 2,453,174(1975);Chem. Abstr., 83, 97360 (1975). 6754.I. Dragutan, S. Serban, P. Obloja, D. Nistor, and V. Dragutan, Rom. Pat. R O 96,132(1989); Chem. Abstr., 113, 212011 (1990). 6755.F. Asinger, M. Thiel, and H. Baltz, Monatsh. Chem., 88, 464 (1957). 6756.A. B. A. Oude, US Pat. 4,281,126(1981);Chem. Abstr., 95, 203986 (1981). 6757.B. A. 0. Alink, US Pat. 4,146,714 (1979);Chem. Abstr., 91, 39523 (1979). 6758.R. Zimmermann, B. Brahler, and H. Hotze, Anyew. Chem., 72, 78 (1960). 6759.E. J. Nikawitz, US Pat. 3,152,122(1964);Chem. Abstr., 62, 1670 (1965). 6760.Chemische Werke Albert, Br. Pat. 848,399(1960);Chem. Abstr., 57, 11215 (1962). 6761.G. A. Boswell and P. H. Williams, US Pat. 3,137,697(1964);Chem. Abstr., 61, 7024 (1964). 6762.H. Petersen, H. Brandeis, and R. Fikentscher, Ger. Pat 1,229,093(1966);Chem. Abstr., 66, 37943 (1967). 6763.G. Zigeuner and W. Rauter, Monatsh. Chem., 96, 1950 (1965). 6764.D. R.Martin, C. M. Merkel, J. U. Mondal, and C. R. Rushing, Inorg. Chim. Acta, 99,81 (1985). 6765.G. Shih, L. S. Gossett, J. F. Worzalla, S. M. Rinzel, G. B. Grindey, P. M. Harrington, and E. C. Taylor, J . Med. Chem., 35, 1109 (1992). 6766.U.Schwenk and A. Becker, Liebigs Ann. Chem., 706, 95 (1967) 6767.H. Petersen, H. Brandeis, and R. Fikentscher, Ger. Pat. 1,230,805(1966);Chem. Abstr., 66, 46435 (1967). 6768.H. Petersen, Synthesis, 1973, 243. 6769.T. Inoue, H. Harada, and S. Miyajima, Jap. Kokai Tokkyo Kohu 31,987(1972);Chem. Abstr., 78, 29809 (1 973).

References

1357

6770. H. H. Hatt, Aust. J . Chem., 23, 577 (1969). 6771. P. H. Boyle and E. O’Brien, Proc. R . Ir. Acad., Sect. B, 83, 13 (1983). 6772. 6773. 6774. 6775. 6776. 6777. 6778. 6779.

A. R. Butler and I. Hussain, J . Chem. Soc., Perkin Trans. 2, 1980, 232. G. E. K. Branch and A. W. Titherly, J . Chem. Soc., 101, 2342 (1912). Shell Research, Belg. Pat 623,714 (1963); Chem. Abstr., 60, 9299 (1964). M. Aya, J. Saito, K. Yasui, and K. Shiokawa, Eur. Pat Appl. E P 86,411 (1983); Chem. Ahstr., 99, 212535 (1983). P. H. Boyle, personal communication. R. M. Khachatryan, S. K. Pirenyan, and S. A. Vartanyan, Arm. Khim. Z h . , 23, 645 (1970); Chem. Ahstr., 74, 112004 (1971). A. R. Hanze, J . Am. Chem. Soc., 89, 6720 (1967). K. S. Chu, G. R. Negrete, and J. P. Konopelski, J . Org. Chem., 56, 5196 (1991).

6780. K. S. Chu, G. R. Negrete, J. P. Konopelski, F. J. Lakner, N.-T. Woo, and M. M. Olmstead, J . Am. Chem. Soc., 114, 1800 (1992). 6781. B. J. Kurtev, M. J. Lyapova, S. M. Mishev, 0. G. Nakova, A. S . Orahovatz, and I. G. Pojarlieff, Org. Magn. Reson., 21, 334 (1983). 6782. R. Baltrussis and I. Mariosius, Khim. Geterotsikl. Soedin., 1969, 120. 6783. R. Baltrussis and I. Mariosius, Khim. Geterotsikl. Soedin., 1969, 904 6784. A. Takamizawa and K. Hirai, Jap. Pat. 1184 (1967); Chem. Ahstr., 66, 55505 (1967). 6785. W. Barbieri, L. Bernardi, F. Luini, and G. Pdlamidessi, Farmaco, Ed. Sci., 24, 561 (1969). 6786. Y. Yamamoto, A. Sakaguchi, H. Yoshida, and K.-Y. Akiba, J . Chem. Soc., Perkin Trans. f, 1988, 725. 6787. H. Singh, P. Singh, and S. Kumar, Indian J . Chem., Sect. 8, 22, 154 (1983). 6788. B. B. Snider and Z. Shi, J . Org. Chem., 57, 2526 (1992). 6789. H. Singh and S. Kumar, Indian J . Chem., Sect. B, 25, 688 (1986). 6790. H. Singh and P. Singh, Tetrahedron, 37, 1215 (1981). 6791. Y. Iwakura, T. Nishiguchi, and A. Nabeya, .I. Orq. Chem., 31, 1651 (1966). 6792. G. Zigeuner, C. Knopp, and H. Blaschke, Monatsh. Chem., 107, 587 (1976). 6793. K. Burger, F. Hein, and G. Jannitsopoulos, Chem. Ber., 113, 3396 (1980). 6794. G. Schulz and W. Steglich, Chem. Ber., 113, 770 (1980). 6795. K.-H. Magosch, Synthesis, 1972, 37. 6796. W. Dowd and P. W. Owen, US Pat. 4,014,880 (1977); Chem. Ahstr., 87, 53301 (1977). 6797. H. Sonnenschein and E. Schmitz, Synthesis, 1989, 443. 6798, I. Brukhardt and K. Hamann, Chem. Ber., 100,2569 (1967). 6799. B. A. M. Oude-Alink, RecL. Trav. Chim. Pays-Bas, 98, 282 (1979). 6800. R. Amoroso, G. Cardillo, and C. Tomasini, Heterocycles, 34, 349 (1992). 6801. R. Amoroso, G. Cardillo, C. Tomasini, and P. Tortoreto, J . Ory. Chem., 57, 1082 (1992). 6802. E. Juaristi, J. Escalante, B. Lamatsch, and D. Seebach, J . Ory. Chem., 57, 2396 (1992). 6803. E. Juaristi, D. Quintana, B. Lamatsch, and D. Seebach J . Org. Chem., 56, 2553 (1991). 6804. P. A. Hunt, C. May, and C . J. Moody, Tetrahedron Lett., 29, 3001 (1988). 6805. L. Gsell, Eur. Pat. Appl. E P 375,613 (1990); Chem. Ahstr., 113, 231399 (1990). 6806. C . N . O’Callaghan and T. B. H. McMurry, J . Chem. Rex, Synop. 345, Minipr. 2712 (1990). 6807. D. E. Fenton, R. Moody, U. Casselato, P. A. Vigato, and R. Graziani, J . Heterocycl. Chem., 22, 1639 (1985). 6808. J. Barluenga, M. Tomis. V. Kouznetsov, J. Jardon, and E. Rubio, Synlett, 1991, 821. 6809. M. Senkus, J . Am. Chem. SOC.,68, 1611 (1946).

1358 6810. 681 I. 6812. 6813. 6814. 6815. 6816. 6817. 6818. 6819. 6820. 6821. 6822. 6823. 6824. 6825. 6826.

References M. Senkus, US Pat. 2,387,043 (1945); Chem. Abstr., 40, 613 (1946). M. B. Winstead, R. G. Strachan, and H. W. Heine, J . Org. Chem., 26, 41 16 (1961). M. Senkus, US Pat. 2,391,847 (1945); Chem. Abstr., 40, 1889 (1946). B. Ganern, Ace. Chem. Res., 15, 290 (1982). R. A. Y. Jones, A. R. Katritzky, and M. Snarey, J . Chem. Soc. (B), 1970, 131. G. Parrinello and R. Miilhaupt, J . Org. Chem., 55, 1772 (1990); [cf. Chem. Ahstr., 112, 138998 (199O)l. M. Scholtz, Ber. Dtsch. Chem. Ges., 32, 2251 (1899). W. L. C. Veer, R e d . Trav. Chim. Pays-Bas, 57, 989 (1938). 1. Y. Poatovskii and N. G. Nosenkova, Zh. Obshch. Khim., 27, 526 (1957); Chem. Ahstr., 51, 15525 (1957). J. H. Billman and L. C. Dorrnan, J . Pharm. Sci., 51, 1071 (1962). J. H. Billrnan and M. S. Khan, J . M e d . Chem., 9, 347 (1966). J. H. Billman and J. L. Meisenheirner, J . Med. Chem., 6, 682 (1963). J. H. Billman and J. L. Meisenheirner, J . M e d . Chem., 8, 540 (1965). J. H. Billrnan and M. S. Khan, J . Med. Chem., 8, 498 (1965). J. H. Billman and M. S. Khan, J . Med. Chem., 11, 312 (1968). J. A. Bell and 1. Dunstan, J . Chem. Soc. (C), 1966, 870. J.-C. Cai, J.-L. Pan, and Y.-F. Ken, Yao Hsueh Hsueh Pao, 14, 52 (1979); Chem. Abstr., 92, 76444 (1 980).

6827. Bayer A.-G.,Neth. Pat. Appl. 6,505,669 (1965); Chem. Ahstr., 64, 11233 (1966). 6828. R. R. Mod, F. C. Magne, G. Sumrell, A. F. Novak, and J. M. Solar, US Pat. 3,872,120(1975); Chem. Abstr., 83, 79272 (1975). 6829. H. Piotrowska, T. Urbanski, and W. Bednarska, Org. Prep. Proced. Int., 3, 21 (1971). 6830. H. Piotrowska and H. Prejzner, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 28, 181 (1980); Chem. Ahstr., 95, 132802 (1981). 6831. H. Piotrowska and H. Prejzner, Pol. J . Chem., 54,2341 (1980); Chem. Abstr., 95,80885 (1981). 6832. W. Popel, G. Faust, H. Furst, G. Dietz, and E. Carstens, J . Prakt. Chem. [4], 38, 339 (1968). 6833. D. S.-C. Black, D. C. Craig, 0.Giitsidis, R. W. Read. A. Selek, and M. A. Sefton, J . Org. Chem., 54, 4771 (1989). 6834. D. S . X . Black, M. Kassiou, and R. W. Read, J . Org. Chem., 56, 4308 (1991). 6835. D. S.-C. Black, D. C. Craig, M. Kassiou, and R. W. Read, Aust. J . Chem., 44, 143 (1991). 6836. A. W. Titherley and G. E. K. Branch, J . Chem. Soc., 103, 330 (1913). 6837. H. Krassig, Makromol. Chem., 17, 77 (1956). 6838. J. N. Shooley, in Third Workshop on N M R and E P R Spectroscopy (Palo Alto, CA, 1959), Pergarnon Press, New York, 1960, p. 40. 6839. J. Okada, K. Nakano, and M. Tsuchiya, Yakugaku Zasshi, 93, 1463 (1973). 6840. J . Oshis, A. A. Anderson, and M. V. Shirnanskaya, Khim. Geterotsikl. Soedin., 1982, 967. 6841. J. Okada, K. Nakano, M. Tsuchiya, and T. Tsukarnoto, Yukugaku Zasshi, 95, 1191 (1975). 6842. N. Yoshirnura, I. Moritani, T. Shimarnura, and S.-I. Murahashi, J . Am. Chem. Soc., 95, 3038 (1973). 6843. R. R. Gaudette, J. L. Ohlson, and P. M. Scanlon, Ger. Pat. Offen. 2,648,354 (1977); Chem. Abstr., 87, 184547 (1977). 6844. R. R. Gaudette, J. L. Ohlson, and P. M. Scanlon, US Pat. 3,988,367 (1976); Chem. Abstr., 86, 105950 (1977). 6845. D. J. Malfer, J. G. Bostick, L. J. Cunningharn, and J. V. Hanlon, Can. Pat. Appl. CA 2,019,047 (1991); Chem. Ahstr., 115, 280048 (1991).

References

1359

6846. V. P. Borovik. A. I . Shadrina, and V. P. Mamaev. Sib. KAim.Zh., 77 (1991); Chem. Ahstr., 116, 214448 (1992). 6847. S. Mager, I. Cristea, L. Craciun, F. Irimie, and M. Diudea, Rev. Roum. Chim., 36, 665 (1991); Chem. Abstr., 116, 214455 (1992). 6848. J. W. Hull and K. Otterson, J . Org. Chem., 57, 2925 (1992). 6849. W. A. W. Stolle, A. E. Frissen, A. T. M. Marcelis, and H. C. van der Plas, J . Org. Chem., 57, 3000 (1992). 6850. H.-J Schulz, J. Liebscher, and G. Maas, Liehigs Ann. Chem., 1992, 411. 6851. J. Chen and G. T. Crisp, Synth. Commun., 22, 683 (1992). 6852. K. Matsumoto, S. Hashimoto, M. Hashimoto, M. Toda, and S. Otani, Synth. Commun., 22, 787 (1992). 6853. R. G. Shepherd, Eur. Pat. Appl. EP 405,932 (1991); Chem. Abstr., 114, 228945 (1991). 6854. C. M. Tice and B. Ganem, J . Org. Chem., 48, 2106 (1983). 6855. H. Braun, B. Bertram, and M. Wiessler, J . Label. Compd. Radiopharm, 13, 375 (1977); Chem. Abstr., 88, 22814 (1978). 6856. J. B. Lambert and M. W. Majchrzak, J . Am. Chem. Soc., 102, 3588 (1980). 6857. B. T. Golding and I. K. Nassereddin, J . Am. Chem. Soc., 104, 5815 (1982). 6858. G. T. Lee, J. C. Amedio, R. Underwood, K. Prasad, and 0. Repic, .I. Org. Chem., 57, 3250 (1992). 6859. E. L. Elicl, W. F. Bailey, L. D. Kopp, R. L. Willer, D. M . Grant, R. Bertrand, K. A. Christensen, D. K. Dalling, M. W. Duch, E. Wcnkert, F. M. Schell, and D. W. Cochran, .I. Am. Chem. SOC.,97, 322 (1975). 6860. M. Hajek, K. Wagner, W. Uerdingen, and W. Wellner, Ger. Pat. Offen. 2,739,313 (1979); Chem. Abstr., 91, 125036 (1979). 6861. J. E. Douglas and R. Dial, Synthesis, 1975, 654. 6862. Y. H. Chang, G. R. Evanega, and W. M. McLamore, US Pat. 3,729,564 (1973); Chem. Abstr., 79, 18762 (1973). 6863. J. Jurczak, in Organic High Pressure Chemistry (W. J. Le Noble, Ed.), Elsevier, Amsterdam, 1988, p. 304. 6864. U. J. Vogelbacher, M. Ledermann, T. Schach, G. Michels, U. Hees, and M. Regitz, Angew. Chem., 100, 304 (1988). 6865. B. Chylinska, Pol. Pat. 73,853 (1975); Chem. Abstr., 85, 177479 (1976). 6866. R. G. Gafurov, S. I. Sviridov, and L. T. Eremenko, Izu. Akad. Nauk S S S R , Ser. Khim., 1973, 1366. 6867. H. Piotrowska, T. Urbanski, and K. Wejroch-Matacz, Rocz. Chem., 45, 1267 (1971); Chem. Ahstr., 76, 34195 (1972). 6868. G. Rembarz and B. Ernst, J . Prakt. Chem. [4], 37, 59 (1968). 6869. H. J. Roth and K. Ergenzinger, Arch. Pharm. (Weinheim, Ger.), 311, 492 (1978). 6870. B. Kamienski, T. Urbanski, and M. Witanowski, Tetrahedron Lett., 1970, 451. 6871. B. Kamienski, R. Kolinski, T. Urbanski, and M. Witanowski, Tetrahedron Lett., 1969, 1281. 6872. M. A. Akhemrov, V. S. Reznik, R. R. Shagidullin, and Y. S. Shvetsov, Izc. Akad. Nauk SSSR, Ser. Khim.,1992, 169. 6873. N. PI&,A. Turck, F. Bardin, and G. Queguiner, J . Heterocycl. Chem., 29, 467 (1992). 6874. H. Mohrle and C. Schnoedelbach, Pharmazie, 30, 699 (1975); Chem Abstr., 84, 59344 (1976). 6875. K. Kawahara, R. Sato, A. Fumita, and T. Miwa, Jap. Pat. 7525 (1961); Chem. Abstr., 58, 13968 (1963). 6876. G. Darnbrough, P. Knowles, S. P. O’Connor, and F. J. Tierney, Tetrahedron, 42, 2339 (1986). 6877. T. Takajo and S. Kambe, Synthesis, 1980, 833.

1360

References

6878. H. Piotrowska, W. Sas, and T. Urbanski, Rocz. Chem., 47, 1233 (1973); Chem. Ahstr., 80,37066 (1974). 6879. H. Piotrowska, W. Sas, and T. Urbanski, Bull. Acud. Pol. Sci., Ser. Sci. Chim., 25, 519 (1977); Chem. Ahstr., 88, 50783 (1978). 6880. W. 0. Bell and A. E. Necker, US Pat. 3,054,797 (1964); Chem. Ahstr., 58, 10216 (1963). 6881. R. F. Evans, in The Pyrimidines: Supplement I (D. J. Brown, Wiley, Ed.), New York, 1970, p. 345. 6882. H. A. Bates. N. Condulis, and N. L. Stein, J . Org. Chem., 1986, 51, 2228; also references 2-15 cited therein. 6883. N. N. Mel’nikov, N. P. Lyalyakina, and N. T. Shvetsov-Shilovskii, Zh. Org. Khim., 5, 390 (1969). 6884. C. Kashirna, M. Shimizu, A. Katoh, and Y. Omote, J . Heterocycl. Chem., 21, 441 (1984). 6885. J. Knabe, W. Geisrnar, and C. Urbahn, Arch. Pharm. (Weinheim, Ger.), 302, 468 (1969). 6886. R. F. Evans, in The Pyrimidines: Supplement I1 (D. J. Brown, Ed.), Wiley, New York, 1985, p. 405ff. 6887. J. G. Keay, A h . Heterocycl. Chem., 39, 1 (1986). 6888. C. 0. Kappe, Liehigs Ann. Chem., 1990, 505. 6889. C. 0. Kappe and G. Fiirber, J . Chem. Soc., Perkin Trans. I , 1991, 1342. 6890. C. 0. Kappe, G. Uray, P. Roschger, W. Lindner, C. Kratky, and W. Keller, 7etrahedron, 48, 5473 (1992). 6891. E. Sato and T. Kanaoka, Tetrahedron Lett., 1969, 3547. 6892. Y. Kondo and B. Witkop, J . Org. Chem., 33, 206 (1968). 6893. C. Kashima, A. Katoh, N. Yoshiwara, and Y. Omote, J . Heterocycl. Chem., 18, 1595 (1981). 6894. T. Tsuji and M. Hard, Chem. Pharm. Bull., 21, 1375 (1973). 6895. M. I. Garcia-Trimifio, A. Macias-Cabrera, and H. Velez-Castro, Synth. Commun., 22, 1319 (1992). 6896. P. S. Manchand, P. Rosen, P. S. Belica, R. V. Oliva, A. V. Perrotta, and H. S. Wong, J . Org. Chem., 57, 3531 (1992). 6897. H.-D. Franken, H. Riiterjans, and F. Miiller, Tetrahedron, 47, 7593 (1991). 6898. S. Frimpong-Manso, K. Nagy, G. Stajer, G. Bernath, and P. Sohar, J . Heterocycl. Chem., 29, 221 (1992). 6899. N. Klempier, A. de Raadt, H. Griengl, and G. Heinisch, J . Heterocycl. Chem., 29, 93 (1992). 6900. T. Akiyarna, R. Yanada, 0. Sakurai, T. Harayama, K. Tanaka, and F. Yoneda, J . Chem. Soc., Chem. Commun., 1989, 910. 6901. R. Yanada, T. Akiyama, T. Harayarna, K. Yanada, H. Meguri, and F. Yoneda, J. Chem. Soc., Chem Commun., 1989, 238. 6902. T. Akiyarna, K. Tanaka, and F. Yoneda, J . Heterocycl. Chem., 26, 877 (1989). 6903. T. Harayama, R. Yanada, T. Akiyama, M. Tanaka, Y. Fujita, and F. Yoneda, Chem. Pharm. Bull., 39, 612 (1991). 6904. F. Yoneda, T. Akiyama, M. Ohno, R. Yanada, and T. Harayarna, Yukugaku Zasshi, 111,284 (1 991). 6905. R. Yanada, K. Bessho, T. Harayama, and F. Yoneda, Chem. Pharm. Bull., 39, 1333 (1991). 6906. M. S. Goodman and S. D. Rose, J . Ory. Chem., 57, 3268 (1992). 6907. R. F. Hartman and S. D. Rose, J . Am. Chem. Soc., 114, 3559 (1992). 6908. H. P. Diogo, A. R. Dias, A. Dhalla, M. E. Minas da Piedade, and T. P. Begley, J . Org. Chem., 56, 7340 (1991). 6909. C. Kashima, A. Katoh, Y. Yokote, and Y. Omote, Heterocycles, 14, 285 (1980).

References

1361

6910. A. S. Morkovnik, E. P. Ivakhne’nko,Y. G. Bogachev, B. A. Tertov, N. T. Berberova, and 0. Y. Okhlobystin, Khim. Geterotsikl. Soedin., 1988, 202. 691 1. T. Shoji and J. Nakaishi, Jap. Kokai Tokkyo Koho, J P 02 11,577 (1990); Chem. Ahstr., 113, 40724 (1990). 6912. N. C. Hancox, Aust. J . Sci. Res., Ser. A , 3, 450 (1950). 6913. M. Habs, H. Habs, and B. Bertram, J . Cancer Res. Clin. Oncol., 105, 191 (1983). 6914. Q. Dai, R. Zhong, and X. Gao, Huanjing Huaxue, 6, l(1987); Chem. Ahstr., 109, 105945 (1988). 6915. R. L. Willer and R. L. Atkins, J . Org. Chem., 49, 5147 (1984). 6916. R. L. Willer and R. L. Atkins, US Pat. 4,614,800 (1986); Chem. Abstr., 106, 20705 (1987). 6917. R. L. Willer and D. W. Moore, Magn. Reson. Chem., 26, 95 (1988). 6918. M. Pickering, J. Rylance, R. W. H. Small, and D. Stubley, Acta Crystallogr., Sect. B, 47, 782 (1991). 6919. A. R. Katritzky, R. Murugan, H. Luce, M. C. Zerner, and G. P. Ford, J . Chem. Soc., Perkin Trans. 2, 1987, 1695. 6920. J. H. Boyer and G. Kumar, Heterocycles, 22, 2351 (1984). 6921. A. R. Katritzky, R . Murugan, H. Luce, B. C. Chen, W. S. Brey, and M . C. Zerner, J . Chem. Soc., Perkin Trans. 2, 1987, 1701. 6922. J. Okada and M . Shimabayashi, Yukugaku Zasshi, 97, 962 (1977). 6923. S.-0. Chua, M. J. Cook, and A. R. Katritzky, J . Chem. Soc., Perkin Trans. 2, 1974, 546. 6924. J. R. Russell, C. D. Garner, and J. A. Joule, J . Chem. Soc., Perkin Trans. I: 1992, 409. 6925. G. Zigeuner, H. Schmidt, and D. Volpe, Monutsh. Chem., 101, 1824 (1970). 6926. G. Zigeuner, H. W. Schramm, A. Fuchsgruber, and W. Wendelin, Monatsh. Chem., 106, 407 (1975). 6927. G. Zigeuner, H. Hamberger, H. Blaschke, and H. Sterk, Monatsh. Chem., 97, 1408 (1966). 6928. F. B. Slezak, Br. Pat. 888,627 (1962); Chem. Abstr., 59,641 (1963). 6929. C. A. Renner and F. D. Greene, J . Org. Chem., 41, 2813 (1976). 6930. A. Takamizawa, K . Hirai, T. Ishiba, and Y. Matsumoto, Chem Pharm. Bull., 15, 731 (1967). 6931. P. N. Gordon, US Pat. 3,219,522 (1965); Chem. Ahstr., 64, 6671 (1966). 6932. R . C. Tweit, US Pat. 3,025,295 (1962); Chem. Abstr., 57, 8589 (1962). 6933. F. d’Angeli, C. di Bello, and V. Giormani, Gazz. Chim. Ital., 94, 1342 (1965). 6934. C. Kashima, M . Shimizu, K . Harada, and Y. Omote, J . Helerocycl. Chem., 25, 1713 (1988). 6935. D. J. Brown, Fused Pyrimidines Part 3: Pteridines, Wiley, New York, 1988, p. 3728 and references cited therein. 6936. S. W. Bailey, S. T. Weintraub, S. M. Hamilton, and J. E. Ayling, J . Biol. Chem., 257, 8253 (1982). 6937. S. W. Bailey and J. E. Ayling, Biochemistry, 22, 1790 (1983). 6938. D. C. Pike, M. T. Hora, S. W. Bailey, and J. E. Ayling, Biochemistry, 25, 4762 (1986). 6939. S. W. Bailey, R. Y. Chandrasekaran, and J. E. Ayling, J. Ory. Chem., 57, 4470 (1992). 6940. M. KoEevar, B. Mlakar, M . Perdih, A. Petrii., S. Polanc, and B. Vertek, Tetrahedron Lett., 33, 2195 (1992). 6941. K. Ladva, U. Dave, and H. Parekh, J . Indian Chem. SOC.,68, 370 (1991). 6942. J.-M. Lehn, M. Mascal, A. de Cian, and J. Fischer, J . Chem. Soc., Perkin Trans. 2, 1992,461. 6943. K. Yoshida and M. Taguchi, J . Chem. Soc., Perkin Trans. I, 1992, 919. 6944. T. Nagamatsu, H. Yamasaki, and F. Yoneda, Heterocycles, 33, 775 (1992). 6945. S. P. Singh, A. R. Mahajan, D. Prajaparti, and J. S. Sandhu, Synthesis, 1991, 1026. 6946. M. G. Jaenecke, H. Voigt, and D. Heydenhauss, 2. Chem., 30, 91 (1990).

1362

References

6947. M. A. El-Hashash, A. F. El-Kafrawy, and S. A. Shiba, Chin. J . Chem., 9, 189 (1991); Chem. Abstr., 115, 114449 (1991). 6948. K. S. Atwal, G. C. Rovnyak, J. Schwartz, S. Moreland, A. Hedberg, J. Z. Gougoutas, M. F. Malley, and D. M. Floyd, J . Med. Chem., 33, 1510 (1990). 6949. A. E. F. G. Hammam, M. A. Salama, N. M. Youssif, and S. F. Mohamed, Egypt. J . Chem., 30, 375 (1987); Chem. Abstr., 114, 62039 (1991). 6950. D. Bozing, P. Benko, L. Petzoc, M. Szecsey, P. Toempe, G. Gigler, I. Gaesalyi, and I. Gyertyan, Eur. Pat. Appl. E P 409,223 (1991); Chem. Abstr., 114, 247302 (1991). 6951. N. G. Kundu and S. G. Khatri, Synthesis, 1985, 323. 6952. A. Crawshaw and A. G. Jones, J . Macromol. Sci., Chem., 5, 1903 11971 (?)I;Chem. Abstr., 73, 131624 (1970). 6953. H. Bohme and M. Dahne, Liebiys Ann. Chem., 723, 41 (1969). 6954. T. Tsuji, Chem. Pharm. Bull., 19, 2551 (1971). 6955. J. Okada and M. Shimabayashi, Chem Pharm. Bull., 28, 3310 (1980). 6956. M. Nicola, A. Donetti, E. Cereda, M. Turconi, G. B. Schiavi, and R. Micheletti, Eur. Pat. Appl. EP 309,425 (1989); Chem. Abstr., 111, 214499 (1989). 6957. 6958. 6959. 6960.

J. Svttlik and F. Turetek, Tetrahedron Lett., 25, 3901 (1984). E. Juaristi and D. Quintana, Tefrahedon:Asymmetry, 3, 723 (1992). J. P. Konopelski, K. S. Chu, and G. R. Negrete, J . Org. Chem., 56, 1355 (1991). R. Amoroso, G. Cardillo, and C. Tomasini, Tetrahedron Lett., 33, 2725 (1992).

6961. R. Baltrusis, V. Mickevicius, I. Bilinskaite, R. M. Zolotoyabko, and E. Liepins, Khim. Geterotsikl. Soedin., 1990, 1096. 6962. C. Kashima, A. Katoh, Y. Yokota, and Y. Omote, J . Heterocycl. Chem., 18, 1469 (1981). 6963. C. Kashima, M. Shimizu, A. Katoh, and Y. Omote, Heterocycles, 24, 3477 (1986). 6964. H. Singh, P. Singh, and K. Deep, Tetrahedron, 39, 1655 (1983). 6965. V. Rakhina, I. B. Blagoeva, I. G. PojcarliefT, and K. Yates, Can. J . Chem., 68, 1676 (1990). 6966. R. V. Kasubick and J. W. McFarland, S. African Pat. 00,516 (1968); Chem. Abstr., 70, 68406 (1969). 6967. J. W. McFarland, S. African Pat. 01,182 (1968); Chem. Abstr., 70, 57880 (1969). 6968. J. Uriach, Spanish Pat. 415,740 (1976); Chem. Abstr., 85, 177476 (1977). 6969. M. L. Aubry, P. Cowell, M. J. Davey, and S. Shevde, Br. J . Pharmacol., 38, 332 (1970). 6970. R. L. Cornwell and M. A. Blore, Ann. Trop. Med. Parasitol., 64, 525 (1970). 6971. S. F. Figdor, M. Schach von Wittenau, J. K. Faulkner, and A. M. Monro, J . Label. Compd., 6, 362 (1970). 6972. S. S. C. Tai, N. Cargile, C. J. Barnes, and P. Kijak, J . Assoc. Ofl Anal. Chem., 1990, 73, 883; Chem. Abstr., 114, 41127 (1991). 6973. J. C. Dore, J. Lacroix, R. Lacroix, and C. Viel, J . Pharm. Belg., 45, 375 (1990); Chem. Abstr., 114, 135581 (1991). 6974. S. Rajappa, M. D.Nair, R. Sreenivasan, and B. G. Advani, Tetrahedron, 38, 1673 (1982). 6975. S. Rajappa and B. G. Advani, J . Chem. Soc.. Perkin Trans. I , 1984, 1631. 6976. G. Zigeuner, A. Frank, and W. Adam, Monatsh. Chem., 101, 1788 (1970). 6977. H. Enders and G. Pusch, Textile Res. J., 36, 322 (1966); Chem. Abstr., 65, 4011 (1966). 6978. A. Iordanova, A. Karparov, and M. Starcheva, Dokl. Bolg. Akad. Nauk, 43, 105 (1990); Chem. Abstr., 115, 110401 (1991). 6979. D. C. Craig, M. Kassiou, and R. W. Read, J . Org. Chem., 57, 3901 (1992). 6980. G. Zigeuner, W. B. Lintschinger, A. Fuchsgruber, and K. Kollmann, Monatsh. Chem., 107,155 (1976).

References

1363

H. Singh, P. Aggarwhal, and S. Kumar, Indian J . Chem., Sect. B, 30, 740 (1991). C. Kashima, M. Shimizu, and Y. Omote, Chem. Pharm. Bull., 35, 2694 (1987). A. Lorente, A. Cosme, P. Coronado, and J. L. Soto, Synthesis, 1988, 739. D. A. Berges and S. J. Schmidt, J . Org. Chem., 49, 4555 (1984). D. A. Claremon and S. A. Rosenthal, Synthesis, 1986, 664. G. Y. Remennikov and S. G. Vishnevskii, Ukr. Khim. Zh. (Russ. Ed.), 57, 82 (1991); Chem. Ahstr., 115, 8726 (1991). 6987. A. D. Shutalev and L. A. Ignatova, Khim. Geterotsikl. Soedin., 1991, 228. 6988. H. Bredereck, F. Effenberger, and H. P. Beyerlin, Chem. Ber., 97,3081 (1964) [cf. Chem. Abstr., 62, 1561 (1965)l. 6989. R. H. B. Galt and S. D. Mills, Chem Br., 1965, 230. 6990. K. M. Reese, Chem. Eng. News, 62, No 28, 132 (1984). 6991. H. R. Seikaly and T. T. Tidwell, Tetrahedron, 42, 2587 (1986). 6992. Z.-T. Huang and 2.-R. Liu, Chem. Ber., 122, 95 (1989). 6993. W.-Y. Zhao and Z.-T. Huang, J . Chem. Soc., Perkin Trans. 2, 1991, 1967. 6994. Z.-T. Huang and M.-X. Wang, Synth. Commun., 21, 1909 (1991). 6995. R. Wayne, S. Cardaciotto, M. Thompson, G. Stockton, W. Millen, J. Conley, L. Davis, S. Rajan, R. Lopata, et al., Iyakuhin Kenkyu, 19,966 (1988); Chem. Ahstr., 110, 187761 (1989). 6996. G. Zigeuner, W. Nischk, and B. Juraszovits, Monatsh. Chem., 97, 1611 (1966). 6997. M. Tomura, N. Matsumura, 0. Mori, H. Chikusa, S. Kamitani, and H. Inoue, J. Heterocycl. Chem., 27, 2215 (1990). 6998. K. Burger, H. Neuhauser, and M. Rudolph, Chem.-Ztg., 114, 251 (1990). 6999. R. W. Alder, D. Colclough, and R. W. Mowlam, Tetrahedron Lett., 32, 7755 (1991). 7000. A. Safavi and A. Massoumi, Microchem. J., 42, 314 (1990); Chem. Abstr., 114, 54969 (1991). 7001. B. Fernindez, I. Perillo, and S. Lamden, J. Chem. Soc., Perkin Trans. 2, 1974, 1416. 7002. I. Perillo, B. Fernandez, and S. Lamden, J. Chem. Soc., Perkin Trans. 2, 1977, 2068. 7003. G. Ferguson, B. Kaitner, D. Lloyd, and H. McNab, J. Chem. Res., Synop. 182, Minipr. 1738 (1984). 7004. F. G. Bordwell, N. R. Vanier, and X. Zhang, J . Am. Chem. Soc., 113, 9856 (1991). 7005. A. L. Weis, 2. Porat, and Z. Luz, J . Am. Chem. Soc., 106, 8021 (1984). 7006. C. Kashima, M. Shimizu, and Y. Omote, Tetrahedron Lett., 26, 5057 (1985). 7007. H. Cho, T. Iwashita, M . Ueda, A. Mizuno, K. Mizukawa, and M. Hamaguchi, J . Am. Chem. Soc., 110, 4832 (1988). 7008. H. Cho, Y. Hamamoto, K. Shima, and Z . Taira, Tetrahedron, 42, 6429 (1986). 7009. Y. H. Kim and B. U. Lim, Tetrahedron Lett., 32, 2057 (1991). 7010. D. Nasipuri, S. Banerjee, B. V. Alaka, and N. P. Daw, Synthesis, 1982, 1073. 701 1. R. Faure, E.-J. Vincent, G. Assef, J. Kister, and J. Metzger, Ory. Magn. Reson., 9, 688 (1977). 7012. R. Jain and H. K. Pardasani, Indian J . Heterocycl. Chern., 1, 79 (1991); Chem. Ahstr., 117, 48461 (1992). 7013. R. F. Evans and C . H. L. Kennard, unpublished results. 7014. D. Seebach, B. Lamatsch, R. Amstutz, A. K. Beck, M. Dobler, M. Egli, R. Fitzi, and 20 others, Helo. Chim. Acta, 75, 913 (1992). 7015. I. J. Ferguson, A. R. Katritzky, and D. M. Read, J . Chem. Soc., Chem. Commun., 1975, 255. 7016. A. R. Katritzky, V. J. Baker, F. M. S. Brito-Palmer, I. J. Ferguson, and I. Angiolini, J. Chem. Soc., Perkin Trans. 2, 1980, 1746. 7017. A. R. Katritzky, R. C. Patel, and F. G. Riddell, J . Chem. Soc., Chem. Commun., 1979, 674; Anyew. Chem., 93, 567 (1981).

6981. 6982. 6983. 6984. 6985. 6986.

1364

References

7018. L. Carballeira, R. A. Mosquera, and M. A. Rios, J . M o l . Struct., 176, 89 (1988). 7019. I. J. Ferguson, A. R. Katritzky, and D. M. Read, J . Chem. Soc., Perkin Trans. 2, 1977, 818. 7020. A. R. Katritzky, V. J. Baker, I. J. Ferguson, and R. C. Patel, J . Chem. Sor., Perkin Trans. 2, 1979, 143. 702 1, R. L. Crumbie, personal communication. 7022. T. D. Bailey and R. L. Crumbie, Royal Australian Chemical Institute 12th National Conference, Brisbane, 1991: Organic Chemistry Division, Poster Abstract M-14. 7023. N. Kalyanam, P. C. Parthasarathy, L. Anathan, S. Manjanatha, and M. A. Likhate, Indian J . Chem., Sect. B, 31, 243 (1992). 7024. E. E. Stashenko, P. I. Zakharov, V. G. Pleshakov, and B. S. Subbotin, Khim. Geterotsikl. Soedin., 1989, 360. 7025. M. Himottu, K. Pihlaja, G. Bernath, G. Stajer. and P. Vainiotalo, Ory. M a s s Spectrom., 25, 277 (1990). 7026. H. Hamdan, M. Scandola, D. Franchi, G. Gaviraghi, and G. Tarzia, Orq. M a s s Spectrom., 27, 240 (1 992). 7027. M. Hamdan, M. Scandola, and G. Tarzia, O r y . Mass Spectrom., 27, 724 (1992). 7028. T. Ushioda and H. Ishibashi, Jap. Pat. 4344 (1967); Chem. Abstr., 67, 82114 (1967). 7029. A. D. Brewer and J. A. Minatelli, Fr. Pat. Dcmande 2,628,741 (1989); Chem. Ahstr., 114, 228638 (1991). 7030. S. Batra and S. Sharma, Indian J . Chem., Sect. B, 29, 1051 (1990). 7031. K. Cooper, PCT Int. Appl. WO 90 11,281; Chem. Ahstr., 114, 143437 (1991). 7032. S. Kumar, S. S. Chimni, and D. Cannoo, fleterocycles, 34, 425 (1992). 7033. F. Zeuner, H.-J. Niclas, G. Reck, and H. Schenk, J . Prakt. Chem., 333, 561 (1991). 7034. L. del Corona, G. Signorelli, S. Mamzardo, A, Pinzetta, and G. Coppi, Eur. J . M e d . Chem., 26, 729 (1991). 7035. Y. S. Sadanandam, M. M. Shetty, and P. V. Diwan, Eur. J . M e d . Chem., 27, 87 (1992). 7036. H. J. Bestmann and R. W. Saalfrank, Chem. Ber., 114, 2661 (1981).

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