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Synthesis and chemical properties of 1,2-dihydropyrrolizines (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Known methods for the synthesis of 1,2-dihydropyrrolizines are presented in a systematized form. Literature data on the chemical properties of 1,2-dihydropyrrolizines are summarized and correlated; and synthetic, physiologically active substances belonging to this group of compounds are examined critically.

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Literature cited

  1. G. R. Clemo and G. R. Ramage, J. Chem. Soc., 49 (1931).

  2. J. Meinwald, Y. C. Meinwald, J. M. Wheeler, T. Eisher, and L. P. Brower, Science, 151, 583 (1966).

    Google Scholar 

  3. W. Flitsch and G. Jones, Adv. Heterocycl. Chem., A. R. Katritzky (ed.), Academic Press, New York, 37, 1 (1984).

    Google Scholar 

  4. A. R. Mattocks, Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, London (1986).

    Google Scholar 

  5. M. M. T. Buckley and R. N. Brogden, Drugs, 39, 86 (1990); Chem. Abstr., 112, 229,187 (1990).

    Google Scholar 

  6. S. Brandänge, B. Luning, and C. Lundin, Acta Chem. Scand., 27, 433 (1973).

    Google Scholar 

  7. R. G. Cooks, F. L. Warren, and D. H. Williams, J. Chem. Soc. C, No. 4, 286 (1967).

    Google Scholar 

  8. A. R. Mattocks and I. N. H. White, Nature (London), New Biol, 231, No. 21, 114 (1971).

    Google Scholar 

  9. A. R. Mattocks and N. H. White, Chem. Biol. Interact., 3, 383 (1971).

    Google Scholar 

  10. C. C. J. Culvenor, J. A. Edgar, L. W. Smith, and H. J. Tweeddale, Austr. J. Chem., 23, 1869 (1970).

    Google Scholar 

  11. C. C. J. Vulvenor, J. A. Edgar, L. W. Smith, and H. J. Tweeddale, Austr. J. Chem., 23, 1853 (1970).

    Google Scholar 

  12. A. R. Mattocks, J. Chem. Res., Synopses, No. 2, 40 (1977).

    Google Scholar 

  13. R. C. Shumaker, M.-T. S. Hsia, J. L. Seymour, and J. R. Allen, J. Labelled Compd. Radiopharm., 15, 227 (1978).

    Google Scholar 

  14. C. C. J. Culvenor, L. W. Smith, J. A. Edgar, M. V. Jago, H. J. Tweeddale, and E. L. French, German Patent 1,940,551; Chem. Abstr., 73, 55, 965 (1970).

    Google Scholar 

  15. A. L. Pereira and E. J. Barreiro, Quim. Nova, 6, No. 2, 74 (1983).

    Google Scholar 

  16. A. R. Mattocks, Chem. Ind., No. 7, 251 (1981).

    Google Scholar 

  17. A. R. Mattocks, J. Chem. Soc. C, No. 8, 1155 (1969).

    Google Scholar 

  18. A. R. Mattocks, Nature, 219, 480 (1968).

    Google Scholar 

  19. A. R. Mattocks, R. Jukes, and J. Brown, Toxicon, 27, 561 (1989); Chem. Abstr., 112, 98,930 (1990).

    Google Scholar 

  20. C. C. J. Culvenor, D. T. Downing, J. A. Edgar, and M. V. Jago, Ann. N. Y. Acad. Sci, 163, Part 2, 837 (1969).

    Google Scholar 

  21. A. R. Mattocks, Nature, 217, 723 (1968).

    Google Scholar 

  22. C. C. J. Culvenor, J. A. Edgar, L. W. Smith, and H. J. Tweeddale, Tetrahedron Lett., 41, 3599 (1969).

    Google Scholar 

  23. A. R. Mattocks, Anal. Chem., 39, 443 (1967).

    Google Scholar 

  24. T. R. Juneja, R. L. Gupta, and S. Samanta, Toxicol Lett., 21, 185 (1984); Chem. Abstr., 101, 49,682 (1984).

    Google Scholar 

  25. A. R. Mattocks, in: Phytochemical Ecology, Proceedings of Phytochemical Society Symposium (1971), J. B. Harborne (ed.), Academic Press, London 91972), p. 179.

    Google Scholar 

  26. A. R. Mattocks, Nature, 228, 174 (1970).

    Google Scholar 

  27. S. J. Armstrong and A. J. Zuckerman, Nature, 228, 569 (1970).

    Google Scholar 

  28. S. J. Armstrong and A. J. Zuckerman, Br. J. Exp. Path., 53, 138 (1972).

    Google Scholar 

  29. J. A. Burguera, G. T. Edds, and O. Osuna, Rev. Fac. Farm., Univ. Los Andes, 23, 65 (1983); Chem. Abstr., 102, 60,915 (1985).

    Google Scholar 

  30. A. R. Mattocks and I. Bird, Chem.-Biol. Interact., 43, 209 (1983).

    Google Scholar 

  31. J. A. Burguera and G. T. Edds, Acta Cient. Venez., 35, 67 (1984); Chem. Abstr., 102, 73,826 (1985).

    Google Scholar 

  32. C. C. J. Culvenor, M. V. Jago, J. E. Peterson, L. W. Smith, A. L. Payne, D. C. Cambell, J. A. Edgar, and J. L. Frahn, Austr. J. Agric. Res., 35, 293 (1984).

    Google Scholar 

  33. B. Kedzierski and D. R. Buhler, Toxicol. Lett., 25, No. 2, 115 (1985).

    Google Scholar 

  34. I. N. H. White, Chem.-Biol. Interact., 16, 169 (1977); Chem. Abstr., 87, 34,046 (1977).

    Google Scholar 

  35. J. Meinwald, Y. C. Meinwald, and P. H. Mazzocchi, Science, 164, 1174 (1969).

    Google Scholar 

  36. J. A. Edgar, C. C. J. Culvenor, and L. W. Smith, Experientia, 27, 761 (1971).

    Google Scholar 

  37. C. C. J. Culvenor and J. A. Edgar, Experientia, 28, 627 (1972).

    Google Scholar 

  38. J. Meinwald, C. J. Boriack, D. Schneider, M. Boppre, W. F. Wood, and T. Eisner, Experientia, 30, 721 (1974).

    Google Scholar 

  39. B. Tursch, J. C. Braekman, and D. Daloze, Experientia, 32, 401 (1976).

    Google Scholar 

  40. D. Schneider, M. Boppre, J. Zweig, S. B. Horsley, T. M. Bell, J. Meinwald, K. Hansen, and E. W. Diehl, Science, 215, 1264 (1982).

    Google Scholar 

  41. V. Carelli, M. Cardellini, and F. Morlacchi, Ann. Chim. (Roma), 51, 604 (1961); Chem. Abstr., 56, 5912 (1962).

    Google Scholar 

  42. V. Carelli, M. Cardellini, and F. Morlacchi, Ann. Chim. (Roma), 53, 309 (1963); Chem. Abstr., 59, 7463 (1963).

    Google Scholar 

  43. S. Brandänge and C. Lundin, Acta Chem. Scand., 25, 2447 (1971).

    Google Scholar 

  44. E. E. Schweizer and K. K. Light, J. Am. Chem. Soc., 86, 2963 (1964).

    Google Scholar 

  45. E. E. Schweizer and K. K. Light, J. Org. Chem., 31, 870 (1966).

    Google Scholar 

  46. E. E. Schweizer and K. K. Light, J. Org. Chem., 31, 2912 (1966).

    Google Scholar 

  47. J. M. Muchowski, S. H. Unger, J. Ackrell, P. Cheung, G. F. Cooper, J. Cook, P. Gallegra, O. Halpern, R. Koehler, A. F. Kluge, A. R. Van Horn, et al., J. Med. Chem., 28, 1037 (1985).

    Google Scholar 

  48. J. Schnekenburger and H. Vollhardt, Arch. Pharm. (Weinheim), 310, 186 (1977).

    Google Scholar 

  49. W. C. Agosta, J. Am. Chem. Soc., 82, 2258 (1960).

    Google Scholar 

  50. W. Flitsch and R. Heidhues, Chem. Ber., 101, 3843 (1968).

    Google Scholar 

  51. W. Flitsch and U. Neumann, Chem. Ber., 104, 2170 (1971).

    Google Scholar 

  52. D. Johnson and G. Jones, J. Chem. Soc., Perkin 1, No. 20, 2517 (1972).

    Google Scholar 

  53. M. E. Cardinali, I. Carelli, and A. Trazza, Electroanal. Chem. Interfacial Electrochem., 48, 277 (1973).

    Google Scholar 

  54. C. Verde and J. Maria, Spanish Patent 549,249; Chem. Abstr., 107, 23,226 (1987).

    Google Scholar 

  55. H. Fischer and M. Neber, Justus Liebigs Ann. Chem., 496, 1 (1932).

    Google Scholar 

  56. H. Volz and R. Draese, Tetrahedron Lett., No. 56, 4917 (1970).

    Google Scholar 

  57. W. Kutscher and O. Klamerth, Chem. Ber., 86, 352 (1953).

    Google Scholar 

  58. H. Shinohara, H. Shiba, M. Sawada, and E. Imoto, Nippon Kagaku Zasshi, 83, 618 (1962); Chem. Abstr., 59, 3866 (1963).

    Google Scholar 

  59. W. Herz, K. Dittmer, and S. J. Cristol, J. Am. Chem. Soc., 70, 504 (1948).

    Google Scholar 

  60. N. J. Leonard and E. H. Burk, J. Am. Chem. Soc., 72, 2543 (1950).

    Google Scholar 

  61. W. Herz and U. Toggweiler, J. Org. Chem., 29, 213 (1964).

    Google Scholar 

  62. A. Hanck and W. Kutscher, Hope-Sayler's Z. Physiol Chem., 338, 272 (1964); Chem. Abstr.,62, 10,505 (1965).

    Google Scholar 

  63. A. D. Josey and E. L. Jenner, J. Org. Chem., 27, 2466 (1962).

    Google Scholar 

  64. A. G. Anderson and M. M. Exner, J. Org. Chem., 42, 3952 (1977).

    Google Scholar 

  65. S. J. Box and D. F. Corbett, Tetrahedron Lett., 22, 3293 (1981).

    Google Scholar 

  66. G. R. Clemo and T. A. Melrose, J. Chem. Soc., No. 7, 424 (1942).

    Google Scholar 

  67. J. M. Patterson, J. Brasch, and P. Drenchko, J. Org. Chem., 27, 1652 (1962).

    Google Scholar 

  68. J. T. Braunholtz, K. B. Mallion, and F. G. Mann, J. Chem. Soc., No. 11, 4346 (1962).

    Google Scholar 

  69. N. W. Gabel, J. Heterocycl. Chem., 4, 627 (1967).

    Google Scholar 

  70. J. Schnekenburger and E. Breit, Arch. Pharm. (Weinheim), 310, 152 (1977).

    Google Scholar 

  71. J. Meinwald and Y. C. Meinwald, J. Am. Chem. Soc., 88, 1305 (1966).

    Google Scholar 

  72. W. Flitsch, J. Koszinowski, and Witthake, Chem. Ber., 112, 2465 (1979).

    Google Scholar 

  73. J. M. Muchowski and S. H. Unger, European Patent 114,632; Chem. Abstr., 101, 210,973 (1984).

    Google Scholar 

  74. H. Carpino, E. Galeazzi, R. Greenhouse, A. Gusman, E. Velarde, Y. Antonio, F. Franco, A. Leon, V. Perez, R. Salas, D. Valdes, J. Ackrell, D. Cho, P. Gallerga, O. Halpern, R. Koehler, M. L. Maddox, J. M. Muchowski, A. Prince, D. Tegg, T. C. Thurber, A. R. Van Horn, and D. Wren, Can. J. Chem., 60, 2295 (1982).

    Google Scholar 

  75. J. M. Muchowski and A. F. Kluge, German Patent 2,731,678; Chem. Abstr., 89, 6215 (1978).

    Google Scholar 

  76. J. M. Muchowski and A. F. Kluge, US Patent 4,097,579; Chem. Abstr., 89, 197,331 (1978).

    Google Scholar 

  77. J. Ackrell, F. Franco, R. Greenhouse, A. Gusman, and J. M. Muchowski, J. Heterocycl. Chem., 17, 1081 (1980).

    Google Scholar 

  78. H. N. Khatri, M. P. Fleming, and G. C. Schloemer, European Patent 275,092; Chem. Abstr., 110, 23, 725 (1989).

    Google Scholar 

  79. A. Padwa and B. H. Norman, Tetrahedron Lett., 29, 3041 (1988).

    Google Scholar 

  80. C. Oritz and R. Greenhouse, Tetrahedron Lett., 26, 2831 (1985).

    Google Scholar 

  81. F. Franco, R. Greenhouse, and J. M. Muchowski, J. Org. Chem., 47, 1682 (1982).

    Google Scholar 

  82. J. M. Muchowski and R. Greenhouse, US Patent 4,347,187; Chem. Abstr., 98, 53,684 (1983).

    Google Scholar 

  83. J. M. Muchowski and R. Greenhouse, US Patent 4,347,184; Chem. Abstr., 98, 16,573 (1983).

    Google Scholar 

  84. J. M. Muchowski and R. Greenhouse, US Patent 4,347,186; Chem. Abstr., 112, 178,658 (1990).

    Google Scholar 

  85. J. M. Muchowski and R. Greenhouse, US Patent 4,873,340; Chem. Abstr., 112, 178,658 (1990).

    Google Scholar 

  86. R. J. P. Corriu, J. J. E. Moreau, and C. Vernhet, Tetrahedron Lett., 28, 2963 (1987).

    Google Scholar 

  87. R. Huisgen, H. Gotthardt, H. O. Bayer, and F. C. Schaefer, Angew. Chem., 76, 185 (1964).

    Google Scholar 

  88. M. T. Pizzorno and S. M. Albonico, J. Org. Chem., 39, 731 (1974).

    Google Scholar 

  89. R. Huisgen, US Patent 3,285,931; Chem. Abstr., 66, 55,380 (1967).

    Google Scholar 

  90. Union Carbide European Research Associates, British Patent 1,099,500; Chem. Abstr., 69, 35,935 (1968).

    Google Scholar 

  91. R. Huisgen, H. Gotthardt, H. O. Bayer, and F. C. Schaefer, Chem. Ber., 103, 2611 (1970).

    Google Scholar 

  92. D. Laduree, J. C. Lancelot, and M. Robba, Tetrahedron Lett., 26, 1295 (1985).

    Google Scholar 

  93. W. K. Anderson and H. L. McPherson, J. Med. Chem., 25, 84 (1982).

    Google Scholar 

  94. J. Rebek and J.-C. E. Gehret, Tetrahedron Lett., No. 35, 3027 (1977).

    Google Scholar 

  95. F. M. Hershenson, J. Org. Chem., 40, 1260 (1975).

    Google Scholar 

  96. J. Rebek and J. C. Gehret, Symp. Heterocycl., T. Kametani (ed.), Sendai, Japan (1977), p. 33; Chem. Abstr., 89, 197,267 (1978).

    Google Scholar 

  97. O. Yebdri and F. Texier, J. Heterocycl. Chem., 23, 809 (1986).

    Google Scholar 

  98. E. K. Kunec and D. J. Robins, J. Chem. Soc., Perkin 1, No. 8, 1437 (1987).

    Google Scholar 

  99. J. J. Karchesy, B. Arbogast, and M. L. Deinzer, J. Org. Chem., 52, 3867 (1987).

    Google Scholar 

  100. W. K. Anderson, C. P. Chang, and H. L. McPherson, J. Med. Chem., 26, 1333 (1983).

    Google Scholar 

  101. J. Rebek, S. H. Shaber, Y.-K. Shue, J.-C. Gehret, and S. Zimmerman, J. Org. Chem., 49, 5164 (1984).

    Google Scholar 

  102. D. J. Robins and S. Sakdarat, J. Chem. Soc., Chem. Commun., No. 24, 1181 (1979).

    Google Scholar 

  103. M. T. Pizzorno and S. M. Albonico, Chem. Ind., No. 10, 349 (1978).

    Google Scholar 

  104. D. J. Robins and S. Sakdarat, J. Chem. Soc., Perkin 1, No. 3, 909 (1981).

    Google Scholar 

  105. W. K. Anderson and P. F. Corey, J. Med. Chem., 20, 8912 (1977).

    Google Scholar 

  106. D. Laduree, J. C. Lancelot, M. Robba, E. Chenu, and G. Mathe, J. Med. Chem., 32, 456 (1989).

    Google Scholar 

  107. H. A. Kelly and D. J. Robins, J. Chem. Soc., Perkin 1, No. 7, 1339 (1989).

    Google Scholar 

  108. I. A. Benages and S. M. Albonico, J. Org. Chem., 43, 4273 (1978).

    Google Scholar 

  109. C. W. Jefford and W. Johncock, Helv. Chim. Acta, 66, 2666 (1983).

    Google Scholar 

  110. E. Galeazzi, A. Guzman, A. Pinedo, A. Saldana, D. Torre, and J. M. Muchowski, Can. J. Chem., 61, 454 (1983).

    Google Scholar 

  111. M. Viscontini and H. Gillhof-Schaufelberger, Helv. Chim. Acta, 54, 449 (1971).

    Google Scholar 

  112. H. Röeder, H. Widenfeld, and T. Bourauel, Ann., No. 8, 1708 (1985).

    Google Scholar 

  113. Z. Yoshida, Jpn. Kokai 78-25596; Chem. Abstr., 89, 24,143 (1978).

    Google Scholar 

  114. Mitsubishi Chemical Industries, Jpn. Kokai Tokkyo Koho 81-154483; Chem. Abstr., 96, 104,084 (1982).

    Google Scholar 

  115. S. Yoneda, H. Hirai, and Z. Yoshida, Heterocycles, 15, 865 (1981).

    Google Scholar 

  116. Mitsubishi Chemical Industries, Jpn. Kokai Tokkyo Koho 81-59774; Chem. Abstr., 95, 187,062 (1981).

    Google Scholar 

  117. G. Dannhardt and R. Obergrusberger, Arch. Pharm. (Weinheim), 312, 896 (1979).

    Google Scholar 

  118. P. W. Hickmott and K. N. Woodward, J. Chem. Soc., Perkin 1, No. 8, 904 (1976).

    Google Scholar 

  119. A. V. Kadushkin, T. V. Stezhko, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 4, 564 (1986).

    Google Scholar 

  120. A. V. Kadushkin, T. V. Stezhko, N. P. Solov'eva, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 12, 1616 (1987).

    Google Scholar 

  121. R. Tressl, D. Rewicki, B. Helak, H. Kampreschröer, and N. J. Martin, Agric. Food Chem., 33, 919 (1985).

    Google Scholar 

  122. H. Shigematsu, S. Shibata, T. Kurata, H. Kato, and M. Fujimaki, J. Agric. Food Chem., 23, 233 (1975).

    Google Scholar 

  123. H. Shigematsu, Nippon Sembai Kosha Chuo Ken-Kyosho Kenkyu Hokoky, 118, 119 (1976); Chem. Abstr., 88, 7217(1978).

    Google Scholar 

  124. R. Tressl, D. Bahri, M. Holzer, and T. J. Kossa, Agric. Food Chem., 25, 459 (1977).

    Google Scholar 

  125. H. Shigematsu, S. Shibata, T. Kurata, H. Kato, and M. Fujimaki, Agric. Biol. Chem., 41, 2377 (1977); Chem. Abstr., 89, 24,664 (1978).

    Google Scholar 

  126. W. Baltes and G. Bochmann, Z. Lehensm.-Unters. Forsch., 184, 478 (1987); Chem. Abstr., 107, 174,544 (1987).

    Google Scholar 

  127. R. Griffith and E. G. Hammond, J. Dairy Sci., 72, 604 (1989); Chem. Abstr., 110, 230,284 (1989).

    Google Scholar 

  128. J.-C. Pommelet, H. Dhimane, J. Chuche, J.-P. Celerier, M. Haddad, and G. Lhommet, J. Org. Chem., 53, 5680 (1988).

    Google Scholar 

  129. M. Tashiro, Y. Kiryu, and O. Tsuge, Bull. Chem. Soc. Jpn., 48, 616 (1975).

    Google Scholar 

  130. S. Mori, M. Watanabe, S. Kajigaeshi, and S. Kanemasa, Heterocycles, 4, 957 (1976).

    Google Scholar 

  131. T. Kobayashi, S. Kajigaeshi, and S. Kanemasa, Heterocycles, 4, 1281 (1976).

    Google Scholar 

  132. Yu. K. Yur'ev, Zh. Obshch. Khim., 6, 972 (1936).

    Google Scholar 

  133. Yu. K. Yur'ev, Uch. Zap. Mask. Gos. Univ., No. 79, 1 (1945).

    Google Scholar 

  134. Yu. K. Yur'ev, Uch. Zap. Mask. Gos. Univ., No. 175, 159 (1956).

    Google Scholar 

  135. F. Sorm and Z. Arnold, Collect. Czech. Chem. Commun., 12, 467 (1947).

    Google Scholar 

  136. A. A. Ponomarev, N. P. Maslennikova, N. V. Alakina, and A. P. Krivenko, Dokl. Akad. Nauk SSSR, 131, 1355 (1960).

    Google Scholar 

  137. A. A. Ponomarev and I. M. Skvortsov, Zh. Obshch. Khim., 32, 97 (1962).

    Google Scholar 

  138. J. M. Patterson and S. Soedigdo, J. Org. Chem., 32, 2969 (1967).

    Google Scholar 

  139. I. M. Skvortsov and I. V. Antipova, Tr. Molod. Uchen., Vyp. Khim. 2 (Izd. Saratov Univ., 1971), p. 158.

  140. A. A. Ponomarev, V. N. Dyukareva, and I. M. Skvortsov, Dokl. Akad. Nauk SSSR, 178, 893 (1968).

    Google Scholar 

  141. A. A. Ponomarev and V. M. Levin, Khim. Geterotsikl. Soedin., No. 5, 939 (1969).

    Google Scholar 

  142. A. A. Ponomarev, I. M. Skvortsov, and A. A. Khorkin, Zh. Obshch. Khim., 33, 2687 (1963).

    Google Scholar 

  143. A. A. Ponomarev, I. M. Skvortsov, and L. N. Astakhova, Dokl. Akad. Nauk SSSR, 155, 861 (1964).

    Google Scholar 

  144. L. N. Astakhova, I. M. Skvortsov, and A. A. Ponomarev, Zh. Obshch. Khim., 34, 2410 (1964).

    Google Scholar 

  145. A. A. Ponomarev and I. M. Skvortsov, Metody Poluch. Khim. Reakt. Prep., No. 17, 65 (1967).

    Google Scholar 

  146. I. M. Skvortsov, I. V. Antipova, Yu. A. Pentin, Tran Suan Khoan', and S. V. Vasil'kovskii, Khim. Geterotsikl. Soedin., No. 8, 1087 (1975).

    Google Scholar 

  147. I. M. Skvortsov and I. V. Antipova, Khim. Geterotsikl Soedin., No. 6, 764 (1978).

    Google Scholar 

  148. I. M. Skvortsov, N. A. Buntyakova, M. I. Kuramshin, and S. A. Filimonov, Khim. Geterotsikl. Soedin., No. 10, 1424 (1983).

    Google Scholar 

  149. A. A. Ponomarev and I. S. Monakhova, Khim. Geterotsikl. Soedin., No. 2, 42 (1970).

    Google Scholar 

  150. P. S. Mariano, M. E. Osborn, D. Dunaway-Mariano, B. C. Gunn, and R. C. Pettersen, J. Org. Chem., 42, 2903 (1977).

    Google Scholar 

  151. L. V. Yerino, M. E. Osborn, and P. S. Mariano, Tetrahedron, 38, 1579 (1982).

    Google Scholar 

  152. R. F. Borch and B. C. Ho, J. Org. Chem., 42, 1225 (1977).

    Google Scholar 

  153. A. Gossauer, The Chemistry of Pyrrole [in German], Springer Verlag, Berlin (1974).

    Google Scholar 

  154. R. A. Jones and G. P. Bean, The Chemistry of Pyrroles, Academic Press, London (1977).

    Google Scholar 

  155. A. A. Ponomarev and L. N. Astakhova, Khim. Geterotsikl. Soedin., No. 2, 221 (1966).

    Google Scholar 

  156. A. A. Ponomarev and L. N. Astakhova, Metody Poluch. Khim. Reakt. Prep., No. 17, 94 (1967).

    Google Scholar 

  157. V. Carelli, M. Cardelini, and F. Morlacchi, Tetrahedron Lett., No. 9, 765 (1967).

    Google Scholar 

  158. S. A. Klesnikov, I. M. Skvortsov, and Yu. Yu. Samitov, Zh. Org. Khm., 7, 1533 (1971).

    Google Scholar 

  159. A. A. Ponomarev, L. N. Astakhova, and V. I. Simontsev, Khim. Geterotsikl. Soedin., No. 1, 81 (1965).

    Google Scholar 

  160. A. A. Ponomarev, L. N. Astakhova, and V. I. Simontsev, Metody Poluch. Khim. Reakt. Prep., No. 17, 70 (1967).

    Google Scholar 

  161. L. N. Astakhova and I. M. Skvortsov, in: Research in the Field of Synthesis and Catalysis of Organic Compounds, V. G. Kharchenko and Yu. N. Usov (eds.), Izd. Saratov. Univ., Saratov (1983), p. 63.

    Google Scholar 

  162. I. M. Skvortsov, L. N. Astakhova, S. N. Kuz'min, and I. Ya. Evtushenko, Khim. Geterotsikl. Soedin., No. 3, 359 (1978).

    Google Scholar 

  163. A. A. Ponomarev, L. N. Astakhova, and V. N. Volkolupov, Metody Poluch. Khim. Reakt. Prep., No. 26, 143 (1974).

    Google Scholar 

  164. A. A. Ponomarev, L. N. Astakhova, and V. N. Volkolupov, Metody Poluch. Khim. Reakt. Prep., No. 26, 190 (1974).

    Google Scholar 

  165. A. A. Ponomarev, V. M. Levin, and N. Ya. Usachev, USSR Inventor's Certificate 344,480; Byull. Izobret., No. 21, 211 (1972).

    Google Scholar 

  166. G. Dannhardt, M. Lehr, and L. Steindl, Chem. Zig., 110, 267 (1986).

    Google Scholar 

  167. G. Dannhardt and L. Steindl, Heterocycles, 23, 1219 (1985).

    Google Scholar 

  168. A. A. Ponomarev, I. M. Skvortsov, and V. M. Levin, Khim. Geterotsikl. Soedin., No. 10, 1339 (1970).

    Google Scholar 

  169. A. A. Ponomarev, I. M. Skvortsov, and V. M. Levin, USSR Inventor's Certificate 221,710; Byull. Izobret., No. 22, 34 (1968).

    Google Scholar 

  170. L. N. Astakhova, I. M. Skvortsov, L. V. Safonova, and V. I. Makukhina, Khim. Geterotsikl. Soedin., No. 3, 320 (1986).

    Google Scholar 

  171. L. Grehn, Chem. Scr., 13, No. 2/3, 67 (1978/1979).

    Google Scholar 

  172. I. M. Skvortsov, S. A. Kolesnikov, Yu. Yu. Samitov, and G. D. Shcherbakova, Khim. Geterotsikl. Soedin., No. 8, 1090 (1977).

    Google Scholar 

  173. I. M. Skvortsov and S. A. Kolesnikov, in: New Developments in Carbene Chemistry: Material from the First All-Union Conference on the Chemistry of Carbenes and Their Analogs, Moscow (1973), p. 205.

  174. G. Dannhardt and M. Lehr, Arch. Pharm., 321, 159 (1988).

    Google Scholar 

  175. G. Dannhardt and M. Lehr, Arch. Pharm., 321, 545 (1988).

    Google Scholar 

  176. F. Bohlmann, W. Klose, and K. Nickisch, Tetrahedron Lett., No. 39, 3699 (1979).

    Google Scholar 

  177. A. A. Ponomarev, V. N. Dyukareva, and I. M. Skvortsov, USSR Inventor's Certificate 201,413; Byull. Izobret., No. 18, 37 (1967).

    Google Scholar 

  178. I. M. Skvortsov and I. V. Antipova, in: Heterogeneous Catalysis in Reactions of Preparation and Conversion of Heterocyclic Compounds, S. A. Giller et al. (eds.) [in Russian], Zinatne, Riga (1971), p. 123.

    Google Scholar 

  179. I. V. Antipova, “Synthesis, stereochemistry, and properties of certain homologs of pyrrolizidine”, Candidate's Dissertation, Saratov (1979).

  180. I. M. Skvortsov and I. V. Antipova, Khim. Geterotsikl Soedin., No. 1, 58 (1979).

    Google Scholar 

  181. I. M. Skvortsov and I. V. Antipova, Zh. Org. Khim., 15, 868 (1979).

    Google Scholar 

  182. I. M. Skvortsov and I. V. Antipova, Vopr. Stereokhim., A. V. Bogatskii (ed), Vishcha Shkola, Kiev, No. 4, 41 (1974).

    Google Scholar 

  183. M. P. Kozina, L. P. Timofeeva, G. L. Gal'chenko, I. M. Skvortsov, and I. V. Antipova, Zh. Obshch. Khim., 51, 451 (1981).

    Google Scholar 

  184. R. Adams, S. Miyano, and D. Fles, J. Am. Chem. Soc., 82, 1466 (1960).

    Google Scholar 

  185. I. M. Skvortsov and S. A. Kolesnikov, Khim. Geterotsikl. Soedin., No. 4, 484 (1976).

    Google Scholar 

  186. I. M. Skvortsov, M. I. Kuramshin, S. N. Kurskov, A. S. Saratikov, and N. S. Livshits, Khim.-farm. Zh., No. 8, 925 (1989).

    Google Scholar 

  187. I. M. Skvortsov and V. M. Levin, Khim. Geterotsikl. Soedin., No. 7, 947 (1973).

    Google Scholar 

  188. I. M. Skvortsov, L. N. Astakhova, I. Ya. Evtushenko, E. V. Cheslavskaya, S. N. Kuz'min, and S. P. Voronin, Khim. Geterotsikl. Soedin., No. 1, 63 (1980).

    Google Scholar 

  189. J. Meinwald and H. C. J. Ottenheim, Tetrahedron, 27, 3307 (1971).

    Google Scholar 

  190. H. S. Aaron, C. F. Rader, and C. E. Wicks, J. Org. Chem., 31, 3502 (1966).

    Google Scholar 

  191. M. Viscontini and H. Buzek, Helv. Chim. Acta, 55, 670 (1972).

    Google Scholar 

  192. V. Carelli, M. Cardellini, and F. Morlacchi, Ann. Chim. (Roma), 57, 1462 (1967).

    Google Scholar 

  193. F. Morlacchi and M. Cardellini, Ann. Chim. (Roma), 57, 260 (1967).

    Google Scholar 

  194. A. Morimoto and T. Watanabe, Japanese Patent 74-27879; Chem. Abstr., 82, 125,416 (1975).

    Google Scholar 

  195. M. Cardellini, V. Carelli, F. Liberatore, and F. Morlacchi, Chim. Ind. (Milan), 50, 455 (1968).

    Google Scholar 

  196. M. E. Cardinali, I. Carelli, G. Ceccaroni, and A. Trazza, J. Electroanal. Chem. Interfacial Electrochem., 42, 49 (1973).

    Google Scholar 

  197. S. H. S. Makoni and J. K. Sugden, Arzneim.-Forsch., 30, 1135 (1980); Chem. Abstr., 93, 220,529 (1980).

    Google Scholar 

  198. A. A. Ponomarev and L. N. Astakhova, Melody Poluch. Khim. Reakt. Prep., No. 26, 159 (1974).

    Google Scholar 

  199. J. B. Doherty, US Patent 4,496,741; Chem. Abstr., 102, 166,728 (1985).

    Google Scholar 

  200. E. Mroszczak and R. Runkel, US Patent 4,397,862; Chem. Abstr., 99, 146,134 (1983).

    Google Scholar 

  201. L. Gu, H. S. Chiang, and D. Johnson, Int. J. Pharm., 41, 105 (1988).

    Google Scholar 

  202. A. A. Ponomarev and V. M. Levin, Khim. Geterotsikl. Soedin., No. 5, 941 (1969).

    Google Scholar 

  203. Z. Yoshida, Jpn. Kokai 78-25559; Chem. Abstr., 89, 109,069 (1978).

    Google Scholar 

  204. A. R. Mattocks and I. Bird, Toxicol. Lett., 16, No. 1/2, 1 (1983).

    Google Scholar 

  205. K. A. Robertson, Cancer Res., 42, 8 (1982).

    Google Scholar 

  206. P. P. Wickramayake, B. L. Arbogest, D. R. Buhler, M. L. Deinzer, and A. L. Burlingame, J. Am. Chem. Soc., 107, 2485 (1985).

    Google Scholar 

  207. J. J. Karchesy and M. L. Deinzer, Heterocycles, 16, 631 (1981).

    Google Scholar 

  208. K. A. Robertson, J. L. Seymour, M. T. Hsia, and J. R. Allen, Cancer Res., 37, 3141 (1977); Chem. Abstr., 88, 1274 (1978).

    Google Scholar 

  209. I. N. H. White and A. R. Mattocks, Biochem. J., 128, 291 (1972).

    Google Scholar 

  210. I. C. Hsu, K. A. Robertson, R. C. Shumaker, and J. R. Allen, Res. Commun. Chem. Pathol. Pharmacol, 11, 99 (1975); Chem. Abstr., 83, 109,531 (1975).

    Google Scholar 

  211. C. C. J. Culvenor and L. W. Smith, Tetrahedron Lett., No. 11, 3603 (1969).

    Google Scholar 

  212. C. C. Curtin, Chem.-Biol. Interact., 10, 133 (1975).

    Google Scholar 

  213. D. N. Black and M. V. Jago, Biochem. J., 118, 347 (1970).

    Google Scholar 

  214. P. S. Sun, M. T. S. Hsia, F. S. Chu, and J. R. Allen, Food Cosmet. Toxicol., 15, 419 (1977); Chem. Abstr., 88, 115,915 (1978).

    Google Scholar 

  215. M. F. Weidner, J. T. Millard, and P. B. Hopkins, J. Am. Chem. Soc., 111, 9270 (1989).

    Google Scholar 

  216. F. Bohlmann, C. Zdero, and M. Grenz, Chem. Ber., 110, 474 (1977).

    Google Scholar 

  217. A. Morimoto and T. Watanabe, Japanese Patent 74-27877; Chem. Abstr., 82, 156, 398 (1975).

    Google Scholar 

  218. A. Morimoto and T. Watanabe, Japanese Patent 74-27878; Chem. Abstr., 82, 140,180 (1975).

    Google Scholar 

  219. G. Dannhardt and L. Steindl, Arch. Pharm. (Weinheim), 318, 663 (1985).

    Google Scholar 

  220. G. S. Gadaginamath, Indian J. Chem. B, 26, 955 (1987).

    Google Scholar 

  221. G. Dannhardt and L. Steindl, Arch. Pharm. (Weinheim), 318, 661 (1985).

    Google Scholar 

  222. A. V. Kadushkin, T. V. Golovko, and V. G. Granik, Khim. Geterotsikl. Soedin., No. 6, 830 (1989).

    Google Scholar 

  223. W. Flitsch, J. Lauterwein, and W. Micke, Tetrahedron Lett., 30, 1633 (1989).

    Google Scholar 

  224. W. H. Rooks, A. J. Tomolonis, P. J. Maloney, M. B. Wallach, and M. E. Schuler, Agents Actions, 12, 684 (1982); Chem. Abstr., 98, 65,202 (1983).

    Google Scholar 

  225. M. N. Chang and T. Biftu, European Patent 96,816; Chem. Abstr., 100, 156,492 (1984).

    Google Scholar 

  226. J. M. Muchowski and A. F. Kluge, German Patent 2,731,662; Chem. Abstr., 88, 136,450 (1978).

    Google Scholar 

  227. S. H. Unger, P. S. Cheung, P. Feigner, and J. M. Muchowski, “QS AR strategies of bioactive compounds,” in: Proceedings of European Symposium on Quantitative Structure — Activity Relationships (1984), J. K. Weydel (ed.), Weinheim (1985), p. 378; Chem. Abstr., 104, 61,666 (1986).

  228. W. H. Rooks, P. J. Maloney, L. D. Shott, M. E. Schuler, H. Sevelius, A. M. Strosberg, L. Ianenbaum, A. J. Tomolonis, M. B. Wallach, et al., Drugs Exp. Clin. Res., 11, 479 (1985); Chem. Abstr., 104, 28,560 (1986).

    Google Scholar 

  229. W. K. Hagmann, European Patent 159,674; Chem. Abstr., 104, 148,732 (1986).

    Google Scholar 

  230. T. Biftu, B. E. Witzel, and P. L. Barker, US Patent 4,536,512; Chem. Abstr., 104, 68,750 (1986).

    Google Scholar 

  231. M. Tsuju, H. Inoue, Y. Tanoue, K. Beppu, I. Shinohara, M. Saita, Y. Tamiguchi, K. Furata, Y. Deguchi, et al., European Patent 330,283; Chem. Abstr., 112, 76,937 (1990).

    Google Scholar 

  232. J. M. Mahoney and L. D. Waterbury, Curr. Eye Res., 4, 531 (1985); Chem. Abstr., 103, 115,887 (1985).

    Google Scholar 

  233. Z. T. Chowhan and L.-H. Chi, Pharm. Technol, 9, 84 (1985).

    Google Scholar 

  234. E. Mroszczak and R. Runkel, PCT Int. Appl. WO 83-01382 (1983); Chem. Abstr., 99, 93,729 (1983).

    Google Scholar 

  235. Beecham Group PLC, Jpn. Kokai Tokyo Koho 58157789; Chem. Abstr., 100, 138,945 (1984).

    Google Scholar 

  236. T. C. Thurber and D. Tegg, European Patent 53,021; Chem. Abstr., 97, 144,766 (1982).

    Google Scholar 

  237. J. M. Muchowski, European Patent 41,711; Chem. Abstr., 96, 181,139 (1982).

    Google Scholar 

  238. D. L. Waterbury, German Patent 3,310,079; Chem. Abstr., 99, 200,515 (1983).

    Google Scholar 

  239. W. K. Anderson, C. P. Chag, P. F. Corey, M. J. Halat, A. N. Jones, H. L. McPherson, J. S. New, and A. C. Rick, Cancer Treat. Rep., 66, 91 (1982).

    Google Scholar 

  240. W. K. Anderson, Cancer Res., 42, 2168 (1982).

    Google Scholar 

  241. W. K. Anderson, J. S. New, and P. F. Corey, Arzneim.-Forsch., 30, 765 (1980); Chem. Abstr., 93, 36,836 (1980).

    Google Scholar 

  242. W. K. Anderson, in: Proceedings of International Congress on Chemotherapy, 13th, K. H. Spitzy et al. (eds.), Vienna (1983), 12, 220/39-220/46; Chem. Abstr., 104, 102,042 (1986).

  243. W. K. Anderson, US Patent 4,734,423; Chem. Abstr., 109, 204,916 (1988).

    Google Scholar 

  244. W. K. Anderson, D. C. Dean, and T. Endo, J. Med. Chem., 33, 1667 (1990).

    Google Scholar 

  245. H. J. Ringold and S. D. Waterbury, US Patent 4,457,941; Chem. Abstr., 101, 116,758 (1984).

    Google Scholar 

  246. J. L. Fabre, D. Farge, C. James, and D. Lave, European Patent 147,317; Chem. Abstr., 103, 160,500 (1985).

    Google Scholar 

  247. T. Biftu, B. E. Witzel, and P. L. Barker, US Patent 4,533,671; Chem. Abstr., 103, 215,161 (1985).

    Google Scholar 

  248. N. Yoshida, K. Tanaka, and Y. Iizuka, Japanese Patent 74-28520; Chem. Abstr., 82, 139,939 (1975).

    Google Scholar 

  249. J. M. Muchowski and R. J. Greenhouse, European Patent 96,583; Chem. Abstr., 100, 156,491 (1984).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh. Soedinenii, No. 2, pp. 147–168, February, 1992.

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Skvortsov, I.M., Astakhova, L.N. Synthesis and chemical properties of 1,2-dihydropyrrolizines (review). Chem Heterocycl Compd 28, 117–134 (1992). https://doi.org/10.1007/BF00473929

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