Skip to main content
Log in

Electrophilic heterocyclization of unsaturated amino compounds in the synthesis of nitrogen-containing heterocycles (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature data on the electrophilic heterocyclization reactions of unsaturated amines, enamines, amidines, amides, and urethanes are correlated. The factors that affect the reactivities of unsaturated amino compounds in electrophilic intramolecular-cyclization reactions are discussed. The problems involved in the regioselectivity of the addition of electrophiles and the stereochemistry of the resulting products are examined, and kinetic data are presented.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 11, 1443 (1982).

    Google Scholar 

  2. V. I. Staninets and E. A. Shilov, Usp. Khim., 40, 291 (1971).

    Google Scholar 

  3. A. Latt, Khim. Geterotsikl. Soedin., No. 1, 7 (1975).

    Google Scholar 

  4. Yu. I. Gevaza and V. I. Staninets, Khim. Geterotsikl. Soedin., No. 7, 867 (1984).

    Google Scholar 

  5. Zh. M. Syurzyur, Khim. Geterotsikl. Soedin., No. 5, 579 (1975).

    Google Scholar 

  6. L. Lagenburg, Ber., 16, 2058 (1883).

    Google Scholar 

  7. G. Merling, Ber., 19, 2688 (1886).

    Google Scholar 

  8. G. Merling, Ann., 264, 310 (1891).

    Google Scholar 

  9. R. Wilstätter, Ber., 33, 365 (1900).

    Google Scholar 

  10. D. Lukes and O. Cervinka, Chem. Listy, 47, 392 (1953).

    Google Scholar 

  11. V. I. Staninets, Doctoral Dissertation, Kiev (1971).

  12. Yu. I. Gevaza, T. A. Degurko, and V. I. Staninets, Ukr. Khim. Zh., 46, 760 (1980).

    Google Scholar 

  13. T. A. Degurko and V. I. Staninets, Dokl. Akad. Nauk Ukr. SSR, No. 3, 245 (1973).

    Google Scholar 

  14. J. Moriyama, D. Doan-Huynh, C. Monneret, and Q. Khuong-Huu, Tetrahedron Lett., No. 10, 825 (1977).

    Google Scholar 

  15. B. Pugin and L. M. Venanzi, J. Organomet. Chem., 214, 125 (1981).

    Google Scholar 

  16. J. Ambuehl, P. S. Pregosin, L. M. Venanzi, G. Ughetto, and L. Zambonelli, J. Organomet. Chem., 160, 329 (1978).

    Google Scholar 

  17. J. Ambuehl and L. M. Venanzi, J. Organomet. Chem., 181, 255 (1979).

    Google Scholar 

  18. O. Wallach, Ber., 38, 2805 (1905).

    Google Scholar 

  19. Wagner-Jauregg and M. Roth, Helv. Chim. Acta, 45, 771 (1962).

    Google Scholar 

  20. H. Cottin, Bull. Soc. Chim. France, No. 9, 2729 (1966).

    Google Scholar 

  21. D. St. C. Black and J. E. Doyle, Austral. J. Chem., 31, 2247 (1978).

    Google Scholar 

  22. D. E. Horning and S. M. Muchowski, Can. J. Chem., 52, 1321 (1974).

    Google Scholar 

  23. C. F. Hammer and J. D. Weber, Tetrahedron, 37, 2173 (1981).

    Google Scholar 

  24. C. F. Hammer, S. R. Heller, and S. H. Craig, Tetrahedron, 28, 239 (1972).

    Google Scholar 

  25. C. F. Hammer, Ali M. McCarthy, and J. D. Weber, Tetrahedron, 29, 1767 (1973).

    Google Scholar 

  26. Yu. I. Gevaza, V. I. Staninets, and E. A. Shilov, Ukr. Khim. Zh., 37, 1185 (1971).

    Google Scholar 

  27. V. I. Staninets and Yu. I. Gevaza, Ukr. Khim. Zh., 39, 358 (1973).

    Google Scholar 

  28. Yu. I. Gevaza, V. I. Staninets, and É. B. Koryak, Khim. Geterotsikl. Soedin., No. 10, 1340 (1976).

    Google Scholar 

  29. Yu. I. Gevaza, Yu. I. Farinyuk, V. I. Staninets, and É. B. Koryak, Ukr. Khim. Zh., 44, 1194 (1978).

    Google Scholar 

  30. M. Miocque, M. Duchon d'Engenieres, and J. Sauzieres, Bull. Soc. Chim. France, Nos. 7–8, 1777 (1975).

    Google Scholar 

  31. V. I. Staninets and Yu. I. Gevaza, Ukr. Khim. Zh., 39, 1291 (1973).

    Google Scholar 

  32. A. Claesson, C. Sahlberg, and K. Luthman, Acta Chem. Scand., Ser. B., 33, 309 (1979).

    Google Scholar 

  33. V. I. Staninets and E. A. Shilov, Ukr. Khim. Zh., 34, 1132 (1968).

    Google Scholar 

  34. G. R. Underwood, J. Org. Chem., 33, 1313 (1968).

    Google Scholar 

  35. H. Iida, U. Uyasa, and C. Kibayashi, Tetrahedron Lett., No. 35, 3591 (1982).

    Google Scholar 

  36. L. S. Hegedus, G. F. Allen, and D. J. Olsen, J. Am. Chem. Soc., 102, 3583 (1980).

    Google Scholar 

  37. L. S. Hegedus, G. F. Allen, J. J. Bozel, and E. L. Waterman, J. Am. Chem. Soc., 100, 5800 (1978).

    Google Scholar 

  38. D. L. J. Clive, C. K. Wong, W. A. Kiel, and S. M. Menchen, Chem. Commun., No. 9, 379 (1978).

    Google Scholar 

  39. Yu. I. Gevasa, Yu. I. Farinyuk, V. I. Staninets, and É. B. Koryak, Ukr. Khim. Zh., 43, 1189 (1977).

    Google Scholar 

  40. Yu. I. Farinyuk, Yu. I. Gevasa, V. I. Staninets, and I. V. Smolanka, Ukr. Khim. Zh., 43, 1223 (1977).

    Google Scholar 

  41. Yu. I. Gevaza, Yu. I. Farinyuk, É. G. Koryak, and V. I. Staninets, Zh. Org. Khim., 13, 1479 (1977).

    Google Scholar 

  42. Yu. Yu. Tsmur and V. I. Ivanik, USSR Inventor's Certificate No. 513031; Byull. Izobret., No. 17, 82 (1976).

  43. Yu. I. Gevaza, T. A. Degurko, and V. I. Staninets, in: New Advances in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 1, Riga (1979), p. 144.

    Google Scholar 

  44. J. S. Oakland and F. Scheinmann, J. Chem. Soc., Perkin I, No. 8, 800 (1973).

    Google Scholar 

  45. É. B. Koryak, Yu. I. Gevaza, and V. I. Staninets, Ukr. Khim. Zh., 46, 178 (1980).

    Google Scholar 

  46. S. R. Wilson and R. A. Sawicki, Chem. Commun., No. 13, 431 (1977).

    Google Scholar 

  47. S. R. Wilson and R. A. Sawicki, J. Org. Chem., 44, 287 (1979).

    Google Scholar 

  48. R. A. Johnson, J. Org. Chem., 37, 312 (1972).

    Google Scholar 

  49. S. R. Wilson and R. A. Sawicki, J. Org. Chem., 44, 330 (1979).

    Google Scholar 

  50. S. R. Wilson and R. A. Sawicki, J. Heterocycl. Chem., 19, 81 (1982).

    Google Scholar 

  51. O. Tatsushi, J. Masataka, F. Keiichire, and K. Tetsuji, Heterocycles, 19, 1605 (1982).

    Google Scholar 

  52. H. F. Campbell, O. E. Edwards, S. W. Elder, and R. J. Kolt, Pol. J. Chem., 53, 27 (1979).

    Google Scholar 

  53. M. Barelle and M. Apparu, Tetrahedron Lett., No. 30, 2611 (1976).

    Google Scholar 

  54. M. Barelle and M. Apparu, Tetrahedron, 33, 1309 (1977).

    Google Scholar 

  55. R. O. Klaus and C. Ganter, Chimia, 31, 61 (1977).

    Google Scholar 

  56. R. O. Klaus and C. Ganter, Helv. Chim. Acta, 63, 2559 (1980).

    Google Scholar 

  57. M. C. Benhamou, V. Speziale, A. Lattes, C. Gonarderes, and J. Cros, Eur. J. Med. Chem.- Chim. Ther., 16, 263 (1981).

    Google Scholar 

  58. I. Monkovic, T. T. Conway, H. Wong, U. G. Perron, I. J. Pachter, and B. Belleau, J. Am. Chem. Soc., 95, 7910 (1973).

    Google Scholar 

  59. I. Monkovic, H. Wong, A. J. Pircio, U. J. Perron, J. J. Pachter, and B. Belleau, Can. J. Chem., 53, 3094 (1975).

    Google Scholar 

  60. G. G. Skvortsova, D. G. Kim, and M. V. Sigalov, Khim. Geterotsikl. Soedin., No. 8, 1147 (1975).

    Google Scholar 

  61. G. G. Skvortsova, D. G. Kim, and M. V. Sigalov, Khim. Geterotsikl. Soedin., No. 6, 858 (1976).

    Google Scholar 

  62. Yu. I. Farinyuk, Yu. I. Gevaza, V. I. Staninets, and I. V. Smolanka, Ukr. Khim. Zh., 42, 1051 (1976).

    Google Scholar 

  63. J. Barluenga, C. Jimenez, C. Najera, and M. Yus, Synthesis, No. 5, 414 (1982).

    Google Scholar 

  64. Yu. V. Melika, V. I. Staninets, and I. V. Smolanka, Ukr. Khim. Zh., 39, 280 (1973).

    Google Scholar 

  65. Yu. V. Melika, I. V. Smolanka, and V. I. Staninets, Ukr. Khim. Zh., 39, 799 (1973).

    Google Scholar 

  66. V. I. Staninets, Yu. I. Gevaza, and V. P. Tikhonov, Dokl. Akad. Nauk Ukr. SSR, No. 1, 52 (1971).

    Google Scholar 

  67. I. I. Ershova, Yu. I. Gevaza, and V. I. Staninets, Ukr. Khim. Zh., 43, 884 (1977).

    Google Scholar 

  68. J. D. Brindle and M. S. Gibson, Chem. Commun., No. 14, 803 (1969).

    Google Scholar 

  69. J. D. Brindle and M. S. Gibson, Can. J. Chem., 57, 3155 (1979).

    Google Scholar 

  70. S. R. Wilson and R. A. Sawicki, Tetrahedron Lett., No. 33, 2969 (1978).

    Google Scholar 

  71. S. R. Wilson, R. A. Sawicki, and J. C. Huffman, J. Org. Chem., 46, 3887 (1981).

    Google Scholar 

  72. H. Szczepanski and C. Ganter, Helv. Chim. Acta, 60, 1435 (1977).

    Google Scholar 

  73. H. Szczepanski and C. Ganter, Helv. Chim. Acta, 59, 2931 (1976).

    Google Scholar 

  74. H. Szczepanski and C. Ganter, Helv. Chim. Acta, 59, 2931 [sic] (1976).

    Google Scholar 

  75. V. I. Staninets and E. A. Shilov, Ukr. Khim. Zh., 34, 372 (1968).

    Google Scholar 

  76. T. A. Degurko and V. I. Staninets, Dokl. Akad. Nauk Ukr. SSR, No. 3, 255 (1974).

    Google Scholar 

  77. S. P. McManus and D. W. Ware, Tetrahedron Lett., No. 48, 4271 (1974).

    Google Scholar 

  78. K. E. Harding and S. R. Burks, J. Org. Chem., 46, 3920 (1981).

    Google Scholar 

  79. W. H. Staas and L. A. Spurlock, J. Org. Chem., 39, 3822 (1974).

    Google Scholar 

  80. I. I. Ershova, V. I. Staninets, and T. A. Degurko, Dokl. Akad. Nauk Ukr. SSR, No. 12, 1099 (1975).

    Google Scholar 

  81. D. E. Worell, J. Am. Chem. Soc., 54, 2061 (1932).

    Google Scholar 

  82. G. Just and P. Rossy, J. Org. Chem., 38, 624 (1973).

    Google Scholar 

  83. I. V. Smolanka, T. A. Krasnitskaya, and E. G. Mel'nik, Ukr. Khim. Zh., 38, 793 (1972).

    Google Scholar 

  84. I. V. Smolanka, T. A. Krasnitskaya, and M. M. Tsitsika, Ukr. Khim. Zh., 38, 587 (1972).

    Google Scholar 

  85. T. A. Krasnitskaya and I. V. Smolanka, Khim. Geterotsikl. Soedin., No. 3, 424 (1973).

    Google Scholar 

  86. D. L. J. Clive, V. Farina, A. Singh, K. Wong, W. A. Kiel, and S. M. Menchen, J. Org. Chem., 45, 2120 (1980).

    Google Scholar 

  87. R. R. Webb and S. Danishefsky, Tetrahedron Lett., No. 13, 1357 (1983).

    Google Scholar 

  88. S. Danishefsky and E. Taniyama, Tetrahedron Lett., No. 1, 15 (1983).

    Google Scholar 

  89. S. Danishefsky, E. Taniyama, and R. R. Webb, Tetrahedron Lett., No. 1, 11 (1983).

    Google Scholar 

  90. T. Aida, R. Legault, D. Dugat, and T. Durst, Tetrahedron Lett., No. 52, 4993 (1979).

    Google Scholar 

  91. A. J. Biloski, R. D. Wood, and B. Ganem, J. Am. Chem. Soc., 104, 3233 (1982).

    Google Scholar 

  92. L. S. Hegedus and J. M. McKearin, J. Am. Chem. Soc., 104, 2444 (1982).

    Google Scholar 

  93. D. E. Korte, L. S. Hegedus, and R. K. Wirth, J. Org. Chem., 42, 1329 (1977).

    Google Scholar 

  94. A. Kasahara, T. Izumi, and O. Saito, Chem. Ind., No. 16, 166 (1980).

    Google Scholar 

  95. C. O'Murchu, Chimia, 29, 508 (1975).

    Google Scholar 

  96. I. K. Yurgevits, É. L. Kupche, and U. Ya. Mikstais, Khim. Geterotsikl. Soedin., No. 7, 972 (1979).

    Google Scholar 

  97. I. K. Yurgevits and É. L. Kupche, Khim. Geterotsikl. Soedin., No. 11, 1474 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–449, April, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gevaza, Y.I., Staninets, V.I. Electrophilic heterocyclization of unsaturated amino compounds in the synthesis of nitrogen-containing heterocycles (review). Chem Heterocycl Compd 21, 359–371 (1985). https://doi.org/10.1007/BF00504390

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00504390

Keywords

Navigation