Skip to main content
SpringerLink
Log in

Catalytic Reduction of Pyridinium, Pyrylium, and Thiopyrylium Salts. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data and the results of the authors' own investigations on the synthesis of six-membered saturated N-, O-, and S-containing heterocycles by catalytic reduction of pyridinium, pyrylium, and thiopyrylium salts are reviewed. The conditions, laws, and special characteristics of the reactions are considered.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. J. Volke, J. Urban, and V. Volkeova, Electrochim. Acta, 39, 2049 (1994).

    Google Scholar 

  2. G. V. Lukova, E. P. Olekhnovich, M. E. Kletskii, A. A. Bumber, and A. D. Garnovskii, Izv. Akad. Nauk. Ser. Khim., 690 (1999).

  3. U. Eisner and J. Kuthan, Chem. Rev., 72, 1 (1972).

    Google Scholar 

  4. A. T. Balaban, C. Bratu, and C. N. Rentea, Tetrahedron 20, 265 (1964).

    Google Scholar 

  5. N. T. Berberova, G. N. Dorofeenko, and O. Yu. Okhlobystin, Khim. Geterotsikl. Soedin., 318 (1977).

  6. S. M. M. Elschafie and A. A. Abd-Elgaber, Z. Phys. Chem., 268, 1049 (1987).

    Google Scholar 

  7. G. A. Reynolds, J. A. Van Allan, and T. H. Reagan, J. Org. Chem., 32, 3772 (1967).

    Google Scholar 

  8. A. T. Balaban, G. Mihai, and C. D. Nenitzesku, Tetrahedron, 18, 257 (1962).

    Google Scholar 

  9. D. D. Tanner and A. Kharrat, J. Org. Chem., 53, 1646 (1988).

    Google Scholar 

  10. A. Nuvole, G. Paglietti, R. Sanna, and M. R. Acheson, J. Chem. Res. Synop., 356 (1984).

  11. J. G. Keay, Adv. Heterocycl. Chem., 39, 2 (1986).

    Google Scholar 

  12. T.-S. Balaban and A. T. Balaban, Tetrahedron Lett., 28, 1341 (1987).

    Google Scholar 

  13. O. Cervinka and O. Kriz, Coll. Czech. Chem. Commun., 30, 1700 (1965).

    Google Scholar 

  14. L. R. Gizzi and M. M. Joulie, Tetrahedron Lett., 3117 (1969).

  15. L. G. Yudin, A. N. Kost, Yu. A. Berdin, and A. E. Shipov, Zh. Obshch. Khim., 27, 3021 (1957).

    Google Scholar 

  16. Yung-Sing Wong, C. Marazano, D. Gnecco, and C. Das Bhupesh, Tetrahedron Lett., 35, 707 (1994).

    Google Scholar 

  17. M. D. Mashkovskii, Medicines[in Russian], Meditsina, Moscow (1986).

    Google Scholar 

  18. R. S. Vartanyan, Khim.-Farm. Zh., 18, 1294 (1984).

    Google Scholar 

  19. J. W. Daly, H. M. Garraffo, and T. F. Spande, The Alkaloids, Academic Press, New York (1993).

    Google Scholar 

  20. D. L. Comins and R. S. Al-awar, J. Org. Chem., 60, 711 (1995).

    Google Scholar 

  21. Yu. A. Baskakov, Zh. Vses. Khim. Obshch. im. D. I. Mendeleeva, 29, 22 (1984).

    Google Scholar 

  22. V. M. Andreev, A. I. Bibicheva, and N. D. Antonova, Zh. Org. Khim., 11, 166 (1975).

    Google Scholar 

  23. S. Matsubara and S. Iwai, US Patent 4145338; Ref. Zh. Khim., 20T600 (1979).

  24. N. Katsuki, M. Abé, M. Mavatari, and M. Igarami, Jpn. Patent Appl. 58-157815; Ref. Zh. Khim., 11S421P (1984).

  25. E. N. Karaulova, in: Production and Properties of Organic Compounds of Sulfur[in Russian] (Ed. L. I. Belen'kii ), (1998), p. 289.

  26. M. A. Ryashentseva and N. S. Prostakov, Khim. Geterotsikl. Soedin., 1443 (1992).

  27. M. A. Ryashentseva, 67, 175 (1998).

  28. E. L. Eliel, M. Manoharan, K. M. Pietrusiewicz, and K. D. Margrave, Org. Magn. Reson., 21, 94 (1983).

    Google Scholar 

  29. L. M. Yudovich, N. S. Smirnova, G. I. Rybina, O. V. Bryukhanova, and V. G. Kharchenko, Zh. Org. Khim., 23, 2333 (1987).

    Google Scholar 

  30. S. K. Klimenko, T. I. Tyrina, and N. N. Sorokin, Khim. Geterotsikl. Soedin., 614 (1987).

  31. B. G. Kharchenko, L. M. Yudovich, O. A. Bozhenova, and A. D. Shebaldova, Khim. Geterotsikl. Soedin., 1187 (1987).

  32. G. V. Grishina and B. M. Potapov, Khim. Geterotsikl. Soedin., 579 (1987).

  33. T. G. Nikolaeva, P. V. Reshetov, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 867 (1997).

  34. A. P. Krivenko (Ed.), Chemistry of Five-and Six-Membered N-and O-Containing Heterocycles[in Russian], Saratov (1997).

  35. F. Potmischil and H. Kalchhauser, Magn. Reson. Chem., 32, 563 (1994).

    Google Scholar 

  36. T. S. Hamilton and R. Adams, J. Am. Chem. Soc., 50, 2260 (1928).

    Google Scholar 

  37. E. B. Maxted and A. G. Walker, J. Chem. Soc., 1093 (1948).

  38. P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press, Orlando, (1979).

    Google Scholar 

  39. I. Utiyama, M. Savaki, S. Kako, and T. Tsukihasi, Jpn. Patent Appl. 54-66684; Ref. Zh. Khim., 4N199P (1980).

  40. M. I. Ushakov and E. V. Yakovleva, Zh. Obshch. Khim., 7, 753 (1937).

    Google Scholar 

  41. M. I. Ushakov, M. I. Ivanova, and N. F. Kosheleva, Zh. Obshch. Khim., 8, 1870 (1938).

    Google Scholar 

  42. M. I. Ushakov and M. Sh. Promyslov, Zh. Obshch. Khim., 17, 1015 (1947).

    Google Scholar 

  43. W. Dietrich, K. Schulze, and M. Muhlstadt, J. Prakt. Chem., 319, 799 (1977).

    Google Scholar 

  44. I. N. Duling and C. C. Price, J. Am. Chem. Soc., 84, 578 (1962).

    Google Scholar 

  45. N. E. Grigor'eva, I. K. Gintse, and T. A. Lyubitskaya, Zh. Obshch. Khim., 30, 1031 (1960).

    Google Scholar 

  46. N. E. Grigor'eva, A. B. Oganes'yan, and I. A. Mysh, Zh. Obshch. Khim., 27, 1565 (1957).

    Google Scholar 

  47. R. E. Lyle, G. H. Warner, and D. A. Nelson, Bol. Soc. Quim. Peru, 31, 89 (1965); Chem. Abstr., 64, 19548 (1966).

    Google Scholar 

  48. N. Sugimoto and H. Kugita, J. Pharm. Soc. Japan, 73, 66 (1953); Ref. Zh. Khim., 491 (1955).

    Google Scholar 

  49. R. E. Lyle, S. A. Leone, H. J. Troscianiec, and G. H. Warner, J. Org. Chem., 24, 330 (1959).

    Google Scholar 

  50. L. H. Sternbach and S. Kaiser, J. Am. Chem. Soc., 74, 2215 (1952).

    Google Scholar 

  51. C.A. Grob and E. Renk, Helv. Chim. Acta, 37, 1672 (1954).

    Google Scholar 

  52. C.A. Grob and E. Renk, Helv. Chim. Acta, 37, 1689 (1954).

    Google Scholar 

  53. R. E. Lyle, E. F. Perlowski, H. J. Troscianiec, and G. G. Lyle, J. Org. Chem., 20, 1761 (1955).

    Google Scholar 

  54. K. Hohenlohe-Oehringen, Monatsh. Chem., 93, 586 (1962).

    Google Scholar 

  55. M. Kawazu, T. Kanno, and S. Saito, J. Med. Chem., 15, 914 (1972).

    Google Scholar 

  56. J. Sam, US Patent 3862937; Ref. Zh. Khim., 22O48P (1975).

  57. N. Sugimoto and S. Oshiro, Jpn. Patent 2377; Chem. Abs., 51, 14827 (1957).

    Google Scholar 

  58. E. Wenkert and B. Wickberg, J. Am. Chem. Soc., 87, 1580 (1965).

    Google Scholar 

  59. E. Wenkert, K, G. Dave, and F. Haglid, J. Am. Chem. Soc., 87, 5461 (1965).

    Google Scholar 

  60. E. Wenkert, K. G. Dave, F. Haglid, R. G. Lewis, T. Oishi, R. V. Stevens, and M. Terashima, J. Org. Chem., 33, 747 (1968).

    Google Scholar 

  61. E. Wenkert, Acc. Chem. Res., 1, 78 (1968).

    Google Scholar 

  62. J. Thesing, H. Ramloch, C. Willersinn, and F. Funk, Angew. Chem., 68, 387 (1956).

    Google Scholar 

  63. C. Schopf, G. Herbert, R. Rausch, and G. Schroder, Angew. Chem., 69, 391 (1957).

    Google Scholar 

  64. N. A. Hughes and H. Rapoport, J. Am. Chem. Soc., 80, 1604 (1958).

    Google Scholar 

  65. J. Thesing and W. Festag, Experientia, 15, 127 (1959).

    Google Scholar 

  66. E. Schlittler and H. Schwarz, Helv. Chim. Acta, 33, 1463 (1950).

    Google Scholar 

  67. H. Schwarz and E. Schlittler, Helv. Chim. Acta, 34, 629 (1951).

    Google Scholar 

  68. E. Schlittler, H. Schwarz, and F. Bader, Helv. Chim. Acta, 35, 271 (1952).

    Google Scholar 

  69. A. Le Hir, R. Goutarel, M.-M. Janot, Compt. Rend., 235, 63 (1953).

    Google Scholar 

  70. T. M. Sharp, J. Chem. Soc., 1353 (1938).

  71. L. Chevolot and H.-P. Husson, J. Heterocycl. Chem., 15, 1509 (1978).

    Google Scholar 

  72. D. R. Howton and D. R. V. Golding, J. Org. Chem., 15, 1 (1950).

    Google Scholar 

  73. L. Chevolot, H.-P. Husson, and P. Potier, Tetrahedron, 31, 2491 (1975).

    Google Scholar 

  74. H.-P. Husson, K. Bannai, R. Freire, and B. Mompon, Tetrahedron, 34, 1363 (1978).

    Google Scholar 

  75. G. Scheuing and L. Winterhalder, Lieb. Ann. Chem., 473, 126 (1929).

    Google Scholar 

  76. R. T. Shuman, P. L. Ornstein, J. W. Paschal, and P. D. Gesellchen, J. Org. Chem., 55, 738 (1990).

    Google Scholar 

  77. M. Honel and F. W. Vierhapper, J. Chem. Soc. Perkin Trans. 1, 2607 (1982).

  78. F. N. Hayes, L. C. King, and D. E. Peterson, J. Am. Chem. Soc., 78, 2527 (1956).

    Google Scholar 

  79. D. Lednicer and C. R. Hauser, J. Am. Chem. Soc., 79, 4449 (1957).

    Google Scholar 

  80. T. A. Yagudeev, E. I. Baishiganov, S. I. Bazhbenova, and G. M. Dzhakiyaev, USSR Author's Certificate 740767; Ref. Zh. Khim., 22O114P (1980).

  81. M. Lounasmaa, T. Tamminen, and R. Jokela, Heterocycles, 23, 1735 (1985).

    Google Scholar 

  82. A. P. Gray, W. L. Archer, E. E. Spinner, and C. J. Cavallito, J. Am. Chem. Soc., 79, 3805 (1957).

    Google Scholar 

  83. J. A. Gautier, R. Epsztein, and M. Olomucki, Compt. Rend., 237, 1533 (1953).

    Google Scholar 

  84. C. F. Koelsch and J. J. Carney, J. Am. Chem. Soc., 72, 2285 (1950).

    Google Scholar 

  85. A. P. Dobbs, K. Jones, and K. T. Veal, Tetrahedron Lett., 38, 5383 (1997).

    Google Scholar 

  86. E. Peichl and T. Kappe, Arch. Pharm., 317, 946 (1984).

    Google Scholar 

  87. T. Kappe, M. Hariri, and E. Pongratz, Monatsh. Chem., 112, 1211 (1981).

    Google Scholar 

  88. G. Fukata, T. Itoh, S. Mataka, and M. Tashiro, J. Chem. Soc. Perkin Trans. 1, 327 (1988).

  89. P. V. Reshetov, S. A. Rozhnova, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 68 (1994).

  90. R. V. Seller, Thesis for Candidate of Chemical Sciences[in Russian], Saratov (2000).

  91. A. G. Golikov, P. V. Reshetov, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 851 (1997).

  92. A. G. Golikov, Thesis for Candidate of Chemical Sciences[in Russian], Saratov (2000).

  93. Kh. Okadzaki, R. Tamura, Kh. Bala, K. Onisi, and K. Soési, Jpn. Patent Appl. 61-275269; Ref. Zh. Khim., 13O68P (1988).

  94. R. V. Seller, E. V. Nikitashin, P. V. Reshetov, and A. P. Kriven'ko, in: Chemistry: State and Prospects of Scientific Investigations at the Threshold of the Third Millennium[in Russian], Izd. Sarat. Un-ta, Saratov (1999).

    Google Scholar 

  95. P. V. Reshetov, O. V. Fedotova, A. P. Kriven'ko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., 608 (1990).

  96. P. V. Reshetov, R. V. Seller, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 1279 (1997).

  97. R. V. Seller, P. V. Reshetov, T. S. Seller, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 1108 (2000).

  98. G. Mihai and T.-S. Balaban, Z. Naturforsch., 41b, 502 (1986).

    Google Scholar 

  99. P. V. Reshetov, R. V. Seller, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., 614 (1998).

  100. A. P. Kriven'ko, O. V. Fedotov, P. V. Reshetov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., 1652 (1984).

  101. P. V. Reshetov, A. P. Kriven'ko, E. I. Boreko, G. V. Vladyko, and L. V. Korobchenko, Khim.-Farm. Zh., 12, 614 (1990).

    Google Scholar 

  102. V. G. Kharchenko, O. A. Bozhenova, and A. D. Shebaldova, Zh. Org. Khim., 18, 2435 (1982).

    Google Scholar 

  103. O. A. Bozhenova, Author's Abstract of Thesis for Candidate of Chemical Sciences[in Russian], Saratov (1984).

Download references

Author information

Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, Saratov, Russia

    R. V. Seller, P. V. Reshetov & A. P. Kriven'ko

Authors
  1. R. V. Seller
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. V. Reshetov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. P. Kriven'ko
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Seller, R.V., Reshetov, P.V. & Kriven'ko, A.P. Catalytic Reduction of Pyridinium, Pyrylium, and Thiopyrylium Salts. (Review). Chemistry of Heterocyclic Compounds 37, 797–821 (2001). https://doi.org/10.1023/A:1012491504815

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012491504815

Search

Navigation