Skip to main content
SpringerLink
Log in

Phase-transfer catalysis in the chemistry of tetrazoles

  • Reviews
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In this review we discuss results obtained in the development of methods for the synthesis of tetrazoles and tetrazolium salts together with studies of alkylation, acylation, and imidoylation of tetrazole and 5-substituted tetrazoles under conditions of phase-transfer catalysis.

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

Literature cited

  1. W. Durckheimer, J. Blumbach, R. Lattrel, and K. H. Scheunemann, Angew. Chem. Int. Ed., No. 3, 183 (1985).

    Google Scholar 

  2. M. D. Mullican, R. J. Sorenson, D. T. Connor, D. O. Thueson, J. A. Kennedy, and M. C. Conroy, J. Med. Chem., 34, 2186 (1991).

    Google Scholar 

  3. A. N. Markaryan, Ya. V. Voznyi, B. B. Dzantiev, and A. M. Egorov, Bioorg. Khim., 13, 263 (1987).

    Google Scholar 

  4. N. N. Karpyshev, Usp. Khim., 57, 1546 (1988).

    Google Scholar 

  5. V. M. Ostrovskaya, I. A. D'yakonova, and T. D. Nikolaeva, Zh. Vses. Khim. Ova, 30, 585 (1985).

    Google Scholar 

  6. S. Rokutanda, A. Tsuchida, and Y. Shigemitsu, Japanese Patent 90 287346 (1990); Chem. Abs., 115, 18522 (1991).

    Google Scholar 

  7. Y. Ishida and M. Ohashi, Japanese Patent 90 280140 (1990); Chem. Abs., 115, 18528 (1991).

    Google Scholar 

  8. A. B. Zhivich, G. I. Koldobskii, and V. A. Ostrovskii, Khim. Geterotsikl. Soedin., No. 12, 1587 (1991).

    Google Scholar 

  9. T. Habu, N. Mil, K. Kuge, H. Manto, and Y. Takamuki, J. Imaging Science, 35, 202 (1991).

    Google Scholar 

  10. V. A. Ostrovskii, N. S. Panina, G. I. Koldobskii, B. V. Gidaspov, and I. Yu. Shirobokov, Zh. Org. Khim., 15, 844 (1979).

    Google Scholar 

  11. E. Fos, J. Vilarrasa, and J. Fernandez, J. Org. Chem. 50, 4894 (1985).

    Google Scholar 

  12. I. Jano, J. Phys. Chem., 95, 7694 (1991).

    Google Scholar 

  13. V. A. Ostrovskii and G. I. Koldobskii, Weak Organic Bases [in Russian], Leningrad University Press, Leningrad (1990), p. 98.

    Google Scholar 

  14. G. I. Koldobskii, V. A. Ostrovskii, and B. V. Gidaspov, Khim. Geterotsikl. Soedin., No. 5, 579 (1988).

    Google Scholar 

  15. G. I. Koldobskii, V. A. Ostrovskii, and B. V. Gidaspov, Khim. Geterotsikl. Soedin., No. 7, 867 (1980).

    Google Scholar 

  16. R. N. Buttler, Adv. Heterocycl. Chem., 21, 323 (1977).

    Google Scholar 

  17. G. I. Koldobskii, V. A. Ostrovskii, and V. S. Poplavskii, Khim. Geterotsikl. Soedin., No. 10, 1299 (1981).

    Google Scholar 

  18. A. I. Lesnikovich, O. A. Ivashkevich, V. A. Lyutsko, G. V. Printsev, K. K. Kovalenko, P. N. Gaponik, and S. V. Levchik, Termochim. Acta, 145, 195 (1989).

    Google Scholar 

  19. A. I. Lesnikovich, O. A. Ivashkevich, G. V. Printsev, P. N. Gaponik, and S. V. Levchik, Termochim. Acta, 171, 207 (1990).

    Google Scholar 

  20. A. I. Lesnikovich, G. V. Printsev, O. A. Lvashkevich, P. N. Gaponik, and V. A. Shandakov, Termochim. Acta, 184, 221 (1991).

    Google Scholar 

  21. E. K. Harvill, R. H. Herbst, E. C. Schreiner, and C. W. Roberts, J. Org. Chem., 15, 622 (1950).

    Google Scholar 

  22. P. K. Kadaba, J. Org. Chem., 41, 1073 (1976).

    Google Scholar 

  23. J. Vaughan and P. A. S. Smith, J. Org. Chem., 23, 1909 (1958).

    Google Scholar 

  24. I. V. Nikonova, G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii, Zh. Obshch. Khim., 61, 1483 (1991).

    Google Scholar 

  25. I. V. Nikonova, G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii, Zh. Obshch. Khim., 61, 2104 (1991).

    Google Scholar 

  26. R. Imhif, D. W. Lander, and J. M. Muchowski, J. Org. Chem., 42, 3709 (1977).

    Google Scholar 

  27. A. B. Zhivich, Preparation, Properties and Uses of 2,3,5-Triaryl-tetrazolium Salts [in Russian], Dissertation, Leningrad (1988).

  28. B. Stanovik, M. Tisler, D. Gabrijelcic, M. Kundver, and J. Zmitek, J. Heterocycl. Chem., 16, 1567 (1979).

    Google Scholar 

  29. I. E. Titova, V. S. Poplavskii, G. I. Koldobskii, V. A. Ostrovskii, V. D. Nikolaev, and G. B. Erusalimski, Khim. Geterotsikl. Soedin., No. 8, 1086 (1986).

    Google Scholar 

  30. W. G. Finnegan, R. A. Henry, and R. Lofquist, J. Am. Chem. Soc., 80, 3908 (1958).

    Google Scholar 

  31. T. F. Osipova, Reactions of Tetrazoles under Conditions of Phase Transfer Catalysis [in Russian], Dissertation, Leningrad (1984).

  32. T. F. Osipova, G. I. Koldobskii, V. A. Ostrovskii, and Yu. E. Myznikov, Khim. Geterotsikl. Soedin., No. 6, 841 (1985).

    Google Scholar 

  33. A. B. Zhivich, G. I. Koldobskii, and V. A. Ostrovskii, Zh. Org. Khim., 24, 225 (1988).

    Google Scholar 

  34. A. B. Zhivich, Yu. E. Myznikov, G. I. Koldobskii, and V. A. Ostrovskii, Zh. Obshch. Khim., 58, 1906 (1988).

    Google Scholar 

  35. S. A. Belyakov, Zh. Org. Khim., 26, 217 (1990).

    Google Scholar 

  36. S. A. Belyakov, Zh. Org. Khim., 25, 2252 (1989).

    Google Scholar 

  37. M. L. Shpak, V. A. Ostrovskii, I. Yu. Shirobokov, G. I. Koldobskii, and B. V. Gidaspov. Zh. Org. Khim., 14, 2444 (1978).

    Google Scholar 

  38. I. Yu. Shirobokov, V. A. Ostrovskii, and G. I. Koldobskii, Zh. Org. Khim., 15, 839 (1979).

    Google Scholar 

  39. I. Yu. Shirobokov, V. A. Ostrovskii, and G. I. Koldobskii, Zh. Org. Khim., 16, 788 (1980).

    Google Scholar 

  40. V. A. Ostrovskii, I. Yu. Shirobokov, and G. I. Koldobskii, Zh. Org. Khim., 17, 146 (1981).

    Google Scholar 

  41. V. S. Poplavskii, I. E. Titova, V. A. Ostrovskii, and G. I. Koldobskii, Zh. Org. Khim., 18, 1981 (1982).

    Google Scholar 

  42. T. F. Osipova, V. A. Ostrovskii, G. I. Koldobskii, and G. B. Erusalimskii, Zh. Org. Khim., 20, 398 (1984).

    Google Scholar 

  43. J. Torres, J. L. Lavandera, P. Cabildo, R. M. Claramunt, and J. Elguero, J. Heterocycl. Chem., 25, 771 (1988).

    Google Scholar 

  44. R. Huisgen, J. Sauer, H. J. Sturm, and J. H. Markgraf, Chem. Ber., 93, 2106 (1960).

    Google Scholar 

  45. T. F. Osipova, G. I. Koldobskii, and V. A. Ostrovskii, Zh. Org. Khim., 20, 1119 (1984).

    Google Scholar 

  46. T. F. Osipova, G. I. Koldobskii, and V. A. Ostrovskii, Zh. Org. Khim., 20, 2468 (1984).

    Google Scholar 

  47. Yu. E. Myznikov, G. I. Koldobskii, I. N. Vasil'eva, and V. A. Ostrovskii, Zh. Org. Khim., 24, 1550 (1988).

    Google Scholar 

  48. L. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York (1967).

    Google Scholar 

  49. L. Fieser and M. Fieser, Reagents for Organic Synthesis, Wiley, New York (1967).

    Google Scholar 

  50. R. Huisgen, J. Sauer, and M. Seidel, Chem. Ber., 93, 2885 (1960).

    Google Scholar 

  51. G. I. Koldobskii, I. V. Nikonova, A. B. Zhivich, V. A. Ostrovskii, and V. S. Poplavskii, Zh. Obshch. Khim., 62, 194 (1992).

    Google Scholar 

  52. P. F. Lindey, G. V. Boyd, and G. A. Nicolaou, Acta Cryst., C46, 1693 (1990).

    Google Scholar 

  53. G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii, Zh. Obshch. Khim., 62, 3 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Saint Petersburg Technological Institute, 198013, Saint Petersburg

    G. I. Koldobskii, Yu. E. Myznikov, A. B. Zhivich, V. A. Ostrovskii & V. S. Poplavskii

Authors
  1. G. I. Koldobskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. E. Myznikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. B. Zhivich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Ostrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. S. Poplavskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 754–761, June, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koldobskii, G.I., Myznikov, Y.E., Zhivich, A.B. et al. Phase-transfer catalysis in the chemistry of tetrazoles. Chem Heterocycl Compd 28, 626–631 (1992). https://doi.org/10.1007/BF00529333

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00529333

Keywords

Search

Navigation