Skip to main content
SpringerLink
Log in

Application of the Schmidt reaction for the preparation of tetrazoles (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The application of the Schmidt reaction with ketones and nitriles for the preparation of tetrazoles is examined. Modern concepts regarding the mechanism of the reaction of ketones and nitriles with hydrazoic acids are discussed. The range of application of the reaction is indicated.

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. C. D. Esplin and N. Woodbury, J. Pharmacol. Exper. Therap.,118, 129 (1956).

    Google Scholar 

  2. V. A. Tsirlin, Farm. i Toksikol.,32, 669 (1969).

    Google Scholar 

  3. R. T. Buckler, J. Med. Chem.,15, 578 (1972).

    Google Scholar 

  4. E. Balieu and E. Bjarnov, Acta Chem. Scand.,27, 1233 (1973).

    Google Scholar 

  5. W. Bossard, J. Voltz, and F. Favre, US Patent No. 2883373 (1959); Chem. Abstr.,54, 3970 (1960).

    Google Scholar 

  6. R. T. Thomson, Phot. Sci. Eng.,3, 272 (1959).

    Google Scholar 

  7. W. G. Schmidt, British Patent No. 796294 (1958); Chem. Abstr.,52, 19, 157 (1958).

    Google Scholar 

  8. E. Roos, F. Lober, and M. Burgdorf, US Patent No. 3007895 (1959); Chem. Abstr.,56, 4968 (1962).

    Google Scholar 

  9. C. Rhykerd, H. W. Gausman, E. S. Scott, and Z. F. Audrieth, Science,118, 192 (1953).

    Google Scholar 

  10. R. M. Herbst and S. F. Froberger, J. Org. Chem.,22, 1050 (1957).

    Google Scholar 

  11. F. R. Benson, Chem. Rev.,41, 1 (1947).

    Google Scholar 

  12. F. R. Benson, in: Heterocyclic Compounds [Russian translation], Vol. 8, Mir, Moscow (1969), p. 7.

    Google Scholar 

  13. G. I. Koldobskii, G. F. Tereshchenko, E. S. Gerasimova, and L. I. Bagal, Usp. Khim.,40, 1790 (1971).

    Google Scholar 

  14. K. F. Schmidt, Ber.,57, 704 (1924).

    Google Scholar 

  15. C. S. Barnes, D. H. R. Barton, J. S. Fawcett, and B. R. Thomas, J. Chem. Soc., 2339 (1952).

  16. P. A. S. Smith, J. Amer. Chem. Soc.,70, 320 (1948).

    Google Scholar 

  17. P. A. S. Smith, in: Molecular Rearrangements (edited by P. Mayo), Vol. 1, J. Wiley, New York (1963), p. 507.

    Google Scholar 

  18. G. F. Tereshchenko, G. I. Koldobskii, and L. I. Bagal, Zh. Organ. Khim.,6, 1132 (1970).

    Google Scholar 

  19. G. I. Koldobskii, G. F. Tereshchenko, and L. I. Bagal, Zh. Organ. Khim.,6, 2395 (1970).

    Google Scholar 

  20. G. F. Tereshchenko, G. I. Koldobskii, A. S. Enin, and L. I. Bagal, Reakts. Sposobnost' Organ. Soedin.,7, 1102 (1970).

    Google Scholar 

  21. V. A. Ostrovskii, A. S. Enin, G. I. Koldobskii, and L. I. Bagal, Zh. Organ. Khim.,8, 46 (1972).

    Google Scholar 

  22. V. A. Ostrovskii, A. S. Enin, and G. I. Koldobskii, Zh. Organ. Khim.,9, 802 (1973).

    Google Scholar 

  23. C. L. Arcus, M. M. Coombs, and I. V. Evans, J. Chem. Soc., 1498 (1958).

  24. P. A. S. Smith, J. Amer. Chem. Soc.,76, 431 (1954).

    Google Scholar 

  25. W. Pritzkow and A. Schuberth, Ber.,93, 1725 (1960).

    Google Scholar 

  26. H. Kawamoto, T. Matsuo, S. Morosawa, and A. Yokoo, Bull. Chem. Soc. Japan,46, 3898 (1973).

    Google Scholar 

  27. G. I. Koldobskii, A. S. Enin, V. N. Naumov, V. A. Ostrovskii, G. P. Tereshchenko, and L. I. Bagal, Zh. Organ. Khim.,8, 242 (1972).

    Google Scholar 

  28. A. S. Enin, G. I. Koldobskii, and L. I. Bagal, Zh. Organ. Khim.,7, 2560 (1971).

    Google Scholar 

  29. A. S. Enin, G. I. Koldobskii, V. A. Ostrovskii, and L. I. Bagal, Zh. Organ. Khim.,8, 1895 (1972).

    Google Scholar 

  30. G. A. Reynolds, T. A. van Allen, and T. F. Tinker, J. Org. Chem.,24, 1205 (1959).

    Google Scholar 

  31. K. Tensen and C. Pederson, Acta Chem. Scand.,15, 991 (1961).

    Google Scholar 

  32. F. R. Benson, L. W. Hartzel, and E. A. Otton, J. Amer. Chem. Soc.,76, 1858 (1954).

    Google Scholar 

  33. Y. Pocker, M. W. Beug, and K. L. Stephens, J. Amer. Chem. Soc.,96, 174 (1974).

    Google Scholar 

  34. R. A. Henry, W. G. Finnegan, and E. Lieber, J. Amer. Chem. Soc.,77, 2264 (1955).

    Google Scholar 

  35. J. Matuieu and J. Valles, Bull. Soc. Chim. Belge, 1509 (1957).

  36. A. N. Nesmeyanov and M. I. Rybinskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 816 (1962).

  37. N. S. Zefirov and N. K. Chapovskaya, Vestnik MGU, Khimiya,5, 113 (1963).

    Google Scholar 

  38. A. I. Tal'vik and V. A. Palm, Zh. Fiz. Khim.,33, 1214 (1959).

    Google Scholar 

  39. V. I. Minkin, J. A. Zdanov, and E. A. Mediantseva, Tetrahedron,23, 3651 (1967).

    Google Scholar 

  40. S. Patai, in: The Chemistry of the Carbon-Nitrogen Double Bond, London-New York (1970).

  41. I. R. Bellobono and G. Favini, J. Chem. Soc., B, 2034 (1971).

  42. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, London, (1965).

  43. N. D. Agibalova, V. A. Ostrovskii, G. I. Koldobskii, and A. S. Enin, Zh. Organ. Khim.,9, 1580 (1973).

    Google Scholar 

  44. J. H. Boyer and F. C. Canter, Chem. Rev.,54, 1 (1954).

    Google Scholar 

  45. G. L. Able, Ind. Chim. Belge,34, 519 (1969).

    Google Scholar 

  46. P. A. S. Smith, J. Amer. Chem. Soc.,76, 434 (1954).

    Google Scholar 

  47. W. P. Norris and R. A. Henry, J. Org. Chem.,29, 650 (1964).

    Google Scholar 

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

    Google Scholar 

  49. N. S. Hjelte and T. Agback, Acta Chem. Scand.,18, 191 (1964).

    Google Scholar 

  50. A. S. Enin, G. I. Koldobskii, and L. I. Bagal, Zh. Organ. Khim.,7, 1672 (1971).

    Google Scholar 

  51. T. A. Bak and E. L. Prestgaard, Acta Chem. Scand.,11, 901 (1957).

    Google Scholar 

  52. N. S. Deno and R. W. Taft, J. Amer. Chem. Soc.,76, 244 (1954).

    Google Scholar 

  53. H. Wai and K. Yates, Can. J. Chem.,47, 2326 (1969).

    Google Scholar 

  54. J. Braun and W. Keller, Ber.,65, 1677 (1932).

    Google Scholar 

  55. R. M. Herbst, C. W. Roberts, and E. J. Harvill, J. Org. Chem.,16, 139 (1951).

    Google Scholar 

  56. A. J. Davies and R. E. Marks, J. Chem. Soc., C, 2703 (1968).

  57. L. Ruzicka, M. W. Goldberg, M. Hurbin, and H. A. Boekenoogen, Helv. Chem. Acta,16, 1323 (1933).

    Google Scholar 

  58. Y. Sakakida, A. S. Kumanireng, H. Kawamoto, and A. Yokoo, Bull. Chem. Soc., Japan, 44, 478 (1971).

    Google Scholar 

  59. J. W. Apsiman and N. R. Hunter, Tetrahedron Lett., 187 (1972).

  60. P. A. S. Smith and W. L. Berry, J. Org. Chem.,26, 27 (1961).

    Google Scholar 

  61. T. Sasaki, S. Eguchi, and T. Tory, J. Org. Chem.,35, 4109 (1970).

    Google Scholar 

  62. T. Sasaki, S. Eguchi, and T. Tory, J. Org. Chem.,36, 2454 (1971).

    Google Scholar 

  63. A. N. Khuthier and J. C. Robertson, J. Org. Chem.,35, 3760 (1970).

    Google Scholar 

  64. N. B. Chapman, H. McCombie, and B. C. Saunders, J. Chem. Soc., 929 (1945).

  65. H. Singh, R. K. Malhotza, and V. V. Parashar, Tetrahedron Lett., 2587 (1973).

  66. R. Huisgen, Ann.574, 171 (1951).

    Google Scholar 

  67. E. K. Harvill, R. M. Herbst, E. C. Schreiner, and C. W. Roberts, J. Org. Chem.,15, 662 (1950).

    Google Scholar 

  68. L. Ruzicka, M. W. Goldberg, and M. Hurbin, Helv. Chim. Acta,16, 1335 (1933).

    Google Scholar 

  69. H. Beckman, Pharmacology, London (1961), p. 3318.

  70. D. Misiti, V. Rimotori, and F. Gatta, J. Heterocyclic Chem.,10, 689 (1973).

    Google Scholar 

  71. W. H. Hayff, J. Org. Chem.,22, 344 (1957).

    Google Scholar 

  72. L. J. Winters, Diss. Abstr.,20, 3963 (1960).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lensovet Leningrad Technological Institute, USSR

    G. I. Koldobskii, V. A. Ostrovskii & B. Z. Gidaspov

Authors
  1. G. I. Koldobskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Ostrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. Z. Gidaspov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–735, June, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koldobskii, G.I., Ostrovskii, V.A. & Gidaspov, B.Z. Application of the Schmidt reaction for the preparation of tetrazoles (review). Chem Heterocycl Compd 11, 626–635 (1975). https://doi.org/10.1007/BF00959947

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00959947

Keywords

Search

Navigation