Chemistry of Heterocyclic Compounds

, Volume 41, Issue 9, pp 1139–1146

Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

  • V. M. Chernyshev
  • V. A. Rakitov
  • V. A. Taranushich
  • V. V. Blinov
Article

Abstract

3-Acylamino-5-amino-1-R-1,2,4-triazoles are formed regioselectively on acylating 3,5-diamino-1-R-1,2,4-triazoles with an equimolar amount of anhydrides, carboxylic acid chlorides, and sulfonyl chlorides. With an excess of anhydride and carboxylic acid chloride 3,5-diacylamino-1-R-1,2,4-triazoles are formed. 3-Acylamino-5-amino-1-R-1,2,4-triazoles do not interact with sulfonyl chlorides. The higher reactivity of the 3-amino group towards acylating agents is determined by electronic and not steric factors.

Keywords

3-acylamino-5-amino-1-R-1,2,4-triazoles 5-amino-3-sulfonylamino-1-R-1,2,4-triazoles amino- 3,5-diamino-1,2,4-triazole 3,5-diacylamino-1,2,4-triazoles 1,2,4-triazole acylation regioselectivity structure 

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REFERENCES

  1. 1.
    B. G. Van Den Boss, Rec. Trav. Chim., 79, 836 (1960).Google Scholar
  2. 2.
    C. D. Selassie, E. J. Lien, and T. A. Khwaja, J. Pharm. Sci., 70, 1281 (1981).Google Scholar
  3. 3.
    M. S. Pevzner, N. V. Gladkova, and T. A. Kravchenko, Zh. Org. Khim., 32, 1230 (1996).Google Scholar
  4. 4.
    M. I. Barmin, O. A. Kolesnikov, V. P. Kononenko, and V. V. Mel'nikov, Zh. Prikl. Khim., 73, 1916 (2000).Google Scholar
  5. 5.
    G. Pellizzari and C. Roncagliolo, Gazz. Chim. Ital., 31, 477 (1901).Google Scholar
  6. 6.
    P. Papini and S. Checchi, Gazz. Chim. Ital., 80, 100 (1950).Google Scholar
  7. 7.
    E. A. Steck. R. P. Brundage, and L. T. Fletcher, J. Am. Chem. Soc., 80, 3929 (1958).CrossRefGoogle Scholar
  8. 8.
    J. Reiter, L. Pongo, T. Somorai, and P. Dvortsak, J. Heterocycl. Chem., 23, 401 (1986).CrossRefGoogle Scholar
  9. 9.
    J. J. Fuentes and J. A. Lenoir, Can. J. Chem., 54, 3620 (1976).Google Scholar
  10. 10.
    V. V. Lipson, S. M. Desenko, V. D. Orlov, O. V. Shishkin, M. G. Shirobokova, V. N. Chernenko, and L. I. Zinov'eva, Khim. Geterotsikl. Soedin., 1542 (2000).Google Scholar
  11. 11.
    J. Reiter, L. Pongo, and P. Dvortsak, J. Heterocycl. Chem., 24, 127 (1987).Google Scholar
  12. 12.
    N. K. Beresneva, V. A. Lopyrev, and K. L. Krupin, Khim. Geterotsikl. Soedin., 1118 (1969).Google Scholar
  13. 13.
    G. L. Starova, O. V. Frank-Kamenetskaya, V. V. Makarskii, and V. A. Lopyrev, Kristallografiya, 25, 1292 (1980).Google Scholar
  14. 14.
    A. Kalman and G. Argay, J. Mol. Struct., 102, 391 (1983).Google Scholar
  15. 15.
    A. Kalman, L. Parkanyi, and J. Reiter, J. Mol. Struct., 118, 293 (1984).Google Scholar
  16. 16.
    W. A. Kleschik, J. E. Dunbar, S. W. Snider, and A. P. Vinogradoff, J. Org. Chem., 53, 3120 (1988).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • V. M. Chernyshev
    • 1
  • V. A. Rakitov
    • 1
  • V. A. Taranushich
    • 1
  • V. V. Blinov
    • 1
  1. 1.South-Russian State Technical UniversityNovocherkasskRussia

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