Skip to main content
SpringerLink
Log in

Synthesis and transformations of 3-azido-5-amino-1,2,4-triazines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of the tetrazolediazonium ion with malonic acid dinitrile and nitroacetonitrile leads to the formation of 3-azido-5-amino-1,2,4-triazine derivatives. According to the mass-spectrometric data and the results of X-ray diffraction analysis, the crystalline compounds exist in the amino form. The facile hydrolysis of the amino and azido groups to azauracils is an argument in favor of the existence of the imino form in solution.

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. M. Tishler and B. Stanovnik, Khim. Geterotsikl. Soedin., No. 5, 579 (1980).

    Google Scholar 

  2. E. J. Gery, M. G. F. Stevens, G. Tehnant, and R. J. S. Vevers, J. Chem. Soc., No. 14, 1496 (1976).

    Google Scholar 

  3. G. I. Migachev and V. A. Danilenko, Khim. Geterotsikl. Soedin., No. 7, 867 (1982).

    Google Scholar 

  4. M. M. Geodman, J. L. Atwood, R. Carlin, W. Hunter, and W. W. Paudler, J. Org. Chem., 41., 2860 (1976).

    Google Scholar 

  5. D. Goldsmith and D. Djerassi, J. Org. Chem., 31, 3661 (1966).

    Google Scholar 

  6. N. A. Klyuev, I. S. Shpileva, L. I. Medvedeva, G. N. Lipunova, and N. P. Bednyagina, Khim. Geterotsikl. Soedin., No. 11, 1506 (1981).

    Google Scholar 

  7. N. A. Klyuev, V. M. Adanin, I. Ya. Postovskii, and Yu. A. Azev, Khim. Geterotsikl. Soedin., No. 4, 547 (1983).

    Google Scholar 

  8. J. L. Anbaganac, P. Campien, and P. Penot, Org. Mass Spectrom., 13, 571 (1978).

    Google Scholar 

  9. J. Svetlic, J. Lesko, and H. Martvon, Monatsh. Chem., 3, 635 (1980).

    Google Scholar 

  10. International Tables for X-ray Crystallography, Vol. 3, Kynoch Press, Birmingham (1964).

  11. M. Chao, E. Schempp, and R. Rosenstein, Acta Crystallogr., B31, 2922 (1975).

    Google Scholar 

  12. M. Chao, E. Schempp, and R. Rosenstein, Acta Crystallogr., B32, 288 (1976).

    Google Scholar 

  13. N. G. Furmanova, Usp. Khim., 50, 1491 (1981).

    Google Scholar 

  14. C. Crystesky and T. Panaitseu, Pharmazie, 18, 336 (1963).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. M. Kirov Ural Polytechnic Institute, 620002, Sverdlovsk

    V. L. Rusinov, T. V. Dragunova, V. A. Zyryanov, G. G. Aleksandrov, N. A. Klyuev & O. N. Chupakhin

  2. All-Union Scientific-Research Institute of Antibiotics, 113105, Moscow

    V. L. Rusinov, T. V. Dragunova, V. A. Zyryanov, G. G. Aleksandrov, N. A. Klyuev & O. N. Chupakhin

Authors
  1. V. L. Rusinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. V. Dragunova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Zyryanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. G. Aleksandrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. A. Klyuev
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. N. Chupakhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 557–561, April, 1984.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rusinov, V.L., Dragunova, T.V., Zyryanov, V.A. et al. Synthesis and transformations of 3-azido-5-amino-1,2,4-triazines. Chem Heterocycl Compd 20, 455–459 (1984). https://doi.org/10.1007/BF00513869

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00513869

Keywords

Search

Navigation