Skip to main content
SpringerLink
Log in

Synthesis of 6,8-substituted derivatives of imidazo[5,1-c][1,2,4]triazines and 1,4-dihydroimidazo[5,1-c][1,2,4]triazin-4-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cyclization of imidazolylhydrazines, synthesized from 5-diazoimidazoles and cyanoacetic acid derivatives, to 4-aminoimidazo[5,1-c][1,2,4]triazines and imidazo[5,1-c][1,2,4]triazin-4-ones has been studied. It was established that electron-withdrawing substituents at position 4 of the imidazole ring had a weak effect on the cyclization process. On the other hand, electron-donating substituents at positions 4 or 2 of this ring inhibited and in some cases completely prevented the formation of bicyclic products.

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

    Google Scholar 

  2. M. H. Elnagdi, E. M. Zayed, and S. Abdou, Heterocycles,19, 559 (1982).

    Google Scholar 

  3. M. F. G. Stevens and G. U. Baig, J. Chem. Soc., Perkin Trans. I, No. 5, 665 (1981).

    Google Scholar 

  4. M. Kocevar, D. Kolman, S. Polanc, B. Porovne, B. Stanovnik, and M. Tisler, Tetrahedron,32, 725 (1976).

    Google Scholar 

  5. G. U. Baig, M. F. G. Stevens, and R. Stone, J. Chem. Soc., Perkin Trans. I, No. 8, 1811 (1982).

    Google Scholar 

  6. T. Novinson, T. Okabe, R. K. Robins, and T. R. Matthews, J. Med. Chem.,19, 517 (1976).

    Google Scholar 

  7. J. F. Shealy, R. F. Struck, L. B. Holum, and J. A. Montgomery, J. Org. Chem.,26, 2396 (1961).

    Google Scholar 

  8. J. Heys and N. Ward, Brit. Pat. 1,373,347; Ref. Zh. Khim., 20069P (1975).

  9. M. F. G. Stevens, J. A. Hickma, N. W. Gibson, G. U. Baig, E. Lunt, and C. G. Newton, J. Med. Chem.,27, 196 (1984).

    Google Scholar 

  10. V. S. Mokrushin, V. I. Ofitserov, T. V. Rapakova, A. G. Tsaur, and Z. V. Pushkareva, Khim. Geterotsikl. Soedin., No. 4, 556 (1976).

    Google Scholar 

  11. V. S. Mokrushin, I. S. Selezneva, T. A. Pospelova, V. K. Usova, S. M. Malinskaya, G. M. Anoshina, T. E. Źubova and Z. V. Pushkareva, Khim.-Farm. Zh., No. 3, 303 (1982).

    Google Scholar 

  12. J. F. Shealy, C. A. Krauth, R. Pitillo, and E. Hunt, J. Pharm. Sci.,56, 147 (1967).

    Google Scholar 

  13. V. I. Nifontov, I. S. Selezneva, V. S. Mokrushin, Z. V. Pushkareva, and V. A. Trofimov, Khim. Geterotsikl. Soedin., No. 7, 984 (1979).

    Google Scholar 

Download references

Authors
  1. M. A. Bezmaternykh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. S. Mokrushin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. A. Pospelova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. S. El'tsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Urals State Technical University (UPI), Ekaterinburg 620002, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 805–815, June, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bezmaternykh, M.A., Mokrushin, V.S., Pospelova, T.A. et al. Synthesis of 6,8-substituted derivatives of imidazo[5,1-c][1,2,4]triazines and 1,4-dihydroimidazo[5,1-c][1,2,4]triazin-4-ones. Chem Heterocycl Compd 34, 702–711 (1998). https://doi.org/10.1007/BF02252280

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02252280

Keywords

Search

Navigation