Skip to main content
SpringerLink
Log in

1,2,4-Triazines – products of reaction of thiocarbohydrazide and its alkyl(aryl)-substituted derivatives with 1,2-dicarbonyl compounds

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of a series of 1,2-dicarbonyl compounds with thiocarbohydrazide and its 1- and 1,4-alkyl-(aryl)-substituted analogs has been studied. Treatment of diacetyl with the polynucleophiles indicated gives monohydrazones and/or 5-methylene-4,5-dihydro-2H-[1,2,4]triazine-3-thiones. Reaction of phenylglyoxal and benzil with thiocarbohydrazide yields 5-hydroxy- or 5-alkoxy-4,5-dihydro-2H-[1,2,4]triazine-3-thiones depending on the nature of the solvent. The products of condensation with 1,1-dimethylthiocarbohydrazide showed a thiocarbonohydrazone – 5-hydroxy-4,5-dihydro-2H-[1,2,4]tri-azine-3-thione ring-chain type equilibrium.

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

Scheme 1

Similar content being viewed by others

References

  1. V. V. Alekseev, K. N. Zelenin, and S. I. Yakimovich, Zh. Org. Khim., 31, 937 (1995).

    CAS  Google Scholar 

  2. P. Ch. Guha and S. Ch. Dey, J. Indian Chem. Soc., 2, 225 (1925).

    Google Scholar 

  3. A. C. Brown, E. C. Pickering, and F. J. Wilson, J. Chem. Soc., 107 (1927).

  4. H. R. Wiley, J. Macromol. Sci. Chem., A25, 231 (1988).

    Article  CAS  Google Scholar 

  5. U. K. Pandey, O. P. Pandey, S. R. Sengupta, and S. C. Tripathi, Polyhedron, 6, 1611 (1987).

    Article  CAS  Google Scholar 

  6. H. D. S. Yadava, S. R. Sengupta, and S. C. Tripathi, Inorg. Chem. Acta, 128, 1 (1987).

    Article  CAS  Google Scholar 

  7. O. P. Pandey, S. R. Sengupta, and S. C. Tripathi, Synth. React. Inorg. Metal-Org. Chem., 17, 567 (1987).

    Article  CAS  Google Scholar 

  8. P. Souzaz, M. A. Mendiola, A. Arguero, V. Fernández, E. Gutiérrez-Puebla, and C. Ruiz-Valero, Z. Naturforsch., 49b, 263 (1994).

    Google Scholar 

  9. P. Souzaz, M. A. Mendiola, A. I. Metesanz, V. Fernández, and A. Arguero, Transition Met. Chem., 20, 157 (1995).

    Google Scholar 

  10. K. N. Zelenin, V. V. Alekseev, K. Pikhlaia, and V. V. Ovcharenko, Izv. Akad. Nauk, Ser. Khim., 197 (2002).

  11. K. N. Zelenin and V. V. Alekseev, Khim. Geterotsikl. Soedin., 267 (1993). [Chem. Heterocycl. Comp., 29, 236 (1993)].

    Google Scholar 

  12. K. N. Zelenin, V. V. Alekseev, T. I. Pekhk, and O. B. Kuznetsova, Khim. Geterotsikl. Soedin., 1288 (1989). [Chem. Heterocycl. Comp., 25, 1080 (1989)].

    Google Scholar 

  13. K. N. Zelenin, O. B. Kuznetsova, and V. V. Alekseev, Khim. Geterotsikl. Soedin., 1418 (1992). [Chem. Heterocycl. Comp., 28, 1211 (1992)].

    Google Scholar 

  14. F. C. Brown, Ch. K. Bradsher, B. F. Moser, and Sh. Forrester, J. Org. Chem., 24, 1056 (1956).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Russian Military Medical Academy, Saint-Petersburg, 194044, Russia

    V. V. Alekseyev & M. B. Yegorova

  2. Scientific Research Test Center (Medical and Biological Defence) of the Federal State Research Test Institute of Military Medicine, Defence Ministry of Russian Federation, Saint-Petersburg, 195043, Russia

    I. V. Lagoda

  3. Saint Petersburg State University, Saint Petersburg, 198504, Russia

    S. I. Yakimovich

Authors
  1. V. V. Alekseyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Lagoda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. I. Yakimovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. B. Yegorova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Alekseyev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1202-1216, August, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alekseyev, V.V., Lagoda, I.V., Yakimovich, S.I. et al. 1,2,4-Triazines – products of reaction of thiocarbohydrazide and its alkyl(aryl)-substituted derivatives with 1,2-dicarbonyl compounds. Chem Heterocycl Comp 46, 971–982 (2010). https://doi.org/10.1007/s10593-010-0610-2

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0610-2

Keywords

Search

Navigation