Skip to main content
Log in

Synthesis and some reactions of 4-carboxy-2-thiazolylhydrazones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of thiosemicarbazones with bromopyruvic acid gives thiazolylhydrazone hydrobromides, which were converted to the free bases. The question of the site of protonation was studied by PMR spectroscopy. The possibility of self-protonation in 4-carboxythiazolylhydrazone crystals is not excluded. The thiazolylhydrazones are brominated in the 5 position. Both cyclization to thiazolyltriazoles and the Chetteueya—Walker reaction are realized in the case of oxidation with lead tetraacetate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. J. V. Metzger (ed.), Thiazole and Its Derivatives, Interscience Publ., New York (1979).

    Google Scholar 

  2. H. Beyer, Z. Chem., No. 10, 361 (1969).

    Google Scholar 

  3. H. Johne, K. Seifert, S. Johne, and E. Bulka, Pharmazie, 33, No. 5, 259 (1978).

    Google Scholar 

  4. G. P. Andronikova, S. V. Usol'tseva, S. L. Nikolaeva, G. M. Anoshina, V. I. Nifontov, and é. M. Emelina, Khim.-farm. Zh., No. 11, 1326 (1988).

    Google Scholar 

  5. J. Emsley, N. J. Freeman, P. A. Bates, and M. B. Hursthouse, J. Chem. Soc., Perkin 1, No. 2, 297 (1988).

    Google Scholar 

  6. M. F. Utinan, R. é. Valter, G. A. Karlivan, é. é. Liepin'sh, and A. S. édzhinya, Khim. Geterotsikl. Soedin., No. 5, 692 (1988).

    Google Scholar 

  7. Yu. P. Kitaev (Ed.), The Chemistry of Hydrazones [in Russian], Nauka, Moscow (1977), p. 40.

    Google Scholar 

  8. G. J. Karabatsos, F. M. Vane, R. A. Taller, and N. Hsi, J. Amer. Chem. Soc., 86, 3351 (1964).

    Google Scholar 

  9. B. I. Buzykin, A. P. Stolyarov, and N. N. Bystrykh, Tetrahedron Lett., 21, 209 (1980).

    Google Scholar 

  10. V. A. Lopyrev, L. I. Larina, and T. I. Vakul'skaya, Usp. Khim., 55, 769 (1986).

    Google Scholar 

  11. R. N. Butler, P. O'Sullivan, and F. L. Scott, J. Chem. Soc., C, 2265 (1971).

  12. R. N. Butler, P. O'Sullivan, and F. L. Scott, J. Chem. Soc., Perkin 1, No. 12, 1519 (1972).

    Google Scholar 

  13. F. L. Scott and T. A F. O'Mahony, Tetrahedron Lett., 1841 (1970).

  14. K. T. Potts and S. Husain, J. Org. Chem., 36, 10 (1971).

    Google Scholar 

  15. J. Mohan and G. S. R. Anjaneyulu, Pol J. Chem., 61, 547 (1987).

    Google Scholar 

  16. B. I. Buzykin, G. P. Sharnin, R. Kh. Fassakhov, A. V. Ladygin, L. P. Sysoeva, and Yu. P. Kitaev, Some Problems in Organic and Physical Chemistry [in Russian], A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Branch, Kazan (1972), p. 49.

    Google Scholar 

  17. Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974).

    Google Scholar 

  18. I. Simiti and M. M. Coman, Bull Soc. Chim. France, 9, 3276 (1969).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 537–543, April, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bredikhina, Z.A., Buzykin, B.I. & Kitaev, Y.P. Synthesis and some reactions of 4-carboxy-2-thiazolylhydrazones. Chem Heterocycl Compd 27, 427–433 (1991). https://doi.org/10.1007/BF00480845

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00480845

Keywords

Navigation