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.
Similar content being viewed by others
Literature Cited
J. V. Metzger (ed.), Thiazole and Its Derivatives, Interscience Publ., New York (1979).
H. Beyer, Z. Chem., No. 10, 361 (1969).
H. Johne, K. Seifert, S. Johne, and E. Bulka, Pharmazie, 33, No. 5, 259 (1978).
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).
J. Emsley, N. J. Freeman, P. A. Bates, and M. B. Hursthouse, J. Chem. Soc., Perkin 1, No. 2, 297 (1988).
M. F. Utinan, R. é. Valter, G. A. Karlivan, é. é. Liepin'sh, and A. S. édzhinya, Khim. Geterotsikl. Soedin., No. 5, 692 (1988).
Yu. P. Kitaev (Ed.), The Chemistry of Hydrazones [in Russian], Nauka, Moscow (1977), p. 40.
G. J. Karabatsos, F. M. Vane, R. A. Taller, and N. Hsi, J. Amer. Chem. Soc., 86, 3351 (1964).
B. I. Buzykin, A. P. Stolyarov, and N. N. Bystrykh, Tetrahedron Lett., 21, 209 (1980).
V. A. Lopyrev, L. I. Larina, and T. I. Vakul'skaya, Usp. Khim., 55, 769 (1986).
R. N. Butler, P. O'Sullivan, and F. L. Scott, J. Chem. Soc., C, 2265 (1971).
R. N. Butler, P. O'Sullivan, and F. L. Scott, J. Chem. Soc., Perkin 1, No. 12, 1519 (1972).
F. L. Scott and T. A F. O'Mahony, Tetrahedron Lett., 1841 (1970).
K. T. Potts and S. Husain, J. Org. Chem., 36, 10 (1971).
J. Mohan and G. S. R. Anjaneyulu, Pol J. Chem., 61, 547 (1987).
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.
Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974).
I. Simiti and M. M. Coman, Bull Soc. Chim. France, 9, 3276 (1969).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 537–543, April, 1991.
Rights 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
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00480845