Abstract
The products of condensation of thiobenzohydrazide with diacetyl and benzil have the structures of the corresponding 1,3,4-thiadiazol-2-ines; the same diketones and phenylthioacetylhydrazine were used to synthesize derivatives that display in solutions the ability to undergo thioacylhydrazone-1,3,4-thiadiazoline tautomerism. A bis derivative, viz., 5-(2′-phenyl-5′-methyl-1,3,4-thiadiazolin-2-yl)-5-methyl-2-phenyl-1,3,4-thiadiazol-2-ine, was obtained in the condensation of excess thiobenzohydrazide with diacetyl.
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K. H. Mayer and D. Lauerer, Ann. Chem., 731, 142 (1970).
V. A. Khrustalev, K. N. Zelenin, V. V. Pinson, and V. V. Alekseev, Zh. Org. Khim., 16, 2237 (1980).
V. V. Alekseev, V. A. Khrustalev, and K. N. Zelenin, Khim. Geterotsikl. Soedin., No. 11, 1569 (1981).
K. N. Zelenin, V. A. Khrustalev, V. V. Alekseev, P. A. Sharbatyan, and A. T. Lebedev, Khim. Geterotsikl. Soedin., No. 7, 904 (1982).
D. M. Evans and D. R. Taylor, Chem. Commun., 188 (1982).
V. A. Khrustalev, K. N. Zelenin, and V. V. Alekseev, Zh. Org. Khim., 17, 2451 (1981).
V. V. Alekseev, K. N. Zelenin, and V. A. Khrustalev, “Tautomerism of thioacylhydrazones,” in: Modern Problems in the Synthesis and Investigation of Organic Compounds [in Russian], Part I, Leningrad (1982), p. 23.
A. Alemagna, T. Bacchetti, and C. Rizzi, Gazz. Chim. Ital., 102, 311 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 769–771, June, 1983.
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Zelenin, K.N., Alekseev, V.V. & Khrustalev, V.A. Ring-chain tautomerism of diacetyl and benzil thioacylhydrazones. Chem Heterocycl Compd 19, 615–617 (1983). https://doi.org/10.1007/BF00523071
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DOI: https://doi.org/10.1007/BF00523071