Abstract
Isatin 2-thiosemicarbazone and its derivatives with one methyl group attached to the nitrogen atoms of the side chain exist in solution primarily in the iminohydrazine tautomeric form. Further substitution of the hydrogen atoms attached to the nitrogen atom in the primary thioamide group or replacement of the hydrogen atom attached to the sulfur atom by a methyl group promotes the formation of the aminohydrazone tautomer.
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A. B. Tomchin, Yu. V. Lapp, and V. S. Dmitrukha, Zh. Organ. Khim., 11, 2347 (1975).
D. Bauer and P. W. Sadler, Brit. J. Pharmacol., 15, 101 (1960).
P. W. Sadler, Ann. New York Acad. Sci., 130, 71 (1965).
A. B. Tomchin, V. S. Dmitrukha, T. N. Timofeeva, and P. S. Pel'kis, Zh. Organ. Khim., 10, 1519 (1974).
A. B. Tomchin and G. A. Shirokii, Zh. Organ. Khim., 10, 2465 (1974).
A. B. Tomchin, I. S. Ioffe, and G. A. Shirokii, Zh. Organ. Khim., 10, 103 (1974).
A. B. Tomchin, I. S. Ioffe, A. I. Kol'tsov, and Yu. V. Lepp, Khim. Geterotsikl. Soedin., 503 (1974).
K. A. Jenssen, U. Antoni, B. Kägi, C. Larsen, and C. Pedersen, Acta Chem. Scand., 22, 1 (1968).
C. Ainsworth, J. Am. Chem. Soc., 78, 1973 (1956).
R. Pummerer, Ber., 44, 338 (1911).
A. Hantzsch, Ber., 55, 3190 (1922).
A. B. Tomchin, I. S. Ioffe, and G. A. Shirokii, Zh. Organ. Khim., 8, 400 (1972).
I. S. Ioffe, A. B. Tomchin, and G. A. Shirokii, Zh. Organ. Khim., 7, 179 (1971).
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See [1] for communication XXXVII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 83–88, January, 1976.
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Tomchin, A.B., Shirokii, G.A. & Dmitrukha, V.S. Semicarbazones and thiosemicarbazones of the heterocylic series XXXVIII. Aminohydrazone-iminohydrazine tautomerism of isatin 2-thiosemicarbazone and its alkyl derivatives. Chem Heterocycl Compd 12, 76–80 (1976). https://doi.org/10.1007/BF00473918
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DOI: https://doi.org/10.1007/BF00473918