Abstract
It was established by means of PMR spectroscopy that, depending on the method of preparation, 2-imino-5-arylidene-4-thiazolidones exist in the form of various geometrical isomers relative to the exocyclic C=N bond. The E isomers are obtained as a result of condensation of 2-imino-4-thiazolidone with the corresponding benzaldehydes, whereas the Z isomers are formed in the solvolysis of hydroxymethyl and piperidinomethyl derivatives. The geometrical isomers retain their individuality in solutions in d6-DMSO and in ethanol. Upon dissolving in alkali with subsequent neutralization the E isomer of 2-imino-5-benzylidene-4-thiazolidinone is converted to the Z isomer. Reverse conversion of the Z isomer to the E isomer occurs when a solid sample is heated to 180 °C.
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S. Yu. Solov'eva-Yavits, S. M. Ramsh, N. A. Smorygo, A. I. Ginak, and E. G. Sochilin, Khim. Geterotsikl. Soedin., 929 (1980).
R. Andreash, Monatsh., 24, 499 (1903).
I. J. Fletcher and A. R. Katritzky, Chem. Commun., 706 (1970).
R. A. Raoul, M. T. Omar, and M. M. El-Attal, Acta Chim. Acad. Sci. Hung., 87, 187 (1975).
R. Knorr, Chem. Ber., 113, 2441 (1980).
S. Kambe, T. Hayashi, H. Yasuda, and A. Sakurai, Nippon Kagaku Zasshi, 92, 867 (1971).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 764–768, June, 1983.
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Ramsh, S.M., Solov'eva, S.Y. & Ginak, A.I. Structure of 2-imino-5-arylidene-4-thiazolidinones. Chem Heterocycl Compd 19, 611–614 (1983). https://doi.org/10.1007/BF00523070
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DOI: https://doi.org/10.1007/BF00523070