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Synthesis of N-Substituted 3-Aminothiazolidin-4-ones Containing Hetaryl Fragments

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Condensation of the N-(3,5-dichloropyridyl-2)- and N-(benzothiazolyl-2-thioacetyl)hydrazones of carbonyl compounds with thioglycolic acid gave the 3-(3,5-dichloropyridyl-2)amino- and 3-[N-(benzothiazolyl-2-thioacetyl)amino]-2-R1-2-R2-thiazolidin-4-ones. Reaction of 1-(benzothiazolyl-2-thioacetyl)-4-R-thiosemicarbazides with chloroacetic acid in the presence of sodium acetate gave the 2-[N-(benzothiazolyl-2-thioacetyl)hydrazono]-3-R-thiazolidin-4-ones. It was found that the N-(benzothiazolyl-2-thioacetyl)hydrazones, both in the solid state and in solution, exist in the form of an equilibrium mixture of the EZ'- and EE'-isomers as a result of hindered rotation around the amide N-CO bond.

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Kelarev, V.I., Silin, M.A., Kotova, I.G. et al. Synthesis of N-Substituted 3-Aminothiazolidin-4-ones Containing Hetaryl Fragments. Chemistry of Heterocyclic Compounds 39, 213–222 (2003). https://doi.org/10.1023/A:1023772509165

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  • DOI: https://doi.org/10.1023/A:1023772509165

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