Synthesis of N-Substituted 3-Aminothiazolidin-4-ones Containing Hetaryl Fragments |
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| Authors: | V. I. Kelarev M. A. Silin I. G. Kotova K. I. Kobrakov I. I. Rybina V. K. Korolev |
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| Affiliation: | (1) I. M. Gubkin Oil and Gas State University, Moscow, 117917, Russia;(2) A. N. Kosygin Moscow State Textile University, Moscow, 117918, Russia |
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| 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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| Keywords: | N-acylhydrazones 1-acylthiosemicarbazides benzothiazole hydrazones dichloropyridines thioglycolic acid thiazolidin-4-one condensation |
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