SYNTHESIS OF N-SUBSTITUTED 3-AMINOTHIAZOLIDIN-4-ONES CONTAINING HETARYL FRAGMENTS

Authors

  • В. И. Келарев I. M. Gubkin Oil and Gas State University, Moscow 117917
  • М. А. Силин I. M. Gubkin Oil and Gas State University, Moscow 117917
  • И. Г. Котова I. M. Gubkin Oil and Gas State University, Moscow 117917
  • K. И. Кобраков A. N. Kosygin Moscow State Textile University, Moscow 117918
  • И. И. Рыбина A. N. Kosygin Moscow State Textile University, Moscow 117918
  • В. К. Королев A. N. Kosygin Moscow State Textile University, Moscow 117918

Keywords:

N-acylhydrazones, 1-acylthiosemicarbazides, benzothiazole, hydrazones, dichloropyridines, thioglycolic acid, thiazolidin-4-one, condensation

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.

How to Cite
Kelarev, V. I.; Silin, M. A.; Kotova, I. G.; Kobrakov, K. I.; Rybina, I. I.; Korolev, V. K. Chem. Heterocycl. Compd. 2003, 39, 213. [Khim. Geterotsikl. Soedin. 2003, 243.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1023772509165

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Published

2003-02-25

Issue

No. 2 (2003)

Section

Original Papers