SPECTROSCOPIC STUDY OF THE KETO-ENOL EQUILIBRIUM OF N-ARYLDIACETYLTHIOACETAMIDES AND THEIR REACTIVITY

Authors

  • B. Zaleska Department of Organic Chemistry, Faculty of Chemistry, Jagiellonian University, 30-060 Kraków
  • M. M. Burgieł Department of Organic Chemistry, Faculty of Chemistry, Jagiellonian University, 30-060 Kraków
  • P. Serda Regional Laboratory of Physicochemical Analysis and Structural Reasearch, 30-060 Kraków

DOI:

https://doi.org/10.1007/7009

Keywords:

anilide of 3-oxoalkanethioic acids, N-aryldiacetylthioacetamide, keto-enol equilibrium, thiazolidin-4-one

Abstract

An NMR study of the equilibrium between keto-enol tautomeric forms of N-aryl- diacetylthioacetamides enables us to estimate their population ratio in solvents of increasing polarity. An X-ray analysis confirmed the structure of the thermodynamically most stable tautomer.  We presume that the course of heterocyclization processes with  N-aryldiacetylthioacetamides  is affected by the structure of the reacting tautomeric form. The treatment of N-aryldiacetylthioacetamides with oxalyl or bromoacetyl bromides leads to thiazolidine derivatives. The reactivity of the 5-methylene group in the obtained thiazolidin-4-one derivatives was investigated.

How to Cite
Zaleska, B.; Burgieł, M. M.; Serda, P.  Chem. Heterocycl. Compd. 2008, 44, 349. [Khim. Geterotsikl. Soedin. 2008, 452.]

For this article in the English edition see DOI 10.1007/s10593-008-0051-3

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Published

2022-08-22

Issue

No. 3 (2008)

Section

Original Papers