Tetrahedron

Reaction of heterocyclic thioamides with dimethyl acetylenedicarboxylate. Synthesis of novel 2-azolyl-5-methoxycarbonylmethylene thiazolin-4-ones

VS Berseneva, YY Morzherin, W Dehaen, I Luyten…

Index: Berseneva, Vera S; Morzherin, Yury Yu; Dehaen, Wim; Luyten, Ingrid; Bakulev, Vasiliy A Tetrahedron, 2001 , vol. 57, # 11 p. 2179 - 2184

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Citation Number: 32

Abstract

A systematic study of the reactions of dimethyl acetylenedicarboxylate (DMAD) with heterocyclic thioamides has been carried out and a number of new 2-isoxazolyl-(8), imidazolyl-(13a, b and 17a), 1, 2, 3-triazolyl-(13d, e) and 1, 2, 3-thiadiazolyl (17b) thiazolines have been prepared. The higher reactivity of the thioamide group in comparison with the amino group in these reactions has been established.