Reactions of 5-mercaptoazoles and pyridine-2-thiones with acetylenic esters. Selectivity of the formation of novel fused thiazin-4-ones and thiazolidin-4-ones / Bakulev V.A., Berseneva V.S., Belskaia N.P., Morzherin Y.Y., Zaitsev A., Dehaen W., Luyten I., Toppet S. // Organic and Biomolecular Chemistry. - 2003. - V. 1, l. 1. - P. 134-139.

ISSN:

14770520

Type:

Article

Abstract:

A systematic study of the reactions of dimethyl acetylenedicarboxylate (DMAD) and methyl propynoate with 5-mercaptoazoles and pyridine-2-thiones has been carried out and as a result, a number of novel imidazo[1,5-b]-thiazin-4-ones 6a,b, pyrazolo[1,5-b] thiazin-4-ones 15a-f, imidazo[1,5-b]thiazol-4-ones 7a,b and thiazolo[3,2-a]-pyridines 21a-c have been prepared. The influence of the size of the ring of the starting "cyclic" thioamides on the size of the fused ring in the reaction products has been established. The preferred formation of a six-membered thiazine ring took place in the reactions of 5-mercaptoazoles. In contrast, the five membered thiazolidine ring is formed in reactions of pyridine-2-thiones. In both cases the product is a five-membered ring fused to a six-membered heterocycle.

Author keywords:

Index keywords:

Esters; Macromolecules; Molecular structure; Reaction kinetics; Mercaptoazoles; Pyridine thiones; Thiazin ones; Thiazolidin ones; Aromatic compounds

DOI:

10.1039/b207854f

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0038791977&doi=10.1039%2fb207854f&partnerID=40&md5=39533996d8df847207846f61d71528db
Affiliations	Dept. of Technol. Organic Synthesis, The Urals State Technical University, 620002, Ekaterinburg, Russian Federation; Department of Chemistry, K.U. Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium
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Correspondence Address	Bakulev, V.A.; Dept. of Technol. Organic Synthesis, The Urals State Technical University, 620002, Ekaterinburg, Russian Federation; email: primavera@ural.org
Language of Original Document	English
Abbreviated Source Title	Org. Biomol. Chem.
Source	Scopus