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 VA,Berseneva VS,Belskaia NP,Morzherin YY,Zaitsev A,Dehaen W,Luyten I,Toppet S // ORGANIC \& BIOMOLECULAR CHEMISTRY. - 2003. - V. 1, l. 1. - P. 134-139.

ISSN/EISSN:

1477-0520 / нет данных

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:

DIMETHYL ACETYLENEDICARBOXYLATE; PRODUCTS; DERIVATIVES; ACID

DOI:

10.1039/b207854f

Web of Science ID:

ISI:000181528500025

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 7
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	DIMETHYL ACETYLENEDICARBOXYLATE; PRODUCTS; DERIVATIVES; ACID
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	primavera@ural.org wim.dehaen@chem.kuleuven.ac.be
ResearcherID-Numbers	Morzherin, Yury/M-7420-2013
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676 Belskaya, Nataliya/0000-0002-2509-7916
Number-of-Cited-References	23
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	4
Journal-ISO	Org. Biomol. Chem.
Doc-Delivery-Number	655AE