Title: 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
Authors: Bakulev, VA ×
Berseneva, VS
Belskaia, NP
Morzherin, YY
Zaitsev, A
Dehaen, Wim
Luyten, I
Toppet, Suzanne #
Issue Date: Jan-2003
Publisher: Royal soc chemistry
Series Title: Organic & biomolecular chemistry vol:1 issue:1 pages:134-139
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.
ISSN: 1477-0520
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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