![5'-Fluoro-[2,3'-biindolinylidene]-2',3-dione structure](https://static.chemtradehub.com/structs/251/251903-00-1-9cb1.webp "5'-Fluoro-[2,3'-biindolinylidene]-2',3-dione structure")
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
Literature Information
Publication Date
2002-12-05
DOI
10.1039/B207854F
Impact Factor
3.876
Authors
Vasiliy A. Bakulev, Vera S. Berseneva, Natalia P. Belskaia, Yury Yu. Morzherin, Andreiy Zaitsev, Wim Dehaen, Ingrid Luyten, Suzanne Toppet
View Original
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.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
![1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure](https://static.chemtradehub.com/structs/141/1412439-82-7-b9a9.webp "1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure")
1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide
CAS Number:
1412439-82-7
Molecular Formula:
C33H31O4P
![1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure](https://static.chemtradehub.com/structs/603/60373-71-9-7dfb.webp "1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure")
1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
CAS Number:
60373-71-9
Molecular Formula:
C19H19N3O
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