A General Approach to 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) via α-(thio)ureidoalkylation of 1,3-diketones or β-oxoesters

A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N -...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2022, Vol.58 (12), p.695-711
Main Authors: Shutalev, Anatoly D., Fesenko, Anastasia A., Strel’tsova, Elena D.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Dehydration
Diketones
Organic Chemistry
Pharmacy
Substitutes
Thioureas
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Summary:A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N -[alkyl(tosyl)methyl]thioureas, N -(azidomethyl)thiourea, and N -[alkyl(tosyl)methyl]ureas followed by TsOH-catalyzed dehydration of the intermediate 4-hydroxyhexahydropyrimidine-2-thiones(ones) without or with isolation of the latter.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-023-03146-6