Alkylation of Tetrahydropyrimidine-2-thiones with Ethyl Chloroacetate

Reaction conditions were found for the alkylation of tetrahydropyrimidine-2-thiones with ethyl chloroacetate, preventing a subsequent cyclization. Only one of the ester groups in the obtained alkylation products was subject to alkaline hydrolysis, while a treatment with ammonia in alcohol resulted i...

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Bibliographic Details
Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 49; no. 11; pp. 1681 - 1686
Main Authors Shiryaev, A. K., Kolesnikova, N. G., Kuznetsova, N. M., Lashmanova, E. A.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.02.2014
Springer Nature
Springer
Subjects
Antifungal agents
Chemical properties
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Esters
Hydrolysis
Organic Chemistry
Pharmacy
Physical Sciences
Science & Technology
dihydropyrimidines
alkylation
thiazolo[3,2
pyrimidines
tetrahydropyrimidine-2-thiones
esters of haloacetic acids
hydrolysis
THIONES
thiazolo[3,2-a]pyrimidines
ONE-POT SYNTHESIS
3,4-DIHYDROPYRIMIDIN-2(1H)-ONES
BIGINELLI-COMPOUNDS
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Summary:Reaction conditions were found for the alkylation of tetrahydropyrimidine-2-thiones with ethyl chloroacetate, preventing a subsequent cyclization. Only one of the ester groups in the obtained alkylation products was subject to alkaline hydrolysis, while a treatment with ammonia in alcohol resulted in thiazolo[3,2-a]pyrimidines.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-014-1420-8