Facile and Rapid Synthesis of 3,4-Dihydropyrimidin-2-(1H)-ones and Thione Derivatives Through the Biginelli Protocol Using N-Methylimidazolium Acetate

Document Type : Research Article

Authors

Department of Chemistry, Faculty of Sciences, Behbahan Khatam Alanbia University of Technology, Behbahan, I.R. IRAN

Abstract

Some protic ionic liquids (PILs) were synthesized by the direct neutralization reaction of N-methylimidazole and 4-N,N-dimethylaminopyridine as nitrogen-containing heterocyclic organic bases with acetic acid and trifluoroacetic acid. The relative acidity of the prepared ionic liquids was evaluated by Hammet's acidity function using UV-Vis spectroscopy. The catalytic effects of the obtained ionic liquids were investigated in the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and thione derivatives through Biginelli reaction. AmongN-methylimidazolium acetate [MImH][OAc], N-methylimidazolium trifluoroacetate [MImH][CF3CO2], 4-N,N-dimethylaminopyridinium acetate [DMAPH][OAc] and 4-N,N-dimethylaminopyridinium trifluoroacetate [DMAPH][CF3CO2], [MImH][OAc] provided the best results. Using 5 mol% of [MImH][OAc] as a catalyst, 3,4-dihydropyrimidin-2-(1H)-ones and thione derivatives were obtained in high to excellent yields at 100 ºC during 15-50 min.

Keywords

Main Subjects

References

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Iranian Journal of Chemistry and Chemical Engineering
Volume 40, Issue 3 - Serial Number 107
May and June 2021
Pages 888-897

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