Affiliation:
1. Department of Organic Chemistry, V.N. Karazin Kharkiv National University, Svobody sq., 4, 61022, Kharkiv, Ukraine
Abstract
4-Alkyl-3,4-dihydropyrimidin-2(1 H)-ones possess a number of important properties in comparison with their 4-aryl analogues. We show that these compounds can be synthesised by a simple one-pot reaction of urea or thiourea, different aliphatic aldehydes (from acetaldehyde to valeraldehyde) and various dicarbonyl compounds (ethyl acetoac-etate, pentane-2,4-dione, N-(4-chlorophenyl)-3-oxobutanamide, acetoacetaldehyde dimethylacetal) in refluxing DMF or HOAc without use of any catalyst. The methylation of 4-alkyl-5-C(O)R-3,4-dihydropyrimidin-2(1 H)-ones leads to 1-methyl derivatives.
Cited by
7 articles.
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1. 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;Chemistry of Heterocyclic Compounds;2022-12
2. A synthesis of 6-functionalized 4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines;Tetrahedron Letters;2017-03
3. Catalyst-free Biginelli-type synthesis of new functionalized 4,7-dihydropyrazolo[1,5-a]pyrimidines;New Journal of Chemistry;2016
4. An effective Biginelli-type synthesis of 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones;Tetrahedron Letters;2015-08
5. Synthesis of 5-Cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones;Synthetic Communications;2014-05-14