Abstract
Abstract Novel N1-substituted 3,4-dihydropyrimidin-2(1H)-one derivatives were synthesized through Biginelli condensation of aromatic aldehydes, β-ketoesters, and monosubstituted (thio)ureas in the presence of copper methanesulfonate at 90°C under solvent-free conditions. The screening of the catalysts showed the copper methanesulfonate was the best. Its catalytic activity remained after three times of use. The products were characterized by IR, 1H NMR, 13C NMR, elemental analysis, and X-ray single crystal diffraction technique. A reasonable reaction mechanism was proposed.
Highlights
Novel N1-substituted 3,4-dihydropyrimidin2(1H)-one derivatives were synthesized through Biginelli condensation of aromatic aldehydes, β-ketoesters, and monosubstitutedureas in the presence of copper methanesulfonate at 90°C under solvent-free conditions
The products were characterized by IR, 1H NMR, 13C NMR, elemental analysis, and X-ray single crystal diffraction technique
The N1-substituted DHPMs were synthesized with aromatic aldehydes, ethyl acetoacetate, and N-substitutedureas using copper methanesulfonate [Cu(CH3SO3)2 · 4H2O, abbreviated as CMS] as a catalyst [Eq (1)]
Summary
Novel N1-substituted 3,4-dihydropyrimidin2(1H)-one derivatives were synthesized through Biginelli condensation of aromatic aldehydes, β-ketoesters, and monosubstituted (thio)ureas in the presence of copper methanesulfonate at 90°C under solvent-free conditions. The N1-substituted DHPMs were synthesized with aromatic aldehydes, ethyl acetoacetate (methyl acetoacetate), and N-substituted (thio)ureas using copper methanesulfonate [Cu(CH3SO3)2 · 4H2O, abbreviated as CMS] as a catalyst [Eq (1)]. The N-substituted (thio)ureas include methylurea, ethylurea, p-tolylurea, and methylthiourea This method avoids the use of a toxic solvent and a high cost. 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) have special therapeutic properties and pharmacological activity. They can be used as calcium channel agents, antiallergic agents, antihypertensive agents and antagonists, and so on [1,2,3,4,5,6].
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