Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control. (4th March 2018)

• Record Type: Journal Article
• Authors: Nematpour, Manijeh; Rezaee, Elham; Jahani, Mehdi; Tabatabai, Sayyed Abbas
• Is Part Of: Journal of sulfur chemistry. Volume 39:Number 2(2018)
• Page Start: 151
• Page End: 163
• Publication Date: 2018-03-04
• Subjects: 3, 4-Dihydropyrimidin-2(1H)-one -- lithium N, N-diisopropylamide -- biginelli- type -- phenylacetone -- urea/thiourea -- kinetic-thermodynamic; Sulfur -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.72305
• DOI: 10.1080/17415993.2017.1402332
• Languages: English
• ISSNs: 1741-5993

Abstract

ABSTRACT: An efficient one-pot regioselective synthesis of various novel 3, 4-dihydropyrimidin-2(1 H )-one (DHPMs) via a three-component Biginelli-type condensation of aldehyde, phenylacetone and urea/thiourea under two different based-catalyzed conditions is described. In kinetic control path, lithium N, N -diisopropylamide (LDA-20 mol % generated in situ from n -BuLi and diisopropylamine) was used as the base, in tetrahydroforane (THF) as the solvent at 0°C. Thermodynamic control path was run with NaH as the base, in EtOH as the solvent under reflux status. The simple procedure, mild base-catalytic reaction conditions, no column chromatography and good to high yields are important features of this protocol. GRAPHICAL ABSTRACT: