TY - DATA T1 - Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control PY - 2017/11/26 AU - Manijeh Nematpour AU - Elham Rezaee AU - Mehdi Jahani AU - Sayyed Abbas Tabatabai UR - https://tandf.figshare.com/articles/journal_contribution/Highly_regioselective_base-catalyzed_biginelli-type_reaction_of_aldehyde_phenylacetone_and_urea_thiourea_kinetic_vs_thermodynamic_control/5633338 DO - 10.6084/m9.figshare.5633338.v1 L4 - https://ndownloader.figshare.com/files/9810289 KW - 3,4-Dihydropyrimidin-2(1H)-one KW - lithium N,N-diisopropylamide KW - biginelli- type KW - phenylacetone KW - urea/thiourea KW - kinetic-thermodynamic N2 - An efficient one-pot regioselective synthesis of various novel 3,4-dihydropyrimidin-2(1H)-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. ER -