1250832-36-0Relevant academic research and scientific papers
Highly regioselective, base-catalyzed, biginelli-type reaction of aldehyde, phenylacetone and urea/thiourea kinetic vs. thermodynamic control
Nematpour, Manijeh,Rezaee, Elham,Jahani, Mehdi,Tabatabai, Sayyed Abbas
, p. 151 - 163 (2018)
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.
Synthesis and Suzuki-Miyaura reactions of 5-halo-3,4-dihydropyrimidin-2(1H) -ones
Zych, Andrew J.,Wang, Hong-Jun,Sakwa, Samuel A.
experimental part, p. 5103 - 5105 (2010/11/16)
A novel synthesis of 6-methyl-4-phenyl-5-substituted-3,4-dihydropyrimidin- 2(1H)-ones from 6-methyl-4-phenyl-5-halo-3,4-dihydropyrimidin-2(1H)-ones via the Suzuki-Miyaura reaction is reported. These previously unknown heterocyclic halides are easily prepared using the Biginelli multicomponent reaction followed by halodecarboxylation. The effect of varied substitution at the C-4 position on the cross-coupling reaction is also examined.
Bronsted base-catalyzed one-pot three-component Biginelli-type reaction: An efficient synthesis of 4,5,6-triaryl-3,4-dihydropyrimidin-2(1H)-one and mechanistic study
Shen, Zhi-Liang,Xu, Xiao-Ping,Ji, Shun-Jun
supporting information; experimental part, p. 1162 - 1167 (2010/04/02)
(Chemical Equation Presented) An efficient one-pot synthesis of 4,5,6-triaryl-3,4-dihydropyrimidin-2(1H)-ones via a three-component Biginelli-type condensation of aldehyde, 2-phenylacetophenone, and urea/thiourea in the presence of a catalytic amount of t-BuOK (20 mol %) is described. The reactions proceeded efficiently at 70 °C to afford the desired products in moderate to good yields. Detailed mechanistic study shows that the Biginelli-type reaction using urea and thiourea proceeds through two totally different pathways. Enone 5 and bis-urea 8 were highly suggested as respective reaction intermediates for reactions involving thiourea and urea as substrates.
