Primary Amine Catalyzed Biginelli Reaction for the Enantioselective Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
نویسندگان
چکیده
منابع مشابه
Solvent-free Biginelli Reaction Catalyzed to Synthesis of Biologically Active 3,4-dihydropyrimidin-2-(1H) –ones/thiones Derivatives
A convenient and highly efficient procedure for the synthesis of 3,4-dihydropyrimidin-2-(1H)-one/thione derivatives via one-pot three-component Biginelli condensation of arylaldehydes,urea/thiourea and ethyl/methyl acetoacetate in the presence of Zn(SO4)2.7H2Oas anefficient, readily and inexpensive catalyst under solvent-free conditions have been studied. Thisprotocol ha...
متن کاملSulfated zirconia-catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) under solventless conditions: competitive multicomponent Biginelli vs. Hantzsch reactions.
The catalytic ability of ZrO(2)/SO(4)(2-) to promote solventless three-component condensation reactions of a diversity of aromatic aldehydes, urea or thoiurea and ethyl acetoacetate was studied. Products resulting from Hantzsch and/or Biginelli multi-component reactions are obtained in the presence of solid acid catalysts using the same reactants but different temperature conditions. The sulfat...
متن کاملHighly enantioselective Biginelli reaction catalyzed by SPINOL-phosphoric acids.
A highly enantioselective Biginelli reaction promoted by chiral spirocyclic SPINOL-phosphoric acids has been developed. Under the optimized conditions with 5 mol% catalyst loading, a wide range of optically active dihydropyrimidinethiones (DHPMs) were obtained in high yields (up to 98%) with good to excellent enantioselectivities (up to 99% ee). The synthetic utility of this method was demonstr...
متن کاملSynthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions
The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone-α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H...
متن کاملD-tartaric acid: a novel catalyst for green and efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones by Biginelli reaction under solvent-free conditions
D-tartaric acid is successfully used as a green and efficient catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions. The developed method has many advantages, including devoid of harmful catalyst and solvents, high yield and easily work-up.
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ژورنال
عنوان ژورنال: European Journal of Organic Chemistry
سال: 2010
ISSN: 1434-193X,1099-0690
DOI: 10.1002/ejoc.201000448