Biginelli反应步骤和反应机理

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    此反应是酸催化的三组分反应,醛,ß-酮酯和脲迅速容易地反应生成二氢嘧啶酮。二氢嘧啶酮是一种非常有用的医药中间体


反应机理:

机理的第一步通常认为是醛和脲先进行缩合,与 Mannich 缩合有些类似。生成的亚胺离子中间体作为亲电试剂,酮酯烯醇式对其进行亲核加成。生成的中间体的酮羰基与氨基进行缩合得到产品。


最新文献:


N-Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of N1-Alkyl-, N1-Aryl-, and N1,N3-Dialkyl-3,4-Dihydropyrimidin-2(1H)-(thi)ones
S. V. Ryabukhin, A. S. Plaskon, E. N. Ostapchuk, D. M. Volochnyuk, A. A. Tolmachev, Synthesis, 2007, 417-427.


Organocatalytic Application of Ionic Liquids: [bmim][MeSO4] as a Recyclable Organocatalyst in the Multicomponent Reaction for the Preparation of Dihydropyrimidinones and -thiones
S. R. Roy, P. S. Jadhavar, K. Seth, K. K. Sharma, A. K. Chakraborti, Synthesis, 2011, 2261-2267.


Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction
I. Cepanec, M. Litvić, A. Bartolinčić, M. Lovrić, Tetrahedron, 2005, 61, 4275-4280.


Ruthenium(III) Chloride-Catalyzed One-Pot Synthesis of 3,4-Dihydro­pyrimidin-2-(1H)-ones under Solvent-Free Conditions
J. H. Schauble, E. A. Trauffer, P. P. Deshpande, R. D. Evans, Synthesis, 2005, 1333-1339.


N-Bromosuccinimide as an Almost Neutral Catalyst for Efficient Synthesis of Dihydropyrimidinones Under Microwave Irradiation
H. Hazarkhani, B. Karimi, Synthesis, 2004, 1239-1242.


Catalysis of the Biginelli Reaction by Ferric and Nickel Chloride Hexahydrates. One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones
J. Lu, Y. Bai, Synthesis, 2002, 466-470.


编译自:Organic Chemistry Portal

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