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比格尼利反应_Biginelli反应_Biginelli Reaction

相关反应

帕氏反应

UGI反应

多组分反应

Related Reactions

Passerini Reaction

Ugi Reaction

Multicomponent Reactions


Biginelli Reaction  比格尼利反应 



在醛、α-酮酯和尿素之间的这种酸催化的三组分反应构成了二氢嘧啶酮的快速和简便的合成,二氢嘧啶酮是具有药物应用潜力的有趣化合物


Biginelli反应的机理

该机理的第一步被认为是醛和尿素之间的缩合,与Mannich缩合有些相似。生成的钐中间体作为亲核试剂用于酮酯烯醇的亲核加成,所得加合物的酮羰基与尿素NH2进行缩合以得到环化产物。




Recent Literature 近期文献


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, Synthesis2007, 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, Synthesis2011, 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, Tetrahedron200561, 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, Synthesis2005, 1333-1339.


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