HBF4-catalyzed Biginelli reaction: One-pot synthesis of dihydropyrimidin-2(1H)-ones under solvent-free conditions

被引:64
作者
Chen, WeiYi [1 ]
Qin, SuDong
Jin, JianRong
机构
[1] Suzhou Univ, Coll Chem & Chem Engn, Suzhou 215123, Peoples R China
[2] JiangShan Pharmaceut Corp, Tech Dept, JingJiang 214500, Peoples R China
关键词
Biginelli reaction; fluoroboric acid; solvent-free; dihydropyrimidin-2(1H)-ones;
D O I
10.1016/j.catcom.2006.05.026
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient synthesis of dihydropyrimidinones from the aldehyde, 1,3-dicarbonyl compound and urea (thiourea) under solvent-free conditions, using fluoroboric acid as the catalyst, is described. Compared with the classical Biginelli reaction conditions, this new protocol has the advantage of high yields, short reaction time and simplicity in the experimental procedure. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:123 / 126
页数:4
相关论文
共 20 条
[1]  
Akiyama T, 2002, ADV SYNTH CATAL, V344, P338, DOI 10.1002/1615-4169(200206)344:3/4<338::AID-ADSC338>3.0.CO
[2]  
2-O
[3]   A highly stereo-divergent Mannich-type reaction catalyzed by Bronsted acid in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
TETRAHEDRON LETTERS, 2001, 42 (24) :4025-4028
[4]   Bronsted acid-catalyzed aza Diels-Alder reaction of Danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
TETRAHEDRON LETTERS, 1999, 40 (44) :7831-7834
[5]   HBF4 catalyzed Mannich-type reaction in aqueous media [J].
Akiyama, T ;
Takaya, J ;
Kagoshima, H .
SYNLETT, 1999, (07) :1045-1048
[6]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].
ATWAL, KS ;
SWANSON, BN ;
UNGER, SE ;
FLOYD, DM ;
MORELAND, S ;
HEDBERG, A ;
OREILLY, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811
[7]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[8]   Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines [J].
Chakraborti, AK ;
Gulhane, R .
TETRAHEDRON LETTERS, 2003, 44 (17) :3521-3525
[9]   Indium(III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction [J].
Fu, NY ;
Yuan, YF ;
Cao, Z ;
Wang, SW ;
Wang, JT ;
Peppe, C .
TETRAHEDRON, 2002, 58 (24) :4801-4807
[10]   An efficient one-pot synthesis of dihydropyrimidinones by a samarium diiodide catalyzed Biginelli reaction under solvent-free conditions [J].
Han, XY ;
Xu, F ;
Luo, YQ ;
Shen, Q .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1500-1503