Biginelli reaction starting directly from alcohols

被引：74
作者：
Garima [1 ]
Srivastava, Vishnu P. [1 ]
Yadav, Lal Dhar S. [1 ]
机构：
[1] Univ Allahabad, Dept Chem, Green Synth Lab, Allahabad 211002, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 49期
关键词：
Biginelli reaction; 3,4-Dihydropyrimidin-2(1H)-ones; Ionic liquids; Cyclocondensation reactions; Alcohols; Oxidation; ONE-POT SYNTHESIS; CALCIUM-CHANNEL BLOCKERS; ACIDIC IONIC LIQUIDS; ACTIVATED ALCOHOLS; MANGANESE-DIOXIDE; OXIDATION; SOLVENT; EFFICIENT; CATALYST; ESTERS;
D O I：
10.1016/j.tetlet.2010.09.141
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient of one-pot oxidative access to 3,4-dihydropyrimidin-2-(1H)-ones directly from aromatic alcohols under mild conditions is reported. The protocol involves 1-methylimidazolium hydrogen sulphate [Hmim]HSO4 catalyzed oxidation of aromatic alcohols to aromatic aldehydes with NaNO3 followed by their cyclocondensation with 1,3-dicarbonyl compounds and urea in the same reaction vessel at 80 degrees C within 2-4 h to afford 3,4-dihydropyrimidin-2-(1H)-ones in 55-97% overall yields. Thus, the present work utilizing alcohols instead of aldehyde in Biginelli reaction is a valid and green alternative to the classical synthesis of 3,4-dihydropyrimidin-2-(1H)-ones. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6436 / 6438
页数：3
相关论文
共 55 条
[41]   Biginelli reactions catalyzed by hydrazine type organocatalyst [J].
Suzuki, Ichiro ;
Wata, Yukari ;
Takeda, Kei .
TETRAHEDRON LETTERS, 2008, 49 (20) :3238-3241
[42]   Tandem oxidation processes using manganese dioxide: Discovery, applications, and current studies [J].
Taylor, RJK ;
Reid, M ;
Foot, J ;
Raw, SA .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (11) :851-869
[43]  
Tietze L.F., 2006, Domino Reactions in Organic Synthesis
[44]   Domino reactions in organic synthesis [J].
Tietze, LF .
CHEMICAL REVIEWS, 1996, 96 (01) :115-136
[45]  
Wang M, 2005, J CHEM RES, P691
[46]  
Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO
[47]  
2-5
[48]  
WASSERSCHEID T, 2003, IONIC LIQUIDS ORGANI
[49]   Room-temperature ionic liquids. Solvents for synthesis and catalysis [J].
Welton, T .
CHEMICAL REVIEWS, 1999, 99 (08) :2071-2083
[50]   Bromodimethylsulfonium bromide (BDMS) in ionic liquid: a mild and efficient catalyst for Beckmann rearrangement [J].
Yadav, Lai Dhar S. ;
Garima ;
Srivastava, Vishnu P. .
TETRAHEDRON LETTERS, 2010, 51 (04) :739-743
123456