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

页码：6436 / 6438

页数：3

共 55 条

[1] 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

[2]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[3]

Blackburn L, 2002, SYNLETT, P215

[4] Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].

Bose, DS ;

Fatima, L ;

Mereyala, HB .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590

[5] Passerini Three-Component Reaction of Alcohols under Catalytic Aerobic Oxidative Conditions [J].

Brioche, Julien ;

Masson, Geraldine ;

Zhu, Jieping .

ORGANIC LETTERS, 2010, 12 (07) :1432-1435

[6] Tandem inverse electron demand Diels-Alder, retro-Diels-Alder and intramolecular Diels-Alder sequences: one-pot synthesis of diaza-polycycles [J].

Bromley, William J. ;

Gibson, Mairi ;

Lang, Stuart ;

Raw, Steven A. ;

Whitwood, Adrian C. ;

Taylor, Richard J. K. .

TETRAHEDRON, 2007, 63 (26) :6004-6014

[7]

Bruce M.A., 1998, PCT Int. Appl. Chem. Abstr, Patent No. [9833791, 9833,791]

[8] Chloroferrate(III) ionic liquid:: Efficient and recyclable catalyst for solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones [J].

Chen, Xiaofen ;

Peng, Yanqing .

CATALYSIS LETTERS, 2008, 122 (3-4) :310-313

[9] Calcium fluoride: an efficient and reusable catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones and their corresponding 2(1H)thione: an improved high yielding protocol for the Biginelli reaction [J].

Chitra, S. ;

Pandiarajan, K. .

TETRAHEDRON LETTERS, 2009, 50 (19) :2222-2224

[10] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].

Cole, AC ;

Jensen, JL ;

Ntai, I ;

Tran, KLT ;

Weaver, KJ ;

Forbes, DC ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963

← 1 2 3 4 5 6 →