Ascorbic acid-Catalyzed One-Pot Three-Component Biginelli Reaction: A Practical and Green Approach towards Synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones

被引:13
作者
Sehout, Imene [1 ]
Boulcina, Raouf [1 ]
Boumoud, Boudjemaa [1 ]
Berree, Fabienne [2 ]
Carboni, Bertrand [2 ]
Debache, Abdelmadjid [1 ]
机构
[1] Univ Constantine 1, Fac Sci Exactes, Dept Chim, Lab Synth Mol Interets Biol, Constantine 25000, Algeria
[2] Univ Rennes 1, UMR CNRS 6226, F-35042 Rennes, France
关键词
Multicomponent reaction; one-pot synthesis; Biginelli reaction; 3; 4dihydropyrimidin-2(1H)-ones/thiones; ascorbic acid; CALCIUM-CHANNEL BLOCKERS; SOLVENT-FREE BIGINELLI; EFFICIENT SYNTHESIS; REUSABLE CATALYST; IMPROVED PROTOCOL; CHLORIDE; DIHYDROPYRIMIDINONES; MILD; 3,4-DIHYDROPYRIMIDIN-2-(1H)-ONES; TRIFLATE;
D O I
10.2174/15701786113109990014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via a three-component Biginelli condensation of aldehyde, ethyl acetoacetate, and urea or thiourea in the presence of a catalytic amount of ascorbic acid (5 mol %) is described. The reaction proceeded efficiently under solvent-free conditions at 80 degrees C to afford the desired products in moderate to good yields.
引用
收藏
页码:463 / 467
页数:5
相关论文
共 49 条
[1]   Iron(III) trifluoro acetate and trifluoromethanesulfonate: Recyclable Lewis acid catalysts for one-pot synthesis of 3,4-dihydropyrimidinones or their sulfur analogues and 1,4-dihydropyridines via solvent-free Biginelli and Hantzsch condensation protocols [J].
Adibi, Hadi ;
Samimi, Heshmat Allah ;
Beygzadch, Mojtaba .
CATALYSIS COMMUNICATIONS, 2007, 8 (12) :2119-2124
[2]   An improved synthesis of Biginelli-type compounds via phase-transfer catalysis [J].
Ahmed, Bahar ;
Khan, Riaz A. ;
Habibullah ;
Keshari, Manoj .
TETRAHEDRON LETTERS, 2009, 50 (24) :2889-2892
[3]   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
[4]   Synthesis and anti-inflammatory activity of some [4,6-(4-substituted aryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]-acetic acid derivatives [J].
Bahekar, SS ;
Shinde, DB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (07) :1733-1736
[5]   Trichloroisocyanuric acid, a new and efficient catalyst for the synthesis of dihydropyrimidinones [J].
Bigdeli, Mohammad A. ;
Jafari, Saeed ;
Mahdavinia, Gholam Hossein ;
Hazarkhani, Hassan .
CATALYSIS COMMUNICATIONS, 2007, 8 (11) :1641-1644
[6]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[7]   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
[8]   Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1H)-ones under solvent-free conditions [J].
De, SK ;
Gibbs, RA .
SYNTHESIS-STUTTGART, 2005, (11) :1748-1750
[9]  
de Souza ALF, 2008, HETEROCYCL COMMUN, V14, P357
[10]   A one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones catalyzed by triphenylphosphine as Lewis base [J].
Debache, Abdelmadjid ;
Amimour, Mouna ;
Belfaitah, Ali ;
Rhouati, Salah ;
Carboni, Bertrand .
TETRAHEDRON LETTERS, 2008, 49 (42) :6119-6121