1-Sulfopyridinium chloride: Green and expeditious ionic liquid for the one-pot synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones under solvent-free conditions

被引:15
作者
Velpula, Ravibabu [1 ]
Banothu, Janardhan [1 ]
Gali, Rajitha [1 ]
Deshineni, Rajitha [2 ]
Bavantula, Rajitha [1 ]
机构
[1] Natl Inst Technol, Dept Chem, Warangal 506004, Andhra Pradesh, India
[2] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
Fused 3,4-dihydropyrimidin-2(1H)-ones; One-pot three component reaction; Solvent-free condition; 1-Sulfopyridinium chloride; Thiones; EFFICIENT SYNTHESIS; BIGINELLI-TYPE; SULFURIC-ACID; SULFAMIC ACID; CATALYST; 3,4-DIHYDROPYRIMIDIN-2-(1H)-ONES/THIONES; DIHYDROPYRIMIDINONES; PROTOCOL;
D O I
10.1016/j.cclet.2014.11.030
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
1-Sulfopyridinium chloride portrayed as an efficient and recyclable ionic liquid for the synthesis of fused 3,4-dihydropyrimidin-2(1H)-ones and thiones via a modified Biginelli reaction involving one-pot three component condensation of 6-methoxy-1-tetralone, arylaldehydes and urea/thiourea under solvent-free conditions. Analytically pure products are formed within 10-20 min in excellent yields. (C) 2014 R. Bavantula. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
引用
收藏
页码:309 / 312
页数:4
相关论文
共 28 条
[1]   Antimalarial activity and synthesis of new trisubstituted pyrimidines [J].
Agarwal, A ;
Srivastava, K ;
Puri, SK ;
Chauhan, PMS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (12) :3130-3132
[2]   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
[3]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[4]   Efficient Biginelli reaction catalyzed by sulfamic acid or silica sulfuric acid under solvent-free conditions [J].
Chen, Wei-Yi ;
Qin, Su-Dong ;
Jin, Jian-Rong .
SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) :47-52
[5]   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
[6]   Searching for a direct preparation of dihydropyrimidine-5-carboxamides under Biginelli reaction conditions [J].
Couto, Irantzu ;
Tellitu, Imanol ;
Dominguez, Esther .
ARKIVOC, 2011, :115-126
[7]   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
[8]   Small molecule modulators of endogenous and co-chaperone-stimulated Hsp70 ATPase activity [J].
Fewell, SW ;
Smith, CM ;
Lyon, MA ;
Dumitrescu, TP ;
Wipf, P ;
Day, BW ;
Brodsky, JL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (49) :51131-51140
[9]   One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Catalyzed by Acidic Ionic Liquids Under Solvent-Free Conditions [J].
Gui, Jianzhou ;
Liu, Dan ;
Wang, Chan ;
Lu, Feng ;
Lian, Jingzhao ;
Jiang, Heng ;
Sun, Zhaolin .
SYNTHETIC COMMUNICATIONS, 2009, 39 (19) :3436-3443
[10]   Unprecedented catalytic three component one-pot condensation reaction: An efficient synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones [J].
Hu, EH ;
Sidler, DR ;
Dolling, UH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3454-3457