Solvent free synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones catalyzed by N,O-bis(trimethylsilyl)acetamide and dicyclohexyl carbodimide

被引:17
作者
Murthy, Y. L. N. [1 ]
Rajack, Abdul [1 ,2 ]
Yuvaraj, Kanithi [1 ]
机构
[1] Andhra Univ, Dept Organ Chem Foods Drugs & Water, Visakhapatnam 530003, Andhra Pradesh, India
[2] MVGR Coll Engn, Dept Sci & Humanities, Vijayanagaram 535005, India
关键词
N; O-Bis(trimethylsilyl)acetamide; Dicyclohexyl carbodimide; Solvent free; 3,4-Dihydropyrimidinones; 3,4-Dihydropyrimidithiones; ONE-POT SYNTHESIS; CALCIUM-CHANNEL BLOCKERS; BIGINELLI-TYPE; EFFICIENT SYNTHESIS; REUSABLE CATALYST; GREEN APPROACH; ACID-ESTERS; DIHYDROPYRIMIDINONES; CONDENSATION; 3-COMPONENT;
D O I
10.1016/j.arabjc.2012.04.046
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein, the usage of N,O-bis(trimethylsilyl) acetamide (BSA) and dicyclohexyl carbodimide (DCC) as two new catalysts for three component condensation of an aldehyde, ethyl acetoacetate and urea/thiourea under solvent free conditions at 100 degrees C to afford the corresponding 3,4-dihydropyrimidine-2-(1H)-ones/thiones (DHPMs) in good to excellent yields. A comparative study of these two catalysts was made and presented. (C) 2012 Production and hosting by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码:S1740 / S1746
页数:7
相关论文
共 57 条
[1]  
Aswal K.S., 1990, J MED CHEM, V33, P2629
[2]  
Atu L. K., 2007, TETRAHEDRON LETT, V48, P4569
[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]  
Bahar Ahmed, 2009, TETRAHEDRON LETT, V50, P2889
[5]   Highly Efficient Solvent-Free Synthesis of Dihydropyrimidinones Catalyzed by Zinc Oxide [J].
Bahrami, Kiumars ;
Khodaei, Mohammad Mehdi ;
Farrokhi, Azita .
SYNTHETIC COMMUNICATIONS, 2009, 39 (10) :1801-1808
[6]   Solvent-free synthesis of dihydropyrimidinones catalyzed by alumina sulfuric acid at room temperature [J].
Besoluk, S. ;
Kucukislamoglu, M. ;
Nebioglu, M. ;
Zengin, M. ;
Arslan, M. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2008, 5 (01) :62-66
[7]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[8]   Antiarrhythmic activity of 4,6-di(het)aryl-5-nitro-3,4-dihydropyrimidin-(1 H)-2-ones and its effects on arterial pressure in rats [J].
Bryzgalov, AO ;
Dolgikh, MP ;
Sorokina, IV ;
Tolstikova, TG ;
Sedova, VF ;
Shkurko, OP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (05) :1418-1420
[9]   Synthesis and in vitro microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones [J].
Chitra, S. ;
Devanathan, D. ;
Pandiarajan, K. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (01) :367-371
[10]  
Christopher B., 2006, BIOORG MED CHEM LETT, V16, P3504