An Efficient Biginelli One-Pot Synthesis of New Benzoxazole-Substituted Dihydropyrimidinones and Thiones Catalysed by Alumina-Supported Trifluoromethane Sulfonic Acid Under Solvent Free Conditions

被引:16
作者
Arjun, M. [2 ]
Sridhar, D. [2 ]
Chari, M. Adharvana [3 ]
Sarangapani, M. [1 ]
机构
[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India
[2] Kakatiya Univ, Univ Coll Pharmaceut Sci, Warangal 506009, Andhra Pradesh, India
[3] Kyung Hee Univ, Dept Appl Chem, Seoul, South Korea
关键词
CALCIUM-CHANNEL BLOCKERS; HIGH-YIELD SYNTHESIS; ANTIHYPERTENSIVE AGENTS; HETEROGENEOUS CATALYST; MICROWAVE IRRADIATION; SILICA; ESTERS; DERIVATIVES; PYRIMIDINES; PROTOCOL;
D O I
10.1002/jhet.29
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of benzoxazole-substituted 3,4-dihydropyrimidinones (DHPMs) using alumina supported trifluoromethane sulfonic acid as the catalyst for the first time from an aldehyde, P-keto ester, and benzoxazole-substituted urea and thiourea under solvent-free conditions is described. When compared with the classical Biginelli reaction conditions, this new method consistently has the advantage of excellent yields (80-93%) and short reaction time (30-120 Minutes) at 120 degrees C temperature.
引用
收藏
页码:119 / 123
页数:5
相关论文
共 37 条
[1]   Tangstophosphoric acid (H3PW12O40):: An efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones [J].
Amini, Mostafa Mohammadpour ;
Shaabani, Ahmad ;
Bazgir, Ayoob .
CATALYSIS COMMUNICATIONS, 2006, 7 (11) :843-847
[2]  
ATWAL KS, 1987, HETEROCYCLES, V26, P1189
[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]   SUBSTITUTED 1,4-DIHYDROPYRIMIDINES .3. SYNTHESIS OF SELECTIVELY FUNCTIONALIZED 2-HETERO-1,4-DIHYDROPYRIMIDINES [J].
ATWAL, KS ;
ROVNYAK, GC ;
OREILLY, BC ;
SCHWARTZ, J .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5898-5907
[5]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[7]   Silica gel/NaHSO4:: An efficient and recyclable heterogeneous catalyst for high yield synthesis of 1,5-benzodiazepine derivatives under microwave irradiation [J].
Chari, M. Adharvana ;
Shobha, D. ;
Syamasundar, K. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (04) :929-932
[8]   Silica gel/FeCl3:: An efficient and recyclable heterogenous catalyst for one step synthesis of 4(3H)-quinazolinones under solvent free conditions [J].
Chari, M. Adharvana ;
Shobha, D. ;
Mukkanti, K. .
CATALYSIS COMMUNICATIONS, 2006, 7 (10) :787-790
[9]   Silicagel supported sodium hydrogensulfate as a heterogenous catalyst for high yield synthesis of 3,4-dihydropyrimidin-2 (1H)-ones [J].
Chari, MA ;
Syamasundar, K .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 221 (1-2) :137-139
[10]  
CHEN W, 2007, J CATAL COMMUN, V8, P123