Efficient Ce(NO3)3•6H2O-catalyzed solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones

被引:56
作者
Adib, Mehdi [1 ]
Ghanbary, Khadijeh [1 ]
Mostofi, Manizheh [1 ]
Ganjali, Mohammad Reza [1 ]
机构
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
关键词
dihydropyrimidinones; cerium(III) nitrate; Biginelli reaction; solvent-free synthesis;
D O I
10.3390/11080649
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Cerium(111) nitrate hexahydrate efficiently catalyzes the three-component Biginelli reaction under solvent-free conditions of an aldehyde, a beta-keto ester or beta-diketone and urea or thiourea to afford the corresponding 3,4-dihydropyrimidin-2(1H)ones or -thiones in excellent yields.
引用
收藏
页码:649 / 654
页数:6
相关论文
共 30 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]   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
[3]   In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia [J].
Barrow, JC ;
Nantermet, PG ;
Selnick, HG ;
Glass, KL ;
Rittle, KE ;
Gilbert, KF ;
Steele, TG ;
Homnick, CF ;
Freidinger, RM ;
Ransom, RW ;
Kling, P ;
Reiss, D ;
Broten, TP ;
Schorn, TW ;
Chang, RSL ;
O'Malley, SS ;
Olah, TV ;
Ellis, JD ;
Barrish, A ;
Kassahun, K ;
Leppert, P ;
Nagarathnam, D ;
Forray, C .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2703-2718
[4]   The Biginelli condensation:: A novel and efficient regioselective synthesis of dihydropyrimidin-2(1H)-ones using lithium bromide [J].
Baruah, PP ;
Gadhwal, S ;
Prajapati, D ;
Sandhu, JS .
CHEMISTRY LETTERS, 2002, (10) :1038-1039
[5]   An efficient, high yield protocol for the one-pot synthesis of dihydropyrimidin-2(1H)-ones catalyzed by iodine [J].
Bhosale, RS ;
Bhosale, SV ;
Bhosale, SV ;
Wang, TY ;
Zubaidha, PK .
TETRAHEDRON LETTERS, 2004, 45 (49) :9111-9113
[6]  
Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360
[7]   Large scale Biginelli reaction via water-based biphasic media: a green chemistry strategy [J].
Bose, AK ;
Manhas, MS ;
Pednekar, S ;
Ganguly, SN ;
Dang, H ;
He, W ;
Mandadi, A .
TETRAHEDRON LETTERS, 2005, 46 (11) :1901-1903
[8]   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
[9]   Dissecting cellular processes using small molecules: identification of colchicine-like, taxol-like and other small molecules that perturb mitosis [J].
Haggarty, SJ ;
Mayer, TU ;
Miyamoto, DT ;
Fathi, R ;
King, RW ;
Mitchison, TJ ;
Schreiber, SL .
CHEMISTRY & BIOLOGY, 2000, 7 (04) :275-286
[10]  
Kappe CO, 1997, TETRAHEDRON, V53, P2803