Three-component coupling reactions in ionic liquids: An improved protocol for the synthesis of 1,4-dihydropyridines

被引:79
作者
Yadav, JS [1 ]
Reddy, BVS [1 ]
Basak, AK [1 ]
Narsaiah, AV [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
D O I
10.1039/b210017g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three-component condensation of aldehyde, beta-ketoester and methyl 3-aminocrotonate proceeds smoothly in 1-n-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF4 or 1-n-butyl-3-methylimidazolium hexafluorophosphate [bmim]PF6 ionic liquids at room temperature under mild conditions to afford the corresponding 1,4-dihydropyridine derivatives in high yields. The recovered activated ionic liquids are recycled for four to five runs with no loss in activity.
引用
收藏
页码:60 / 63
页数:4
相关论文
共 27 条
[1]   SYNTHESIS OF 1,4-DIHYDROPYRIDINES UNDER MICROWAVE IRRADIATION [J].
ALAJARIN, R ;
VAQUERO, JJ ;
NAVIO, JLG ;
ALVAREZBUILLA, J .
SYNLETT, 1992, (04) :297-298
[2]  
BOCKER RH, 1986, J MED CHEM, V29, P1596
[3]   Hydrophobic, highly conductive ambient-temperature molten salts [J].
Bonhote, P ;
Dias, AP ;
Papageorgiou, N ;
Kalyanasundaram, K ;
Gratzel, M .
INORGANIC CHEMISTRY, 1996, 35 (05) :1168-1178
[4]   1,4-DIHYDROPYRIDINES - A BASIS FOR DEVELOPING NEW DRUGS [J].
BOSSERT, F ;
VATER, W .
MEDICINAL RESEARCH REVIEWS, 1989, 9 (03) :291-324
[5]   Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].
Cole, AC ;
Jensen, JL ;
Ntai, I ;
Tran, KLT ;
Weaver, KJ ;
Forbes, DC ;
Davis, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963
[6]   1,4-DIHYDROPYRIDINES AS ANTAGONISTS OF PLATELET-ACTIVATING-FACTOR .1. SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF 2-(4-HETEROCYCLYL)PHENYL DERIVATIVES [J].
COOPER, K ;
FRAY, MJ ;
PARRY, MJ ;
RICHARDSON, K ;
STEELE, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (17) :3115-3129
[7]   QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS FOR 1,4-DIHYDROPYRIDINE CALCIUM-CHANNEL ANTAGONISTS (NIFEDIPINE ANALOGS) - A QUANTUM CHEMICAL/CLASSICAL APPROACH [J].
GAUDIO, AC ;
KOROLKOVAS, A ;
TAKAHATA, Y .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (08) :1110-1115
[8]   Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines [J].
Gordeev, MF ;
Patel, DV ;
Gordon, EM .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :924-928
[9]   Approaches to combinatorial synthesis of heterocycles: Solid phase synthesis of pyridines and pyrido[2,3-d]pyrimidines [J].
Gordeev, MF ;
Patel, DV ;
Wu, J ;
Gordon, EM .
TETRAHEDRON LETTERS, 1996, 37 (27) :4643-4646
[10]   New developments in catalysis using ionic liquids [J].
Gordon, CM .
APPLIED CATALYSIS A-GENERAL, 2001, 222 (1-2) :101-117