A Microwave-Assisted Bismuth Nitrate-Catalyzed Unique Route Toward 1,4-Dihydropyridines

被引:54
作者
Bandyopadhyay, Debasish [1 ]
Maldonado, Stephanie [1 ]
Banik, Bimal K. [1 ]
机构
[1] Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78539 USA
关键词
microwave; 1,4-dihydropyridines; catalysis; green synthesis; bismuth nitrate; POLYCYCLIC AROMATIC-COMPOUNDS; ORGANIC-CHEMISTRY APPLICATION; N-SUBSTITUTED PYRROLES; ONE-POT SYNTHESIS; HANTZSCH 1,4-DIHYDROPYRIDINES; ANTICANCER AGENTS; ELECTROPHILIC SUBSTITUTION; MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; BETA-LACTAMS;
D O I
10.3390/molecules17032643
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
The classical Hantzsch reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful 1,4-dihydropyridine derivatives. Bismuth nitrate pentahydrate under microwave irradiation is proven to act as a very efficient catalyst for a one-pot, three-component synthesis of 1,4-dihydropyridines in excellent yields from diverse amines/ammonium acetate, aldehydes and 1,3-dicarbonyl compounds within 1-3 min under solvent-free conditions. The present environmentally benign procedure for the synthesis of 1,4-dihydropyridines is suitable for library synthesis and it will find application in the synthesis of potent biologically active molecules. The excellent yield and extreme rapidity of the method is due to a concurrent effect of the catalyst and microwave irradiation.
引用
收藏
页码:2643 / 2662
页数:20
相关论文
共 74 条
[1]
Abrego D, 2011, HETEROCYCL LETT, V1, P94
[2]
Molecular iodine-catalyzed one-pot synthesis of some new Hantzsch 1,4-dihydropyridines at ambient temperature [J].
Akbari, J. D. ;
Tala, S. D. ;
Dhaduk, M. F. ;
Joshi, H. S. .
ARKIVOC, 2008, :126-+
[3]
Andoh-Baidoo R., 2011, Heterocycl Lett, V1, P107
[4]
LONG-ACTING DIHYDROPYRIDINE CALCIUM-ANTAGONISTS .1. 2-ALKOXYMETHYL DERIVATIVES INCORPORATING BASIC SUBSTITUENTS [J].
ARROWSMITH, JE ;
CAMPBELL, SF ;
CROSS, PE ;
STUBBS, JK ;
BURGES, RA ;
GARDINER, DG ;
BLACKBURN, KJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (09) :1696-1702
[5]
Bandyopadhyay D., 2011, HETEROCYCL LETT, P65
[6]
Bandyopadhyay D, 2011, HETEROCYCL LETT, V1, P71
[7]
Polycyclic aromatic compounds as anticancer agents: Evaluation of synthesis and in vitro cytotoxicity [J].
Bandyopadhyay, Debasish ;
Granados, Jose C. ;
Short, John D. ;
Banik, Bimal K. .
ONCOLOGY LETTERS, 2012, 3 (01) :45-49
[8]
An Effective Microwave-Induced Iodine-Catalyzed Method for the Synthesis of Quinoxalines via Condensation of 1,2-Diamines with 1,2-Dicarbonyl Compounds [J].
Bandyopadhyay, Debasish ;
Mukherjee, Sanghamitra ;
Rodriguez, Robert R. ;
Banik, Bimal K. .
MOLECULES, 2010, 15 (06) :4207-4212
[9]
An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions [J].
Bandyopadhyay, Debasish ;
Mukherjee, Sanghamitra ;
Banik, Bimal K. .
MOLECULES, 2010, 15 (04) :2520-2525
[10]
Microwave-Induced Stereocontrol of β-Lactam Formation with an N-Benzylidene-9,10-dihydrophenanthren-3-amine via Staudinger Cycloaddition [J].
Bandyopadhyay, Debasish ;
Banik, Bimal K. .
HELVETICA CHIMICA ACTA, 2010, 93 (02) :298-301