Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide

被引:168
作者
Hasaninejad, Alireza [1 ]
Zare, Abdolkarim
Shekouhy, Mohsen [1 ]
Rad, Javad Ameri [1 ]
机构
[1] Persian Gulf Univ, Fac Sci, Dept Chem, Bushehr 75169, Iran
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 06期
关键词
SOLVENT-FREE SYNTHESIS; TETRASUBSTITUTED IMIDAZOLES; SUBSTITUTED IMIDAZOLES; HIGHLY-EFFICIENT; 1,2,4,5-TETRASUBSTITUTED IMIDAZOLES; CONJUGATE ADDITION; SILICA-GEL; 4-COMPONENT; REAGENT; DIHYDROXYLATION;
D O I
10.1021/cc100097m
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A catalyst-free one-pot four component methodology for the synthesis of 1,2,4,5-substituted imidazoles under conventional heating and microwave irradiation using 1-butyl-3-methylimidazolium bromide, [Bmim]Br, as a neutral reaction media is described. A broad range of structurally diverse aldehydes (aromatic aldehydes bearing electron withdrawing and/or electron releasing groups as well as heteroaromatic aldehydes) and primary amines (aromatic and aliphatic) were applied successfully, and corresponding products were obtained in good to excellent yields without any byproduct.
引用
收藏
页码:844 / 849
页数:6
相关论文
共 60 条
[1]  
ABRAHAMS SL, 1989, J PHARMACOL EXP THER, V249, P359
[2]   Characterizing ionic liquids on the basis of multiple solvation interactions [J].
Anderson, JL ;
Ding, J ;
Welton, T ;
Armstrong, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14247-14254
[3]   One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation [J].
Balalaie, S ;
Arabanian, A .
GREEN CHEMISTRY, 2000, 2 (06) :274-276
[4]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[5]  
2-A
[6]  
Chauvin Y, 1995, ANGEW CHEM INT EDIT, V34, P2698
[7]   An efficient synthesis of tetrasubstituted imidazoles from N-(2-oxo)-amides [J].
Claiborne, CF ;
Liverton, NJ ;
Nguyen, KT .
TETRAHEDRON LETTERS, 1998, 39 (49) :8939-8942
[8]   An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O [J].
Das Sharma, Salkat ;
Hazarika, Parasa ;
Konwar, Dilip .
TETRAHEDRON LETTERS, 2008, 49 (14) :2216-2220
[9]   The action of ammonia on benzil [J].
Davidson, D ;
Weiss, M ;
Jelling, M .
JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :319-327
[10]   An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature [J].
Deb, WL ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2006, 47 (09) :1441-1443