Room temperature ionic liquid promoted improved and rapid synthesis of 2,4,5-triaryl imidazoles from aryl aldehydes and 1,2-diketones or α-hydroxyketone

被引:291
作者
Siddiqui, SA [1 ]
Narkhede, UC [1 ]
Palimkar, SS [1 ]
Daniel, T [1 ]
Lahoti, RJ [1 ]
Srinivasan, KV [1 ]
机构
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
关键词
2,4,5-triaryl imidazoles; ionic liquid (IL); ammonium acetate; benzaldehydes; 1,2-diketones; alpha-hydroxyketone;
D O I
10.1016/j.tet.2005.01.116
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved and rapid one-pot synthesis of 2,4,5-triaryl imidazoles in a room temperature ionic liquid is described, which does not need any added catalyst. Different ionic liquids based on 1-n-butyl and 1,3-di-n-butyl imidazolium salts were screened and their efficacy in terms of acidity and polarity have been correlated with yields and reaction period. The one-pot methodology resulting in excellent isolated yields in short reaction times is characterized by simple work up procedures and efficient recovery and recycling of the ionic liquid, which acts as a promoter. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3539 / 3546
页数:8
相关论文
共 39 条
[1]   A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation [J].
Balalaie, S ;
Hashemi, MM ;
Akhbari, M .
TETRAHEDRON LETTERS, 2003, 44 (08) :1709-1711
[2]   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
[3]   Parallel synthesis of substituted imidazoles from 1,2-aminoalcohols [J].
Bleicher, KH ;
Gerber, F ;
Wüthrich, Y ;
Alanine, A ;
Capretta, A .
TETRAHEDRON LETTERS, 2002, 43 (43) :7687-7690
[4]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[5]   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
[6]  
CLARK NG, 1975, TETRAHEDRON LETT, P2717
[7]   Parallel synthesis of 1,2,4-trisubstituted imidazoles via N-alkyl-N-(β-keto)amides using a carbazate linker [J].
Cobb, JM ;
Grimster, N ;
Khan, N ;
Lai, JYQ ;
Payne, HJ ;
Payne, LJ ;
Raynham, T ;
Taylor, J .
TETRAHEDRON LETTERS, 2002, 43 (42) :7557-7560
[8]   The action of ammonia on benzil [J].
Davidson, D ;
Weiss, M ;
Jelling, M .
JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :319-327
[9]  
Debus H., 1858, LIEBIGS ANN CHEM, V107, P199, DOI [10.1002/jlac.18581070209, DOI 10.1002/JLAC.18581070209]
[10]   Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids [J].
Deshmukh, RR ;
Rajagopal, R ;
Srinivasan, KV .
CHEMICAL COMMUNICATIONS, 2001, (17) :1544-1545