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：293

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

来源：

TETRAHEDRON | 2005年 / 61卷 / 14期

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

页码：3539 / 3546

页数：8

共 39 条

[21]

Maier T., 1989, Google Patents, Patent No. [4820335A, 4820335, 1154820335 A]

[22] THALLIUM IN ORGANIC SYNTHESIS .21. DIRECT CONVERSION OF CHALCONES INTO BENZILS WITH THALLIUM(III) NITRATE (TTN) [J].

MCKILLOP, A ;

SWANN, BP ;

TAYLOR, EC .

TETRAHEDRON LETTERS, 1970, (60) :5281-+

[23] Room temperature ionic liquid promoted regioselective synthesis of 2-aryl benzimidazoles, benzoxazoles and benzthiazoles under ambient conditions [J].

Nadaf, RN ;

Siddiqui, SA ;

Daniel, T ;

Lahoti, RJ ;

Srinivasan, KV .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 214 (01) :155-160

[24] Ionic liquid-promoted regiospecific Friedlander annulation: Novel synthesis of quinolines and fused polycyclic quinolines [J].

Palimkar, SS ;

Siddiqui, SA ;

Daniel, T ;

Lahoti, RJ ;

Srinivasan, KV .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9371-9378

[25]

PERRIN DD, 1982, IONIZATION CONSTANT

[26]

PHILLIPS AP, 1982, Patent No. 58890

[27] Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions [J].

Rajagopal, R ;

Jarikote, DV ;

Srinivasan, KV .

CHEMICAL COMMUNICATIONS, 2002, (06) :616-617

[28] Ionic liquid promoted regioselective monobromination of aromatic substrates with N-bromosuccinimide [J].

Rajagopal, R ;

Jarikote, DV ;

Lahoti, RJ ;

Daniel, T ;

Srinivasan, KV .

TETRAHEDRON LETTERS, 2003, 44 (09) :1815-1817

[29] Imidazole libraries on solid support [J].

Sarshar, S ;

Siev, D ;

Mjalli, AMM .

TETRAHEDRON LETTERS, 1996, 37 (06) :835-838

[30]

Schmierer R., 1987, German Patent, Patent No. 361464

← 1 2 3 4 →