Bronsted acidic ionic liquid catalyzed an efficient and eco-friendly protocol for the synthesis of 2,4,5-trisubstituted-1H-imidazoles under solvent-free conditions

被引：34

作者：

Banothu, Janardhan ^{[1
]}

Gali, Rajitha ^{[1
]}

Velpula, Ravibabu ^{[1
]}

Bavantula, Rajitha ^{[1
]}

机构：

[1] Natl Inst Technol, Dept Chem, Warangal 506004, Andhra Prades, India

来源：

ARABIAN JOURNAL OF CHEMISTRY | 2017年 / 10卷

关键词：

Eco-friendly; Imidazole; Ionic liquid; Solvent-free; Three component reaction; ONE-POT SYNTHESIS; HIGHLY SUBSTITUTED IMIDAZOLES; SULFONIC-ACID; DERIVATIVES; SYSTEM; CONDENSATION; ANALOGS; MILD;

D O I：

10.1016/j.arabjc.2013.10.022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple, highly efficient and eco-friendly protocol for the synthesis of 2,4,5-trisubstituted-1H-imidazoles via one-pot three component condensation of benzil/benzoin, aldehydes and ammonium acetate under solvent-free conditions has been achieved utilizing Bronsted acidic ionic liquid, (4-sulfobutyl)tris(4-sulfophenyl) phosphonium hydrogen sulfate as catalyst. The remarkable features of this methodology are excellent yields in shorter reaction times, cleaner reaction profile, and environmentally benign nature, use of non-toxic, readily synthesizable, inexpensive and recyclable catalyst. (C) 2013 King Saud University. Production and hosting by Elsevier B.V.

引用

页码：S2754 / S2761

页数：8

共 38 条

[1]

Ali R.K., 2012, MOL DIVERS, V14, P635

[2] Analogues of 4,5-bis(3,5-dichlorophenyl)-2-trifluoromethyl-1H-imidazole as potential antibacterial agents. [J].

Antolini, M ;

Bozzoli, A ;

Ghiron, C ;

Kennedy, G ;

Rossi, T ;

Ursini, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :1023-1028

[3] Bronsted acidic ionic liquid catalyzed highly efficient synthesis of chromeno pyrimidinone derivatives and their antimicrobial activity [J].

Banothu, Janardhan ;

Bavanthula, Rajitha .

CHINESE CHEMICAL LETTERS, 2012, 23 (09) :1015-1018

[4] BIOMIMETIC CHEMISTRY AND ARTIFICIAL ENZYMES - CATALYSIS BY DESIGN [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :146-153

[5] Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles [J].

Chary, Mahankhali Venu ;

Keerthysri, Nallani Chakravarthula ;

Vupallapati, Srinivasu V. N. ;

Lingaiah, N. ;

Kantevari, Srinivas .

CATALYSIS COMMUNICATIONS, 2008, 9 (10) :2013-2017

[6] Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles in water using p-dodecylbenzenesulfonic acid as catalyst [J].

Das, Biswanath ;

Kashanna, Jajula ;

Kumar, Rathod Aravind ;

Jangili, Paramesh .

MONATSHEFTE FUR CHEMIE, 2013, 144 (02) :223-226

[7] 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

[8] Bronsted acid ionic liquid [Et3NH][HSO4] as an efficient and reusable catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles [J].

Deng, Xiaocui ;

Zhou, Zhongqiang ;

Zhang, Aiqing ;

Xie, Guangyong .

RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) :1101-1108

[9] Ionic liquids. Green solvents for the future [J].

Earle, MJ ;

Seddon, KR .

PURE AND APPLIED CHEMISTRY, 2000, 72 (07) :1391-1398

[10]

Freedman J., 2009, NEW THERAPEUTIC AGEN, V3th

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