Choline chloride/urea as a deep eutectic solvent/organocatalyst promoted three-component synthesis of 3-aminoimidazo-fused heterocycles via Groebke-Blackburn-Bienayme process

被引：42

作者：

Shaabani, Ahmad ^{[1
]}

Hooshmand, Seyyed Emad ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Fac Chem, GC, POB 19396-4716, Tehran, Iran

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 03期

基金：

美国国家科学基金会;

关键词：

Deep eutectic solvents; GBB reaction; Multicomponent reactions; Isocyanide chemistry; SULFURIC-ACID; IONIC LIQUIDS; SOLVENTS; EFFICIENT; MIXTURES; CATALYST; FACILE; DERIVATIVES; IMIDAZOLE; ALDEHYDES;

D O I：

10.1016/j.tetlet.2015.12.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic activity of urea-, metal- and organic acid-based/choline chloride deep eutectic solvents/organocatalysts was investigated for the synthesis of 3-aminoimidazo-fused heterocycles via a one-pot domino reaction of an aldehyde, an isocyanide and 2-aminoheterocycles. The urea-based/choline chloride system exhibited significant catalytic activity for the reaction and could be reused in four consecutive reactions with no considerable loss in catalytic activity. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：310 / 313

页数：4

共 54 条

[1] Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids [J].

Abbott, AP ;

Boothby, D ;

Capper, G ;

Davies, DL ;

Rasheed, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :9142-9147

[2] Novel solvent properties of choline chloride/urea mixtures [J].

Abbott, AP ;

Capper, G ;

Davies, DL ;

Rasheed, RK ;

Tambyrajah, V .

CHEMICAL COMMUNICATIONS, 2003, (01) :70-71

[3] Catalyst-free three-component reaction between 2-aminopyridines (or 2-aminothiazoles), aldehydes, and isocyanides in water [J].

Adib, Mehdi ;

Mahdavi, Mohammad ;

Noghani, Mahsa Alizadeh ;

Mirzaei, Peiman .

TETRAHEDRON LETTERS, 2007, 48 (41) :7263-7265

[4] DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY [J].

ALMIRANTE, L ;

POLO, L ;

MUGNAINI, A ;

PROVINCIALI, E ;

RUGARLI, P ;

BIANCOTTI, A ;

GAMBA, A ;

MURMANN, W .

JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) :305-+

[5] A facile acidic choline chloride-p-TSA DES-catalysed dehydration of fructose to 5-hydroxymethylfurfural [J].

Assanosi, Amhamed A. ;

Farah, Mohamed M. ;

Wood, Joseph. ;

Al-Duri, Bushra .

RSC ADVANCES, 2014, 4 (74) :39359-39364

[6] Greener synthesis of spirooxindole in deep eutectic solvent [J].

Azizi, Najmedin ;

Dezfooli, Sahar ;

Hashemi, Mohammad Mahmoudi .

JOURNAL OF MOLECULAR LIQUIDS, 2014, 194 :62-67

[7] An atom-economic and odorless thia-Michael addition in a deep eutectic solvent [J].

Azizi, Najmedin ;

Yadollahy, Zahra ;

Rahimzadeh-Oskooee, Amin .

TETRAHEDRON LETTERS, 2014, 55 (10) :1722-1725

[8] Greener construction of 4H-chromenes based dyes in deep eutectic solvent [J].

Azizi, Najmedin ;

Mariami, Mahboobe ;

Edrisi, Mahtab .

DYES AND PIGMENTS, 2014, 100 :215-221

[9] Synthesis of imidazo[1,2-a]pyridines: a decade update [J].

Bagdi, Avik Kumar ;

Santra, Sougata ;

Monir, Kamarul ;

Hajra, Alakananda .

CHEMICAL COMMUNICATIONS, 2015, 51 (09) :1555-1575

[10]

Bienaymé H, 1998, ANGEW CHEM INT EDIT, V37, P2234, DOI 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO

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