Synthesis of imidazo[1,2-a]pyridine in the presence of iodine-water catalytic system

被引：37

作者：

Siddiqui, I. R. ^{[1
]}

Rai, Pragati ^{[1
]}

Rahila ^{[1
]}

Srivastava, Anushree ^{[1
]}

Shamim, Shayna ^{[1
]}

机构：

[1] Univ Allahabad, Dept Chem, Lab Green Synth, Allahabad 211002, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 06期

关键词：

Imidazo[1,2-a]pyridine; Iodine; Aqueous medium; Eco-friendly; Multicomponent reaction; ONE-POT SYNTHESIS; MOLECULAR-IODINE; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; EFFICIENT; DERIVATIVES; 2-AMINOTHIAZOLES; INHIBITORS; ALDEHYDES; AGONISTS;

D O I：

10.1016/j.tetlet.2013.12.088

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have devised an expedient, cleaner, and environmentally friendly approach for 'on water' mediated synthesis of imidazo[1,2-a]pyridine derivatives. The synthesis involves in situ formation of imines followed by addition of alkyne to give the desired products in excellent yield. (C) 2014 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1159 / 1163

页数：5

相关论文

共 43 条

[1] A novel class of orally active non-peptide bradykinin B2 receptor antagonists.: 1.: Construction of the basic framework [J].

Abe, Y ;

Kayakiri, H ;

Satoh, S ;

Inoue, T ;

Sawada, Y ;

Imai, K ;

Inamura, N ;

Asano, M ;

Hatori, C ;

Katayama, A ;

Oku, T ;

Tanaka, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (04) :564-578

[2] An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines [J].

Adib, Mehdi ;

Sheibani, Esmail ;

Zhu, Long-Guan ;

Mirzaei, Peiman .

TETRAHEDRON LETTERS, 2008, 49 (34) :5108-5110

[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] Efficient synthesis of imidazo[1,2-a]pyridin-3(2H)-ones [J].

Adib, Mehdi ;

Mahdavi, Mohammad ;

Abbasi, Alireza ;

Jahromi, Amin Haghighat ;

Bijanzadeh, Hamid Reza .

TETRAHEDRON LETTERS, 2007, 48 (18) :3217-3220

[5] Pd-Cu catalyzed heterocyclization during Sonogashira coupling:: synthesis of 2-benzylimidazo[1,2-a]pyridine [J].

Bakherad, Mohammad ;

Nasr-Isfahani, Hossein ;

Keivanloo, Ali ;

Doostmohammadi, Nesa .

TETRAHEDRON LETTERS, 2008, 49 (23) :3819-3822

[6] An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions [J].

Bandyopadhyay, Debasish ;

Mukherjee, Sanghamitra ;

Banik, Bimal K. .

MOLECULES, 2010, 15 (04) :2520-2525

[7] General and Efficient Copper-Catalyzed Three-Component Coupling Reaction towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem [J].

Chernyak, Natalia ;

Gevorgyan, Vladimir .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (15) :2743-2746

[8] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[9] Recent progress in the pharmacology of imidazo[1,2-a]pyridines [J].

Enguehard-Gueiffier, Cecile ;

Gueiffier, Alain .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2007, 7 (09) :888-899

[10] Imidazo[1,2-a]pyrimidines as functionally selective and orally bioavailable GABA-α2/α3 binding site agonists for the treatment of anxiety disorders [J].

Goodacre, SC ;

Street, LJ ;

Hallett, DJ ;

Crawforth, JM ;

Kelly, S ;

Owens, AP ;

Blackaby, WP ;

Lewis, RT ;

Stanley, J ;

Smith, AJ ;

Ferris, P ;

Sohal, B ;

Cook, SM ;

Pike, A ;

Brown, N ;

Wafford, KA ;

Marshall, G ;

Castro, JL ;

Atack, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (01) :35-38

← 1 2 3 4 5 →