Iodine-ammonium acetate promoted reaction between 2-aminopyridine and aryl methyl ketones: a novel approach towards the synthesis of 2-arylimidazo[1,2-a]pyridines

被引：41

作者：

Kour, Dilpreet ^{[1
]}

Khajuria, Rajni ^{[1
]}

Kapoor, Kamal K. ^{[1
]}

机构：

[1] Univ Jammu, Dept Chem, Jammu 180006, India

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 40期

关键词：

Intramolecular cyclization; Ortoleva-King intermediate; 2-Aminopyridine; Aryl methyl ketones; NH4OAc; 2-Arylimidazo[1,2-a]pyridines; ONE-POT SYNTHESIS; MULTICOMPONENT SYNTHESIS; DIVERGENT SYNTHESIS; ANTIVIRAL ACTIVITY; EASY ACCESS; DERIVATIVES; FUNCTIONALIZATION; PYRIDINE; CYCLIZATION; ZOLIMIDINE;

D O I：

10.1016/j.tetlet.2016.08.058

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

I-2-NH4OAc was found to be an efficient system for the metal-free synthesis of diversely substituted imidazo[1,2-a]pyridines 3a-r from 2-aminopyridine 1 and aryl methyl ketones 2a-r in one pot. 2-Arylimidazo[1,2-a]pyridines 3a-r were obtained in good to excellent yields via in situ generation of an Ortoleva-King intermediate (pyridinium iodide), followed by NH4OAc-assisted cyclization. (C) 2016 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4464 / 4467

页数：4

相关论文

共 64 条

[1] 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-+

[2] 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

[3] Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale [J].

Bagdi, Avik Kumar ;

Rahman, Matiur ;

Santra, Sougata ;

Majee, Adinath ;

Hajra, Alakananda .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) :1741-1747

[4] Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397 [J].

Boggs, Sharon ;

Elitzin, Vassil I. ;

Gudmundsson, Kristjan ;

Martin, Michael T. ;

Sharp, Matthew J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2009, 13 (04) :781-785

[5] Imidazo[1,2-α]pyridines.: Part 2:: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors [J].

Byth, KF ;

Culshaw, JD ;

Green, S ;

Oakes, SE ;

Thomas, AP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2245-2248

[6] Synthesis and evaluation of two 18F-labeled 6-iodo-2-(4′-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine derivatives as prospective radioligands for β-amyloid in Alzheimer's disease [J].

Cai, LS ;

Chin, FT ;

Pike, VW ;

Toyama, H ;

Liow, JS ;

Zoghbi, SS ;

Modell, K ;

Briard, E ;

Shetty, HU ;

Sinclair, K ;

Donohue, S ;

Tipre, D ;

Kung, MP ;

Dagostin, C ;

Widdowson, DA ;

Green, M ;

Gao, W ;

Herman, MM ;

Ichise, M ;

Innis, RB .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (09) :2208-2218

[7] Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy [J].

Cai, Qun ;

Liu, Mei-Cai ;

Mao, Bi-Ming ;

Xie, Xuan ;

Jia, Feng-Cheng ;

Zhu, Yan-Ping ;

Wu, An-Xin .

CHINESE CHEMICAL LETTERS, 2015, 26 (07) :881-884

[8] Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines [J].

Cai, Zhong-Jian ;

Wang, Shun-Yi ;

Ji, Shun-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (13) :2686-2692

[9] Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization [J].

Cao, Hua ;

Zhan, Haiying ;

Lin, Yuanguang ;

Lin, Xiulian ;

Du, Zuodong ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2012, 14 (07) :1688-1691

[10] 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

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