Metal- and base-free synthesis of imidazo[1,2-a]pyridines through elemental sulfur-initiated oxidative annulation of 2-aminopyridines and aldehydes

被引：31
作者：
Tan, Jing [1 ]
Ni, Penghui [1 ]
Huang, Huawen [1 ]
Deng, Guo-Jun [1 ,2 ,3 ]
机构：
[1] Xiangtan Univ, Coll Chem, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environm Friendly Chem & Applicat,Minist, Xiangtan 411105, Peoples R China
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; C-N; CYCLIZATION; HETEROCYCLES; DERIVATIVES; ZOLPIDEM; OXIDANT; KETONES; ACCESS; FUNCTIONALIZATION;
D O I：
10.1039/c8ob00981c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The elemental sulfur-promoted oxidative cyclization reaction for the efficient synthesis of substituted imidazo[1,2-a]pyridines has been developed. Easily available 2-aminopyridines and aldehydes were directly assembled in a highly atom-economical fashion through oxidative annulation under metal- and base-free conditions. Besides arylacetaldehydes, aliphatic aldehydes were also compatible with this system to deliver the alkyl-substituted imidazo[1,2-a]pyridines in excellent yields with the capability of gram-scale synthesis.
引用
收藏
页码：4227 / 4230
页数：4
相关论文
共 45 条
[1]   THE REACTION OF 2-AMINOPYRIDINE WITH ALPHA-HALO KETONES [J].
ADAMS, R ;
DIX, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (17) :4618-4620
[2]   Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines [J].
Adiyala, Praveen Reddy ;
Mani, Geeta Sai ;
Nanubolu, Jagadeesh Babu ;
Shekar, Kunta Chandra ;
Maurya, Ram Awatar .
ORGANIC LETTERS, 2015, 17 (17) :4308-4311
[3]   A Novel Solvent-Free Approach to Imidazole Containing Nitrogen-Bridgehead Heterocycles [J].
Attanasi, Orazio A. ;
Bianchi, Luca ;
Campisi, Linda A. ;
De Crescentini, Lucia ;
Favi, Gianfranco ;
Mantellini, Fabio .
ORGANIC LETTERS, 2013, 15 (14) :3646-3649
[4]   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
[5]   DABCO catalyzed highly regioselective synthesis of fused imidazo-heterocycles in aqueous medium [J].
Bangade, Vikas M. ;
Reddy, B. Chennakesava ;
Thakur, Pramod B. ;
Babu, B. Madhu ;
Meshram, H. M. .
TETRAHEDRON LETTERS, 2013, 54 (35) :4767-4771
[6]   The cyclopropylimine rearrangement/Povarov reaction cascade for the assembly of pyrrolo[3,2-c]quinoline derivatives [J].
Cai, Jinhui ;
Li, Feifei ;
Deng, Guo-Jun ;
Ji, Xiaochen ;
Huang, Huawen .
GREEN CHEMISTRY, 2016, 18 (12) :3503-3506
[7]   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
[8]   One-Pot Regiospecific Synthesis of Imidazo[1,2-a]pyridines: A Novel, Metal-Free, Three-Component Reaction for the Formation of C-N, C-O, and C-S Bonds [J].
Cao, Hua ;
Liu, Xiaohang ;
Zhao, Limin ;
Cen, Jinghe ;
Lin, Jingxin ;
Zhu, Qiuxia ;
Fu, Minling .
ORGANIC LETTERS, 2014, 16 (01) :146-149
[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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