(Diacetoxy)iodobenzene-Mediated Oxidative C-H Amination of Imidazopyridines at Ambient Temperature

被引:84
作者
Mondal, Susmita [1 ]
Samanta, Sadhanendu [1 ]
Jana, Sourav [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
N BOND FORMATION; ONE-POT SYNTHESIS; METAL-FREE CONDITIONS; COUPLING REACTIONS; DIRECT ACCESS; FUNCTIONALIZATION; ARENES; IODINE; IMIDAZOHETEROCYCLES; BENZOXAZOLES;
D O I
10.1021/acs.joc.7b00564
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Diacetoxy)iodobenzene (PIDA)-mediated direct oxidative C-H amination for the synthesis of 3-amino substituted imidazopyridines has been achieved under metal free conditions at room temperature in short reaction times. This methodology is also applicable for the regioselective amination of indolizines. Experimental results suggest that the reaction likely proceeds through a radical pathway.
引用
收藏
页码:4504 / 4510
页数:7
相关论文
共 47 条
[1]   Organocatalytic, Oxidative, Intramolecular C-H Bond Amination and Metal-free Cross-Amination of Unactivated Arenes at Ambient Temperature [J].
Antonchick, Andrey P. ;
Samanta, Rajarshi ;
Kulikov, Katharina ;
Lategahn, Jonas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8605-8608
[2]   Design, Synthesis, and Functionalization of Imidazoheterocycles [J].
Bagdi, Avik Kumar ;
Hajra, Alakananda .
CHEMICAL RECORD, 2016, 16 (04) :1868-1885
[3]   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
[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]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[6]  
Boursalian GB, 2016, NAT CHEM, V8, P810, DOI [10.1038/nchem.2529, 10.1038/NCHEM.2529]
[7]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[8]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[9]   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
[10]   Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].
Cho, Seung Hwan ;
Yoon, Jungho ;
Chang, Sukbok .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005