Metal-free C-H arylation of imidazoheterocycles with aryl hydrazines

被引:21
作者
Jana, Sourav [1 ]
Samanta, Sadhanendu [1 ]
Bagdi, Avik K. [2 ]
Shirinian, Valerii Z. [3 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati A Cent Univ, Dept Chem, Santini Ketan 731235, W Bengal, India
[2] TDB Coll, Dept Chem, Burdwan 713347, W Bengal, India
[3] Zelinsky Inst Organ Chem RAS, 47 Leninsky Prosp, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
CATALYZED DIRECT ARYLATION; FREE COUPLING REACTIONS; RADICAL ARYLATION; BOND FORMATION; C-3; ARYLATION; ONE-POT; PALLADIUM; COPPER; ARYLHYDRAZINES; FUNCTIONALIZATION;
D O I
10.1039/c8ra01474d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient metal-free arylation of imidazo[1,2-a] pyridines at the C-3 position with arylhydrazine has been achieved at room temperature under ambient air conditions. Various 2,3-disubstituted imidazopyridines and imidazothiazoles were synthesized with high yields. The present methodology demonstrates the usefulness of commercially available aryl hydrazine as an arylating agent.
引用
收藏
页码:12360 / 12367
页数:8
相关论文
共 51 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[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]   A facile access to 2-methylthio/alkoxy/amino-3-acylimidazo[1,2-a]pyridines based on cupric chloride promoted oxidative ring closure of α-oxoketene N,S-, N,O-, and N,N-acetals [J].
Barun, HO ;
Ila, H ;
Junjappa, H ;
Singh, OM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1583-1587
[6]   Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].
Baudoin, Olivier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911
[7]   Switch in Site of Inhibition: A Strategy for Structure-Based Discovery of Human Topoisomerase IIα Catalytic Inhibitors [J].
Baviskar, Ashish T. ;
Amrutkar, Suyog M. ;
Trivedi, Neha ;
Chaudhary, Vikas ;
Nayak, Anmada ;
Guchhait, Sankar K. ;
Banerjee, Uttam C. ;
Bharatam, Prasad V. ;
Kundu, Chanakya N. .
ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (04) :481-485
[8]   Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes [J].
Bhunia, Anup ;
Yetra, Santhivardhana Reddy ;
Biju, Akkattu T. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) :3140-3152
[9]   Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators [J].
Bischoff, Francois ;
Berthelot, Didier ;
De Cleyn, Michel ;
Macdonald, Gregor ;
Minne, Garrett ;
Oehlrich, Daniel ;
Pieters, Serge ;
Surkyn, Michel ;
Trabanco, Andres A. ;
Tresadern, Gary ;
Van Brandt, Sven ;
Velter, Ingrid ;
Zaja, Mirko ;
Borghys, Herman ;
Masungi, Chantal ;
Mercken, Marc ;
Gijsen, Harrie J. M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (21) :9089-9106
[10]   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