Palladium-catalyzed dehydrogenative annulation of imidazo[1,2-a]pyridines with diarylalkynes

被引:23
作者
Ghosh, Monoranjan [1 ]
Naskar, Aswini [1 ]
Mishra, Subhajit [1 ]
Hajra, Alakananda [1 ]
机构
[1] Visva Bharati, Dept Chem, Santini Ketan 731235, W Bengal, India
关键词
Palladium; Dehydrogenative annulation; C-H activation; Alkynes; Imidazo[1,2-a]pyridines; C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; OXIDATIVE ANNULATION; INTERNAL ALKYNES; FLUORESCENT; ACTIVATION; ACCESS; ARYL; IMIDAZOHETEROCYCLES; HETEROCYCLES;
D O I
10.1016/j.tetlet.2015.05.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed direct dehydrogenative annulation of imidazo[1,2-a]pyridines with diarylalkynes through dual cleavage of C-H bonds has been developed. This new strategy offers a straightforward route for the synthesis of pi-conjugated polyaromatic heterocycles from readily accessible imidazo[1,2-a]pyridine. An array of 2,3,4-triarylphenyl-1,7b-diaza-cyclopenta[cd]indene derivatives with broad functionalities are obtained in high yields by this protocol. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4101 / 4104
页数:4
相关论文
共 69 条
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[3]   Ruthenium-Catalyzed Oxidative Synthesis of 2-Pyridones through C-H/N-H Bond Functionalizations [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ORGANIC LETTERS, 2011, 13 (12) :3278-3281
[4]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[5]   The larger acenes: Versatile organic semiconductors [J].
Anthony, John E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :452-483
[6]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[7]   Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate [J].
Bagdi, Avik Kumar ;
Mitra, Shubhanjan ;
Ghosh, Monoranjan ;
Hajra, Alakananda .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (11) :3314-3320
[8]   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
[9]   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
[10]  
Bras J. L., 2014, SYNTHESIS-STUTTGART, V46, P1555