Rhodium-catalyzed annulation between 2-arylimidazo[1,2-a]pyridines and alkynes leading to pyrido[1,2-a]benzimidazole derivatives

被引:42
作者
Peng, Haibo [1 ]
Yu, Jin-Tao [1 ]
Jiang, Yan [1 ]
Wang, Lei [1 ]
Cheng, Jiang [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Jiangsu Prov Key Lab Fine Petrochem Engn, Changzhou 213164, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; N BOND FORMATION; POLYSUBSTITUTED NAPHTHALENE DERIVATIVES; RH(III)-CATALYZED OXIDATIVE ANNULATION; INTERNAL ALKYNES; DIRECTING GROUP; SUBSTITUTED NAPHTHALENES; REGIOSELECTIVE SYNTHESIS; ISOQUINOLONE SYNTHESIS; MOLECULAR-OXYGEN;
D O I
10.1039/c5ob00450k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed annulation between 2-arylimidazo[1,2-a] pyridines and alkynes was developed, leading to pyrido[1,2-a] benzimidazole derivatives in moderate to excellent yields. Notably, the ring C in pyrido[1,2-a] benzimidazole and the naphthalene framework were constructed consecutively, which provided a potential pathway leading to such a structure. This procedure tolerated chloro, bromo, cyano and methoxycarbonyl groups.
引用
收藏
页码:5354 / 5357
页数:4
相关论文
共 63 条
[51]   Synthesis of Azaheterocycles from Aryl Ketone O-Acetyl Oximes and Internal Alkynes by Cu-Rh Bimetallic Relay Catalysts [J].
Too, Pei Chui ;
Chua, Sze Hui ;
Wong, Siong Heng ;
Chiba, Shunsuke .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) :6159-6168
[52]   Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes [J].
Too, Pei Chui ;
Wang, Yi-Feng ;
Chiba, Shunsuke .
ORGANIC LETTERS, 2010, 12 (24) :5688-5691
[53]   An efficient waste-free oxidative coupling via regioselective C-H bond cleavage: Rh/Cu-catalyzed reaction of benzoic acids with alkynes and acrylates under air [J].
Ueura, Kenji ;
Satoh, Tetsuya ;
Miura, Masahiro .
ORGANIC LETTERS, 2007, 9 (07) :1407-1409
[54]   Fluorescent naphthyl- and anthrylazoles from the catalytic coupling of phenylazoles with internal alkynes through the cleavage of multiple, C-H bonds [J].
Umeda, Nobuyoshi ;
Tsurugi, Hayato ;
Satoh, Tetsuya ;
Miura, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (21) :4019-4022
[55]   Rhodium-Catalyzed Oxidative 1:1, 1:2, and 1:4 Coupling Reactions of Phenylazoles with Internal Alkynes through the Regioselective Cleavages of Multiple C-H Bonds [J].
Umeda, Nobuyoshi ;
Hirano, Koji ;
Satoh, Tetsuya ;
Shibata, Naoto ;
Sato, Hirofumi ;
Miura, Masahiro .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :13-24
[56]  
Viswanathan GS, 2002, ANGEW CHEM INT EDIT, V41, P2138, DOI 10.1002/1521-3773(20020617)41:12<2138::AID-ANIE2138>3.0.CO
[57]  
2-T
[58]   Direct Intramolecular C-H Amination Reaction Cocatalyzed by Copper(II) and Iron(III) as Part of an Efficient Route for the Synthesis of Pyrido[1,2-a]benzimidazoles from N-Aryl-2-aminopyridines [J].
Wang, Honggen ;
Wang, Yong ;
Peng, Changlan ;
Zhang, Jiancun ;
Zhu, Qiang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13217-13219
[59]   Synthesis of 1-Aminoisoquinolines via Rh(III)-Catalyzed Oxidative Coupling [J].
Wei, Xiaohong ;
Zhao, Miao ;
Du, Zhengyin ;
Li, Xingwei .
ORGANIC LETTERS, 2011, 13 (17) :4636-4639
[60]   Synthesis of Pyrido[1,2-a]benzimidazoles through a Copper-Catalyzed Cascade C-N Coupling Process [J].
Wu, Zhiqing ;
Huang, Qing ;
Zhou, Xiangge ;
Yu, Lintao ;
Li, Zhengkai ;
Wu, Di .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) :5242-5245