Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-Heterobenzimidazoles

被引:99
作者
Lv, Xin [1 ]
Bao, Weiliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
关键词
COUPLING REACTIONS; C-N; REGIOSELECTIVE SYNTHESIS; NITROGEN-HETEROCYCLES; AZOLIUM AZOLATE; BENZIMIDAZOLES; DERIVATIVES; ARYL; INHIBITORS; DISCOVERY;
D O I
10.1021/jo900743y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient one-pot synthesis of various N-substituted 2-heterobenzimidazoles has been developed. Through a Cu(I)-catalyzed cascade intermolecular addition/intramolecular C-N coupling process, a wide variety of 2-heterobenzimidazoles could be synthesized from o-haloarylcarbodiimides and N- or O-nucleophiles.
引用
收藏
页码:5618 / 5621
页数:4
相关论文
共 59 条
[51]   A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles [J].
Yao, Pei-Yuan ;
Zhang, Yu ;
Hsung, Richard P. ;
Zhao, Kang .
ORGANIC LETTERS, 2008, 10 (19) :4275-4278
[52]   A one-pot coupling/hydrolysis/condensation process to pyrrolo[1,2-a]quinoxaline [J].
Yuan, Qiliang ;
Ma, Dawei .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (13) :5159-5162
[53]   Discovery of pyrimidine benzimidazoles as Lck inhibitors: Part I [J].
Zhang, Guobao ;
Ren, Pingda ;
Gray, Nathanael S. ;
Sim, Taebo ;
Liu, Yi ;
Wang, Xia ;
Che, Jianwei ;
Tian, Shin-Shay ;
Sandberg, Mark L. ;
Spalding, Tracy A. ;
Romeo, Russell ;
Iskandar, Maya ;
Chow, Donald ;
Seidel, H. Martin ;
Karanewsky, Donald S. ;
He, Yun .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) :5618-5621
[54]   Copper-catalyzed regiospecific synthesis of N-alkylbenzimidazoles [J].
Zheng, Nan ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (23) :4749-4751
[55]   A palladium-catalyzed regiospecific synthesis of N-aryl Benzimidazoles [J].
Zheng, Nan ;
Anderson, Kevin W. ;
Huang, Xiaohua ;
Nguyen, Hanh Nho ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) :7509-7512
[56]   Synthesis of 2-fluoroalkylbenzimidazoles via copper(I)-catalyzed tandem reactions [J].
Zhu, Jiangtao ;
Xie, Haibo ;
Chen, Zixian ;
Li, Shan ;
Wu, Yongming .
CHEMICAL COMMUNICATIONS, 2009, (17) :2338-2340
[57]   N-1-HYDROXYAMIDINES - SYNTHESES AND REACTIONS WITH ISOCYANATES AND 1,1'-CARBONYLDIIMIDAZOLE [J].
ZINNER, G ;
PERNER, M ;
GRUNEFELD, J ;
SCHECKER, HG .
ARCHIV DER PHARMAZIE, 1986, 319 (12) :1073-1079
[58]   Cascade Coupling/Cyclization process to n-substituted 1,3-dihydrobenzimidazol-2-ones [J].
Zou, Benli ;
Yuan, Offlang ;
Ma, Dawei .
ORGANIC LETTERS, 2007, 9 (21) :4291-4294
[59]   Synthesis of 1,2-disubstituted benzimidazoles by a Cu-catalyzed cascade aryl amination/condensation process [J].
Zou, Benli ;
Yuan, Qiliang ;
Ma, Dawei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) :2598-2601