Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles

被引：77
|
作者：
Rasheed, Sk. [1 ,2 ]
Rao, D. Nageswar [1 ,2 ]
Das, Parthasarathi [1 ,2 ]
机构：
[1] Acad Sci & Innovat Res AcSIR, Jammu 180001, India
[2] CSIR, Div Med Chem, Indian Inst Integrat Med, Jammu 180001, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 18期
关键词：
CROSS-COUPLING REACTIONS; ARYL BORONIC ACIDS; ARYLBORONIC ACIDS; ANTITUMOR EVALUATION; CUPRIC ACETATE; DNA-BINDING; ARYLATION; DERIVATIVES; PALLADIUM; N-ARYL-2-AMINOPYRIDINES;
D O I：
10.1021/acs.joc.5b01396
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Cu (II)-catalyzed, inter/intramolecular C-N bond formation for the synthesis of various benzimidazole-fused heterocycles in a concise manner has been reported. The robustness of this reaction is demonstrated by the synthesis of a series of benzimidazole-fused heteroaromatics (e.g., pyrido[1,2-a] benzimidazole, benzimidazo[1,2-a]quinolines, benzimidazo [1,2-a]pyrazine, benzo[4,5] imidazo[2,1-b]thiazoles) directly from 2-aminoheteroarenens and 2-iodoarylboronic acids in one-pot. The novel cascade protocol for C-N bond formation operates via unique combination of Chan-Lam type coupling followed by Ullmann-type reaction.
引用
收藏
页码：9321 / 9327
页数：7
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