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

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]...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-09, Vol.80 (18), p.9321-9327
Main Authors: Rasheed, Sk, Rao, D. Nageswar, Das, Parthasarathi
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01396