Access to C4-Functionalized Quinolines via Copper-Catalyzed Tandem Annulation of Alkynyl Imines with Diazo Compounds

An efficient synthesis of C4-functionalized quinolines through copper-catalyzed tandem annulation of alkynyl imines with diazo compounds is described. This transformation involves an in situ formation of allene and intramolecular electrocyclization, which features high efficiency, mild reaction cond...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-09, Vol.81 (17), p.7539-7544
Main Authors: Zhu, Ruifeng, Cheng, Guolin, Jia, Chunqi, Xue, Lulu, Cui, Xiuling
Format: Article
Language:English
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Summary:An efficient synthesis of C4-functionalized quinolines through copper-catalyzed tandem annulation of alkynyl imines with diazo compounds is described. This transformation involves an in situ formation of allene and intramolecular electrocyclization, which features high efficiency, mild reaction conditions, easy operation, and broad functional-group tolerance. A wide variety of C4-functionalized quinolines were provided in up to 92% yield for 33 examples.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01227