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Issue 35, 2017
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Synthesis of quinolines via copper-catalyzed domino reactions of enaminones

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Abstract

Quinoline derivatives were obtained from enaminones and 2-bromo- or 2-iodobenzaldehydes via copper-catalyzed domino reactions consisting of the aldol reaction, C(aryl)–N bond formation and elimination. The electronic effect of aldehydes played a major role in the reaction outcome. Two simple protocols are disclosed to achieve various quinolines from both cyclic and acyclic enaminones in good yields. With the less-reactive acyclic enaminones, diethyl-2-(2-bromobenzylidene)malonate was shown to be more compatible than the benzaldehydes.

Graphical abstract: Synthesis of quinolines via copper-catalyzed domino reactions of enaminones

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Supplementary files

Article information


Submitted
27 Jul 2017
Accepted
18 Aug 2017
First published
18 Aug 2017

Org. Biomol. Chem., 2017,15, 7387-7395
Article type
Paper

Synthesis of quinolines via copper-catalyzed domino reactions of enaminones

B. Kaewmee, V. Rukachaisirikul and J. Kaeobamrung, Org. Biomol. Chem., 2017, 15, 7387
DOI: 10.1039/C7OB01867C

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