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Synthesis of quinolines via copper-catalyzed domino reactions of enaminones†
Benyapa Kaewmee,Vatcharin Rukachaisirikul,Juthanat Kaeobamrung
Organic & Biomolecular Chemistry Pub Date : 08/18/2017 00:00:00 , DOI:10.1039/C7OB01867C
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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