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. 2019 Apr 2;9(18):10340-10344.
doi: 10.1039/c9ra01481k. eCollection 2019 Mar 28.

An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp3)-H bond activation mediated by Selectfluor

Yejun Gao  1   2 , Robert C Hider  3 , Yongmin Ma  1   2
Affiliations

An efficient 3-acylquinoline synthesis from acetophenones and anthranil via C(sp3)-H bond activation mediated by Selectfluor

Yejun Gao et al. RSC Adv. .

Abstract

An efficient method for the synthesis of 3-functionalized quinolines from commercially available acetophenones and anthranil has been described. Selectfluor propels the C(sp3)-H bond activation of the acetophenones and aza-Michael addition of anthranil resulting in annulated 3-acylquinolines in moderate to high yields. DMSO acts not only as a solvent but also as a one carbon donor in the reaction.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Examples of biological active quinoline derivatives.
Scheme 1
Scheme 1. Conversion of 3-acylquinoline into biologically active molecules.
Scheme 2
Scheme 2. Control experiments.
Scheme 3
Scheme 3. Proposed reaction mechanism.
See this image and copyright information in PMC

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