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Issue 20, 2020
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Gold(iii)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

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Abstract

A gold-catalyzed 6-endo-dig azide-yne cyclization/O–H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs.

Graphical abstract: Gold(iii)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

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Supplementary files

Article information


Submitted
10 Apr 2020
Accepted
28 Apr 2020
First published
28 Apr 2020

Org. Biomol. Chem., 2020,18, 3888-3892
Article type
Paper

Gold(III)-catalyzed azide-yne cyclization/O–H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

J. Huang, H. Su, M. Bao, L. Qiu, Y. Zhang and X. Xu, Org. Biomol. Chem., 2020, 18, 3888
DOI: 10.1039/D0OB00745E

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