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Issue 98, 2019
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Gold-catalyzed cyclization of 1-(2′-azidoaryl) propynols: synthesis of polysubstituted 4-quinolones

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Abstract

An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-activated triple bonds in a 6-endo-dig manner and subsequent gold-assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.

Graphical abstract: Gold-catalyzed cyclization of 1-(2′-azidoaryl) propynols: synthesis of polysubstituted 4-quinolones

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Article information


Submitted
27 Aug 2019
Accepted
14 Nov 2019
First published
15 Nov 2019

Chem. Commun., 2019,55, 14769-14772
Article type
Communication

Gold-catalyzed cyclization of 1-(2′-azidoaryl) propynols: synthesis of polysubstituted 4-quinolones

X. Wu, L. Zheng, L. Zhao, C. Zhu and Y. Li, Chem. Commun., 2019, 55, 14769
DOI: 10.1039/C9CC06652G

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