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Synthesis of 3-(2-quinolyl) chromones from ynones and quinoline N-oxides via tandem reactions under transition metal- and additive-free conditions

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Abstract

A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- and additive-free conditions and can be amplified to the gram level in 91% yield. 3-(1-Isoquinolyl) and 3-(2-pyridyl) chromones are also successfully synthesized using isoquinoline and pyridine N-oxides under basic conditions. Various heteroarene-contaning chromones were afforded in 30–98% yields, which are difficult to be obtained and are compounds of interest in pharmaceutical chemistry and chemical biology.

Graphical abstract: Synthesis of 3-(2-quinolyl) chromones from ynones and quinoline N-oxides via tandem reactions under transition metal- and additive-free conditions

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Article information


Submitted
06 Dec 2019
Accepted
02 Mar 2020
First published
02 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Synthesis of 3-(2-quinolyl) chromones from ynones and quinoline N-oxides via tandem reactions under transition metal- and additive-free conditions

J. Liu, D. Ba, Y. Chen, S. Wen and G. Cheng, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09460A

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