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Construction of 4-Acyl-2-quinolones through Sc(OTf)3-Catalyzed Ring-Closing Alkyne-Carbonyl Metathesis

Zhenjie Su and Shaozhong Wang*

*School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China, Email: wangsznju.edu.cn

Z. Su, S. Wang, J. Org. Chem., 2022, 87, 16873-16881.

DOI: 10.1021/acs.joc.2c02077


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Abstract

A Sc(OTf)3-catalyzed ring-closing alkyne-carbonyl metathesis enables an atom-economical construction of densely substituted 4-acyl-2-quinolones from N-(2-alkynylphenyl)-α-ketoamides. Mechanistic studies support a formation of an oxetene intermediate and an electrocyclic ring-opening of the oxetene.

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proposed mechanism



Key Words

2-quinolones


ID: J42-Y2022