4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 24, Pages 16873-16881

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02077

Keywords

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Funding

  1. National Natural Science Foundation of China
  2. [21871132]
  3. [21572098]

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An atom-economical protocol utilizing Sc(OTf)3 as the catalyst has been developed to synthesize densely substituted 4acyl-2-quinolones. Mechanistic experimental studies suggest the involvement of coordinative interaction between Sc(OTf)3 and the substrate, formation of an oxetene intermediate, and an electrocyclic ring-opening of the oxetene.
An atom-economical protocol to construct densely substituted 4acyl-2-quinolones from N-(2-alkynylphenyl)-alpha-ketoamides has been developed through Sc(OTf)3-catalyzed ring-closing alkyne-carbonyl metathesis. Mechanistic experimental studies support that coordinative interaction between Sc(OTf))3 and the substrate, the formation of an oxetene intermediate, and an electrocyclic ring-opening of the oxetene might be involved.

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