Construction of 4-Acyl-2-quinolones through Sc(OTf)<sub>3</sub>-Catalyzed Ring-Closing Alkyne–Carbonyl Metathesis
Zhenjie Su, Shaozhong Wang
Abstract
An atom-economical protocol to construct densely substituted 4-acyl-2-quinolones from N-(2-alkynylphenyl)-α-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.
Topics & Concepts
AlkyneCatalysisRing-closing metathesisRing (chemistry)ChemistryMetathesisMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryPolymerizationPolymerSynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisOrganometallic Complex Synthesis and Catalysis