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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2022-12, Vol.87 (24), p.16873-16881
Hauptverfasser: Su, Zhenjie, Wang, Shaozhong
Format: Artikel
Sprache:eng
Schlagworte:
4-Quinolones
Alkynes
Catalysis
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02077