A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

Caixia Xie; Di Yang; Xinfeng Wang; Chen Ma

doi:10.1021/acs.joc.0c01662

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

J Org Chem. 2020 Dec 4;85(23):14937-14944. doi: 10.1021/acs.joc.0c01662. Epub 2020 Nov 4.

Authors

Caixia Xie^{1

2}, Di Yang², Xinfeng Wang², Chen Ma²

Affiliations

¹ School of Chemistry and Chemical Engineering, Shandong University of Technology, Zibo 255049, P. R. China.
² School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, P. R. China.

PMID: 33146531
DOI: 10.1021/acs.joc.0c01662

Abstract

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.