HFIP Mediated Synthesis of C4-Aryl-2-quinolones through Serial Oxidation

Abstract

A practical, efficient approach for the synthesis of C4-arylated 2-quinolones from propargylic chlorides and anilines has been developed. The synthesis process involves subsequent oxidations of the initial products, tetrahydroquinolines and quinolinium ions, eventually leading to desired quinolones. A mechanism for the transformation is proposed based on a meticulous examination of intermediates and comprehensive control experiments. With a thorough understanding of the reaction mechanism, the applicability of the reaction scope is expanded. © 2023 Wiley-VHCA AG, Zurich, Switzerland.