Iron(III)-Catalyzed Amine-Release Triple Condensation of Enaminones to C3-Alkenylated Dihydroquinolinones

By:Wang, Qiaoqiao ； Yuan, Xu ； Sun, Haoyang ；Yang, Jimei ；Yang, Xingjiang ；Lin, Jun ；Jin, Yi

Journal of Organic Chemistry

DOI：https://doi.org/10.1021/acs.joc.4c00750

Published：2024-JUL

Abstract

      C3-functionalized dihydroquinolinones represent a class of important biologically active compounds. Although methods for synthesizing C2/4-functionalized dihydroquinolinones have been extensively reported, research on the synthesis of C3-functionalized dihydroquinolinone is extremely rare. Herein, we report for the first time a method for C3-alkenylated dihydroquinolinones via iron(III)-catalyzed amine-release triple condensation of enaminones. These reactions exhibit broad substrate scope and offer operationally simple, low-cost catalyzed procedures in a single step. Subsequent intramolecular and intermolecular additions to the alkene moiety provide diverse C3-functionalized dihydroquinolinone derivatives.