Synthesis of Functionalized Indolobenzazepinones via Sc(OTf)3-Induced Ring Expansion/Annulation Reactions of 4-Diazoisoquinolin-3-ones with Isatins

J Org Chem. 2022 Dec 2;87(23):15938-15946. doi: 10.1021/acs.joc.2c02076. Epub 2022 Nov 17.

Abstract

Herein, we report an unexpected cascade ring expansion/annulation reaction between 4-diazo-1,4-dihydroisoquinolin-3-ones and a variety of isatin derivatives in the presence of Sc(OTf)3 catalyst. A series of novel indolobenzazepinones were synthesized in good to excellent yields with the exclusion of nitrogen and carbon dioxide gases. High bond-forming efficiency, novel reaction mechanism, readily available starting materials, commercially available cheap catalyst, broad substrate scope, and mild reaction conditions are the prominent features of this method.