Molecular editing of 3-hydroxyphenyl oxindole derivatives via formal O-insertion and N-insertion: synthesis of dioxolane spirooxindoles and quinoxalin-2(1H)-ones

Abstract

Molecular editing represents a powerful tool for rapid access to privileged skeletons. Described herein for the first time was the single-atom molecular editing of 3-hydroxyphenyl oxindole derivatives through light/acid-promoted formal O-insertion and FeBr₃-catalyzed formal N-insertion. Two kinds of biologically significant scaffolds-dioxolane spirooxindoles and quinoxalin-2(1H)-ones-were synthesized in moderate to good yields. The developed methods expanded the reactivity profiles of 3-aryl oxindoles, featuring broad functional group tolerance, operational simplicity, and the ability to synthesize analogs of anticonvulsant and Eis inhibitory compounds.