Synthesis of 4-amino-7-oxyindoles via dearomatization of 4-alkyl-2-alkynylanilines and dual fragment incorporation with O-benzoylhydroxylamines

Abstract

O-Benzoylhydroxylamines have been widely used as important amination reagents in C–N bond construction reactions; however, these reactions have exclusively focused on utilizing the amino group, with the benzoyloxy moiety often discarded as waste. Herein, we achieved the incorporation of both the NH₂ and benzoyloxy fragments of O-benzoylhydroxylamines into indole scaffolds via dearomatization of 4-alkyl-2-alkynylanilines and subsequent treatment with single-electron transfer (SET) reagents. The resulting 4-amino-7-oxyindoles allow for further selective structural modifications at the C-4 and C-7 positions as needed, facilitating drug screening investigations.