Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene

Abstract A photo-induced intramolecular electrophilic aromatic substitution (SEAr) of N-acyloxyamides using FeCl3 in 1,4-dioxane is reported for the synthesis of biologically interesting benzoxazin-3(4H)-ones. It is believed that irradiation with a blue LED facilitates the reaction, serving as a source of energy. The SEAr reaction pathway is ascribed to the electronic effects present in the aryl ring of the substrates. The reaction is also applicable for the synthesis of useful scaffolds possessing a quinolin-2-one core, such as an anticancer reagent and analogues of brexipiprazole and cilostamide.