Photo-Induced Electrophilic Aromatic Substitution of Ferric Acyl Nitrene

A photo-induced intramolecular electrophilic aromatic sub-stitution (SEAr) of N-acyloxyamides using FeCl3 in 1,4-dioxane is report-ed for the synthesis of biologically interesting benzoxazin-3(4H)-ones. Itis believed that irradiation with a blue LED facilitates the reaction, serv-ing as a source of energy. The SEAr reaction pathway is ascribed to theelectronic effects present in the aryl ring of the substrates. The reactionis also applicable for the synthesis of useful scaffolds possessing a quin-olin-2-one core, such as an anticancer reagent and analogues of brexip-iprazole and cilostamide