Deconstructive annulation mediated one-pot synthesis of xanthene derivatives

Abstract

Direct conversion of naphthoxazines to diverse xanthene derivatives was achieved under one-pot operation through deconstructive annulation methodology. Sequential oxidative C(sp³)–O/C(sp³)–N cleavage followed by intramolecular/intermolecular annulation reaction was carried out under aerobic reaction conditions. Mechanistic analyses performed on the substrate revealed that the C(sp³)–O bond cleavage supersedes the C(sp³)–N bond scission. The in situ generated Betti base intermediate through the C(sp³)–O cleavage was successfully isolated. Based on a molecular docking investigation, the intermolecular annulated products demonstrated good α-glucosidase inhibitory properties.