Nitroallylic acetates react with naphthols and electron‐rich phenols under mild conditions (TEA, DCM, room temp.) to afford arenopyrans in moderate to excellent yields. Such (3+3) annulation of a 1,3‐bielectrophilic nitroallylic acetate and a 1,3‐binucleophilic arenol involving an SN2′ reaction and an intramolecular 6‐endo‐trig cyclization takes place in a regio‐ and stereoselective manner. Surprisingly, the reaction of arenethiols under the same conditions provided nitroallylic thioethers instead of the expected arenothiopyrans presumably through a direct SN2 reaction.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.