Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols

Abstract

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.