Tandem 1,6-Addition/Annulations of Alkynyl p-Quinone Methides with Bis-nucleophiles: Entry to Functionalized Furans, Isoxazoles, Pyrazoles, and Pyridines

Abstract

The reaction of alkynyl p-quinone methide (pQM) with keto-methylenes through a base-mediated tandem 1,6-addition/annulation sequence, [2 + 3] annulation, affording the furans is reported for the first time. A variety of functionalized furans, including fused derivatives, were obtained in good to excellent yields under mild reaction conditions. The efficacy of alkynyl pQMs is highlighted by extending their use to access isoxazoles, pyrazoles via [3 + 2] annulation, and pyridines through [3 + 3] annulation in the presence of different bis-nucleophiles.