Synthesis of Azocane- and Oxocane-Annulated Furans by a [2+2] Photocycloaddition–Ring-Opening Cascade

Dedicated to Professor Paul Knochel on the occasion of his 65th birthday

Abstract

The title compounds were synthesized from readily available quinolone and coumarin derivatives by a cascade reaction (12 examples, 90–98% yield). The cascade comprised a [2+2] photocycloaddition which occurred upon sensitized irradiation at λ = 420 nm (or direct UV irradiation at λ = 366 nm) and a subsequent acid-catalyzed ring-opening reaction. A variety of substituents are compatible with the conditions and a 3-alkyl group in the coumarin (or quinolone) is crucial to achieve a high chemoselectivity. Key to the success of the ring opening is the formation of a 4,5,5a-trihydrocyclobuta-2H-furan containing a strained bridgehead double bond which stems from the allenyl group tethered to the 4-position of the starting materials.

Key words

azocane - cycloaddition - domino reaction - heterocycles - oxocane - photochemistry - ring expansion

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