Sulfur-Promoted Oxidative Cyclization of Pentan-1-ones: Direct Access to Tetrasubstituted Furans from Deoxybenzoins and Chalcones.

ABSTRACT

Furan is an important heterocyclic scaffold in natural product, bioorganic, and medicinal chemistry as well as in materials science. The system S8/DABCO/DMSO was found to efficiently mediate the oxidative cyclization of 1,2,3,5-tetraarylpentan-1-ones A, which were obtained in situ as the Michael adducts of chalcones 1 and deoxybenzoins 2, to furan 3. The strategy provided convenient and direct access to tetrasubstituted furans 3 from readily available starting materials with high functional group tolerance.