Sulfur-Promoted Oxidative Cyclization of Pentan-1-ones: Direct Access to Tetrasubstituted Furans from Deoxybenzoins and Chalcones
Van Phu Nguyen, Nhu Ngan Ha Nguyen, Nang Duy Lai, Dinh Hung Mac, Pascal Retailleau, Thanh Bình Nguyễn
Abstract
Furan is an important heterocyclic scaffold in natural product, bioorganic, and medicinal chemistry as well as in materials science. The system S 8 /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.
Topics & Concepts
ChemistryFuranDABCOAdductOxidative phosphorylationNatural productSulfurCombinatorial chemistryOrganic chemistryCatalysisBiochemistrySulfur-Based Synthesis TechniquesSynthesis of Organic CompoundsSynthesis and biological activity