Preparation of Substituted 2 H -Pyrans via a Cascade Reaction from Methyl Coumalate and Activated Methylene Nucleophiles

The reaction of methyl coumalate with a wide range of methylene active compounds, such as keto-esters or keto-sulfones and cyclic or acyclic diketones, afforded more than 30 2,3,5,6-tetrasubstituted 2H-pyrans. The reaction proceeds via a cascade reaction involving a Michael addition-6 pi-electrocyclic ring opening-proton transfer and 6 pi electro-cyclization, in which a variety of functional groups were tolerated.