Synthesis of Diketohexenoic Acid Derivatives by Alkenylation of Indoles and Pyrroles with 4-Pyrones.

A new synthesis of functionalized (Z)-6-hetaryl-2,4-dioxo-5-hexenoic acids based on acid-catalyzed alkenylation of indoles and pyrroles with derivatives of 5-substituted 4-pyrone-2-carboxylic acid in 37-82% yields has been developed. Coupling between isochelidonic acid and indoles followed by decarboxylation afforded biologically important (E)-6-indolyl-2,4-dioxo-5-hexenoic acids. These ring-opening reactions proceed with high regioselectivity through nucleophilic attack at the C-6 position of the pyrone ring. Reactions of ethyl 6-indolyl-2,4-dioxo-5-hexenoate with nucleophiles are useful for the production of different β-(indolyl)vinyl-containing azaheterocycles.