title: Synthesis of Diketohexenoic Acid Derivatives by Alkenylation of Indoles and Pyrroles with 4-Pyrones.
abstract: 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.
authors.affiliation: Department of Chemistry, Institute of Natural Sciences, Ural Federal University , 620000 Ekaterinburg, Russian Federation.
authors.forename: Dmitrii L
authors.identifier: 0000-0002-6659-9832
authors.initials: DL
authors.lastname: Obydennov
authors.affiliation: Department of Chemistry, Institute of Natural Sciences, Ural Federal University , 620000 Ekaterinburg, Russian Federation.
authors.forename: Ekaterina O
authors.initials: EO
authors.lastname: Pan'kina
authors.affiliation: Department of Chemistry, Institute of Natural Sciences, Ural Federal University , 620000 Ekaterinburg, Russian Federation.
authors.forename: Vyacheslav Y
authors.initials: VY
authors.lastname: Sosnovskikh