title: Studies on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone: reactions with indole derivatives and other C-nucleophiles.
abstract: [reaction: see text] Thermal decomposition of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone (lawsone) in the presence of indole derivatives affords 3-acylated indoles existing in their enol forms, through a ring contraction and alpha,alpha'-dioxoketene formation reaction. The same reactants afford 3-(3-indolyl)-2-hydroxy-1,4-naphthoquinones in a copper-catalyzed reaction. Enamines, among other C-nucleophiles tested, give analogous results.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, University of Thessaloniki, Greece.
authors.forename: Sofia
authors.initials: S
authors.lastname: Koulouri
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Malamidou-Xenikaki
authors.forename: Spyros
authors.initials: S
authors.lastname: Spyroudis
authors.forename: Maria
authors.initials: M
authors.lastname: Tsanakopoulou
mesh_terms: D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D009861:Onium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D007211:Indoles; D009285:Naphthoquinones; D009861:Onium Compounds; C510883:phenyliodonium; C030374:indole; C005090:lawsone