Studies on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone: reactions with indole derivatives and other C-nucleophiles |
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Authors: | Koulouri Sofia Malamidou-Xenikaki Elizabeth Spyroudis Spyros Tsanakopoulou Maria |
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Institution: | Laboratory of Organic Chemistry, Department of Chemistry, University of Thessaloniki, Greece. |
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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. |
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