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Please use this identifier to cite or link to this item: http://hdl.handle.net/10277/536

Authors: Ieronimo, Gabriella
Internal Tutor: PENONI, ANDREA
Title: Synthesis and funcionalization of indole skeleton compunds via nitrosoarene-alkyne cycloadditions.
Abstract: Indoles are one of the most important and abundant classes of N-heterocycles, being present in the form of innumerable natural products and bioactive compounds. A class of indole derivatives which have received considerable attention in recent years are N-hydroxyindoles. The biological role of N-hydroxyindoles is still an area of active investigation since they have been shown to possess biological activity in certain cases. 3-Aroylindoles are another class of indole derivatives, known as bioactive compounds with interesting properties. Not many indolization procedures are known to afford directly 3-acylindoles starting from commercially available reactants. Our general interest in this topic lead us to disclose a novel and regioselective indole synthesis by annulation reaction between nitro- and nitrosoarenes with alkynes. Indoles, N-hydroxy- and N-alkoxyindoles were afforded in moderate to excellent yields and good regioselectivity. Using conjugated alkynones as starting materials the reaction proceeded with the regioselective formation of 3-acylindoles and/or N-hydroxy-3-acylindoles. Highly functionalizable indole derivatives were synthesized and different derivatization reactions were developed.
Keywords: Indole, nitrosoarenes, alkynes.
Issue Date: 2014
Language: eng
Doctoral course: Scienze Chimiche
Academic cycle: 26
Publisher: Università degli Studi dell'Insubria
Citation: Ieronimo, G.Synthesis and funcionalization of indole skeleton compunds via nitrosoarene-alkyne cycloadditions. (Doctoral Thesis, Università degli Studi dell'Insubria, 2014).

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