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.

Synthesis and funcionalization of indole skeleton compunds via nitrosoarene-alkyne cycloadditions / Ieronimo, Gabriella. - (2014).

Synthesis and funcionalization of indole skeleton compunds via nitrosoarene-alkyne cycloadditions.

Ieronimo, Gabriella
2014-01-01

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.
Indole, nitrosoarenes, alkynes.
Synthesis and funcionalization of indole skeleton compunds via nitrosoarene-alkyne cycloadditions / Ieronimo, Gabriella. - (2014).
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2090375
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