The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between o-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.

A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N-O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products

MASPERO, ANGELO;PALMISANO, GIOVANNI;GALLI, SIMONA;TOLLARI, STEFANO;MASCIOCCHI, NORBERTO;PENONI, ANDREA
2013-01-01

Abstract

The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between o-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.
2013
Alkynes; Annulation; Indoles; N-Heterocycles; Nitrosoarenes
Ieronimo, Gabriella; Mondelli, Alessandro; Tibiletti, Francesco; Maspero, Angelo; Palmisano, Giovanni; Galli, Simona; Tollari, Stefano; Masciocchi, Norberto; Nicholas, Kenneth M.; Tagliapietra, Silvia; Cravotto, Giancarlo; Penoni, Andrea
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/1850319
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