Tetrahedron

A simple, efficient, regioselective and one-pot preparation of N-hydroxy-and N–O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic …

…, N Masciocchi, KM Nicholas, S Tagliapietra, G Cravotto…

Index: 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 Tetrahedron, 2013 , vol. 69, # 51 p. 10906 - 10920

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Citation Number: 9

Abstract

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 ...