Synlett

A new general synthesis of N-hydroxyindoles

M Belley, D Beaudoin, G St-Pierre

Index: Belley, Michel; Beaudoin, Daniel; St-Pierre, Gabriel Synlett, 2007 , # 19 p. 2999 - 3002

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Citation Number: 5

Abstract

We recently reported that catalytic hydrogenation of 2-nitrophenylacetonitriles bearing an electron-withdrawing group (EWG) or an aryl substituent α to the nitrile, using a mixture of Pd/C and (Ph 3 P) 4 Pd, afforded N-hydroxy-2-aminoindoles in good to excellent yields (Scheme [1] ). [13] In the absence of the EWG, we observed that the reductive cyclization to form the indole ring does not occur. Instead, we isolated mixtures of anilines and hydroxylamines ...