Synlett

One-Pot Synthesis of Highly Functionalized Oxindoles under Swern Oxidation Conditions

P López-Alvarado, J Steinhoff, S Miranda…

Index: Lopez-Alvarado, Pilar; Steinhoff, Judith; Miranda, Sonia; Avendano, Carmen; Menendez, J. Carlos Synlett, 2007 , # 18 p. 2792 - 2796

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Abstract

Abstract The reaction of indole derivatives bearing a 3-or 4-hydroxyalkyl chain with dimethyl sulfoxide and oxalyl chloride under Swern conditions led to a one-pot process involving three different synthetic transformations, namely oxidation of indole to oxindole, introduction of a chlorine substituent at the oxindole C-3 position, and substitution of the hydroxyl group in the side chain by chlorine. In spite of its mechanistic complexity, this synthetically useful ...