Tetrahedron

Efficient, one-pot transformation of indoles into functionalized oxindole and spirooxindole systems under Swern conditions

P Lopez-Alvarado, J Steinhoff, S Miranda, C Avendano…

Index: Lopez-Alvarado, Pilar; Steinhoff, Judith; Miranda, Sonia; Avendano, Carmen; Carlos Menendez Tetrahedron, 2009 , vol. 65, # 8 p. 1660 - 1672

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Citation Number: 16

Abstract

The reaction of indole derivatives bearing a 3-or 4-hydroxyalkyl chain with dimethylsulfoxide and oxalyl chloride under Swern conditions led to a one-pot, three-component 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 good to excellent overall yields. The same ...

~93%

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