Oxidative Conversion of Sulfonyl Indoles into 3-Alkylidene-2-oxindoles under Flow Chemical Conditions

Abstract Sulfonyl indoles were converted into 3-alkylidene-2-oxindoles using NCS as the sole reagent under flow chemical conditions. The conjugated oxindole derivatives were generally obtained as E stereoisomers in moderate to satisfactory yields. The transformation entails the oxidation of the indo...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-01, Vol.50 (2), p.371-376
Main Authors: Petrini, Marino, Chiurchiù, Elena, Rossi, Federico V., Palmieri, Alessandro
Format: Article
Language:English
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Summary:Abstract Sulfonyl indoles were converted into 3-alkylidene-2-oxindoles using NCS as the sole reagent under flow chemical conditions. The conjugated oxindole derivatives were generally obtained as E stereoisomers in moderate to satisfactory yields. The transformation entails the oxidation of the indole ring by NCS followed by elimination of arylsulfinic acid in order to install the exocyclic unsaturation.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588584