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Synthesis 2018; 50(02): 371-376
DOI: 10.1055/s-0036-1588584
DOI: 10.1055/s-0036-1588584
paper
Oxidative Conversion of Sulfonyl Indoles into 3-Alkylidene-2-oxindoles under Flow Chemical Conditions
Further Information
Publication History
Received: 30 July 2017
Accepted after revision: 12 September 2017
Publication Date:
04 October 2017 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588584.
- Supporting Information
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Sulfonyl indoles 3 are prepared by a three-component condensation of indoles with aldehydes and p-toluenesulfinic acid under acidic conditions: