Synthesis
DOI: 10.1055/s-0036-1588584
paper
© Georg Thieme Verlag Stuttgart · New York

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

Marino Petrini, Elena Chiurchiù, Federico V. Rossi, Alessandro Palmieri*
  • Green Chemistry Group, School of Sciences and Technology, Chemistry Division, University of Camerino, Via S. Agostino n. 1, 62032 Camerino (MC), Italy   Email: alessandro.palmieri@unicam.it
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Publication History

Received: 30 July 2017

Accepted after revision: 12 September 2017

Publication Date:
04 October 2017 (eFirst)

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