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Oxidative Conversion of Sulfonyl Indoles into 3-Alkylidene-2-oxindoles under Flow Chemical Conditions
Synthesis ( IF 2.6 ) Pub Date : 2017-10-04 , DOI: 10.1055/s-0036-1588584
Alessandro Palmieri , Marino Petrini , Elena Chiurchiù , Federico Rossi

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.

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.



中文翻译:

流动化学条件下磺酰基吲哚氧化转化为3-亚烷基-2-氧吲哚

摘要

在流动化学条件下,使用NCS作为唯一试剂,将磺酰基吲哚转化为3-亚烷基-2-吲哚。通常以中等至令人满意的产率以E立体异构体形式获得共轭的羟吲哚衍生物。该转化需要NCS氧化吲哚环,然后消除芳基亚磺酸,以安装环外不饱和键。

在流动化学条件下,使用NCS作为唯一试剂,将磺酰基吲哚转化为3-亚烷基-2-吲哚。通常以中等至令人满意的产率以E立体异构体形式获得共轭的羟吲哚衍生物。该转化需要NCS氧化吲哚环,然后消除芳基亚磺酸,以安装环外不饱和键。

更新日期:2017-10-04
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