Synthesis of 2‐Oxindoles from Substituted Indoles by Hypervalent‐Iodine Oxidation

A practical conversion of indoles into the corresponding 2‐oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2‐oxindoles in up to 90 % yield...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2018; no. 12; pp. 1437 - 1442
Main Authors Jiang, Xinpeng, Zheng, Cong, Lei, Lijun, Lin, Kai, Yu, Chuanming
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 29.03.2018
Wiley Subscription Services, Inc
Subjects
Chemistry
Chemistry, Organic
Hypervalent compounds
Indoles
Iodine
Nitrogen heterocycles
Oxidation
Parkinson's disease
Physical Sciences
Reagents
Science & Technology
Substitutes
Synthesis
DESIGN
REAGENTS
ONE-POT SYNTHESIS
Hypervalent compounds
OXINDOLES
KINASE INHIBITORS
DISCOVERY
Nitrogen heterocycles
ASSIGNMENT
Oxidation
Indoles
DERIVATIVES
Iodine
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Summary:A practical conversion of indoles into the corresponding 2‐oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2‐oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method. The practical and efficient conversion of indoles into the corresponding 2‐oxindoles is achieved under neutral conditions using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701807