Synthesis of 2‐Oxindoles from Substituted Indoles by Hypervalent‐Iodine Oxidation. Issue 12 (26th March 2018)

• Record Type: Journal Article
• Authors: Jiang, Xinpeng; Zheng, Cong; Lei, Lijun; Lin, Kai; Yu, Chuanming
• Is Part Of: European journal of organic chemistry. Issue 12(2018)
• Page Start: 1437
• Page End: 1442
• Publication Date: 2018-03-26
• Subjects: Nitrogen heterocycles -- Hypervalent compounds -- Iodine -- Indoles -- Oxidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701807
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : 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.