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    • Fulltext

       

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/131/12/0119

    • Keywords

       

      a-Thioesters; a-selenoesters; 3-diazoindolin-2-ones; S-ylide; Se-ylide; oxindoles; Sommelet-Hauser rearrangement.

    • Abstract

       

      Efficient rhodium-catalyzed Sommelet-Hauser type rearrangement of 3-diazoindolin-2-ones with a-thioesters has been accomplished for the synthesis of C4-thioalkylated oxindoles. The developed reaction offers the selective functionalization of C4-position of oxindole via generation of S-ylide and [2, 3]-sigmatropic rearrangement and allows access to diverse C4-thioalkylated oxindoles in good to excellent yield. Furthermore, the method was successfully extended to the synthesis C4-selenoalkylated oxindoles employingthe corresponding a-selenoester.

    • Author Affiliations

       

      ANGULA CHANDRA SHEKAR REDDY BHOJKUMAR NAYAK PAZHAMALAI ANBARASAN1

      1. Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, Tamilnadu, India

    • Dates

       
      Published
      December 2019
      Manuscript received
      30 July 2019
      Manuscript revised
      31 October 2019
      Accepted
      4 November 2019

    • Supplementary Material

       

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