Synthesis 2025; 57(09): 1583-1591
DOI: 10.1055/a-2492-3240
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Synthesis of Isatins via Oxone®/TBAI-Mediated On-Water Oxidation of Indoles

Authors

  • Pratiksha Khajuria

    a   Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu and Kashmir 180001, India
    b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
  • Debojyoti Bag

    a   Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu and Kashmir 180001, India
    b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
    c   Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India
  • Sanghapal D. Sawant

    a   Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu and Kashmir 180001, India
    b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
    c   Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India

This work was financially supported by the Council of Scientific and Industrial Research, India (CSIR, India) via Project Nos. HCP23 and HCP50. P.K. thanks CSIR for a fellowship. D.B. thanks CSIR-IIIM and CSIR-NCL for fellowships.


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Abstract

Isatins and their derivatives are important scaffolds in a wide range of pharmaceuticals, bioactive compounds, and functional materials. Herein we describe a new strategy for the synthesis of isatins from indoles via Oxone®/TBAI-mediated oxidative dearomatization of indoles in water. The strategy works well with a variety of N-protected indoles and azaindoles.

Supporting Information



Publication History

Received: 25 September 2024

Accepted after revision: 28 November 2024

Accepted Manuscript online:
28 November 2024

Article published online:
07 January 2025

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