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Synthesis of Oxindoles, Spirooxindoles, and Isatins with Prominent Bioactive Probes Review

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  • Omprakash H Nautiyal

    (Professor and Consulting scientist, India)

Abstract

3-Hydroxy-2-oxindoles (Figure 1) are biologically useful active molecules, and efficient methods are needed for their synthesis under mild conditions. Wen-Ting Wei, have developed a base- and metal-free C (sp3)-H hydroxylation of 2-oxindoles. The reaction is promoted by TEMPO (2, 2, 6, 6-tetramethylpiperidine N-oxide) and synthesized under atmospheric air as a hydroxylation reagent in THF (tetrahydrofuran) at room temperature. Reaction mechanism proposed involves TEMPO reacting with the enol form of the 2-oxindole, followed by a reaction with O2 that generates a superoxide anion. This anion regenerates TEMPO and is converted to peroxide. Finally, the peroxide is cleaved to give the desired product. This concord provides a mild and simple strategy for the construction of C-O bonds from moderate to good yields. A wide range of substituted 2-oxindoles could be converted with a variety of functional groups.

Suggested Citation

  • Omprakash H Nautiyal, 2018. "Synthesis of Oxindoles, Spirooxindoles, and Isatins with Prominent Bioactive Probes Review," Organic & Medicinal Chemistry International Journal, Juniper Publishers Inc., vol. 5(5), pages 126-137, March.
    • Handle: RePEc:adp:jomcij:v:5:y:2018:i:5:p:126-137
    DOI: 10.19080/OMCIJ.2018.05.555671
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