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

Omprakash H Nautiyal
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Omprakash H Nautiyal: Professor and Consulting scientist, India

Organic & Medicinal Chemistry International Journal, 2018, vol. 5, issue 5, 126-137

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.

Keywords: juniper publishers:Medicinal Chemistry; Biochemistry Journal; Pharmacology Journal; biochemical pharmacology; molecular pharmacology; biochemistry; open access journals; peer reviewed journals; Open Access; Journal of Molecular Biochemistry; International Research Journal of Pure and Applied Chemistry; World Journal of Biological Chemistry; Biochemistry and Analytical Biochemistry; Biochemistry & Physiology: Open Access; Molecular Biology International; Plant Biochemistry & Physiology; International Journal of Molecular Sciences; Journal of Clinical and Medical Genomics; Environmental Analytical Chemistry; Medicinal Chemistry; Juniper publishers reivews (search for similar items in EconPapers)
Date: 2018
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Persistent link: https://EconPapers.repec.org/RePEc:adp:jomcij:v:5:y:2018:i:5:p:126-137

DOI: 10.19080/OMCIJ.2018.05.555671

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