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Issue 42, 2014
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An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

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Abstract

A novel molecular I2-catalyzed synthesis of isatins through C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated.

Graphical abstract: An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

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Article information


Submitted
24 Jul 2014
Accepted
05 Sep 2014
First published
08 Sep 2014

Org. Biomol. Chem., 2014,12, 8512-8518
Article type
Paper

An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)–H oxidation and intramolecular C–N bond formation of 2′-aminoacetophenones

V. Rajeshkumar, S. Chandrasekar and G. Sekar, Org. Biomol. Chem., 2014, 12, 8512
DOI: 10.1039/C4OB01564A

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