Direct Amidation of 2′-Aminoacetophenones Using I₂-TBHP: A Unimolecular Domino Approach toward Isatin and Iodoisatin

Andivelu Ilangovan* and Gandhesiri Satish

*School of Chemistry, Bharathidasan University, Tiruchirappalli 620024, India, Email: ilangovanbduyahoo.com

A. Ilangovan, G. Satish, J. Org. Chem., 2014, 79, 4984-4991.

DOI: 10.1021/jo500550d

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Abstract

The use of a catalytic amount I₂ and TBHP as stoichiometric oxidant enables a simple and atom economic one-pot synthesis of isatins from 2′-aminoacetophenones via oxidative amido cyclization of the sp³ C-H bond. In the presence of a stoichiometric amount of iodine, the reaction yields iodoisatines. The reaction proceeds through sequential iodination, Kornblum oxidation, and amidation in one pot.

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Copper-Mediated Selective C-H Activation and Cross-Dehydrogenative C-N Coupling of 2′-Aminoacetophenones

A. Ilanovan, G. Satish, Org. Lett., 2013, 15, 5726-5729.

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Key Words

isatins, TBHP

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ID: J42-Y2014