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 (free Supporting Information)
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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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A. Ilanovan, G. Satish, Org. Lett., 2013, 15, 5726-5729.