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Iodine-Catalyzed C-N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions

Abhishek Gupta, Mahesh Subhashrao Deshmukh and Nidhi Jain*

*Department of Chemistry, Indian Institute of Technology, New Delhi 110016, India, Email: njainchemistry.iitd.ac.in

A. Gupta, M. S. Deshmuk, N. Jain, J. Org. Chem., 2017, 82, 4748-4792.

DOI: 10.1021/acs.joc.7b00464 (free Supporting Information)


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Abstract

A metal-free cross-dehydrogenative coupling between quinoxalinones and amines in the presence of catalytic iodine yields 3-aminoquinoxalinones in good yields under ambient conditions in dioxane as solvent and aqueous tert-butyl hydroperoxide as the terminal oxidant. The reaction is highly versatile and exhibits good functional group tolerance with a range of primary and secondary amines.


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Key Words

quinoxalinones, TBHP


ID: J42-Y2017