Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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

Iodine-Catalyzed C–N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions
Abhishek Gupta, Nidhi Jain, Mahesh Subhashrao Deshmukh
A metal-free cross-dehydrogenative coupling between quinoxalinones (sp2 C–H) and amines (N–H) in the presence of catalytic iodine is reported. The reaction yields 3-aminoquinoxalinones in moderate to high yields under ambient conditions in dioxane as solvent and aqueous tert-butyl hydroperoxide (TBHP) as the terminal oxidant. The reaction is highly versatile and exhibits good functional group tolerance with a range of primary and secondary amines. It provides a practical access to pharmaceutically active 3-aminoquinoxalinone derivatives. Preliminary mechanistic studies reveal in situ iodination of the amine as the putative mode of activation.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00464

DOI: 10.1021/acs.joc.7b00464

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