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One-Pot Synthesis of Quinoxalinones via Tandem Nitrosation/Cyclization of N-Aryl Cyanoacetamides

Fang Wang, Bo-Lun Hu, Lizhi Liu*, Hai-Yong Tu and Xing-Guo Zhang*

*Guangzhou Center for Disease Control and Prevention, Guangzhou 51440; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email: pearms12126.com, zxgwzu.edu.cn

F. Wang, B.-L. Hu, L. Liu, H.-Y. Tu, X.-G. Zhang, J. Org. Chem., 2017, 82, 11247-11252.

DOI: 10.1021/acs.joc.7b01930 (free Supporting Information)


Abstract

A tandem nitrosation/cyclization reaction of N-aryl cyanoacetamides with tert-butyl nitrite provides quinoxalin-2-ones in good yields with good functional group tolerance. The dehydrogenative N-incorporation is achieved through a sequence of nitrosation, tautomerization, and cyclization.

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proposed mechanism



Note

In a model reaction in N2 atmosphere, almost the same yield was obtained. These results suggest that O2 in air has no obvious influence on reaction yield.

Xing-Guo Zhang, August 5, 2018


Key Words

quinoxalinones, tert-butyl nitrite


ID: J42-Y2017