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Transition-metal-free direct C-3 cyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate as the “CN” source

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Abstract

A novel avenue of C–CN bond construction was facilely achieved via the TBHP-mediated oxidative coupling reaction between quinoxalin-2(1H)-one derivatives and ammonium thiocyanate without any metal catalyst. Applying this protocol, a variety of 3-cyanoquinoxalin-2(1H)-one derivatives were prepared in moderate to good yields with good functional-group tolerance under mild conditions. Additionally, this methodology featured a broad substrate scope, excellent regioselectivity and operational simplicity.

Graphical abstract: Transition-metal-free direct C-3 cyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate as the “CN” source

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Publication details

The article was received on 28 Aug 2019, accepted on 19 Nov 2019 and first published on 19 Nov 2019


Article type: Research Article
DOI: 10.1039/C9QO01055F
Org. Chem. Front., 2020, Advance Article

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    Transition-metal-free direct C-3 cyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate as the “CN” source

    J. Wang, B. Sun, L. Zhang, T. Xu, Y. Xie and C. Jin, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO01055F

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