Ni-Catalyzed radical cyclization of vinyl azides with cyclobutanone oxime esters to access cyanoalkyl containing quinoxalin-2(1)-ones.

Org Biomol Chem

Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.

Published: June 2021

A nickel-catalyzed cascade addition/cyclization of 2-azido-N-arylacrylamides and cyclobutanone oxime esters for the construction of 3-cyanoalkylated quinoxalin-2(1H)-ones is developed. This reaction proceeds under mild conditions with good functional group tolerance and broad substrate scope. A preliminary mechanistic experiment indicated that the cyanoalkyl radical might be involved in this transformation.

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http://dx.doi.org/10.1039/d1ob00610jDOI Listing

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