Issue 7, 2022

Metal-free three-component cyanoalkylation of quinoxalin-2(1H)-ones with vinylarenes and azobis(alkylcarbonitrile)s

Abstract

We have unveiled an efficient synthesis of cyanoalkylated quinoxalin-2(1H)-ones via a three-component radical cascade reaction of quinoxalin-2(1H)-ones with vinylarenes and azobis(alkylcarbonitrile)s. K2S2O8 takes part in the reaction as a sole oxidant under base, additive, and metal-free conditions, producing the three-component products in moderate to good yields. The protocol also works with phenylacetylene in the absence of vinyl arenes and provides the respective product. Furthermore, different control experiments with radical scavengers like 2,2,6,6-tetramethylpiperidine-1-oxyl and diphenyl ethylene prove the generation of radicals during the reaction.

Graphical abstract: Metal-free three-component cyanoalkylation of quinoxalin-2(1H)-ones with vinylarenes and azobis(alkylcarbonitrile)s

Supplementary files

Article information

Article type
Paper
Submitted
01 Nov 2021
Accepted
18 Jan 2022
First published
19 Jan 2022

Org. Biomol. Chem., 2022,20, 1462-1474

Metal-free three-component cyanoalkylation of quinoxalin-2(1H)-ones with vinylarenes and azobis(alkylcarbonitrile)s

M. Bhuyan, S. Sharma and G. Baishya, Org. Biomol. Chem., 2022, 20, 1462 DOI: 10.1039/D1OB02143E

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