Issue 30, 2021, Issue in Progress

Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Abstract

Here, we report iron-catalyzed one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Knölker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated in situ. Trimethylamine N-oxide was used to activate the iron complex. Various unsymmetrical and symmetrical vicinal diols were applied for transfer hydrogenation, resulting in quinoxaline derivatives in 49–98% yields. A plausible mechanism was proposed based on a series of control experiments. The major advantages of this protocol are that no external redox reagents or additional base is needed and that water is liberated as the sole byproduct.

Graphical abstract: Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Supplementary files

Article information

Article type
Paper
Submitted
31 Mar 2021
Accepted
13 May 2021
First published
20 May 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 18225-18230

Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

R. R. Putta, S. Chun, S. B. Lee, J. Hong, D. Oh and S. Hong, RSC Adv., 2021, 11, 18225 DOI: 10.1039/D1RA02532E

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