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Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols
Cited 11 time in
Web of Science
Cited 12 time in Scopus
- Authors
- Issue Date
- 2021-06
- Publisher
- Royal Society of Chemistry
- Citation
- RSC Advances, Vol.11 No.30, pp.18225-18230
- Abstract
- Here, we report iron-catalyzed one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (eta 4-cyclopentadienone) iron complex, which is well known as the Knolker 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.
- ISSN
- 2046-2069
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