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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

Putta, Ramachandra Reddy; Chun, Simin; Lee, Seok Beom; Hong, Junhwa; Oh, Dong-Chan; Hong, Suckchang

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
URI
https://hdl.handle.net/10371/201994
DOI
https://doi.org/10.1039/d1ra02532e
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products

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