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

SUBMITTER: Putta RR 

PROVIDER: S-EPMC9033394 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature