Préparation, réduction chimique et électrochimique d'α-nitrostyrylcétones — synthèse d'hétérocycles azotés
Year: 1981
Type: article
Abstract: Nitration of styryl ketones with nitrogen peroxide leads to the corresponding α-nitroethylenic ketones in good yield. However, the presence of methoxy groups involves a nitration on the aromatic nucleus.LiAlH4 reduction of α-nitrostyrylketones yields the corresponding racemic erythro- and threo-aminoalcohols; after acylation and cyclisation a dihydro-quinoline or a 2-oxazoline is obtained.Electrochemical reduction of these nitrostyryl-ketones selectively provides the α-ketoximes, which are themselves reduced electrolytically to α-aminoketones. These latter compounds dimerise in neutral medium to dihydro-2,5-pyrazines which aromatise to the corresponding pyrazines. In acid medium an α-ketol is obtained.A mechanism for the reduction is proposed implicating an enaminol intermediate.
Source: Canadian Journal of Chemistry
DOI: 10.1139/v81-179
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W1990275035