Synthesis and Antiradical Properties of 4-Aryl-3,4-Dihydroquinolin-2-(1H)-Ones, Aza Analogs of Neoflavonoids

Chemistry of Heterocyclic Compounds 2014
Inese Mieriņa, Agnese Stikute, Māra Jure

A convenient one-pot method is proposed for the synthesis of 4-aryl-3,4-dihydroquinolin-2(1H)-ones from the monoanilides of malonic acid and aromatic aldehydes. The antiradical activity of the synthesized 4-aryl-3,4-dihydroquinolin-2(1H)-ones was examined (tests on the inhibition of 2,2-di-phenyl-1-picrylhydrazyl and galvinoxyl). It was found that the highest antiradical activity is exhibited by derivatives of syringaldehyde; the activity of the other compounds is moderate or low, however in the 2,2-diphenyl-1-picrylhydrazyl inhibition test it is comparable with or higher than for the widely used antioxidant Ionol.

Keywords
antioxidant, 4-aryl-3,4-dihydrocarbostyril, 4-aryl-3,4-dihydroquinolin-2(1H)-one, arylidene-malonic acid monoanilide, 4-aryl-2-oxo-1,2,3,4-tetrahydroquinoline, malonic acid monoanilides, antiradical activity, hydroarylation
DOI
10.1007/s10593-014-1574-4
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-014-1574-4

Mieriņa, I., Stikute, A., Jure, M. Synthesis and Antiradical Properties of 4-Aryl-3,4-Dihydroquinolin-2-(1H)-Ones, Aza Analogs of Neoflavonoids. Chemistry of Heterocyclic Compounds, 2014, Vol.50, No.8, pp.1137-1146. ISSN 0009-3122. e-ISSN 1573-8353. Available from: doi:10.1007/s10593-014-1574-4

Publication language
English (en)