Agnese Stikute

Synthetic approaches to 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones

This review summarizes strategies for the synthesis of 4-(het)aryl-3,4-dihydroquinolin-2(1H)-ones which are of interest due to their biological activity. It covers methods elaborated particularly for obtaining the title heterocycles, as well as procedures where these compounds are formed as side products. 4-Aryl-3,4-dihydroquinolin-2(1H)-one derivatives have been used for the synthesis of valuable molecules, e.g., anticancer drug tipifarnib.

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

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.

Crystal structure of 3-hy­droxy-2-(4-hy­droxy-3-meth­oxy­phenyl­methyl)-5,5-di­methyl­cyclo­hex-2-enone

In the title dimedone derivative, the 4-hydroxy-3-methoxybenzyl substituent adopts a sofa conformation. In the crystal, molecules are assembled into a sheet structure parallel to the ab plane via O—H⋯O hydrogen bonds.