Solvent-free mechanochemical synthesis of arylcyanomethylenequinone oximes from phenylacetonitriles and 4-unsubstituted nitroaromatic compounds using KF/nano-γ-Al2O3 as catalyst

Abstract

Solvent-free condensation of phenylacetonitriles with 4-unsubstituted nitroaromatic compounds to produce a series of arylcyanomethylenequinone oximes was described in the presence of KF/nano-γ-Al₂O₃ under high-speed vibration milling conditions, and the products were obtained in moderate to excellent yields at short reaction times. Moreover, the product α-(3-methyl-4-(hydroxyimino)-2,5-cyclohexadien-1-ylidene) benzeneacetonitrile 3b has been confirmed by X-ray diffraction analysis. The formation of nitroso isomer from oxime was measured by ¹H NMR in acetone-d₆ under different temperatures. In vitro antitumor studies showed that several arylcyanomethylenequinone oximes displayed strong antitumor activity against Caki-1 and 769-P.