Synthesis of 2-(hetero)arylquinazolinones in aqueous media

Abstract

Mechanochemical treatment of N-unsubstituted or N-methyl anthranilamide with benzaldehyde yielded their Schiff bases derivatives which could be easily cyclized to the corresponding 2-phenyl-2,3-dihydroquinazolinones via thermal rearrangement in water. On the basis of the above findings, an eco-friendly method was applied to prepare quinazolin-4(1H)-one derivatives from anthranilamides and a number of (hetero)aryl aldehydes. Heating the aqueous mixture of starting compounds to 90 °C resulted in the products in 81-94% yields. All products precipitated from the reaction mixture and were isolated by simply filtration. No further work-up or purification was necessary.