Synthesis of Some New Hydrazones from Quinazolinone Moiety

Abstract

Methyl α-[(4-oxoquinazolin-2-yl)thio]acetate (4) is one of the important heterocyclic compounds. It isused as a precursor to synthesis new derivatives of quinazolin-4-one moiety. The compound (4) was synthesized via a series of steps from anthranilic acid. The anthranilic acid was converted to its methyl ester (1) by esterification with methanol under acidic condition. The ester (1) was reacted with chloroacetyl chloride to produce methyl α-chloroacetamido benzoate (2). The chloro compound (2) was converted to the corresponding thiocyanato compound (3) by its reaction with ammonium thiocyanate. The thiocyanato compound (3) was cyclized to the target precursor (4) by boiling of compound (3) for 12 h. compound (4) was reacted with aromatic aldehydes under boiling condition to produce different hydrazones derivatives (5-12). The hydrazones compounds (5-12) were reacted with Chloroacetyl chloride to afforded the Azetedines compounds (13-20). The synthesized compounds were identified via the physical and spectral data.