The facile synthesis of 2-(2'-4-anisoylvinyl)-3-arylquinazolin-4-ones (2a, b) involves the condensation of 2-toluidine or 4-phenylenediamine with the corresponding 2-[2'-(4-anisoylvinyl)]-4H-3,1-benzoxazine-4-one (1). Reaction of compound 2 with aldehydes, bromine, alcohols, hydrazine hydrate, urea and thiourea are discussed. The former structure of the products have been characterized by elemental analysis and spectral data. Preliminary screening of some selected compounds for antimicrobial activity is reported.