Abstract
Behaviour of 2-(4-oxo-4H-benzo[d][l,3]oxazin-2-yl)-benzoic acid (1) towards nitrogen nucleophiles namely, hydrazine hydrate, in different solvents, ammonium acetate, and o-phenylenediamine has been investigated to give aminoquinazolin-4-one, benzotriazepinone, spiro-type compound, and nitrogen bridgehead compounds 3-5, respectively. Also, reactivity of the aminoquinazolin-4-one 2 towards carbon elec-trophiles such as ethyl acetoacetate, ethyl phenylacetate, ethyl chloroacetate, and aromatic aldehydes has been discussed. Reaction of Schiff s base 8 with sulfur nucleophiles namely o-aminothiophenol and/or thio-glycolic acid afforded Michael type adducts. Structural assignments, of products 1-24 have been confirmed by elemental analysis and spectral data (1H- and 13C -NMR and MS fragmentation). The bioassay indicates that some of the target compounds obtained have good selective anticancer activity.
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