Regioselectivity and Regiospecificity of Benzoxazinone (2-Isopropyl4 H -3,1-Benzoxazinone) Derivatives toward Nitrogen Nucleophiles and Evaluation of Antimicrobial Activity

The reaction of the benzoxazinone 3 with various nitrogen nucleophiles such as formamide and hydrazine hydrate and also the reaction of the isopropylquinazolinone 4 with hydrazonyl chloride have been shown to proceed with a high degree of regioselective at C(2). Spiro heterocycles have been found to play fundamental roles in biological processes and have exhibited diversified biological activity and pharmacological and therapeutical properties, thus reaction of the acetohydrazide 10a-c afforded the spiro compounds 11a-c .

The acetohydrazide derivative 7 reacted with carbon electrophiles such as acetylacetone, ethyl acetoacetate, acid chlorides and benzaldehyde to give some interesting heterocyclic compounds 12-16 , respectively. The structures of all the synthesized compounds were inferred by IR, 1 H-NMR and MS spectra as well as elemental analyses. The antimicrobial activities of some of the synthesized products were preliminarily evaluated.