Synthesis and Reactions of 1-(p-Tolyl)-5,6,7, 8-Tetrabromeo-3,2-Benzoxazin-4-One

Abstract

The oxime's (2a-g) has been obtained from the reactions of titled compound (1) with benzylamine, p-toluidine, acetylhydrazide, salicylohydrazide and with aromatic and/or aliphatic hydrocarbons under Friedel-Crafts and Grignard reaction conditions. 3-Phthalazin-4-one derivatives (3a-h) and (4) has been obtained from the reactions of benzoxazone (1) with p-anisidine, benzoylhydrazide, cyclization product of oximes (2c and d) and from the reaction of (1) with hydrazine. Fusion of (1) with ammonium acetate and/or with phenylacetic acid leads to formation of phthalazinone (Sa) and (6) respectively. Also reaction of compound (1) with P₂S₅ and active methylene compounds are described. The reaction of chlorophthalazine derivatives (5b) with nitrogen nucleophiles has been investigated.