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Abstract This thesis describes the studying of behavior of [4-(3-bromo-4-methyl) phenyl] phthalazin-1(2H)-one towards some electrophiles and nucleophile sand some studies with the products to produce new phthalazine derivatives with the aim to evaluate their anti corrosion activities. The thesis consists of the following parts: 1) Summary 2) Introduction: In this section brief literatures review of the different methods of preparation and the reactions of phthalazine derivatives. 3) Results and Discussion: It deals with the discussion of the experimental methods adopted for the synthesis of the designed compounds as well as the different analytical methods applied for the characterization of the new compounds. Schemes A-C illustrates the synthetic pathways followed in the preparation of target compounds. In this part the author synthesis 2-(3-bromo-4-methyl benzoyl) benzoic acid (I) by the reaction of o-bromo toluene with phthalic anhydride under Friedel Craft’s condition. Condensation of benzoic acid derivative (I) with hydrazine hydrate in boiling ethanol afforded the target compound 4-(3-bromo-4-methyl phenyl) -2H-phthalazin-l-one (II). I. A. Behavior of 4-(3-bromo-4-methyl phenyl) -2H-phthalazin-l-one (II) towards carbon electrophiles: (Scheme A) 1. Reaction with ethyl cyanoacetate: When the phthalazinone (II) was allowed to react with ethyl cyanoacetate in sodium ethoxide cyanoacetylation takes place and yielded 2-Cyanoacetyl-4-(3-bromo-4-methyl phenyl)-2H-phthalazin-1-one (III). 2. Reaction with ethyl bromoacetate: Phthalazinone (II) was treated with ethyl bromoacetate to afford the corresponding phthalazine acetic acid ethyl ester (IV). On other hand, the structure of the esters (IV) was established chemically via: 1. The interaction with hydrazine hydrate and afforded [4-(3-bromo-4-methyl phenyl)-l-oxo-2H-phthalazin-2-yl] acetic acid hydrazide (V). 2. The interaction with benzaldhyde in the presence of sodium methoxide and yielded the Claisen Schmidt product (VI). 3. Interaction with sodium hydroxide solution and afforded the 2-(4-(3-bromo-4-methylphenyl)-1-oxophthalazin-2(1H)-yl) acetic acid (VII). I. B. Behavior of [4-(3-bromo-4-methyl) phenyl] phthalazin-1(2H)-one (II) towards phosphorous pentasulphide: When the phthalazinone derivative (II) reacted with phosphorus pentasulphide in dry xylene, it yielded the thione derivative (VIII). The structure of compound (VIII) was inferred chemically from its reaction with hydrazine hydrate in boiling ethanol to afford the hydrazine phthalazine derivative (IX). |