BEHAVIOR OF SOME PHTHALAZINONE DERIVATIVES TOWARD SOME CARBON ELECTROPHILES :"SYNTHESIS OF SOME NOVAL PHTHALAZINONE DERIVATIVES FOR ANTICANCER AND ANTIMICROBIAL EVALUATION"

Abstract

This thesis studies the behavior of 4-(5,6,7,8-tetrahydronaphthalen-2-yl) phthalazin-1(2H)-one towards some electrophiles and nucleophiles and evaluate their antimicrobial activities and antifungal 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 their different analytical methods applied for the characterization of the new compounds. Schemes (1-2) illustrate the synthetic pathways followed in the preparation of target compounds. In this part the author synthesis 4-(5,6,7,8-tetrahydronaphthalen-2-yl) benzoic acid (1) by the reaction of 1,2,3,4-tetrahydronaphalene with phthalic anhydride under Friedel Craft’s condition. Condensation of benzoic acid derivative (1) with hydrazine hydrate in boiling ethanol afforded the target compound 4-(5,6,7,8-tetrahydronaphthalen-2-yl) phthalazin-1(2H)-one (2). b . SUMMARY I. Behavior of 4-(5,6,7,8-tetrahydronaphthalen-2-yl) phthalazin-1(2H)-one (2) towards carbon electrophiles (Scheme 1): 1. Reaction with benzoyl chloride: When phthalazinone (2) and benzoyl chloride was heated under reflux for 24h the product obtained was identified as 2-benzoyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)phthalazin-1(2H)-one (3) . 2. Reaction with allyl bromide: When the phthalazinone (2) was heated under reflux for 24h with allyl bromide, the product obtained was identified as 2-allyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)phthalazin-1(2H)-one (4). 3. Reaction with 2-chloroethanol: The phthalazinone (2) was heated under reflux for 24h with 2-chloroethanol, the product obtained was identified as 2-(2-hydroxyethyl)-4-(5,6,7,8-tetrahydronaphthalen-2-yl) phthalazin-1(2H)-one (5) On other hand , the structure of (5) was established chemically via the interaction with : (a) phenol and afforded 2-(2-hydroxyphenethyl)-( 5,6,7,8-tetrahydronaphthalen-2-yl)phthalazin-1(2H)-one (6a). (b) Catachol and afforded 2-(3,4-dihydrhydroxyphenethyl)-(5,6,7,8-tetrahydronaphthalen-2-yl)phthalazin-1(2H)-one (6b) . Treating compound (6b) with acetic anhydride gave 4-(2-(1-oxo-4-(5,6,7,8-tetrahydronaphthalen-yl) phthalazin-1(2H)-yl)ethyl)-1,2-phenylene diacetate (7) .