Synthesis and characterization of new phthalimides and succinimides substituted with 1,3,4-oxadiazole ring

Abstract

A series of new phthalimides and succinimides connected to 1,3,4-oxadiazole moietywere synthesized via multistep synthesis. The first step involved synthesis of six 5- substituted 2-amino-1,3,4-oxadiazoles by oxidative cyclization of substituted semicarbazones under treatmentwith bromine and anhydrous sodium acetate in glacial acetic acid.The synthesized 2-amino-1,3,4-oxadiazoles were introduced in reaction with phthalic or succinic anhydride in the second stepproducing six N - ( 5- substituted-1,3,4-oxadiazole-2-yl) phthalamic acids and six N-(5-substituted-1,3,4-oxadiazole-2-yl) succinamic acids which in turn were dehydrated in the third step via fusionmethod or using acetic anhydride and anhydrous sodium acetate as dehydrating agent to affordthe desirable N-(5-substituted -1,3,4-oxadiazole -2-yl) phthalimides and N-(5- substituted -1,3,4-oxadiazole -2-yl) succinimides respectively.Structures of the prepared compounds were confirmed byspectroscopic analysis and C.H.N analysis.Some of the synthesized compounds were screened fortheir antibacterial activity against two microorganisms, staphylococcus aureous (Gram positive) andEscherichia coli (Gram negative) and the results indicated that they exhibit good to moderate