111| International Journal of Pharmaceutical Research | Oct -Dec 2019 | Vol 11 | Issue 4 Research Article Synthesis and characterization of some new Pyrazolin,Triazolin and Tetrazolin derivatives of 1,8- naphthal imide and evaluate their anti-microbial activity MOHAMMED G.A AL-KHUZAIE 1* , AAD M.H. AL-MAJIDI 1 1 Department of Chemistry, College of Science, Baghdad University, Baghdad, Iraq Email id :alibaderosmania@gmail.com,mgabbas89@gmail.com Received: 12.07.19, Revised: 12.08.19, Accepted: 12.09.19 ABSTRACT New pyrazolin, triazolin and tetrazolin derivatives of 1,8-naphthalimide had been synthesized from 1, 8-naphthalic anhydride by reactionwith p-phenylenediamine to give 1,8-naphthalimide derivative [1], that converted into its diazonium salt derivative by using sodium nitrite and acetic acid. Then, the diazonium salt reacted at the first time with acetylacetone to give compound [2] that react with hydrazine derivative to produce pyrazolin derivatives [3-7]. At the second time, diazonium salt reacted with sodium azide to produce azide derivative [8] that react with unsaturated carbonyl compounds to obtained 1,2,3-triazolin derivatives [9-13]. Also, azide derivative [8] react with some of Schiff’s bases derivatives [14-18] of compound [1] to produce tetrazolin derivatives [19-23]. The New pyrazolin, triazolin,andtetrazolin derivatives had been identified by [ 1 H-NMR, 13 C-NMR, and FTIR] and by measuring of characteristic physical properties and specific reactions. Moreover, the biological effect of all prepared compounds was tested on fungicidal and some of the bacteria. Keywords: 1,8-naphthalic anhydride, triazolin, tetrazolin, pyrazolin, anti-microbial activity. INTRODUCTION 1,8-naphthalimidederivatives have adeep investigation in past years because of their unique structural and photophysical properties astheyhave wide use in biological, biochemical and chemical field. Until now (1, 2) , 1,8-naphthalimide derivatives are used as dyes in industries (3) , fluorescent probes of chemosensors (4) , fluorescent cell markers used in biomedical application (5) andantimicrobial (6) .1,8-naphthalimide derivatives widely used as DNAintercalating agents because they have a flat structure with intense aromatic system make them bind easily to DNA by insertion between the two base pairs of the DNA double helix (7) . Also,1,8-naphthalimide derivatives are antitumor agents because of their good intercalation ability that separates the base pairs of DNA vertically and destroys the sugar-phosphate back bone (8) .Pyrazolin, triazolin,andtetrazolin are heterocyclic compoundscharacterized by a 5-membered ring consist of carbon and nitrogen atoms.They are the most studied compounds among azole family. Indeed, they have huge and different synthetic methods have been reported over the last years (9) . Pyrazolin,triazolinand tetrazolin systems, as biomolecules, have been attractedthe attention of scientists because of their special pharmacological properties. In particular, they are widely usas antimicrobial (10) ,anticancer (11) , antioxidant (12) andantitubercular (13) agents. Experimental Instruments All chemicals used are supplied from BDH, Merck, Fluka and Sigma Aldrich. Melting points had been measured using SMP3 melting point apparatus and left uncorrected. FTIR spectra had been studied on SHIMAZU FTIR-8400 spectrophotometer by using KBr disc in the (4000-600) cm -1 spectrum range. 1 HNMR and 13 CNMR spectra had been recorded on ECA 600 MHz by using TMS as referenceand DMSOd 6 as a solvent. TLC was performed for all prepared compounds. Synthesis of N-(4-aminophenyl)-1,8- naphthalimide [1] (14) (5g, 0.025mol) of 1,8-Naphthalic anhydride dissolved in (20mL) DMSO with heating. Then, (2.72g, 0.025mol) p-phenylenediamine added and the mixture refluxed for (18hrs). Finally, the mixture of reaction poured into iced water and stirred, then the solid precipitated was filtered and recrystallized by acetic acid. Compound [1] physical properties listed in the table (1). Synthesis of N-(4-(2-(2,4-dioxopentan-3- ylidene)hydrazinyl)phenyl)-1,8-naphthalimide[2] (15) Compound [1] (2 g, 0.007mol) was dissolved in concentrated acetic acid (18mL) and distilled water (18 mL), then cooled in an ice bath until reach the temperature to(0-5) °C, then Sodium nitrite solution (0.47g, 0.007 mol in (5mL) water) was added very slowlyto the mixture and stirred for (10minutes). Finally, the mixture was added drop-by-drop to the solution of acetyl acetone (0.7 mL, 0.007 mol) and sodium acetate (0.57 g, 0.007 mol) in (25mL) of ethanol and stirred for (30 min.). The solid green product was filtered and washed with water and ethanol. The physical properties are listed in Table (1). Synthesis of N-(4-((3,5-dimethyl-1-subs.phenyl-pyrazolin- 4-yl)diazenyl)phenyl)-1,8-naphtha -limide [3-7] (16)