Microsoft Word - 86-101 86 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Synthesis and Characterization of New Phthalimides Containing 1, 2, 4-triazole and Imine Group Khalid F.Ali Eman M.Hussain Rana S.Ahmed Dept. of Chemistry/ College of Education for pure sciences (Ibn –Al-Haitham)/ University of Baghdad Received in: 11 January 2015, Accepted in: 23 Fubrury2015 Abstract Several new derivatives of 1, 2, 4-triazoles linked to phthalimide moiety were synthesized through following multisteps. The first step involved preparation of 2, 2-diphthalimidyl ethanoic acid [2] via reaction of two moles of phthalimide with dichloroacetic acid. Treatment of the resulted imide with ethanol in the second step afforded 2,2-diphthalimidyl ester[3] which inturn was introduced in reaction with hydrazine hydrate in the third step ,producing the corresponding hydrazide derivative[4] .The synthesized hydazide was introduced in different synthetic paths including treatment with carbon disulfide in alkaline solution then with hydrazine hydrate to afford the new 1,2,4-triazole[10] .Reaction of compound [10] with different aldehydes produced a new Schiff base derivatives[11,12] .Reaction of derivative [4] with different aldehydes produced a new derivatives [5-8].All the synthesized compounds have been characterized by melting points ,FTIR ,1HNMR(some of them ) and mass spectroscopy of compound [2]. Derivatives [5, 6, 7, 10, 11, 12] were tested against inhibition of E-coli, staphyloccus aureus and were all found to be active. Schem1,2 illustrated the reaction steps. Keywords: synthesis, imide, 1, 3, 4-triazole, Schiff bases. 87 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Introduction During the last few decades, a considerable attention has been devoted to the synthesis of .for example, a large (1)bioactivitiestriazole derivatives possessing comprehensive -1,2,4 number of 1,2,4-triazoles have been incorporated into a wide variety of therapeutically , )(5analgesic, (4)antioxidant (2,3)inflammatory-antiincluding candidatesinteresting drug (10) ntifungal activitiesa, and , anticancer)9-(6antimicrobial Among the bicyclic non aromatic nitrogen heterocycles, phthalimide is interesting functionality due to its wide presence in the natural products and in the pharmacologically active compounds. Compounds containing phthalimide moiety are distinguished by their potent fungicidal action (11, 12) Schiff bases are also known to have biological activities such as antimicrobial (13), antifungal (14), and antitumor (15) and as herbicider (16).Keeping in view the facts mentioned we thought it is worthwhile to synthesize new Schiff bases containing phthalimide moiety which were predicated to have useful biological activities. Experimental Instruments Ftir Spectra Were Performed On A Shimadzu Ftir 8400 Fourier Transform Infrared Spectrophotometer. 1hnmr Spectra Were Recorded On A Bruker, Ultrashield 300 Mhz Spectrometer And Mass Spectroscopy Were Recorded On A Gcms Qp2010 Ultra(Gas)Chromatograph Mass Spectrometer Shimdzu Japan. Melting Points Were Determined On Gallenkamp Melting Apparatus And Were Uncorrected. Chemicals All chemicals were of analytical reagent grade and were used without further purification -Synthesis of 2, 2- diphthalimidyl ethanoic acid [2] (11) Phthalimide (1g, 0.007 mole) was dissolved in aqueous potassium hydroxide (0.57g , 0.01 mole) 50mL distilled water then added dichloroacetic acid (0.438g , 0.003 mole ). The reaction mixture was heated on sand bath for (4 hrs). The reaction mixture was cooled to room temperature and acidified with dilute HCI to precipitate the acetic acid derivative. The crud product was recrystallized from ethanol. -Synthesis of ethyl -2, 2- diphthalimidyl ethanoate[3](12) Methyl -2, 2- diphthalimidyl acetic acid [2] (4.0g, 0.01 mole) was dissolved in ethanol (70mL).concentration sulfuric acid (4mL) was added. The reaction mixture was refluxed for (6 hrs.). After completion of the reaction (monitored by T.L.C), the reaction mixture was poured on to ice-cold water then neutralized with (2%) KOH .The mixture was extracted with ethyl acetate (2X30 mL), combined organic layer dried over magnesium sulphate and the solvent was removed to give compound [2] as a syrup. 88 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Synthesis of 2,2 diphthalimidyl ethanoic hydrazide [4] (17,18) Compound [3] (1.8g, 0.004 mole) and hydrazine hydrate (4.0mL) were dissolved in (25mL) of ethanol. The reaction mixture was refluxed for (20 hrs). The precipitate which separated on cooling was filtered and recrystallized from ethanol to give compound [3] Diphthalimidyl ethanoic hydrazone methyl substituted phenyl (5-8) (19) Compound [4] (0.01 mol.) was dissolved in 50 mL of absolute ethanol. Appropriate aldehyde (0.01mol.) was added gradually, 2-3 drops of glacial acetic acid was added. The reaction mixture was refluxed for (7 hrs.) After completion of the reaction (monitored by T.L.C) and cooled, the product was precipitated filtered off and recrystallized from appropriate solvent, Table-1. showed the physical properties for Schiff base derivatives (4-7) Synthesis of 2,2 diphalimido methyl xanthate [9] (20) Compound [4] (3.8g , 0.05 mole) was dissolved in solution of potassium hydroxide (0.6g , 0.01 mole) in ethanol (100mL) and the reaction mixture was stirred for 1 hrs.at room temperature. Then carbon disulfide (3.8g, 0.05mole) was added slowly at 0-5 c. The reaction mixture was stirred for overnight at room temperature. The xanthate [13] was filtered, washed with ether. Synthesis of 3-(2,2- diphthalimidyl – methyl) -4- amino – 1,2,4- triazole -5- thione [10] (20) Compound [9] (3.4g, 0.01) was dissolved in (40mL) of water. Then excess amount of hydrazine hydrate was added. The mixture was refluxed for 20 hrs. The reaction was cooled, and then neutralized with 10 % HCl. The separated crude produced was filtered, dried and recrystallized from ethanol. Synthesis of 3-(2,2-diphthalimidyl – methyl ) -4- arylidenimino 1,2,4- triazole -5-thione [11-12] (19) Compound [10] (0.6, 0.01 mole) was dissolved in 250 mL of methanol. Appropriate aldehyde (0.02 moles) was added gradually and (2-3) drops of glacial acetic acid were added. The mixture was refluxed for (16 hrs.). On cooling the separated solid was filtered dried and recrystallized from methanol .Table (1) showed the physical properties for compounds (2- 12).derivatives. While the tables (2 and 3) include the structures and nomenclatures for compounds (2-12). Result and Discussion Chemistry The present work is directed towards synthesis of new heterocyclic derivatives of phthalimides Containing 1, 2, 4-triazole and imine group derivatives. Performing this target was achieved through following multi step synthesis which its steps are outlined in scheme (1) and (2). The first step involved the synthesis of 2,2-diphthalimidyl ethanoic acid which was prepared via reaction of two moles of phthalimide potassium salt [1] with dichloroacetic acid according to Gabriel Synthesis. The structure of the white crystals of compound (2) was assigned on the basis of mass and FTIR spectral data. The spectrum of electron ionization mass spectroscopy (EIMS) for compound2, 2- diphthalimidyl ethanoic acid figure (1) displayed the molecular ion at m/z= 350 also the base peak appeared at m/z=166. In addition of these, the other fragments were in agreement with the suggested structure of compound 2, 2- diphthalimidyl ethanoic acid. Furthermore, the patron of these fragments and the rearrangements which appeared are in 89 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 agreements with most literatures that study the mass fragmentations of the substituted phthalamide (16-18). (Scheme 3) dedicated the most important fragments. In EIMs losing molecular of CO or 2CO beside the CO2 from phathalmide attached with acetic acid are widely known (18, 19). In our compound the molecular ion appeared as exactly expect (M. +), however in some literatures the molecular ion was either ( M.+-CO) and ( M.+-CO2) [4] or M.+-N2 (20)instead of M.+. The FTIR spectrum showed clear absorption bands at (3400-2500) cm-1 due to v (O-H) acid, v (1693) cm-1 , (1770) cm-1 due to vasy and vsy (C=O) imide respectively,(1687) cm- 1due to v (C=O)acid. And the mass spectrum supported this compound. Synthesis of compound 4 involved two steps; in the first one compound [2] was converted to its ester derivatives [3] by the reaction of with ethanol in the presence of sulphric acid. The resulted ester [3] was introduced in reaction with hydrazine hydrate in ethanol absolute under reflux condition in the second step producing the desired hydrazide derivative [4]. FTIR Spectrum of compound [3] showed disappearance of absorption bands due to v (C=O) carboxylic acid at (1687) cm-1 and v (O-H) acid at (3400-2500) cm-1with appearance of v (C=0) ester at v (1726) and v (C-O) ester at (1281) cm-1 FTIR Spectrum of compound [4] showed disappearance of absorption due to v (C=0) and v (C-O-C) ester at (1726) cm-1 and (1281)cm-1respectively with the appearance of v(NH- NH2)absorption band at (3429-3167)cm-1proving success of hydrazide formation .The FTIR showed other bands (1732)cm-1,(1660) cm-1 due to vsy and vasy(C=0)imide and (1602) cm-1,(1558) cm-1 ,(1377) cm-1due to v(C=0)amide, v(C=C)aromatic, v(C-N)imide respectively. The next step in this work involved introducing of compound (4) in different synthetic two paths the first path introduced various new schiff bases [5-8]( scheme1) and the second path produced new heterocyclic (1, 3, 4- triazole) [10](scheme2) all of them contain two phthalimides moiety.The first synthetic path involved introducing of compound [4] in reaction with different aromatic aldehydes in ethanol in the presence of few drops of glacial acetic acid under reflux producing the new Schiff base (5-8). FTIR Spectra of compound [5-8] respectively showed disappearance of absorption bands due to v (NH2) absorption at (3429,3313)cm-1. The IR Spectra showed absorption at v (NH) absorption bands at (3173-3120) cm-1. Also the IR Spectra showed absorption at (1674- 1643) cm-1,( 1745-1735) cm-1,( 1616-1597) cm-1,( 1552-1512) cm-1 ,( 1375-1348) cm-1 due to v (C=0)amide, v (C=0)imide v (C=N)imine , v (C=C)aromatic, v (C-N)imide, respectively. 1HNMR spectrum of compound [7] figure(2) is shown δ 3.4 ppm( 1,S, CHCO) proton, δ 2.3ppm (1,S,CH3) protons, δ 8.67ppm (1,S, NH), δ (7.3-7.78)ppm(13,m, aromatic and imine proton ) The second path involved introducing of compound [4] in reaction with carbon disulfide in presence of potassium hydroxide to producing salt [9] F.T.IR Spectrum of compound [9] showed the disappearance absorption band at the (3429, 3167) cm-1due to asymmetric and symmetric stretching vibration of the (NH-NH2) group. Appearance band at (1205) cm-1due to (C=S) also appearance band at (1442) cm-1due to (-N-C=S). These bands are good evidence for the presence of this compound. Treatment of compound [9] with access amount hydrazine hydrate produced compound [10]. F.T.IR spectrum compound [10] showed absorption band due to v (NH) indicates (the presence of tautomerism).The weak band at (2582) cm-1due to v (S-H), (3307-3163) cm-1due to v (NH,NH2).Other bands (1730, 1705)cm-1 due to vsy and vasy 90 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 (C=O)imide. Reaction of 5-(N, N –diphthalimidyl) methyl -3-thion-1, 2, 4triazole with different substituted aldehyde produced compounds [11,12] . F.TIR Spectrum of compound [11] showed the disappearance of v (NH) group due to the possibility of hydrogen bonding ,(1614)cm-1for v (C=N)imine,(1267)cm-1for v (C=S) and (1450) cm-1for v (-N-C=S). F.TIR Spectrum of derivative [12] showed single stretching band due to (NH) group appeared at (3140) cm-1, (1608) cm-1due to v (C=N) imine, (1269) cm-1due to v (C=S), and(1431) cm-1due to v (-N-C=S).cm-1, (1552) cm-1 (1375) cm-1, due to v (C=0) imide, v (C=C) aromatic, v (C- N) imide. 1HNMR for compound [11],figure(3) shown δ 3.4 ppm(1,S,CHCO) proton , δ 11ppm (1,S,OH)protons, δ 9 ppm (1,S,NH)proton , δ (6.9-7.7ppm aromatic protons and imine proton. Biological Activity The effect of compounds [5, 6, 7, 10, 11,and 12] prepared in (10% DMF solution) were tested against two types of bacteria Escherichia coli and staphylococcus aureus the experiment was conducted by using nutrient agar plates(26). The plates were incubated at 37 C0 for 24 hrs. The study showed all compounds have a varying biological activity toward mentioned bacteria accept compound [12] has no biological activity toward the E.coli Reference 1. 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María Blanco, M. ; Alejandra Salerno; and Perillo, I. A., (2010)Mass spectrometry of aromatic cyclic imides and amides. Part II: electron ionization induced decomposition of N- substituted 3,4-pyridinedicarboximides. ARKIVOC , xi, 215-231. 25. W E I Jun-hua; DON G D e-w en; i-qiang, L. I. Z.; andShu2ying, L. I., (1999) Fragm en ta tion of Som e Substituted Phtha lim ides on Electron Im pact Ion iza tion. Chem ical Research in Chinese U niversitie, 15, (2). 26. Frank Knefeli; Mayer Klaus ,K. ; and Wiegrebe ,W. , (1989)Electron Impact Induced Loss of C-5/C-8 Substituents of 1,2,3,4-Tetrahydroisoquinolines, V:Synthesis and Mass Spectrometric Fragmentation of Dihydroisoindole Derivatives Arch. pharm. 322, 419-426. 27. Amina, A.F., Ph. D. Thesis, College of Education for pure science Ibn- Al- Haitham, university of Bagdad (2008).     93 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table NO. (1) Physical properties of compounds (2-12)                         Com No. Molecular Formula M.W G/Mole M.P. C Yield % color Solvent recryst 2 C18H10N2O6 350 195-200 80 White Ethanol 3 C20H14N2O6 364 - 99 Oil - 4 C18H12N4O5 364 300 dec- 75 White Greenish Methanol- 5 C27 H21 N5O5 495 250-253 80 Yellow Aceton 6 C25 H16 N4O6 468 210-215 76 Yellow Aceton 7 C26 H18 N4O5 466 130-132 75 Yellow Methanol 8 C25 H15 N5O7 497 300 dec 60 Reddish Yellow Methanol 9 C19 H11 N4O5S2K 407 110-112 90 Greenish-yellow - 10 C19 H12 N6O4S 420 300dec 80 White Methanol 11 C26H16N6O5S 524 190-193 75 Yellow Methanol 12 C26H15N6O4SBr 583 170 - 175 75 Yellow Methanol 94 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table N0. (2): the compound structure and nomenclature of (5-8) Com No. Compound Structure compound name 5 C C N O O C C N O O CHCONHN CH (H3C)2N diphthalimidyl ethanoic acid (2-dimethyl amino-benzlidene) hydrazine 6 C C N O O C C N O O CHCONHN CH HO diphthalimidyl ethanoic acid (2-hydroxy-benzlidene)hydrazine 7 C C N O O C C N O O CHCONHN CH CH3 diphthalimidyl ethanoic acid (4-methyl-benzlidene)hydrazine 8 C C N O O C C N O O CHCONHN CH NO2 diphthalimidyl ethanoic acid (4-nitro-benzlidene) hydrazine           95 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table No. (3): The compound structure and nomenclature of (9-12) Comp. No. Compound Structure Compound name 9 CC N OO C C N O O CHCONHNH(CS)SK 2,2 diphalimido methyl xanthate 10 C C N O O C C N O O CH NHN N NH2 S 4-amino-5-(2,2diphthalimidyl-methyl)2,4-dihydro- 1,2,4-triazole-3-thione 11 C C N O O C C N O O CH NN N (Z) N H C HO S H 5-(2,2diphthalimidyl-methyl)-4-(2-hydroxy benzlidene -amino)2,4-dihydro-1,2,4-triazole-3-thione 12 C C N O O C C N O O CH NHN N S N H C Br 5-(2,2diphthalimidyl-methyl)-4-(2-bromo benzlidene amino)2,4-dihydro-1,2,4-triazole-3-thione 96 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table No. (4) : result of biological activity for compounds [5-7] and [10-12]                   Table No (4 ) result of biological activity for compounds [5-7] and [10-12]     Comp.No. E.coli Staphylococcus aureus Control Solvent DMF 11 mm --- 5 15 mm 20 mm 6 14 mm 16 mm 7 17 mm 18 mm 10 11 mm 15 mm 11 13 mm 18 mm 12 -- 14 mm Comp.No. E.coli Staphylococcus aureus Control Solvent DMF 11 mm --- 5 15 mm 20 mm 6 14 mm 16 mm 7 17 mm 18 mm 10 11 mm 15 mm 11 13 mm 18 mm 12 -- 14 mm 97 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015   C C N O O C C N O O CHCOOH Cl2CHCOOH C NH C O O 2 KOH C NK C O O H2O [1] [2] H2SO4 CH3CH2OH C C N O O C C N O O CHCOOC2H5 [3] NH2NH2.H2O CC N OO C C N O O CHCONHNH2 2 H C C N O O C C N O O CHCONHN CH R= 2- (CH3)2N, 2-OH, 4-CH3 , 4-NO2 [5-8] R (Scheme 1): Synthetic pathway for prepration of imine group     CC N OO C C N O O CHCONHNH2 [4] CS2 /KOH CC N OO C C N O O CHCONHNH(CS)SK [9] NH3NH2.H2O C C N O O C C N O O CH NHN N S NH2 C C N O O C C N O O CH NN N SH NH2 CHO R C C N O O C C N O O CH NHN N S N C H R R= OH,Br [10] [11-12] (Scheme 2): Synthetic pathway for prepration of 1,2,4-triazole   98 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 N N O O O O O OH M+ =350 N N O O O O O m/z: 321 N N O O O O N N O O O m/z 291 m/z 264 N N O m/z= 219 N O O O HO m/z= 204 N O O m/z= 160 N O m/z= 132 O m/z= 104 N O O H m/z= 148 N O O O OH NH2 m/z= 219 N O O O OH2 m/z= 192 OH NH O m/z= 148 N N O O O OH m/z= 295 H N H NH2 OH HO m/z= 166 100% N OH O O H m/z= 164 N O O O H N O O m/z= 148 HN m/z= 93 m/z= 79 H H - 2CO CO2 -CO -HCN -H (Scheme 3): the most important fragments for compound [2] 99 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015     Figure (1) mass spectrum for compound [2]                           100 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015   Figure (2): 1HNMR spectrum for compound [7]   Figure (3): 1HNMR spectrum for compound [11] 101 | Chemistry ٢٠١٥عام ) 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 ١،٢،٤حضير وتشخيص فثال ايمايدات معوضة جديدة تحتوي مشتقات ت ترايزول ايمينومجموعة خالد فھد علي إيمان محمد حسين رنا سامي أحمد / جامعة بغداد)ابن الھيثم ( للعلوم الصرفة ة التربيةيقسم الكيمياء / كل ٢٠١٥شباط ٢٣،قبل البحث في:٢٠١٥كانون الثاني ١١استلم البحث في: الخالصة الجديده المشتقة من مركب فثال ايمايد .حضرت ھذه ترايازول -٤،٢،١تم في ھذا البحث تحضير عدد من مركبات ]من ٢فثال ايمايديل حامض االيثانول [٢،٢المركبات باتباع عدة خطوات حيث تضمنت الخطوة االولى تحضير المركب ب الناتج خالل تفاعل مولين من جزيئة الفثال ايمايد مع مول واحد من ثنائي حامض كلورواسيتك وفي خطوة ثانية المرك ] وھذا بدوره تم معاملته مع الھدرازين المائي ادى الى ٣ري له عملية استرة انتج مشتق استر ثنائي فثال ايمايديل استيت[اج ]في خطوة ثالثة .ومشتق الھدرازايد تم ادخاله في مسارات تحضيريه حيث عومل مع ثاني٤تكوين مشتق الھدرازايد [ ] الذي اسفرت تفاعالته ١٠ترايزول [-٤،٢،١لھايدرازين المائي لتكوين مشتقكبريتيد الكاربون قي الوسط القاعدي ثم مع ا ]مع الديھايدات مختلفة اعطى مشتقات ٤] وعند مفاعلة المشتق [١١،١٢مع الديھايدات مختلفه تكوين قواعد شف جديدة[ و استافيلوكوكس واظھرت ]بكتريا ايكوالي١٢،١١،١٠،٧،٦،٥] . تمت دراسة الفعالية البايلوجية للمشتقات [٥-٨جديدة [ جميعھا فعالية بايلوجية . قواعد شف ترايزول، ٤،٣،١،تحضير، ايمايد مفتاحية:كلمات