Conseguences of soil crude oil pollution on some wood properties of olive trees Chemistry |84 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Synthesis of New beta-lactam , 2-thioxoimidazolidin-4-one and Imidazole-5-one Derivatives from thiosemicarbazide and Their Biological Activity Study Roaa Majid Abdul-Amir Hamid Dept. of Chemistry/ College of Science/AL- Mustansirya University Received in:21/Aril/2016,Accepted in:5/October/2016 Abstract New derivatives of thiosemicarbazide were synthesized by reaction of different aromatic aldehydes and ketones with thiosemicarbazide to give schiff-bases 1(a-d) . schiff-bases have been used for synthesized the thioimidazolidine 2(a-d) by reaction of schiff-bases with ethyl chloroacetatein in presence of anhydrous sodium acetate that transformed part of it in to Beta- lactam 3(a-b) compounds with phenyl acetic acid and thionyl chloride , The compounds 4(a- b) came from the reactor of 4-bromobenzaldehyde with compounds 2(a-b) , as well as reaction of compounds 2(b-d) with methyl iodide and anhydrous potassium carbonate to give 5 (b-d) , then added hydrazine hydrate formed 6(b-d) , then reaction with acetic anhydride to prepare 7(b-d) , The biological activity of the synthesized compounds was also studied . All newly compounds were characterized by using the proton nuclear magnetic resonance ( 1 H- NMR) ,mass spectra (Ms) , fourier transform infrared spectroscopy (FTIR) ,ultraviolet (UV) spectroscopy spectra , and studied their physical properties. Keywords: thiosemicarbazide ,imidazole , imidazole-5-one , beta lactame Chemistry |85 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Introduction Thiosemicarbazide is one of N-Aminothiourea compounds , as well it considers an effective control for bacterial leaf blight of rice also as a reagent for ketones , certain metals[1], of photography and as a rodenticide . In organic chemistry aldehyde or ketone condensation reaction with semicarbazide to form semicarbazone derivatives . such as Nitrofurazone used antibiotics[1] . when oxygen atom changes to sulfur atom in a semicarbazone we get thiosemicarbazone[1]. In past years thiosemicarbazone derivedes from related aldehydes and 2-formylpyridine have been of great interest because of their antineoplastic action [2] . Thiosemicarbazone derivatives have wide pharmaceutical interest and exhibit various biological activities such as anticancer , antifungal, rheumatism , antibacterial , coccidiodis, leprosy , antimalarial , antiviral and trypanosomiasis[2,3] . in organic synthesis Imidazol-thione derivatives are playing very important role and they have many applications as therapeutics and the methods for the synthesis of imidazole-2-thiones are classified according to reaction types including cyclization, reactions of halo- and oxoimidazole derivatives with sulfur-containing nucleophiles, and direct insertion of sulfur into position 2 of the imidazole ring [4-6] as well as herbicides and fungicides [7] .The 5- diphenylimidazolidin-2,4-dione and phenylimidazolone were used as anticonvulsants [8] . S- glucosylatedimidazolones[9] exhibit high activity against the human-immune deficiency virus[10] , the herpes simple virus[11] , The 1-aminoimidazolone used for the treatment of urinary tract infections as antimicrobial drug[12] , and as muscle relaxant drug for cardiac arrhythmia[13], Imidazolone-thione derivatives were reported as inhibitors of liver glycogen phosphorylases[14] . and serine protease[15] , Imidazole ring found in many drugs such as nitro imidazole which is used antifungal drugs[16,17], and the sedative midazolam[18] , more over some of these activities are antibacterial activites [19-22]. Chemistry |86 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Synthesis of new compounds 1(a-d)- 7(b-d) from thiosemicarbazide Ar - O R NH2 NH S NH2+  EtOH Ar - R N NH S NH2 ClCH2CO2Et Ar - R N N NH S O O H Br Ar - R N N NH S O Br Ar - R N N NH S Oph O MeI K2CO3 EtOH Ar - R N N N O S CH3 NH2 NH2 Ar - R N N N O NH NH2 Ar - R N N N O NN CH3 CH3 O O O CH3 1(a-d) 2(a-d) 3(a-b) 4(a-b) 5(b-d) 6(b-d) 7(b-d) Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - PhCH2COOH SOCl 2 Chemistry |87 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Experimental Instruments Melting point was determined in open capillary tube on gallenkamp melting point apparatus and are uncorrected . The FT-IR spectra were recorded by using a perkin –Elmer 1600-series FT-IR spectrometer, mass spectra (Ms) . 1 HNMR spc. were recorded onavariar –Mercury 200 µHZ spectrometer and solvents (DMSO-d6) in Jordan University . Chemicals The chemical materials that were used (Fluka, BDH) brand, it is pure substances . Synthesis of N'-Arylidenehydrazinecarbothioamide1(a-d) To a stirring solution of thiosemicarbazide(0.01 mole) in absolute ethanol (20 ml), aromatic aldehyde or ketone (o-chlorobenzaldehyde , m-nitrobenzaldehyde , p- chloroacetophenon , p- methoxyacetophenon) (0.01 mole) were added. The mixture was refluxed for 4hrs., then cooled. The precipitate was filtered and recrystallized from appropriate solvent Tables (1) and (2). Synthesis of N'-Arylideneamino-2- thioxoimidazolidin-4-one 2(a-d) A mixture of 1(a-d) (0.01mol) and ethyl chloroacetate (0.01mol) in ethanol (50 ml) in presence of anhydrous sodium acetate (0.03mol) was heated under reflux for 4 hr. After cooling to room temperature, the reaction mixture was poured into ice water. The resulting solid was filtered off, washed with hot water, dried and recrystallized from appropriate solvent Tables (1) and (2). Synthesis of 3-[2-( Arylidene)-4-oxo-3-phenylazetidin-1-yl]-2- thioxoimidazolidin-4-one(3a ,3 b) To a stirring mixture of phenyl acetic acid (0.01mol) and triethylamin (2.02gm) in (40ml) chloroform with (0.01mol) compounds (2a or 2b ) in ice bath was added drop wise of thionyl chloride (5ml) in 20ml chloroform then the reaction was stirred for (10 hrs) . After that the mixture was washed with (30ml,1NHCL) and three times with water, dried by Na2SO4(5g), recrystallized from appropriate solvent Tables (1) and (2). Synthesis of 5-arylidene-3-substituted-2-thiohydantoins (4a,4b) A mixture of (2a or 2b) (0.01mol) , appropriate aromatic aldehydes (4- bromobenzaldehyde) (0.01mol) and triethylamine (1 ml) was heated at 120-125 o C for 1hr without solvent. The reaction mixture was then left to cool at room temperature and acidified with dilute hydrochloric acid (2%). The crude product was filtered off, washed with water, dried and purified by recrystallization from the suitable solvent to give compounds (4a,4b), Tables (1) and (2). Synthesis of 2-(methylsulfanyl)-3-[(Arylidene)amino]-3,5-dihydro-4H- imidazol-4-one 5(b-d) A mixture of 2(b-d) (0.01mol) , methyl iodide (0.01mol) and anhydrous potassium carbonate (0.03 mol) in ethanol (50 ml) was heated under reflux for 4hrs. The reaction mixture was then cooled and poured in to water. The solid formed was filtered off, washed with water, dried and recrystallized from appropriate solvent Tables (1)and(2) [23]. Chemistry |88 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Synthesis of 2-hydrazinyl-3-[( Arylidene)amino]-3,5-dihydro-4H-imidazol- 4-one 6(b-d) Hydrazine hydrate (99%)(10 ml) was added to a mixture of compound (5(b- d)) (0.001 mole) in abs. ethanol (30 ml). The reaction mixture was refluxed for 8 hrs. Then, the mixture was allowed to cool to room temperature .The solid formed was filtered off , washed with ethanol and recrystallized from appropriate solvent Tables (1)and(2) [23]. Synthesis of 3-methyl-7-[(Arylidene)amino]-5H-imidazo[2,1-c][1,2,4]triazol- 6(7H)-one 7(b-d) A solution of 6(b-d) (0.01mol) in acetic anhydride (25 ml) was heated under reflux for 4 hr, then cooled and poured into ice-water (50 mL) .The solid formed was filtered off , washed with water, dried and recrystallized from appropriate solvent Tables (1)and(2) [23] . Antimicrobial evaluation The newly synthesized heterocyclic compounds, as shown in Table 3 were tested for their antimicrobial activity against the following microorganisms :Escherichia coli,klebsiella pneumonia ,staphylococcus aureus,Streptococcus lactis , and Candida albicans. The preliminary screening of the investigated compounds was performed using the holes method. and the results are summarized in Table (3). Results and discussion The research includes the preparation of N'-Arylidenehydrazinecarbothioamide 1(a-d) through aromatic aldehyde or ketone different interacts with thiosemicarbazide showed spectra FTIR(ν, cm -1 ) frequency bands belonging to the (C=N) at (1608-1585) and (NH2) at (3415 - 3232),λmax (EtOH)(nm) at (220-248) responsible for (n→ π ⃰ ) transition of (N and O) atoms and at (298-320) due to ( π → π ⃰), and then added ethyl chloroacetate to synthesis of N'-Arylideneamino-2-thioxoimidazolidin-4-one 2(a-d) diagnosed by spectra of FTIR(ν, cm -1 ) that gave the frequency bands characteristic belonging to a group (C=O)amid at (1720-1706) and the disappearance of the frequency (NH2) group in Schiff-bases, λmax (EtOH)(nm) at (221- 242) responsible for (n → π ⃰) transition of (N and O) atoms and at (315-342) due to (π →π ⃰),and diagnosed of 3-[2-(Arylidene)-4-oxo-3-phenylazetidin-1-yl]-2-thioxoimidazolidin- 4-one (3a, 3b) that attended by the reactance of (2a,2b) with phenyl acetic acid and thionyl chloride has shown FTIR(ν, cm -1 )(1761) return to the group (C=O) in the ring Beta-lactam and the disappearance of the shades (C = N) group . 1 H-NMR(δ,ppm)showed 6.87- 8.54(m,9H,ArH),4.12-4.31(s,1H,CH)amid,7.00-7.12 (s,1H,NH)amid,4.36- 4.46(d,1H,CH)Lactam,5.60-5.61(d,1H,CH-N)Lactam, as shown in Figure (1) for 3a ,Synthesis of 5- arylidene-3-substituted-2-thiohydantoins(4a,4b) attended the interaction (2a,2b) with 4- bromobenzaldehyde has shown Spectra of FTIR(ν, cm -1 ) have frequency peaks at (C=O)amid 1710- 1701, (C=C) 1649-1587,(C-Br) 810-806,and 1 HNMR (DMSO-d6)(δ,ppm),6.37- 8.39(m,8H,ArH),8.49-8.79 (s,1H,CH=N), 6.50-6.96 (s,1H, CH=CH), 2.10-2.25 (s,1H, NH)amid,as shown in Figure (2) for 4b , either synthesis of 2-(methylsulfanyl)-3- [(Arylidene)amino]-3,5-dihydro-4H-imidazol-4-one 5(b-d) came from reacting methyl iodide and anhydrous potassium carbonate to 2(b-d) where it showed FTIR(ν, cm -1 ) (C=O)amid 1710- 1718, (C=C) 1487-1597,(C=N) 1610-1674, MS (m/z) %: 278 (M - , 98.50) for (5b), as shown in Figure (3) for 5d,then reaction with Hydrazine hydrate to synthesis of 2-hydrazinyl-3- [(Arylidene)amino]-3,5-dihydro-4H-imidazol-4-one 6(b-d) characterized by FTIR (ν, cm -1 ) (C=O)amid 1712-1718,(NH2) 3250-3493,(C=N)1602-1618 and the disappearance of the frequency (C-S) group and MS (m/z) %: 262(M + ,19.90)for (6d), as shown in Figure (4) for 6c then added acetic anhydride to prepare the derivatives 3-methyl-7-[(Arylidene)amino]-5H- imidazo[2,1-c][1,2,4]triazol-6(7H)-one7(b-d).The FTIR spectra for derivatives 7(b-d) showed stretching bands at (ν, cm -1 )(C=O)amid 1714-1720,(C=N)1602-1684 and the disappearance of the frequency (NH2),MS (m/z) %: 289 (M - ,98.60)for(7C), as shown in Figure (5) for 7b, Tables (2).The study of biological activity of all new prepared compounds were listed in the Chemistry |89 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Table (3) . All prepared compounds happened according to the following mechanisms: Mechanism synthesis of 1(a-d): (Nucleophilic addition reaction) Mechanism synthesis of 2(a-d): (cyclization mechanism) Ar - C O R + NH2 NH R 1 .. Ar - C O - + NH2 NH R 1 R Ar - C OH NH NH R 1 R Ar - C N NH R 1 R P.T.-H2O  Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - R 1 = C S NH2. Ar - C N NH C R S NH2 + Cl CH2 C O OC2H5.. Ar - C N NH C R S + NH2 C ClCH2 OC2H5 O - Ar - C N NH C R S NH C Cl CH2 O + O - C2H5 H P.T. -C 2 H 5 OH Ar - C N NH C R S NH C ClCH2 O .. -HcL N NHAr - C N R S O Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - Chemistry |90 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Mechanism synthesis of 3(a-d): (cyclization mechanism) Ar - C N R 2 R + C C O Ph H .. C C N + C o - R 2 Ar - Ph RH CC Ar - Ph RH C N O R 2 Ph CH2 C O OH + S O Cl Cl H C Ph H C O O S OH Cl Cl .. OH S OH Cl Cl +C C O Ph H Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - R 2 = .N NH S O Chemistry |91 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Mechanism synthesis of 4(a-d): (Nucleophilic substitution reaction) Mechanism synthesis of 5(a-d):(SN2) Mechanism synthesis of 6(a-d): (Nucleophilic substitution reaction) N NHAr - C N R S O N NHAr - C N R S OH N + NH C - Ar - C N R S OH Tout. Br C O HN + NHAr - C N R S OH C Br H O - Tout.N NHAr - C N R S O C Br H OH -H 2 O N NHAr - C N R S O C Br H Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - N NHAr - C N R S O Tout. N NAr - C N R O SH K 2 CO 3 N NAr - C N R O S - CH 3 -I N NAr - C N R O H3C-S Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - N NAr - C N R O H3C-S + NH2 NH2 .. N N - Ar - C N R O H3C-S + NH2 NH2 N NAr - C N R O NH NH2 +CH3SH Ar = 2-ClC6H4 , 3-NO2C6H4 , 4-ClC6H4 , 4-CH3OC6H4 R H , CH3= - Chemistry |92 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Mechanism synthesis of 7(a-d): (Nucleophilic substitution reaction) References 1- DimmockJ.R.,and VashishtaS.C. 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H.(2012) Synthesis and Characterization of New 1,3-Oxazol-5-(4H)-one Derivatives , American Journal of Organic Chemistry, 2,6,(143-150). 18- Prasanthy, G.; VenkataRamana,V. ;Reddy, K.;Nirmala, K. and Kumar, R.(2011) Synthesis and biological evaluation of 1- substitution imidazole derivatives , International Research Journal of Pharmacy, 1,2,( 92-99). 19- ZalaSh.P.; Badmanaban, R.;Sen,D.J.and Patel, Ch.N.(2012)Synthesis and biological evaluation of 2,4,5-triphenyl-1H-imidazole-1-yl Derivatives, Journal of Applied Pharmaceutical Science,8,(202-208). 20- Yu-Ting Liu;Xiao-Ming Sun;Da-Wei Yin;and YuanF.(2012)Syntheses and biological activity of chalcones-imidazole derivatives,Research on Chemical Intermediates,8,3,(309- 316). 21- Lambab, H.S.;Narwalc, S.;Singhc, G.;Sainid, D.R.,Kaurd, A. and Narwal, S.(2012)Synthesis of Novel Imidazole Compounds and Evaluation of Their Antimicrobial Activity , Indo Global Journal of Pharmaceutical Sciences,2,2,(147-156). 22- Tashtoush, H.;Al-Soud Y.;Masla, A.T.;Shkoor, M. and Al-Talib, M.(2007) Synthesis and Biological Activity of Some New 5-Sulphanyl-4-nitroimidazole Derivatives,Jordan Journal of Chemistry,2,1,(11-20). http://link.springer.com/search?facet-author=%22Yu-Ting+Liu%22 http://link.springer.com/search?facet-author=%22Xiao-Ming+Sun%22 http://link.springer.com/search?facet-author=%22Da-Wei+Yin%22 http://link.springer.com/search?facet-author=%22Fang+Yuan%22 http://link.springer.com/journal/11164 Chemistry |94 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 23- Hussein, A. AL-Tamamy and Abdel Fattah M.E.(2010)Synthesis and antibacterial activity of some new imidazole, Imidazo[2,1-c]triazole and Imidazo[1,2-e]tetrazole derivatives, Oriental Journal of Chemistry, 26,2,(421-427). Table (1):Physical properties of newly synthesized compounds Comp. No. M.P (C°) & State and colour Recryst-solvent & Mol. formula(M. wt) Yield % chemical name of scientific 1a 216 Solid ,White Ethanol:H2o(2:1) C8H8ClN3S (213.68) 94 2-(2-chlorobenzylidene)hydrazinecarbothioamide 1b 244 Solid ,White Ethanol:H2o(2:1) C8H8N4O2S (224.24) 90 2-(3-nitrobenzylidene)hydrazinecarbothioamide 1c 197 Solid ,White Ethanol C9H10ClN3S (227.71) 89 2-[1-(4- chlorophenyl)ethylidene]hydrazinecarbothioamide 1d 176 Solid ,White Ethanol:H2o(1:1) C10H13N3OS (223.29) 91 2-[1-(4- methoxyphenyl)ethylidene]hydrazinecarbothioamide 2a 250 Solid ,White Ethanol C10H8ClN3OS(253.70) 83 3-[(2-chlorobenzylidene)amino]-2- thioxoimidazolidin-4-one 2b 216 Solid ,White Ethanol:H2o(2:1) C10H8N4O3S (264.62) 80 3-[(3-nitrobenzylidene)amino]-2-thioxoimidazolidin- 4-one 2c 267 Solid ,White Ethanol:H2o(1:1)C11H10Cl N3OS (267.73) 82 3-{[1-(4-chlorophenyl)ethylidene]amino}-2- thioxoimidazolidin-4-one 2d 184 Solid ,White Ethanol C12H13N3O2S (263.31) 85 3-{[1-(4-methoxyphenyl)ethylidene]amino}-2- thioxoimidazolidin-4-one 3a 240 Solid ,yellow Ethanol C18H14ClN3O2S (371.84) 72 3-[2-(2-chlorophenyl)-4-oxo-3-phenylazetidin-1-yl]- 2-thioxoimidazolidin-4-one 3b Decompose Solid ,orange Benzene C18H14N4O4S (382.39) 77 3-[2-(3-nitrophenyl)-4-oxo-3-phenylazetidin-1-yl]-2- thioxoimidazolidin-4-one 4a 240 Solid ,orange Ethanol:H2o(1:1) C17H11BrClN3OS (420.71) 65 (5Z)-5-(4-bromobenzylidene)-3-[(2- chlorobenzylidene)amino]-2-thioxoimidazolidin-4- one 4b 230 Solid ,yellow Ethanol C17H11BrN4O3S (431.26) 72 (5Z)-5-(4-bromobenzylidene)-3-[(3- nitrobenzylidene)amino]-2-thioxoimidazolidin-4-one 5b 161 Solid ,orange Ethanol:H2o(1:1) C11H10N4O3S (278.28) 52 2-(methylsulfanyl)-3-[(3-nitrobenzylidene)amino]- 3,5-dihydro-4H-imidazol-4-one 5c 169 Solid ,orange Ethanol C12H12ClN3OS (281.76) 62 3-{[1-(4-chlorophenyl)ethylidene]amino}-2- (methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one 5d 138 Solid ,orange Acetone C13H15N3O2S (277.34) 70 3-{[1-(4-methoxyphenyl)ethylidene]amino}-2- (methylsulfanyl)-3,5-dihydro-4H-imidazol-4-one 6b Oil,Brown C10H10N6O3 (262.22) 63 2-hydrazinyl-3-[(3-nitrobenzylidene)amino]-3,5- dihydro-4H-imidazol-4-one 6c 171 Solid ,Pink Ethanol C11H12ClN5O (265.69) 81 3-{[1-(4-chlorophenyl)ethylidene]amino}-2- hydrazinyl-3,5-dihydro-4H-imidazol-4-one 6d 165 Solid ,White Ethanol C12H15N5O2 (261.27) 78 2-hydrazinyl-3-{[1-(4- methoxyphenyl)ethylidene]amino}-3,5-dihydro-4H- imidazol-4-one 7b 167 Solid ,orange Ethanol C12H10N6O3 (286.24) 74 3-methyl-7-[(3-nitrobenzylidene)amino]-5H- imidazo[2,1-c][1,2,4]triazol-6(7H)-one 7c 160 Solid ,Brown Ethanol C13H12ClN5O (289.72) 50 7-{[1-(4-chlorophenyl)ethylidene]amino}-3-methyl- 5H-imidazo[2,1-c][1,2,4]triazol-6(7H)-one 7d 129 Solid ,orange Ethanol C14H15N5O2 (285.30) 62 7-{[1-(4-methoxyphenyl)ethylidene]amino}-3- methyl-5H-imidazo[2,1-c][1,2,4]triazol-6(7H)-one Chemistry |95 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Table (2): Spectral data of the new synthesized compounds Comp.No. Spectral data IR (ν, cm -1 ) UV (EtOH)& 1 H NMR (DMSO-d)& MS(m/z , 100) 1a (C = N) 1608 (NH2) 3414-3244 (C-Cl) 750 UV (EtOH)(Wavelength(nm)/Abs): 320/1.689, 220/0.405 1b (C = N) 1604 (NH2) 3392-3232 (NO2) 1523-1346 UV (EtOH)(Wavelength(nm)/Abs): 315/0.737, 222/0.410 1c (C = N) 1585 (NH2) 3400-3240 (C-Cl) 765 UV (EtOH)(Wavelength(nm)/Abs):320/0.523 , 245/1.216 1d (C = N) 1604 (NH2) 3400-3251 (C-O) 1245 UV (EtOH)(Wavelength(nm)/Abs):298/0.388 , 248/0.712 2a (C = O)amid 1720 (C=C) 1637 (C=S) 1327 UV (EtOH)(Wavelength(nm)/Abs):315/3.296, 222/0.403 2b (C = O)amid 1706 (C=C) 1639 (NO2) 1517-1348 UV (EtOH)(Wavelength(nm)/Abs):320/2.643, 221/0.405 2c (C = O)amid 1712 (C=C) 1610 (C=S) 1392 UV (EtOH)(Wavelength(nm)/Abs):324/0.425 , 223/1.226 2d (C = O)amid 1720 (C=C) 1622,1602 (C=S) 1336 UV (EtOH)(Wavelength(nm)/Abs):342/0.013 , 242/0.394 3a (C = O)lactam 1761 (C = O)amid 1728 (C=C) 1654,1602 UV (EtOH)(Wavelength(nm)/Abs):344/0.038 , 224/0.408 1 HNMR (DMSO-d6) (δ) ,6.87-7.46ppm (m, 9H, ArH), 4.31ppm (S,1H,CH)amid, 7.00ppm (S,1H, NH) amid, 4.46ppm (d,1H,CH)Lactam, 5.61ppm (d,1H, CH-N) Lactam 3b (C = O)lactam 1761 (C = O)amid 1712 (C=C) 1654,1585 (NO2) 1529-1346 UV (EtOH)(Wavelength(nm)/Abs):364/0.040 , 224/0.224 1 HNMR (DMSO-d6) (δ) ,7.44-8.54ppm (m, 9H, ArH), 4.12ppm (S,1H,CH)amid, 7.12ppm (S,1H, NH) amid, 4.36ppm (d,1H,CH)Lactam, 5.60ppm (d,1H, CH-N) Lactam 4a (C = O)amid 1710 (C=C) 1649,1606 (C-Br) 810 UV (EtOH)(Wavelength(nm)/Abs):346/0.020 , 285/0.316 1 HNMR (DMSO-d6) (δ) ,6.37-7.50ppm (m, 8H, ArH), 8.49ppm (S,1H,CH=N), 6.50ppm (S,1H, CH=CH), 2.10ppm (S,1H, NH) amid 4b (C = O)amid 1701 (C=C) 1639,1587 (NO2) 1527-1348 UV (EtOH)(Wavelength(nm)/Abs):355/0.049 , 290/0.214 1 HNMR (DMSO-d6) (δ) ,7.54-8.39ppm (m, 8H, ArH), 8.79ppm (S,1H,CH=N), 6.96ppm (S,1H, CH=CH), 2.25ppm (S,1H, NH) amid 5b (C = O)amid 1710 (C=C) 1579,1554 (C=N) 1622 UV (EtOH)(Wavelength(nm)/Abs):335/0.004 , 236/0.949 MS (m/z) %: 278 (M - , 98.50) 5c (C = O)amid 1718 (C=C) 1573,1487 (C=N) 1610 UV (EtOH)(Wavelength(nm)/Abs):303/0.723 , 238/1.237 MS (m/z) %: 281 (M - , 97.50) Chemistry |96 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. 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Vol. 30 (2) 2017 5d (C = O)amid 1716 (C=C) 1597,1556 (C=N) 1674 UV (EtOH)(Wavelength(nm)/Abs):298/0.853 , 241/1.401 MS (m/z) %: 277 (M + , 100) 6b (C = O) 1712 (NH2) 3493-3250 (C=N) 1618 UV (EtOH)(Wavelength(nm)/Abs):350/0.015 , 272/0.032 MS (m/z) %: 266 (M - , 95.50) 6c (C = O) 1718 (NH2) 3404-3281 (C=N) 1612 UV (EtOH)(Wavelength(nm)/Abs):278/0.272 , 237/0.526 MS (m/z) %: 265 (M - , 96.80) 6d (C = O) 1714 (NH2) 3412-3352 (C=N) 1602 UV (EtOH)(Wavelength(nm)/Abs):288/0.646 , 241/1.252 MS (m/z) %: 262 (M + , 19.90) 7b (C = O)amid 1720 (C=C) 1595,1556 (C=N) 1612 UV (EtOH)(Wavelength(nm)/Abs):336/0.008 , 276/0.016 MS (m/z) %: 286 (M - , 97.60) 7c (C = O)amid 1714 (C=C) 1597,1556 (C=N) 1684 UV (EtOH)(Wavelength(nm)/Abs):334/0.004 , 238/0.468 MS (m/z) %: 289 (M - , 98.60) 7d (C = O)amid 1718 (C=C) 1577,1510 (C=N) 1602 UV (EtOH)(Wavelength(nm)/Abs):311/0.156 , 242/0.347 MS (m/z) %: 285(M + , 19.90) Chemistry |97 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Table (3): Biologicalactivities of newly synthesized compounds Zone of Inhibition (mm) Comp. NO. Fungi Gram-positive Gram-negative Candida albicans Staphylococcus A. Steroptococcus SP. Klebsiella P. E.coli 500 1000 500 1000 500 1000 500 1000 *500 *1000 0 0 7 4 0 0 9 10 0 14 1a 0 0 0 5 20 12 19 19 11 19 1b 0 12 0 10 5 10 0 0 8 13 1c 0 0 8 9 10 12 15 18 12 10 1d 9 7 11 7 14 10 0 5 16 13 2a 0 0 8 10 22 17 0 0 6 12 2b 0 0 3 7 15 9 0 0 9 12 2c 0 0 0 0 12 10 21 19 12 14 2d 14 15 14 13 15 17 0 0 10 10 3a 0 0 9 13 12 8 0 0 12 11 3b 0 0 5 9 10 18 0 0 0 0 4a 0 0 2 9 6 10 0 0 10 12 4b 0 0 10 8 12 10 0 0 11 10 5b 10 0 3 7 4 12 6 0 9 11 5c 0 0 0 5 3 0 0 0 0 2 5d 0 0 4 0 5 9 5 0 10 16 6b 0 0 5 8 10 12 0 3 7 11 6c 0 0 4 0 0 5 0 0 0 3 6d 0 0 0 5 12 15 0 0 15 18 7b 0 0 5 2 8 10 0 0 9 4 7c 0 0 0 3 5 12 0 0 3 8 7d 0 0 0 0 19 10 0 0 0 10 Flagyl E.coli = Escherichia coli , Klebsiella P.= klebsiella pneumonia , Steroptococcus SP.=streptococcus species ,Staphylococcus A.= staphylococcus aureus The sensitivity of microorganisms to the tested compounds is identified in the following manner: Highly sensitive = Inhibition zone 3–22 mm Not sensitive = Inhibition zone: 0 mm *Concentration= 1000,500 ppm Chemistry |98 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Figure (1): Proton nuclear magnetic resonance spectroscopy of 3a . Figure (2): Proton nuclear magnetic resonance spectroscopy of 4b . Chemistry |99 2017(عام 2العدد ) 30هجلة إبن الهيثن للعلىم الصرفة والتطبيقية الوجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 30 (2) 2017 Figure (3): Mass spectra of 5d. Figure (4): Mass spectra of 6c . Figure (5): Mass spectra of 7b.