Microsoft Word - 126-135 126 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Solvent -Free One -Pot Multicomponent, Synthesis, Characterization and Anti-bacterial activity, of some 2- substituted-3-cyano-Pyridine Derivatives Zakaria H. Aiube Muna S. Al-rawi Ahmed K. Ebrahem Dept. of Chemistry/ College of Education for Pure Science (Ibn Al-Haitham)/ University of Baghdad. Received in: 18 March 2015, Accepted in: 14 April 2015 Abstract Solvent- free thermal heating, one-pot condensation of acetophenone, ethyl cyanoacetate or malononitrle and substituted Aromatic aldehyde, ammonium acetate give, 2- oxo-3-cyano-4-substituted Aryl-6-phenyl pyridine [I]a-h , or 2-amino-3-cyano-4-substituted Aryl-6-phenyl pyridine derivatives[II]a-f , respectively. Treatment of compounds 2-oxo-3-cyano-4-substituted Aryl-6-phenyl pyridine with phosphorous penta sulphide (P2S5), give 2-thioxo-3-cyano-4-substituted Aryl-6-phenyl pyridine derivatives[III]a-c . All prepared compounds are characterized by, C.H.N.S-elmental analysis, melting points, FTIR-and1H-NMR-spectral analysis . Antibacterial examination of synthesized compounds [I]a-c , [II]a-c and [III]a-c against five types of, (G-) and (G+) bacterial . in comparison with common antibiotic like Ampicillin, Amoxicilin and Lincomycin the result shows 2-thioxo-3-cyano-4-substituted Aryl-6-phenyl pyridine derivatives are more reactive than 2-oxo-3-cyano pyridine derivatives or 2-amino-3-cyano pyridine derivatives . Key words: Solvent-free, one-pot, pyridine derivatives . 127 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Introduction   One-pot multi-component reactions, is an important synthetic methodology for a broad spectrum of biological and pharmaceutical organic compounds, in which the simultaneous interaction of three or more components in a sequence of steps to afford the final product [1- 4]. 3-Cyano-2-pyridone derivatives draw a special attention for their wide spectrum biological activities along with their importance and utility as intermediates in preparing variety of heterocyclic compounds [5-7]. In recent years much attention has been developed of 3-cyanopyridine derivatives because of interesting pharmaceutical and biological activities, such as antimicrobial [8-13] , analgesic anti- inflammatory [14]; and antitumor agents [15]. In view of the above mentioned facts, and giving attention to the antimicrobial effects of 3-cyanopyridines derivatives, we use the thermal heating solvent-free one-pot multicomponent reaction as a synthetic methodology for synthesis of three different types of 3-cyano pyridine with different substituted in position-2, like 2-oxo-3-cyanopyridine, 2- amino-3-cyanopyridine and 2-thioxo-3-cyanopyridine derivatives, and antibacterial activities examination against five different types of (G-) and (G+) bacteria species . N CN X ZHPh Y CN + CHO + COCH3 CH3COONH4 N H CN X ZPh [I] , [II] N H CN X SPh P2S5 N CN X SHPh [III] Y = CN , COOEt Z= [ I ]= O , [ II ]= NH In case Z = O X= 3-Br IIb = 4-Cl IIc = 4-N(CH3)2 IId = 4-NO2 IIe = 3-NO2 IIf = 4-OH IIg = 2-NO2 IIh = 4-OH , 3-OCH3 The scheme for synthesized compounds [ I ]a-h , [ II ]a-f , [ III ]a-c ,,,,,,, X + 128 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Experimental Materials and instruments All chemicals were supplied from Merck , Fluka and Aldrich Chemicals Co. and used as received . FTIR spectra were recorded using potassium bromide discs on a Shimadzo (IR prestige-21) FTIR spectrophotometer . 1HNMR spectra were carried out by company : Bruker , model: ultra shield 400 MHz , origin : Switzerland and are reported in ppm(δ) duterated, DMSO was used as a solvent with TMS as an internal standard . Elemental analysis (C.H.N.S) were carried out using an EuroEA Elemental Analyzer at ( The Central Service Laboratory-College of Education For Pure Science Ibn Al- Haitham). Uncorrected melting points were determined by using Hot-Stage, Gallen Kamp melting point apparatus .  The biological activity was performed in Center for Market Research and Consumer Protection , University of Baghdad . Synthesis Methods Synthesis 2_oxo _3 _ cyano _ 4 _substituted Aryl _ 6 _ phenyl pyridine [I] a-h. A- Solvent-free one-pot multicomponent condensation at 140 0C          A stirred mixture of acetophenone (0.01 mol, 1.17 ml), ethyl cyanoacetate (0.01 mol ,1.1 ml) , substituted benzldehyde (0.01 mol) and ammonium acetate ( 0.01 , 0.77 g ) was heated at ( 140 C°) in oil bath for 15- minute , progress of reaction was monitored by TLC ( petroleum ether : ethyl acetate eluent ) . Dough was formed , solidified upon cooling , Then Ethanol was added , a precipitate began to form , left in ice-chest for an hour , then filtered , washed with water and ethanol , dried to give a very good yield (80-90 %) . Recrystallized from ethanol . The physical data of these compounds are listed in Table 1. Anal. Calcd. for compound [I]a C18H11N2OBr : C, 61.53; H, 3.13; N, 7.97 Found: C, 61.88; H, 3.20; N,8.21 , for Calcd. compound [II]h C19H14N2O3 : C, 71.69 ; H, 4.40; N, 8.80 Found: C, 71.82; H, 4.48 ; N, 8.86 . B-ethanol reflux one-pot multicomponent condensation of acetophenone, ethyl cyanoacetate, substituted aromatic aldehyde and ammonium acetate for 8 h give poor yield (20-45)% of product . Synthesis 2_amino _3 _ cyano _4 _substituted Aryl _6 _ phenyl pyridine[II]a-f . A-Solvent-free one-pot multicomponent condensation at 140 oC        A stirred mixture of acetophenone (0.01mol , 1.17 ml), malononitrle (0.01mol, 0.66 g) , substituted benzldehyde (0.01mol), and ammonium acetate (0.01mol, 0.77 g) was heated (140 C°) in oil bath for 20 minute , progress of reaction was monitored by TLC (petroleum ether: ethyl acetate eluent). Dough was formed , solidified upon cooling , Then ethanol was added a precipitate began to form , then left in ice-chest for an hour , then filtered , washed with water then ethanol , dried to give a very good yield (75-87 %) . Recrystallized from ethanol and acetic acid. 129 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 B-ethanol reflux one-pot multicomponat condensation of acetophenone, malononitrle, substituted aromatic aldehyde and ammonium acetate for 8 h give poor yield . The physical data of these compounds are listed in Table 1. Anal. Calcd. For compound [II]a C18H12N3Br: C, 61.71; H, 3.42; N, 12.00; Found: C, 61.85 ; H, 3.49; N, 12.28 and Calcd. for compound [II]b C18H12N3Cl : C, 70.70 ; H, 3.92; N, 13.74; Found: C,71.11; H,4.01; N, 13.86 . Synthesis 2_ thioxo _3 _ cyano _4 _substituted Aryl _6 _ phenyl pyridine [III]a-c .          A mixture of 2-oxo3-cyano-4-(xʹ-substituted phenyl)-6- phenyl -2(1H)-pyridinones [II]a-c (0.01 mol) and Phosphorous pentasulphide (P2S5) (0.01 mol) in pyridine (10 mL) was refluxed for 5 h . Then reaction mixture was poured into ice-cold water. The separated solid was filtered off and washed with dilute HCl to afford the corresponding thione derivative , which was crystallized from ethanol . The physical data of these compoundes are listed in Table 1. Anal. Calcd. For compound [III]a C18H11N2 SBr: C,58.85; H, 2.99; N, 7.62; S, 8.71; Found: C, 59.12 ; H, 3.17; N, 7.88; S,8.98 and Calcd. for compound [III]c C20H17N3S : C,72.50; H, 5.13; N, 12.68; S, 9.66; Found: C, 72.72 ; H, 5.29; N, 12.92; S,9.90. Evaluation of Antibacterial Activity Antibacterial activity of synthesized compounds was determined using a disc diffusion method 30 µl of each Gram negative  Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis and gram positive Bacillus subtilis, Staphylo coccus aureus bacterial suspension of approximately 108 colony cell/ml was incubated at 37 oC for 24 h, were spread on Muller- Hintone agar using sterile collon. Swaks . 30 mg/ml solution of synthesized compounds in DMSO, were prepared and placed into occulted plates . The plates were incubated aerobically at 37oC for 24 h then inhibition zone diameter (mm) were measured. Results and Discussion Thermal-heating one-pot multicomponent condensation of equimolecular amounts of substituted benzaldehyde and acetophenon with ethylcyanoacetate and anhydrous ammonium acetate at 140 oC for less than 15 min ; afforded an excellent yield of 2-oxo- cyanopyridin derivatives [I]a-h (80-90)%. FTIR-spectral analysis of compounds[I]a-h, showed disappearance of carbonyl stretching bands of acetophenone, substituted benzaldehyde, ethyl cyanoacetate ester and ammonium acetate, and appearance of secondary amide carbonyl stretching band (C=O) at 1643-1699cm-1, besides the secondary amide (N-H) stretching bands at 3130- 3150cm-1 and cyano stretching bands at 2214-2225cm-1, as well as the appearance of (NO2) a symmetrical and symmetrical stretching bands of compounds [I]d 1516 and 1350cm-1 , [I]e at 1531,1350cm-1 and [I]g at 1527,1353 cm-1, respectively , while compound [I]f , [I]h showed (O-H) stretching band at 3338 and 3429cm-1, respectively. The other data of functional groups which are characteristics of these compounds are given in Table 2. The 1HNMR spectrum (in DMSO), of compound [I]b showed  pyridine ring proton at C5 as a singlet signal at 6.82 ppm , aromatic proton (9H) of phenyl groups at C4 and C6 of pyridine ring as a multiplet signal at 7.5-7.9 ppm : equivalent to 9-protons , and secondary amide (N-H) proton as a singlet signal at 12.89 ppm, While 1HNMR-spectrum of compound [I]g, showed pyridine ring proton at C5 as a singlet signal at 6.9 ppm , aromatic proton (9H) of phenyl groups at C4 and C6 of pyridine ring as a multiplet signal at 7.5-8.3 ppm : equivelant to 9-protons , and secondary amide (N-H) proton as a singlet signal at 13.0 ppm .   130 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Thermal heating one-pot multicomponent reaction of equimolar amounts of acetophenone, substituted benzaldehyde, malononitrle, ammonium acetate at 140 °C for less than 20 minute give a very good yield (75-87%), with high purity of 2_amino - 3 -cyano- 4(xʹ_substituted phenyl) - 6 - phenyl pyridine[II]a-f , which were characterized , (C.H.N.S) elemental analysis , FTIR-spectral analysis and 1H.NMR-spectral analysis . The FTIR absorption spectra of compound [II]a, showed the disappearance of absorption bands of the starting materials together with appearance of ( C=N) of pyridine ring at1610- 1643cm-1and a symmetrical and symmetrical stretching bands of amino group (NH2) at 3460- 3487cm-1 and 3305-3375cm-1 , respectively, and cyano group (CN ) stretching band 2206- 2214 cm-1. Moreover, the 1HNMR spectrum (in DMSO), of compound [II] a showed pyridine ring proton at C 5 as a singlet signal at 6.8 ppm , (NH2) proton as a singlet signal at 6.9 ppm (equivalent to 2-proton ) and Aromatic proton (9H) of phenyl groups at C4 and C6 of pyridine ring as a multiplet signal at 7.5-7.7 ppm (equivalent to 9-proton) . Treatment of compounds 2- oxo-3 –cyano-4(xʹ -substituted phenyl) -6 - phenyl (2H) pyridine[I] a-c with phosphorous penta sulfide (P2S5) in pyridine under reflux give correspounding 2- thioxo-3 –cyano- 4(xʹ -substituted phenyl) -6 - phenyl (2H) pyridine[III]a-c . Structure of compounds [III]a-c has been characterized by its melting points ,(C.H.N.S) elemental analysis , FTIR and 1H.NMR-spectral analysis. FTIR-spectral of compounds [III]a-c , showed disappearance of carbonyl stretching bands of 2-oxo pyridine starting material and appearance of 2-thioxo pyridine (C=S) stretching bands at 1199 , 1188, 1184 cm-1 , respectively, besides the appearance of secondary thioxo amide (N-H) stretching bends at 3433, 3398, 3394 cm-1, respectively and cyano (CN) 2218 , 2218 , 2210 cm-1 , respectively . 1H.NMR-spectral analysis of compound [III]a , showed a singlet signal of C5-pyridine ring proton at 7.1 ppm, secondary thioxo amide (N-H) proton at 8.7 ppm, and aromatic proton (9H) of phenyl groups substituted at C4 and C6 of pyridine ring as a multiplet signal at 7.3- 8.1 ppm (equivalent to 9-protons ) . While the 1H.NMR-spectrum of compound [III]b, showed C5- pyridine ring proton as singlet signal at 7.1 ppm , secondary thioxo amide (N-H) proton as singlet signal at 8.9 ppm , and aromatic proton (9H) of phenyl groups substituted at C4 and C6 of pyridine ring as a multiplet signal at 7.5-8.0 ppm. All the spectral data of FTIR spectroscopy of synthesized compounds are listed in Table (2). Biological Activity Antibacterial activity of synthesized compounds 2_oxo _3 _ cyano _ 4 _substituted Aryl _ 6 _ phenyl pyridine [I] a-c , 2_amino_3 _ cyano _ 4 _substituted Aryl _ 6 _ phenyl pyridine [II ]a-c , 2_thioxo _3 _ cyano _ 4 _substituted Aryl _ 6 _ phenyl pyridine [III] a-c respectively in comparison with common antibiotic, Ampicillin, Amoxicilin and Lincomycin against Gram negative  Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis and gram positive Bacillus subtilis, Staphylo coccus aureus.pathogenic species . are given in table (3). Result showed stronger activity exhibition of compounds [III]a-c against Pseudomonas aeruginosa, Escherichia coli and Staphylo coccus , this may be due to presence of thioxo- group (C=S) at position 2 , of 3-cyanopyridine derivatives . While all synthesized compounds showed stronger activity against Pseudomonas aeruginosa bactiria . 131 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 References: 1- Ming-Yue Yin.; A Mei-Mei Zhang.; B Wei Wang,a Yu-Ling Li,a and Xiang-Shan Wang., (2011), An efficient synthesis of 8-aryl-9H-cyclopenta[a][4,7]phenanthroline derivatives catalyzed by iodine. arkivoc, (xi) 51-59 , 2- Chebanov V.A.; Sakhno, Y.I.; Desenko, S.M.; Chernenko,V.N; Musatov, V.I.; Shishkina, S.V.; Shishkin O.V. and Kappe C.O., 2007, One-Pot, Multicomponent Route to Pyrazoloquinolizinones, Tetrahedron, 63, 1229. 3- Aggarwal, R., Kumar, V.; Bansal, A. and Sanz,D. Claramunt, R.M., 2012, Multi- component solvent-free versus stepwise solvent mediated reactions: regioespecific formation of 6-trifluoromethyl and 4-trifluoromethyl-1H-pyrazolo[3,4-b ]pyridines Journal of Fluorine Chem., 140, 31. 4- El-borai, M.A.; Rizk ,H.F. and Abd-Aal ,M.F., El-Deeb, I.Y., (2012), Synthesis of pyrazolo[3,4-b]pyridines under microwave irradiation in multi-component reactions and their antitumor and antimicrobial activities - Part 1Eur. J. Med. Chem., 48, 92. 5- Swelam, S. A.; El-Said, N. S; Aly, A. and Abdel-Fatth, A. (2009), Facile and Simple Syntheses of Heterocyclic Compounds Based on Pyridine and Pyrazolopyridine Derivatives Int.J. PharmTech Res. 1(3). 6- Kamlesh, K.; Taslimahemad, K. and Praful, P. (2013), One Pot Synthesis of Bioactive Novel Cyanopyridones Journal of the Korean Chemical Society,. 57 ( 4) . 7- Zahira Kibou1 ; Nawel Cheikh1,2, Didier Villemin2; Noureddine Choukchou-Braham1 ; Bachir Mostefa-Kara1 and Mohamed Benabdallah, (2011), A Simple and Efficient Procedure for a 2-Pyridones Synthesis under Solvent-Free Conditions, International Journal of Organic Chemistry, 1, 242-249 . 8- Hassan, A. El-Sayed, and Nabil, H. Ouf, (2012), An Efficient and Facile Multicomponent Synthesis of 4,6-Diarylpyridine Derivatives under Solvent-Free Conditions, Nature and Science;10(9). 9- Smith, A.; Owen, J.; Borgman, K.; Fish, F. and Kannankeril, P., (2011), Relation of milrinone after surgery for congenital heart disease to significant postoperative tachyarrhythmias.Am. J. Card., 108, 1620 10- Sedzani ,A. N. and Teunis ,V. R.,(2014), ʻʻSynthesis and Antimalarial Activities of Some Novel 2-Pyridonesʼʼ, Arabian Journal for Science and Engineering,. 39, 9. 6595-6598. 11- Hussein, F.; Zohdi, Nora, M. Rateb and Tamer, A. Khlosy , (2014), Synthesis, reaction and antimicrobial activity of some pyridinethione derivatives containing benzimidazole nucleus, International Journal of Advanced Research 2, 4 ,861-872 12- Mahmoud, M.R.; El-Bordany, E.A.A.; Hassan, N.F. Abu El-Azm(2007), Utility of Nitriles in Synthesis of Pyrido[2,3-d]pyrimidines, Thiazolo[3,2-a]pyridines, Pyrano[2,3-b]benzopyrrole, and Pyrido[2,3-d]benzopyrrolesPhosphorus Sulfur Silicon 182, 2507-2521.   13- Mungra, D.C.; Patel, M.P.;Patel, R.G. (2009), ''Microwave-assisted multi-component synthesis of indol-3-yl substituted pyrano[2,3-c]pyrazoles and their antimicrobial activit'', Arkivoc XIV: 64-67 14- Bekhit, A.A.; Fahmy, H.T.; Rostom, A.El-Din S.A and Bekhit, A., (2010), Synthesis and biological evaluation of some thiazolylpyrazole derivatives as dual anti-inflammatory antimicrobial agents, Eur J. Med Chem., 45, 6027. 15- Lin, R.; Chiu, G.; Yu Y.; Connolly, P.J.; Li, S.; Lu, Y.; Adams, M.; A.R. Pesquera, Greenberger S.L.E., (2007), synthesis, and evaluation of 3,4-disubstituted pyrazole analogues as anti-tumor CDK inhibitors.Bioorg., Med. Chem. Lett., 17, 4557. Design 132 | Chemistry ٢٠١٥) عام 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 synthesized compounds [I]a-h, [II]a-f and [III]a-c comp. No. Molecular Formula M.P C٠ Yield% solvent- free At 140 oC Yield% in ethanol reflux [II]a Br3N12H18C 240-242 87 25 [II]b C18H12N3Cl 252-253 75 18 [II]c C20H18N4 222-224 80 11 [II]d C18H12N4O2 230-231 84 14 [II]e C18H12N4O2 218-220 80 14 [II]f C18H13N3O 233-235 78 16 [I]a OBr2N11H18C >300 90 45 [I]b OCl2N11H18C >300 88 33 [I]c C20H17N3O >300 83 25 [I]d C18H11N3O3 >300 86 28 [I]e C18H11N3O3 >300 80 36 [I]f C18H12N2O2 >300 85 28 [I]g C18H11N3O3 >300 82 20 [I]h C19H14N2O3 >300 87 22 [III]a SBr2N11H18C 228-230 [III]b SCl2N11H18C 238-239 [III]c C20H17N3S 195-197 133 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table No.(2):Characteristic FTIR absorption bands of synthesized compounds [I]a-h ,[II]a-f and [III]a-c Comp. No. 1-H)cm-υ(N 1-H)cm-υ(C -)cmNCυ( 1 -C=N) cm(υ 1 -υ(C=O)cm 1 -υ(C=S).cm 1 1-υ(C=C).cm a]I[ 3138 3028- 3055 2214 1608 1643 - 1570-1531 b]I[ 3140 3066-3028 2214 1608 1643 - 1573-1531 c]I[ 3130 3077-3040 2206 1610 1699 - 1564-1517 d]I[ 3150 3062-3020 2210 1608 1674 - 1577-1500 e]I[ 3140 3082-3028 2214 1604 1651 - 1577-1500 f]I[ 3134 3062-3028 2225 1608 1649 - 1575-1519 g]I[ 3148 3077 -3040 2218 1603 1643 - 1519-1502 h]I[ 3136 3066 -3016 2218 1604 1643 - 1573-1525 a[II] 3358 –3483 3051-3100 2214 1629 - - 1591-1571 b[II] 3354 -3480 3037-3003 2214 1643 - - 1573-1544 c[II] 3350 -3464 3116-3080 2206 1612 - - 1566- 1523 d [II] 3375-3487 3078-3062 2210 1635 - - 1570 -1554 e[II] 3305 -3475 3100-3080 2206 1639 - - 1573- 1550 f[II] 3311 -3468 3064 -2988 2210 1629 - - 1571-1544 a[III] 3433 3080-3055 2218 1608 - 1199 1573-1554 b[III] 3433 3100-3059 2218 1608 - 1188 1573-1539 c[III] 3394 3089-3985 2210 1608 - 1184 1573-1554 134 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 Table No.(3): Antibacterial activity of synthesized compounds against five pathogenic Species. Comp. no. Mean of Inhibition zone Diameter (mm) S. aureus P.aerugina E. coli P. mirabilis B.subtilis [I]a 8 27 2 7 4 [I]b - 10 - 5 3 [I]c - 22 - 5 3 [II]a - 20 - - - [II]b - 26 22 - - [II]c - 17 - - - [III]a 17 28 30 7 4 [III]b 16 6 22 - - [III]c 16 22 17 - - Ampicillin 5 - - - - Amoxicilin 15 3 - - - Lincomycin 9 - - - - DimethylSulfoxie 0.0 0.0 0.0 0.0 0.0 135 | Chemistry ٢٠١٥) عام 2العدد ( 28مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham J. for Pure & Appl. Sci. Vol. 28 (2) 2015 -٣-معوض-٢) لبعض مشتقات متعدد المكوناتخليق (بدون مذيب بوعاء واحد ت سيانو بريدين ودراسة خواصھا البايولوجية وفعاليتھا. ھادي ايوبزكريا سعيدمنى سمير احمد خميس ابراھيم جامعة بغداد /) الھيثمابن (كلية التربية للعلوم الصرفة /قسم الكيمياء ٢٠١٥نيسان ١٤البحث في : قبل ،٢٠١٥اذار ١٨استلم البحث في: الخالصة االمونيوم بوعاء تكاثف االسيتوفينون وخالت سيانو اثيل او مالونونايتريل مع األلدھايدات األروماتية المعوضة وخالت فنيل -٦- اريل معوض-٤-سيانو- ٣-اوكسو-٢ليعطي المركبات oم ١٤٠واحد وبدون مذيب بالتسخين المباشر عند درجة -٤- سيانو-٣- اوكسو - ٢] عند معاملة مركبات II[f-aفنيل بريدين -٦- اريل معوض-٤-سيانو- ٣-امينو-٢ ،] h-a]Iبريدين فنيل - ٤-سيانو-٣-ثايوكسو -٢) ليعطي مركبات 5S2Pخامس كبريتيد الفسفور( مع ]c-a]Iفنيل بريدين -٦-اريل معوض .]c-a]IIIفنيل بريدين -٦- معوض ) ( CHNS تحليل العناصر الدقبقدرست خواص جميع المركبات المحضرة من خالل قياس درجات اانصھارھا، .)FTIR ،NMR H1( طياف االشعة تحت الحمراء والرنين النووي المغناطيسيوا ) و -G(اظھرت دراسة الفعالية البايلوجية (كمضادات حيوية) للمركبات المحضرة مع خمسة انواع من البكتريا )G+( ،و ان سين كومالينوال االموكسيلينتمت مقارنة الفعالية البايولوجية لھذه المركبات مع المضادات الحيوية األمبيسلين . تمتلك فعالية بايلوجية قوية جدا ] c-a]IIIفنيل بريدين -٦-اريل معوض -٤- سيانو-٣-ثا يوكسو-٢مركبات .البريدينمشتقات واحد،بوعاء مذيب،بدون :المفتاحيةالكلمات