Synthesis and Characterization of Some O-[2-{''2- Substituted Aryl (''1,''3,''4 thia diazolyl) ['3,'4-b]-'1,'2,'4- Triazolyl]-Ethyl]-p- chlorobenzald oxime Derivatives. Eman M.Hussain Department of Chemistry, College of Education for Pure Science, Ibn Al Haitham University of Baghdad Received in : 12January 2014, Accepted in : 14 April 2014 Abstract In this study new derivatives of O-[2-{''2-Substituted Aryl (''1,''3,''4 thia diazolyl) ['3,'4- b]-'1,'2,'4- Triazolyl]-Ethyl]-p- chlorobenzald oxime (6-11) have been synthesized from the starting material p-chloro – E- benzaldoxime 1. Compound 2 was synthesized by the reaction of p-chloro – E- benzaldoxime with ethyl acrylate in basic medium. Refluxing compound 2 with hydrazine hydrate in ethanol absolute afforded 3. Derivative 4 was prepared by the reaction of 3 with carbon disulphide, treated of compound 4 with hydrazine hydrate gave 5. The derivatives (6-11) were prepared by the reaction of 5 with different substitutes of aromatic acids. The structures of these compounds were characterized from their melting points, infrared spectroscopy, elemental analysis and 1HNMR (some of them). Compounds (6-11) were exhibited biological activity against E- coli bacteria. Compound 9 exhibited higher degree of activity than the other. Key words:Synthesis of new derivatives of thiaduazol and triazol compounds. Introduction Heterocyclics bearing a triazole or 1,3,4- thiadiazole moiety are reported to show biological properties such as antibacterial, anti- inflammatory, anticonvalsant, anticonvulsant, analgesic and antitumoral [1,2]. Banday and Rouf [13] have prepared some new 1, 2, 4- triazole derivative with antimicrobial activity. Neslihan [14] has synthesized compounds incorporating both 1, 2, 4-triazole and 1,3,4 thia diazole due to their possible diverse pharmacological properties. Cherkupally et al [15] synthesized a new series of triazoloe and thiadiazole derivatives. All the symthesized compounds were tested for in vitro activities against certain strains of bacteria such as staphylococcus aureus, Baccillus subtills, Escherichia coil and fungi such as Aspergillus niger Aspergillus nodulans , Alternaria alternate some of these derivatives showed marked inhibition of bacterial and fungal growth. The other new compounds also showed appreciable activity against the test bacteria and fungi. Gowramma et al [16] synthesized a series of 1, 3, 4- thiadiazole derivatives .All the compounds were evaluated for antibacterial and antifungal activities. Most of the compounds have shown significant antibacterial and antifungal activity when compared with the standard drugs. In this study, we decided to synthesize new derivatives of thiadiazole and triazole for their biological activity. 188 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 Experimental Materials: All chemical used were supplied from Riedel-De Hean AG, BDH chemicals, Acros Organics, Janssen chemical, Merk chemicals Fluka AG Hopkin and wiliams. Elemental analyzer were carried out by using carlo Erba/Mod 1106, Infrared spectra were recorded using Shimadzu-408 (KBr disc), 1HNMR spectra were recorded in Hitachi Perkin Elmer, R-24 B at 60MHz and melting points were recorded using Electrothermal melting point apparatus. The biometerials were obtained from Biomerieux Ltd. Synthesis of O-[2-Ethoxy carbonyl) ethyl –p-chloro- bemzaldoxime] [18]. 2 A mixture of (0.01 mole) of ethyl acrylate and 1.2 ml of 2N KOH solution in EtOH was added dropwise into a solution of (0.01 mole) of p-chloro- E-benzaldoxime 1 in EtOH (8ml). The mixture was heated at 38 C° for 15 hrs. and the solvent was removed under reduced pressure. The residue was dissolved in diethyl ether, treated with 10% NaOH solution and H2O. The organic layer was dried and removed to give 2 as solid. Compound 2 was recrystallized from ethyl acetate. Synthesis of O-(ethyl hydrazide) –p-chloro benzaldoxime. 3 A mixture of (0.005 mole) of compound 2 and (1ml) of hydrazine hydrate 98% in 10 ml of EtOH absolute was refluxed for 2hrs. After cooling the precipitate was fromed, filtered and recrystallized from EtOH to give derivative 3 as solid. Synthesis of O-2-[΄5 thiol- ΄1, ΄3, ΄4- oxadiazole-΄2- yl) - ethyl] –p- chloro benzaldoxime. 4 Compound 3 was dissolved in (20ml) of EtOH, a solution of (0.5g) KOH in (5ml) water and (0.03 mole) of CS2 was added. The reaction mixture was heated under reflux until the evaluation of hydrogen sulphide ceased. The reaction mixture was cooled, diluted with cold water (30ml) and acidified with HCL 10%. The precipitate was formed, collected by filtration, washed with water and recrystallized from (ethanol- DMF 9:1) mixture. Synthesis of O-[2-΄4 N-amino -΄5 – thiol -΄1, ΄2, ΄4- triazole- ΄3-yl) ethyl] –p- chloro benzaldoxime. 5 A mixture of compound 4 (0.01 mole) and hydrazine hydrate 98% (0.01 mole) in dry pyridine (15ml) was refluxed for 2hrs. Reaction mixture was cool and neutralized with dilute HCL. The precipitate was formed filtered and recrystallized from DMF. 1HNMR (CDCl3) δ 3.4 (1H, s, CH=NO); 7.4 (2H, d, Aromatic); 7.8 (2H, d, Aromatic); 4.4 (2H, t, O*CH2 CH2); 3.3 (2H, t, OCH2 *CH2) Synthesis of O-[2 {''2-p-Substituted –phenyl (''1, ''3, ''4- thiadiazoly) ['3,'4] - ''1, ''2, ''4- triazolyl} ethyl] p-chloro benzaldoximc. 6-11 General procedure: A mixture of compound 5 (0.01) mole, substituted benzoic acid (0.01 mole) and POCL3 (15ml) was refluxed for 6hrs, cooled and poured in to crushed ice with stirring. The solid which separated, filtered, washed successively with aqueous Na2CO3 solution and cold water. The product was dried and recrystallized from methanol. 1HNMR (CDCl3) for derivative 6:𝛿3.2 (1H, s, CHNO) 7.3-7.8 (9H, m, aromatic), 4.5(2H, t, O *CH2 CH2); 3.4 (2H, t, OCH2 *CH2), 5.2 (2H, s, NH2); 5.5(1H, s, 5H). Results and discussion The synthesis of the compounds [2-11] is depicted in the scheme 1 we used E-isomer of the oxime 1 as starting material. Compound 1 was synthesized according to known procedure [17]. Compound 2 was synthesized by the reaction of 1 with ethyl acrylate by Michale- type addition [18]. The IR spectrum of 2 showed a strong stretching band at 1725cm-1 due to (C=O) of the ester group, another stretching band was observed at 1195cm-1 for (OC2H5). Tables (1) and (2) showed the characteristic IR absorption and physical properties for all new derivatives. Gatterman method [19] was used for the synthesis of derivative 3. The derivative 189 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 3 was indicated by its melting point and infrared spectrum which showed displacement of (CO) group to low frequency at 1650 cm-1 with appearance of stretching band at 3355 cm-1 for (NH2) group. The cyclization of compound 3 with Carbone disulphide in alkaline medium gave the oxadiazole derivative 4. Derivative 4 was characterized from its melting point and IR spectrum. The IR spectrum of 4 showed two distinct peaks, the first stretching band at 1050 cm-1 due (C=S) [20] and the second weak band at 3410 cm-1 due to (NH) stretching [21], another stretching band at (1650 cm-1) was also obtained for (C=N) of the oxadiazole ring. Treatment of compound 4 with hydrazine hydrate 98% gave the triazole 5which was characterized from its melting point, IR spectrum and 1HNMR . The IR spectrum showed stretching bands at 3390 cm-1, 3280 cm-1 due to (NH2) group, other bands at 2800 [22] cm-1 for (SH) and 1610 cm-1 for (C=N). The 1HNMR of compounds 5 exhibited a singlet at 𝛿 3.4 due to (CH=NO) proton, two doublets at 𝛿 (7.4 and 7.8) integrating for four aromatic protons; triplet at 𝛿 4.4 for (O *CH2 CH2) protons and triplet at 𝛿 3.3 for (O CH2 *CH2) protons. Scheme 2 explains the suggested mechanism for derivative 5. The derivatives (6-11) were synthesized from the reaction of compound 5 with different substituted aromatic carboxylic acids in POCl3. Derivatives 6-11 were characterized from their m.p., IR and CHN- analysis, IR spectra showed the disappearance of the (NH2) and (SH) stretching bands for triazole with appearance of a weak bands in the range (1600-1640) cm-1 attribute to the (C=N) group. A strong bands were appeared in the range (1490-1498) cm-1 attributed to the (S-C=N) stretching in thiadiazole ring [23]. Compound 6 was also characterized by 1HNMR. The 1HNMR of 6 exhibited a singlet at 𝛿 3.2 due to (CH=NO) proton, multiplet at 𝛿 (7.3 - 7.8) integrating for nine aromatic protons, triplet at 𝛿 4.5 for (O *CH2 CH2) and triplet at 𝛿 3.4 (O CH2*CH2) protons. Scheme 3 explains the suggested mechanism for compounds (6-11). Compounds 6-11 exhibited a biological activity against E-Coli bacteria. Compound 9 exhibited higher degree of activity than the others table (3). References 1. Sedar,M.; Gumaukcuoglu,N.; Karaoglu, S.A. and Demirbas, N. (2007)"Synthesis of some novel 3, 5- diaryl -1,2,4- triazole derivatives and investigation of their antimicrobial activites", Turk. J. Chem., 31:315-326. 2. Palaska, E.; Sahin,G.; Kelicen,P.; Durlu,N.T. and Altionk, G.(2002) "Synthesis and anti-inflammatory activity of 1-thio semicarbazides, 1,3,4- oxadialzoles, 1,3,4-triazoles and 1,2,4-triazole-3- thiones, Farmaco, 57(2): 101-7. 3. Dua, R. and Srinivas,S.K. (2010) "Synthesis several new 2-('2- substittutedbenzylidene-hydrazino-acetyl)-mercapto-5-methyl-1,3,4-thiadiazoles, International Jornal of pharma and bio Sciences, 1(2). 4. Singh,A.K.; Lahani,M. and Singh,U.P.(2011) "Synthesis a series of new 5-Substituted- [1,3,4-thiadia- zole-2-yl] benzamid as antimicrobial activity". Pak. J. Pharm. Sci. 24 (4): 571-574. 5. Jamal,G.S.; Khan,S.A.;Alam,O. and Siddiqui,N.;(2011) "Synthesis a series of 6- substituted1,2,4-triazolo- [3,4-b]-1,3,4-thiadiazole derivatives". Acta Poloniae Pharmacetica- Drug Research, 68(2): 205-211. 6. Demirbas,N.; Alpay Karaoglu,S.; Demibas.A. and Sancak,K.(2004) "Synthesis and antimicrobial activites of some new 1,2,4-triazole derivatives", Eur- J. Med. Chem. 39:793-804. 7.Demirbas,N.;Demirbas,A.;Karaoglu,S.A. and Celik,E.(2005) "Synthesis and antimicrobial Activities of some new [1,2,4] triazolo [3,4-b] [1,3,4] thiadiazines" ARKIVOC (i):75-91. 8. Demirbas ,N.; Demirbas, A. and Karoglu, S.A.(2005) "Synthesis and biological activity of new 1, 2, 4- triazol-3-one derivatives", Russian J. Bioorg. Chem. 39:387-97. 190 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 9.Rajasekaran,A.;Murugesan,S. and Anaudara-Jagopal,K.(2006)"Antibacterial,antifungal and anticonvulsant evaluation of newly synthesized 1-1-[2- (1H-tetrazol-5-yl) ethyl]-1 H-benzol [d] [1,2,3] triazoles", Arch. Pharm. Res, 29,535-540. 10. Rajasekaran,A. and Rajagopal,K.A.(2009)"Synthesis of some novel triazol derivatives as anti-nociceptive and anti- inflammatory agents", Acta Pharm, 59:355-364. 11. Kadi,A.A.; Al-Abdullah,E.S.; Shehata,I.A.; Habib,E.E.; Ibrahim,T.M. and El- Emam,A.A.(2010)" Synthesis a new series of 1- adamanyl- 1,3,4-thiadiazole derivatives as antimicrobial agents", Eur. J. Med. Chem., 45:5006-5011 12. Baharam,L.; Negar,M.; Ali,A.; Alireza,F.(2011) "Synthesis and in vitro antibacterial activity of new 2-(1-methyl-4-nitro-1H-imidazol-5-yl-sulfonyl-1,3,4-Thiadiazoles", E. Journal of chemistry, 8, 1120-1123. 13. Banday,M.R. and Rauf,A.(2009) "Substituted 1,2,4-triazoles and thiazolidinones from Fatty acids : Spectral aracterization and antimicrobial activity", Indian Journal of Chemistry, 48B, 97-102. 14. Demirbas,N.(2005) "Synthesis and characterization of new triheterocylic compounds consisting of 1,2,4-triazol-3-one, 1,3,4-thiadiazole and 1,3,4-oxadiazole rings", Turk. J. Chem.; 29: 125-133. 15. Reddy,C.S; Rao,L.S.; Kumar,G.R. and Nagaraj,A.(2011) "Synthesis of new series of6-caryl/heteryl)-3 (5-methyl -1-phemyl- 1 H-4-pyrazolyl) [1,2,4] triazolo [3,4-b] [1,3,4 thiadiazoles", Chem. Pharm. Bull.; 1328-1331. 16. Gowramma,B; Gomaty;S and Kalirajan,R;(2011) "Synthesis, characterization and antimicrobial evaluations of some 1,3,4-thiadiazole"; IJPSR, 2(6), 1476-1479. 17. Lapucci,A.; Macchia,A.M. and Baldacci,M.M.(1994) "Synthesis, ant-inflammatory activityand molecular orbital studies of a series of benzylidene aminoxypropionic acids substituted on the phenyl ring", Eur. J. Med. Chem., 29:33. 18: Macchia,B.; Balsomo,A. and Lapucci,A. (1990) "Molecular design, synthesis, and antiinflammatory activity of a series of beta-aminoxy propionic acids", J. Med. Chem.; 33, 1423. 19. Gatterman,L. and Wieland,H.(1952) "Laboratory method of organic chemistry", Macillon Co.; P. 135. 20. Mahmoud, M.J. and Mustafa, I.F. (1996) "synthesis and characterization of some dioxadiozoles and their methyl and ethyl thioether" Mu'tah Journal for Research and studies; 11(5),155-170. 21. Williams,D.H. and Fleming,I.F.(1973) "Spectroscopic methods in organic chemrstry" 2nd Edit. Me, Graw Hill, London, 64. 22. Rani, H.S. ; Mogilaiah Rao and Sreenivasulu, B. (1996) "Synthesis and antibacterial activity of 6-aryl-3-( - methyl - , - naphthyridin- -yl)-1,2,4- triazolo-[3,4-b] [1,3,4] thiadiazoloes"; Indian Journal of Chemistry; 35B,745-747. 23. Koji,N. (1962) "Infrared Spectroscop", Nankodo Company Limited, Tokyo, PP. 54. 191 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 Table (1): Characteristic IR absorption bands of the new derivatives Compound No. Infrared data (𝜇𝑚𝑎𝑥𝑐𝑚−1) KBR (disc) 2 (C=O) 1725; (CH aliphatic) 2910, 2930; (C-O) 1195; (C=C) 1610; (C=C) out of plan (C-H) aromatic 820. 3 (C=O) 1650; (NH)3150; (NH2) 3300; (C=C) 1610; (C=C) ) out of plan (C-H) aromatic 815. 4 (NH) 3310; (C=N) 1605; (C=S) 1050; (-N.C=S) 1495; (C=C) 1595; (C=C) bending 820. 5 (NH2) 3370; (SH) 2800; (C=N) 1610; (C=N)1610, (C=C) 1590; (C=C) ) out of plan (C-H) aromatic 815; (-N.C=S1)1490. 6 (C=N) 1600; (C=C) 1595; (C=C) ) out of plan (C-H) aromatic 835. 7 (C=N) 1620; (C=C) 1590; (C=C) ) out of plan (C-H) aromatic 850; (- OCH3) 2830 8 (C=N) 1640; (C=C) 1600; (C=C) ) out of plan (C-H) aromatic 830. 9 (C=N) 1625; (C=C) 1610; (C=C) ) out of plan (C-H) aromatic 820. 10 (OH) 3630; (C=N) 1630; (C=C) 1600; (C=C) ) out of plan (C-H) aromatic 810. 11 (-NO2) (1345 and 1515); (C=N) 1615; (C=C) 1610: (C=C) ) out of plan (C-H) aromatic 820. Table (2): Physical properties for all new derivatives Compound No. Formula Melting point ℃ Elemental analysis calculated (found) Yield % C% H% N% 2 C12H14NO3Cl 179 56.47 (56.27) 5.49 (5.41) 5.49 (5.53) 60 3 C10H12N3O2Cl 195 49.79 (49.68) 4.97 (5.00) 17.42 (17.33) 55 4 C11H10N3O2ClS 225 46.64 (46.62) 3.53 (3.61) 14.84 (14.90) 75 5 C11H12N5OClS 284 44.44 (44.60) 4.04 (3.91) 23.56 23.73 86 6 C18H15N5OClS 228 59.01 (59.11) 4.29 (4.02) 19.12 (19.11) 65 7 C19H17N5O2ClS 222 57.57 (57.21) 3.66 (3.31) 17.67 (17.15) 70 8 C18H14N5OCl2S 219 56.54 (56.21) 3.66 (3.31) 18.32 (18.11) 68 9 C18H14N5OClSBr 221 48.64 (48.41) 3.15 (3.01) 15.76 (15.51) 62 10 C18H14N5O2ClS 252 56.54 (56.32) 3.92 (3.81) 18.32 (18.21) 67 11 C18H14N6O3ClS 231 52.55 (52.42) 3.40 (3.21) 20.43 (20.22) 58 192 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 Table (3): Effect of antimicrobial agents on Escherichia Coli No. compound Effect of new derivatives on the growth of E-Coli bacteria 1 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.09 Concentration gm/ml 6 _ _ _ _ _ _ + 7 _ _ _ _ _ + 8 _ _ _ _ _ _ _ + 9 _ _ _ _ _ _ _ _ _ _ + 10 _ _ _ _ _ _ _ _ + 11 _ _ _ _ _ _ _ _ _ + Blank + (-) No growth (+) Growth 193 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 (Scheme 1) Where Ar = Phenyl p-methoxy phenyl p-chloro phenyl p-bromo phenyl p- hydroxy phenyl p- nitro phenyl Compound No. 6 7 8 9 10 11 a: b: 𝐍𝐇𝟐𝐍𝐇𝟐, 𝐄𝐭𝐎𝐇 c: 𝐂𝐒𝟐, 𝐊𝐎𝐇 d: 𝐍𝐇𝟐𝐍𝐇𝟐, 𝐏𝐲𝐫𝐢𝐝𝐢𝐧𝐞 e: 𝐀𝐫𝐂𝐎𝐎𝐇, 𝐏𝐎𝐂𝐥𝟑 Cl CH N OH Cl N O CH2 CH2 COOEt 1 2 CL CH N O CH2 CONHNH2 a C CH N O CH2 CH2 NN O SHCL 4a CL CH N O CH2 CH2 CH N O CH2 CH2 NN N SHCL 5 NN O H S d 4b NH2 Cl CH N O CH2 CH2 NN N N S Ar 6-11 b CH2 3 e CH CH2 CH C OEt O KOH, 194 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 NN O R SH O NH2 NN SH NH2 + P - T N N N R SH H2O R HN NN SHR -H2O NN N R SH NH2 NH2 - NH2 - NH2 HH2O .. .. HO NN NH R SH + NH2 - H+ NH2 195 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 (Scheme 3) Pocl3Ar-COOH C O NN N NH2 SH Ar CLR NN N SH R NCAr H O NN N SH R NCAr O H enol NN N R S C NAr H O H NN NS C NAr R + - H2O C O Ar CL N N N NH2 SH R C O Cl Ar PT N N N NH SH R C O Cl Ar H -HCL 196 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014 O-[2 {2'' – معوض اریل تحضیر ودراسة بعض مشتقات اثیل] -ترایزولیل} - '4,'2, '1-[b-'4,'3] (1'',3'' ,4''- )ثایادایزولیل باراكلورو بنزالدوكزیم ایمان محمد حسین جامعة بغداد/ ابن الھیثم -كلیة التربیة للعلوم الصرفة /قسم الكیمیاء 2014نیسان 14،فبل البحث في : 2014كانون الثاني 12استلم البحث في : الخالصة -1' ,2',4' )ثایادایزولیل (1'',3'' ,4''- معوض اریل O-[2 {2'' – تم في ھذا البحث تحضیر مشتقات جدیدة من [b-'4,'3] - {كلورو -لمركب بارااستعمل ا. وقد 6-11بنزالدوكزیم واثیل] باراكلور -ترایزولیل--E مادة 1بنزالدوكزیم مع 2مع االثیل اكریلیت في وسط قاعدي. مفاعلة المركب 1حضر من تفاعل المركب 2اولیة في التحضیر. المركب 4. معاملة المشتق 4مع ثنائي كبریتید الكاربون، اعطى المركب الحلقي 3. تم مفاعلة المركب 3اعطى المشتق الھیدرازین مع حوامض اورماتیة 5من تفاعل المشتق حضرت 6-11. المشتقات 5 مع الھیدرازین بوجود البریدین اعطى المشتق كما شخص .وتحلیل العناصر IRالمشتقات الجدیدة من درجة انصھارھا وباستخدام طیف شخصت مختلفة التعویض. قولون وكان اكثرھا ضد بكتریا ال 6-11الفعالیة البایولوجیة للمشتقات من درست . 1HNMRوباستخدام 6,5المركب .9فاعلیة المشتق جدیدة لمركبات الثایادیازول و الترایازولتحضیر مشتقات مفتاحیة :الكلمات ال 197 | Chemistry @a@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹127@@ÖÜ»€a@I2@‚b«@H2014 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (2) 2014