Microsoft Word - 10 435 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Synthesis and Characterization New Schiff Bases,Pyrazole and Pyrazoline Compounds Derived From Acid Hydrazide Containing Isoxazoline Ring Nebras M.Jamel Dhuha F. Hussein Jumbad H.Tomma Dept.of Chemistry/College of Education For Pure Science (Ibn Al Haitham)/University of Baghdad Received in: 15 June2014,Accepted in: 29 September 2014 Abstract The work involves synthesis of new Schiff bases ( [V]a, b and [VI]a, b), pyrazoles[VII]a, b and pyrazolines[VIII]a, b derivatives containing isoxazoline unit starting with chalcones. 4- bromoacetophenone was reacted with 4-hydroxybenzaldehyde or 4-hydroxyacetophenone was reacted with 4-bromobenzaldehyde in basic medium to give chalcone by Claisen-Schemidt reaction. The chalcons [I]a, b was reacted with hydroxylamine hydrochloride to form isoxazolines [II]a, b. which were reacted with ethyl chloro acetate in basic medium to get ester compounds[III]a, b .The condensation new ester[III]a, b with hydrazine hydrate80% yieldedacid hydrazide [IV]a, b.The later compound refluxing with 4-substituted benzaldehyde in dry benzene to give Schiff bases([V]a, band [VI]a, b)while the reaction of acid hydrazide [IV]a, b with acetylacetone or ethyl aceto acetate to get pyrazole[VII]a, b , pyrazolone[VIII]a, b ,respectively.The synthesized compounds were characterized by melting points, FTIR, mass and 1H NMR spectroscopy(of someof them). Key Words:chalcones, Schiff bases, isoxazoline, pyrazole, pyrazoline. 436 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Introduction Chalcones were prepared by condensation of acetophenone with aromatic aldehydes in presence of basic medium [1]. The Chalcone derivatives are important intermediate and also act as precursor for the synthesis of novel cyanopyridines, pyrazolines, isoxazoles,pyrimidines and tetrazole [2]. Five-member heterocyclic compounds isoxazoline are important for pharmaceutical industry and material science due to their various applications. Isoxazoline are present in the structures of many natural products. In fact, isoxazoline have a broad spectrum of their biological and pharmacological activities [3-6]. Pyrazoles are one of the important members of heterocyclic compounds with two adjacent nitrogens in a five-membered ring system. Because of their aromaticity and wide application in pharmaceutical and material industry, they have gained significant interest among the scientist [7-10]. Also the pyrazoline showed a wide spectrum of biological activities such as anti-bacterial, antifungal, herbicidal and anti-choligenic [11-14]. In the view of the varied biological , pharmacological and industry applications, we have planned to synthesis some isoxazoline derivatives containing imine, pyrazole or pyrazoline unit. Experimental Chemicals All chemicals were supplied by fluka, GCC, merck and sigma-Aldrich chemicals Co. and used as received. Techniques FTIR spectra were recorded using potassium bromide discs on a Shimadzu(Ir prestige - 21) 1HNMR spectra were carried out by company:Bruker,model: ultra-shield 400MHz,origin: Switzerland and are reported in ppm(δ) DMSO were used as a solvent with TMS as an internal standard,measurements were made at Chemistry Department, science and Technology University, Jordan. The mass spectrum was recorded on shimadzu model 6CMS QL 1000 EX, made in Japan. Uncorrected melting points were determined by using Hot-Stage,Gallen Kamp melting point apparatus. Synthesis New compounds are synthesized according to scheme1 Synthesis of (chalcones) 3-(4-hydroxyphenyl)(4¯-bromophenyl)-2-propene-1-one[I]a and 3-(4¯-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one[I]b Equimolar quantities of 4-bromo or 4-hydroxy acetophenone (0.01 mol),and 4-bromo or4- hydroxy benzaldehyde (0.01 mol) were dissolved in minimum amount of alcohol. Sodium hydroxide solution (0.02 mol) was added slowly and the mixture became cold. Then the mixture was poured slowly into 400 mL of ice water with constant stirring and kept in refrigerator for 24 hrs. The precipitate obtained was filtered [15],washed and recrystallized from ethanol . Synthesis of 4-(3-(4`-bromophenyl)-4,5-dihydroisoxazol-5-yl)phenol [II]a and 4-(5-(4`- bromophenyl)-4,5-dihydroisoxazol-3-yl)phenol[II]b A mixture of chalcone (0.02 mol) , hydroxylamine hydrochloride (0.02 mol , 1.39 gm) and sodium hydroxide solution (0.5 g NaOH in 25 mL of water) in ethanol (60 mL) was refluxed for 6hrs. The mixture was concentrated under vacuum and poured into ice water[16]. The precipitate obtained was filtered, washed and recrystallized from chloroform. Synthesis of new ester derivatives[III] A mixtuer of compound [II]a, b(0.01mol) ,ethyl α- chloro acetate (0.01 mol) and fused sodium acetate (0.03mol,2.46gm) in ethanol 25mL was refluxed for 4 hrs .Then cooled and 437 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 poured into cold water, the resulting soiled was filtered and from recrystallized ethanol [17] to give a new ester. C O X Cy O H NaOH X C O CH CH X N O NH OH .HCl y ClCH CO Et Br N O N O OCH2CONHN NaOH EtOH y OCH2CO2Et OCH2CONHNH2Br N O CH3 Br CH R 4-R C H CHO6 4 OCH2COBr N O N N CH3H3C OCH2COBr N O N N CH3O Ethyl aceto acetate Acetyl acetone [I] [II] [III] [IV] [V] [VII [VIII] a a,b a ,b a a a ,b a and [VI]a ,b ] 2 2 2 NH NH .H O2 2 2 ClCH CO Et2 2 EtO2CH2CO N O Br [III]b EtOH NH NH .H O2 2 2 Br N O H2NHNOCH2CO [IV] b R NHNOCH2CO N O BrHC 4-R C H CHO6 4 Br N O OCH2CONN CH3H3C [VII] b Br N O OCH2CONN H3C O [VIII] b x= Br, y = OH ;[I] ,[II] and[III]a a a x= OH, y = Br ;[I] ,[II] and[III] b b b R=NO ,Br 2 Acetyl acetone Ethyl aceto acetate Scheme (1) Synthesis of hydrazid derivatives [IV]a, b A solution of ester [III]a, b (0.06 mol) and hydrazine hydrate(15mL) in(25mL) of ethanol was heated to reflux during 4hrs. The mixture was then cooled to room temperature[18] ,and the solid obtained was filtered and recrystallized from ethanol. The physical properties of synthesized compounds [I]-[IV] were given in Table 1. Synthesis of Schiff base derivatives[V]a, b , [VI] a, b A mixture of new hydrazide[IV]a, b (0.01 mol) , different aromatic aldehyde (0.012 mol) , dry benzene (10 mL) and 2drops of glacial acetic acid was refluxed for 3hrs . The solvent was evaporated under vacuum and the residue crystallized from chloroform[19]. Synthesis of pyrazole and pyrazoline derivatives [VII]a, b,[VIII]a, b 438 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 A mixture of new hydriozide [IV]a, b (0.0028 mol) and CH3COCH2COCH3or CH3COCH2CO2Et (0.0028 mol) in abs. EtOH(20mL) was refluxed for 3hrs. the reaction mixture was cooled and the formed precipitate was filtered off and recrystallized to give new pyrazoles [VII]a, b or pyrazoline[VIII]a, b ,respectively. The physical properties of synthesized compounds [V]-[VIII] were listed in Table 2. Results and Discussion The chalcones [I]a, b were synthesized by Claisen-Schemidt reaction from condensation aromatic aldehyde with  acetophenone in NaOH. The compounds [I]a, b were characterized by melting points, FTIR spectroscopy .The FTIR spectra of compound[I]a, b showed appearance broad band ν O-H between (3448-3250)cm-1, absorption sharp stretching band in the region(1681-1645)cm-1 due to C=O stretching with the appearance band between (1654-1610) cm-1 due to ν C=C of chalcone unit and a stretching band at (680-675)cm-1due to C-Br.Also the spectra showed disappearance characteristic bands of starting materials. The isoxazoline compound [II]a, b was synthesized by the reaction of compound[I]a, b with hydroxylamine hydrochloride in basic medium .The FTIR spectra of compound [II]a showed disappearance the bands of C=O and C=C for chalcone moiety with the appearance of new bands for ν C-Haliph. in the region (2920-2854) cm-1 and appearance of a stretching band at (1643-1640) cm-1 due to ν C=N of isoexaline ring (endo cyclic) and ν C-O of isoexaline ring between (1095-1070) cm-1 . The ester compounds [III]a, b were synthesized by the reaction of compounds [II]a, b with ethylα-chloro acetate in fused sodium acetate. The FTIR spectra of compounds [III]a, b showed a significant band at 1735cm-1 which could be attributed to stretching vibration of the carbonyl of ester group ,together with disappearance absorption band due to ν O-H group for compound[III]a, b .The1HNMR spectrum of ester compound [III]a (in DMSO as a solvent), Figure(1) showed the following characteristics chemical shifts: a singlet signal at δ4.25 ppm for two protons of OCH2 group while the aquaterale signal of protons of CH2 group appear at δ (3.12-3.20) ppm, and a triplet signal at δ1.79 ppm due to three protons of CH3group. Also the spectrum showed many signals in the region δ (6.79-8.04) ppm could be attributed to eight aromatic protons , a triplet signal at δ (3.95-4.05) ppm and doublet of doublet at δ (2.95- 3.02) ppm were assigned to one proton at C-5 and two protons at C-4,respectively of isoxazoline ring. The condensation of ester with hydrazine hydrate to get new acid hydrazides[IV]a, b. The FTIR spectra of compounds[IV]a, b showed a shift in the carbonyl stretching band to ester group of compound[III]a, b to 1645cm-1 for amide group of hydrazide[IV]a, b also showed three bands in the range(3334-3115) cm-1 which is assigned to asymmetric and symmetric bands of NH2and NH groups. The1HNMR spectrum of acid hydrazide[IV]b (in DMSO as a solvent), Figure(2) exhibited a sharp singlet at δ4.21 ppm for two proton of OCH2 group, two signals at δ3.83 ppm and δ 4.46 ppm due to two protons at C-4 and one proton at C-5 ,respectively of isoxazoline ring. A broad signal at δ3.4 ppm could be assigned for two protons of NH2 group and another broad signal at δ11.3 ppm due to proton of NH group. Finaly many signals between δ (6.63-7.87) ppm for eight aromatic protons. The new Schiff bases compound [V]a, b and[VI] a, b were synthesized by the refluxing of compound [IV]a, b with different aromatic aldehydes in benzene. The compounds were characterized by melting points, FTIR spectroscopy . The characteristic FTIR absorption bands of compounds [V]a, b and[VI] a, b as Figure(3) showed the disappearance of two absorption bands due to NH2 stretching of acid hydrazide together with the appearance of a 439 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 stretching bands at (1682-1671)cm-1 assignable to ν C=N The characteristics FTIR absorption bands of new Schiff bases [V]a, b and [VI] a, b were listed in Table 3.The refluxing hydrazide [IV] with acetyl acetone led to form new pyrazoles [VII]a, b .These compounds were characterized by melting points and FTIR spectroscopy. The FTIR spectra as Figure(4) showed the disappearance of three absorption bands due to NH2 and NH groups together with the appearance of the stretching bands near (1645) cm-1 assignable to ν C=N group and 1371 cm-1 due to N-N for pyrazole ring .Also pyrazoline [VIII]a, b is produced from the reaction hydrazide with Ethyl aceto acetate. This compound is identified by melting points , FTIR spectra and mass spectroscopy .The FTIR spectra as Figure(5) showed the disappearance of three absorption bands due to NH2 and NH groups together with the appearance of the a stretching band around 1650 cm-1 due to ν C=N band and new absorption band at (1735-1729)cm-1 due to C=O (endo cyclic) . The mass spectrum of compound [VIII]a Figure(6) showed the most fragments in scheme 2. Br N O OCH2 N N CH3O C O Br N O OCH2 NC O O Br N O OCH2 C O Br N O O Br N O Br N O Br C N C N Br NH O N N OH3C C O CH2OH2 N N OH3C C O CH2 N N OH3C C O N N OH3C H3C N NH m/z = 456 m/z = 415 m/z = 359 m/z = 317 m/z = 301 m/z = 225 m/z = 182 m/z = 102 m/z = 77 m/z = 156 m/z = 120 base peak m/z = 155 m/z = 139 m/z = 125 -14 -28 m/z = 97 m/z = 56 -Br -CH2 -CO m/z = 65 m/z = 51                                           Scheme (2) 440 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 References 1.Elarfi,M. and Al-Difar, H. (2012) “Synthesis of some heterocyclic compounds derived from chalcones” ,Scientific Reviews and Chemical Communications,2(2):103-107. 2.Selvakumar, S.; Babu,I. and Chidambaranathan, N. (2012) “Pharmacological evaluation of some potent 2-substituted benzimidazolyl chalcones for analgesic, anti- inflammatory,anthelmintic and central nervoussystem activities”,International Journal of Phytopharmacology,3(2): 163-172. 3.Chakraborty,B. ;Samanta,A.; Sharma,C.and Khatun,N. (2014) “Synthesis of some novel class of isoxazoline and isoxazolidine derivative in ionic liquid via 1,3-dipolar cycloaddition reaction of dihydropyran derived nitrones and their antimicrobial activities”,Indian Journal of Chemistry,53B: 218-226. 4.Kumar,K.; Govindaraju, M. and Kumar, G. (2014) “Synthesis and Antimicrobial activity of Novel Isoxazolines by 1, 3-Dipolar Cycloaddition Reactions”, International Journal of ChemTech Research,(6)2: 886-890. 5. Jadhav,S.(2010) “Synthesis and antimicrobial studies of some novel isoxazoline derivatives”,International Journal of Applied Biology and Pharmaceutical Technology,I(3): 939-945. 6. Baseer, M.; Shah, N.; Shaikh,S. and Kendre M.( 2013) “Synthesis and antimicrobial studies of some new halogenated isoxazoline derivatives”,International Journal of Pharmaceutical Sciences and Research,4(3): 1183-1185. 7.Banerjee, M.; Kumar, H.; Sahu, S.; Das, A. and Parasar, P. (2011) “Synthesis and in-vitro protein denaturation screening of novel substituted isoxazole/ pyrazole derivatives”, RASAYAN J.Chem.,4(2):413-417. 8. Jahan Siddiqui,N.; Idrees,M.; Khati, N. and Dhonde M. (2013) “Synthesis and Antimicrobial Activities of Some New Pyrazoles, Oxadiazoles and Isoxazole Bearing Benzofuran Moiety” , S. Afr. J. Chem., 66: 248–253. 9.Kumar, K. and Jayaroopa, P. (2013) “Pyrazoles: Synthetic Strategies and Their Pharmaceutical Applications-An Overview”,International Journal of PharmTech Research,5(4): 1473-1486. 10. Runja,C.; Pavani, B.; Deepthi, G.; Sharma,J. and Vykuntam, U.(2013) “Synthesis, Characterization andAnalgesic Activity of New Isoxazole and Pyrazole Derivatives”, Journal of Pharmaceutical and Biological Sciences,1(1): 8-11. 11.Intodia,k.; Gupta,A.; Sharma ,B. and Wasi,A. (2013) “Ecofriendly synthesis of some bioactive pyrazoline and isoxazoline derivatives from α, β-unsaturated cyclohexanone ”, Int. J. Chem. Sci., 11(4): 1621-1635. 12.Chawla,R.; Sahoo,U.; Anshu,A.; Sharma,P. and Shnan, V. (2010) “Microwave assisted synthesis of some novel 2-pyrazoline derivatives as possible antimicrobial agents ”, Acta Poloniae Pharmaceutica - Drug Research, 67 (1) :55-61. 13.Shah,V.; Dangar,V.and Borkhataria,K. (2014) “Synthesis,characterization and antimicrobial activity of pyrazoline and amino cyanopyridine derivatives of with vanillin ”, Scientific Reviews and Chemical Communications,4(1):31-37. 14.Dawane,B.; Konda,S.; Valekar,A.; Lomate,S.and Lokhande,P. (2010) “Synthesis and antibacterial studies of some new pyrazoline and isoxazoline derivatives”,Journal of Chemical and Pharmaceutical Research,2(5): 1-6. 15. Kalirajan , R.; Sivakumar , S. ;Jubie , S. ; Gowramma, B. and Suresh, B. (2009) “ Synthesisand Biological Evaluation of Some Heterocyclic Derivatives of Chalcones” , InternationalJ. of Chem Tech Research 1(1) :27-34. 16.Khazaal, M. and Tomma, J. (2011) “Synthesis and Characterization of Novel Schiff Bases Containing Isoxazoline or Pyrazoline Unit”,Ibn Al- Haitham J. for Pure & Appl. Sci,24 (2) :128-141. 441 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 17.Muhsen,T.; Tomma, J. and Mukhlus, A. J. (2012) “Synthesis and Characterization of Novel Compounds Containing of Imidazolidinone and Oxazepine Rings ” ,Ibn Al-Haitham Journal for Pure and Applied Science,25(3):276-283. 18. Tomma, J. ; karam, N.; and Al-Dujaili , A. (2006) “ Synthesis a New Series of Compounds Containing Oxadiazole Rings” ,National Journal of Chemistry,21:63-72 19. Tomma, J.; Khazaal, M. and Al-Dujaili,A. (2014) “Synthesis and characterization of novel Schiff bases containing pyrimidine unit” , Arabian Journal ofChemistry, 7:157–163. Table No. (1) The physical properties of Chalcones [I]a, b and compounds [II]a, b-[IV]a, b Com .No. Nomenclature Structural formula Molecular formula M. P 0C Yie ld % Color [I]a 3-(4`-hydroxyphenyl)(4``- bromophenyl)-2-propene- 1-one Br C O CH CH OH C15H11O2Br 158-160 45 Yellow [I]b 3-(4`-bromophenyl)-1- (4``- hydroxyphenyl) -2- propen-1-one HO C O CH CH Br C15H11O2Br 178-180 90 white [II]a 3-[4`-bromophenyl )-5- (4``-hydroxy phenyl)-4,5- dihydroisoxazole N O OHBr Br2NO12H15C 68-70 42 Yellow [II]b 3-[4`-hydroxy phenyl)-5- (4``-bromophenyl)-4,5- dihydroisoxazole N O BrHO C15H12NO2Br 130-132 60 Off white [III]a Ethyl 2-{4-[3-(4`bromo phenyl)-4,5-dihydro isoxazol-5-yl]phenoxy} acetate N O OCH2CO2EtBr C19H18NO4Br 100-102 59 Yellow [III]b Ethyl 2-{4-[5-(4`-bromo phenyl)-4,5- dihydro isoxazol-3-yl]phenoxy} acetate N O BrEtO2CH2CO C19H18NO4Br 155-158 70 Off white [IV]a 2-{4-[3-(4`- bromophenyl)-4,5- dihydroisoxazol-5-yl] phenoxy}acetohydrazide N O OCH2CBr O NHNH2 C17H16 N3O3Br 85-88 61 Pale green [IV]b 2-{4-[5-(4`- bromophenyl)-4,5- dihydroisoxazol-3-yl] phenoxy}acetohydrazide N O BrCH2CO O H2NHN C17H16N3O3Br 120-122 65 Pale green 442 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Table No.(2) The physical properties of compounds [V]a, b-[VIII]a, b Com. No. Nomenclature Structural formula Molecular formula M. P 0C Yie ld % Color [V]a {4-[3-(4`-bromophenyl) - 4,5-dihydro-isoxazol-5- yl]phenoxy}(4``-nitro benzylidine)acetic hydrazide. N O OCH2CBr O NHN HC NO2 C24H19N4O5Br 288- 290 82 Brown [V]b {4-[5-(4`-bromophenyl) - 4,5-dihydro-isoxazol-3- yl]phenoxy}(4``-nitro benzylidine)acetic hydrazide. N O BrCH2CO O =NHNO2N CH C24H19N4O5Br 276- 279 46 Yellow [VI]a {4-[3-(4`-bromophenyl) - 4,5-dihydro-isoxazol-5- yl]phenoxy}(4``- bromobenzylidine) acetichydrazide. N O OCH2CBr O NHN HC Br C24H19 N3O3Br2 158- 160 82 Brown [VI]b {4-[5-(4`-bromophenyl) - 4,5-dihydro-isoxazol-3- yl]phenoxy}(4``- bromobenzylidine) acetichydrazide. N O BrCH2CO O =NHNBr CH C24H19 N3O3Br2 110- 114 92 Pale Brown [VII]a 2-{4-[3-(4`-bromo phenyl )-4,5-dihydroisoxazol-5- yl]phenoxy}-1- (3,5dimethyl-pyrazol -1- yl)ethanone. N O OCH2CBr O N N H3C CH3 C22H 20 N3O3Br 190- 192 43 Brown [VII]b 2-{4-[5-(4`-bromo phenyl )-4,5-dihydro isoxazol-3- yl]phenoxy} -1- (3,5dimethyl-pyrazol -1- yl)ethanone. N O BrCH2CO O NN H3C CH3 C22H 20 N3O3Br 100- 103 89 Brown a[VIII] 2(2-{4-[3-(4`-bromo phenyl)-4,5-dihydro- isoxazol-5-yl]phenoxy} - acetyl)-5-methyl - pyrazolin-3-one N O OCH2CBr O N N CH3O C21H18 N3O4Br 60-62 67 Brown [VIII]b 2(2-{4-[5-(4`-bromo phenyl)-4,5-dihydro- isoxazol-3-yl]phenoxy} - acetyl)-5-methyl - pyrazolin-3-one N O BrCH2CO O NN H3C O C21H18 N3O4Br 107- 109 83 Brown 443 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Table No.(3):Characteristic FTIR absorption band of compounds[V]a, b -[VIII]a, b Comp. No. Characteristic bands FTIR spectra(cm-1) νNH νC-H aromat ic νC-H aliphati c ν C=O endocycli c ν C=O exocycli c νC=C aromati c Other [V]a 3271 3066 2957- 2854 1662 1594 ν C=N 1671 νNO2;1517,1390 [V]b 3245 3077 2968- 2843 1660 1595 ν C=N 1682 νNO2;1521,1375 [VI]a 3259 3065 2954- 2843 1654 1589 ν C=N 1682 [VI]b 3248 3071 2956- 2854 1652 1588 ν C=N 1680 [VII]a 3066 2954- 2850 1675 1591 ν C=N(pyrazole) 1645 [VII]b 3077 2954- 2854 1665 1573 ν C=N(pyrazole) 1650 [VIII]a 3066 2978- 2854 1735 1712 1595 νC=N(pyrazoline ) 1651 [VIII]b 3077 2980- 2861 1729 1711 1607 νC=N(pyrazoline ) 1650 Figure No.(1): 1HNMR-Spectrum of compound [III] 444 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Figure No. (2) :1HNMR-Spectrum of compound [IV]b Figure No. (3): FTIR-Spectrum of compound [V]b 445 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Figure No. (5): FTIR-Spectrum of cmpound [VIII]b Figure No. (4) :FTIR-Spectrum of compound [VII]a 446 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 Figure No. (6): Mass - spectrum of compound [VIII]a Target@ 5.8 min (95⁰ C) Target @ 8.5 min (200⁰ C) 447 | Chemistry 2014) عام 3العدد ( 27مجلة إبن الھيثم للعلوم الصرفة و التطبيقية المجلد Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 27 (3) 2014 مشتقة تحضير و تشخيص مركبات قواعد شف و بايارازول و بايارازولين جديدة من حامض الھيدرازيد الحاوي على حلقة األيزوكزولين. نبراس مظفر جميل ضحى فاروق حسين جمبد ھرمز توما للعلوم الصرفة (ابن الھيثم)/جامعة بغداد–قسم الكيمياء /كلية التربية 2014ايلول 29,قبل البحث في: 2014حزيران 15ستلم البحث: ا الخالصة a, b [VII],بايرازول a, b[VI]و a, b[V]شف تحضير مشتقات جديدة لقواعد البحث ھذا يتضمن -4ستعمال الجالكون مادة أساسية ,يحضر الجالكون من تفاعل باتحتوي على وحدةااليزوكزولين a, b[VIII]وبايرازولين برومو بنزالديھايد في وسط -4ھيدروكسي أسيتوفينون مع - 4ھيدروكسي بنزالديھايد أوتفاعل -4برومو أسيتوفينون مع a, [II]مع ھيدروكسيل أمين ھايدروكلورايد ليعطي االيزوكزولين a, b[I]الجالكون . يتفاعل بتفاعل كلسين شمدت قاعدي b الذي تمت مفاعلتة مع أثيل كلورو أسيتيت في وسط قاعدي لنحصل على مركب أستري,a, b[III] وحدة تكثيف األستر الذي يصعد عكسيا مع البنزلديھايد المعوض ليعطي قواعد a, bV][Iالناتج مع الھايدرازين نحصل على حامض الھايدرازايد ومن تفاعل حامض الھايدرازايد مع أستيل أسيتون أو أثيل أسيتو أستيت نحصل على a, b[VI] a, b [V]شيف على التوالي .شخصت جميع المركبات المحضرة بوساطة قياس درجات a,b[VIII]و بايارازولين a,b[VII]بايارازول (لبعض منھا)H NMR1و FTIRأنصھارھا ,طيف يزوكزولين, البايارازول, البايارازوليناأل, قواعدشف,الجالكون :المفتاحية الكلمات