Synthesis and Characterization of Heterocyclic Compounds Derived From 4- Hydroxy and 4-Amino Acetophenone Nisreen H. Karam Jumbad H. Tomma Ammar H. AL-dujaili Dept. of Chemistry /College of Education For Pure Science (Ibn Al- Haitham)/ University of Baghdad Received in : 23 June 2013 , Accepted in :26 August 2013 Abstract Two series of Schiff Bases [VI]n and thiazolidin-4-one derivatives[VII]n were synthesized by many steps starting from cyclization of 4- hydroxyacetophenon with thiourea in iodine to yield 1,3-thiazole compound which was reacted with pentoxy bromide in anhydrous potassium carbonate to converted compound[II] and this reacted with Phenol to yield azo compound[III]. The azo compound reacted with ethyl chloro acetate in basic medium to get a new easter compound[IV] which is converted to their acid hydrazid[V]. The later compound condensation with n-alkoxy benzaldehyde to give new Schiff bases[VI]n . Imine group undergoes addition cyclization with thioglycolic acid to get thiazolidinone compounds[VII]n .Also, two new series of Schiff Bases [XII]n and their thiazolidin-4-one derivatives[XIII]n were synthesized by using the same steps given for synthesis Schiff bases [VI]n and thiazoidinone [VII]n except using 4- aminoacetophenon instead of 4- hydroxyacetophenon(see scheme 2) .The synthesized compounds were characterized by melting points , FTIR ,C.H.N.S analysis , 1HNMR and Mass spectroscopy (of some of them) . Keywords: Thiazole, thiazolidinone, heterocyclic compounds , Schiff bases 296 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Introduction The thiazolidin-4-one ring have reported to a wide range of pharmacologic activities which include antimicrobial[1] ,antifungal[2], antitumor[3] ,antidiabetic activity [4], anti- inflammatory[5] and stomach toxicity [6]. Over views of their synthesis , properties , reactions and applications have been published [7,8] . Fuloria et al [9] synthesized 2-(4-chloro-3-methylphenoxy)-N-(4-oxo-2-arylthiazolidin-3- yl) acetamide (1) by Cyclization N-(substituted benzylidiene)-2-(4-chloro-3- methylphenoxy)acetamide with thioglycolic acid in the presence of zinc chloride. O O Cl S N Ar O N H Ar=C6H5, 4-ClC6H4, 4-HOC6H4 or 4-(CH3)2NC6H4 (1) While, Patel et al[10] synthesized a series of novel thiazolidinones(2) by reaction of various Schiff bases of coumarin with thioglycolic acid in dry benzene. OO S N Ar OHN Ar=C6H5, 4-NO2C6H4, 3-NO2C6H4, 4-ClC6H4 or 4-CH3C6H4 (2) On the other hand, Vinay et al[11] synthesized new derivatives of thiazolidinone(3) by reaction of hydrazone compound with thioglycolic acid in DMF as a solvent. X=N(CH3)2 or Cl X S HN O C N O N (3) Recently, Kumar et al [12] synthesized new thiazolidinones derivatives 3-(2-(5-benzoyl- 1H-benzo[d][1,2,3]imidazol-1-yl)acetyl)-2- alkylthiazolidin-4-one (4) by cyclocondensation of the corresponding Schiff bases compounds with thioglycolic acid in anhydrous ZnCl2 297 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 S N R O H N N O Ph CH3 C O NH (4) R=C6H5, 4-CH3 C6H4, 4-HO-C6H4 or 4-CH3O-C6H4 In this paper , synthesis and characterization of new thiazolidinones derived from new Schiff bases containing another heterocyclic ring(1,3-thiazole). Experimental Chemicals All chemicals were supplied by fluka, merek and Aldrich chemicals Co. and used as received. Techniques FTIR spectra were recorded using potassium bromide discs on a Shimadzo(Ir prestige-21) 1HNMR spectra were carried out by company: Bruker , model: ultra-shield 300 MHz , origin : Switzerland and are reported in ppm(δ), DMSO and CDCl3were used as a solvent with TMS as an internal standard,measurements were made at Chemistry Department, Al-albyat University. Elemental micro-analyses of some compounds were performed on a (C.H.N.S) Company: Euro vector, model EA 3000A origin: Italy. University of Al-albayt, Jordan. Mass spectrum were recorded on IEOL JMS-7 high resolution instrument , Jordan. uncorrected melting points were determined by using Hot-Stage, Gallen Kamp melting point apparatus. 298 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Synthesis New compounds are synthesized according to scheme1 and scheme2: NH2 S NOH NH2 S NC5H11O S N N N OH ClCH2CO2C2H5 CH3CO2Na OCH2CO2C2H5 OCH2CONHNH2 NH2NH2 OCH2CONHN CH OCH2CONH S N N N S N N N S N N N S N N N C5H11O C5H11O C5H11O C5H11O HSCH2COOH dry bebzene C5H11O OH C I2 CH3 O C S H2N NH2 CHN O S EtOH EtOH EtOH C5H11Br K2CO3 acetone H3PO4/HNO3 NaNO2 PhOH + 4-CnH2n+1OC6H4CHO OCnH2n+1 OCnH2n+1 n=1,3-8 [I] [II] [III] [IV] [V] [VI]n [VII]n Scheme1 299 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 S N N N N N OCH2CONHN CH CH NNHCOCH2O S N N N N NH2NHNOCOCH2O OCH2CONHNH2 S N N N N N OCH2CO2C2H5 C2H5OCOCH2O NH2 S NNH2 S N N N N NHO OH C I2 CH3 O C S H2N NH2 H2N CHN O SS N N N N NNHCOCH2O OCH2CONH S O NCH ClCH2CO2C2H5 CH3CO2Na NH2NH2 HSCH2COOH dry bebzene 2H3PO4/2HNO3 2NaNO2/2PhOH [IX] + [XIII]n [XII]n 2 2 2 4-CnH2n+1OC6H4CHO2 2 EtOH EtOH EtOH [X] [XI] [VIII] n= 1, 3,4, 6 CnH2n+1O CnH2n+1O OCnH2n+1 OCnH2n+1 Scheme2 Synthesis of 4-n-Alkoxybenzaldehyde Dissolved 4-hydroxybenzaldehyde (10.61g, 0.087 mol) and potassium hydroxide (4.87g, 0.087mol) in 50 mL of absolute ethanol, and added n-alkyl bromide (0.13 mol), the mixture was refluxed for 6 hrs., and potassium bromide was precipitated after that added 50 mL water and 50 mL diethyl ether. The mixture was extracted, and take the organic phase, washed with 25 mL of water and 25 mL of 10% sodium hydroxide solution, then 25 mL of water. Dried the organic phase over magnesium sulphate [13] , then the filtered evaporated to yield 4- alkoxybenzaldehyde yields (75-80%). 300 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Synthesis of 2-Amino 4-(4`-hydroxylphenyl)-1,3-thiazole[I] In a flask of 250 mL added iodine (7.61g, 0.03mol), thioura (4.56g ,0.006mol) and 4- hydroxyacetophenone (4.08g, 0.003 mol), the mixture was heated for 8 hrs. on the water bath. Cooled, washed by diethyl ether and solution of sodium thiosulfate ,the precipitated was filtered[14]and recrystalized from ethanol . Yield 89%, m.p= 148-155 oC Synthesis of 2-Amino 4-(4`-n- pentoxyphenyl)-1,3-thiazole [II] A mixture of compound [I] (0.28g ,0.0015mol) and anhydrous potassium carbonate ( 0.80g, 0.012mol) dissolved in acetone 20 mL ,then n-pentyl bromide (0.004 mol) was added, the mixture was refluxed overnight .Afterward, the mixture was poured into ice water the precipitate was filtered and washed with water,dried and recrystalized from ethanol. Yield =74% ,m.p= 98-99 oC Synthesis of 2-( 4`-Hydroxylphenylazo)-4-([4``-n-pentoxy phenyl)-1,3- thiazole [III] Compound [II]5 ( 0.44 g, 0.0017 mol) was dissolved by heating and stirring in 8 mL of 85% phosphoric acid. The solution was cooled to 0oC in an ice bath, and then concentrated nitric acid 4 mL and a solution of sodium nitrite (0.10 g, 0.0017mol) in water 2 mL were added. The mixture was stirred vigorously and maintained at below 5oC for10 minutes. Afterwards phenol (0.15g, 0.0017mol) in water 0.5mL was added dropwise with stirring. The brown solid was filtered, washed several times with water, then dissolved in 30mL 10% NaOH, the solution filtered, the crude product precipitated during neutralization with 10%HCl [13], then filtered and washed with water several times , recrystallized from ethanol.Yield 78%, m.p = 60-62 oC. Synthesis of 2-(4`-Oxyethylacetate phenylazo)-4-(4``-n-pentoxy phenyl)-1,3- thiazole [IV] A mixture of compound[III](0.36g,0.001 mol), ethyl α -chloroacetate (0.001 mol) and fused sodium acetate(0.246g,0.003 mol) in ethanol 5 mL was refluxed for 4 hrs. then cooled and poured into cold water . The resulting was filtered and purified by ethanol to give new ester,yield73%, m.p> 295 oC. Synthesis of 2-(4`-Oxy acidhydrazide phenylazo)-4-(4``-n-pentoxy phenyl)- 1,3- thiazole[V] A solution of compound [IV] (2.71g,0.006 mol) and hydrazine hydrate 1.5 mL(80%) in absolute ethanol 2.5 mL was heated to reflux during 3 hrs[15]. The mixture was cooled to room temperature, evaporation of solvent and recrystalized from ethanol to yield pale brown compound, yield 80%. Synthesis of 2-[4`-(4``-Substutiedbenzaledine amino)-oxyacetamide] phenyl azo-4-(4```-n-pentoxy phenyl)-1,3- thiazole [VI]n A mixture of compound [V] (0.43g,0.001mol) and different aromatic aldehyde (0.001 mol) dissolved in (15 mL) of absolute ethanol was refluxed for (3-4 hrs.) and cooled to room temperature . The solid product was filtered and recrystallized by ethyl acetate to give new schiff bases.The physical properties are listed in Table1. Synthesis of Thiazolidin-4-one derivatives[VII]n A mixture of Schiff bases[VI]n (0.01mol) and thioglycolic acid (0.01 mol) was refluxed in dry benzene (10 mL) for 12 hrs. The solvent was evaporated and the reaction mixture was neutrilized with sodium bicarbonate solution, the product was filtered off and recrystallized from acetone .The physical properties are listed in Table 2. Synthesis of 2- Amino 4-(4`-amino phenyl)-1,3-thiazole [VIII] 301 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 This compound was synthesized by using the same procedure given for compound [I], except using 4-aminoacetophenone instead of 4-hydroxyacetophenone [14], recrystalized by ethanol. Yield 83%,m.p= 110-111 oC. Synthesis of 2-(4`-Hydroxyphenyl azo)-4-[4``(4```- hydroxy phenyl azo) phenyl ]-1,3-thiazole [IX] This compound was synthesized by using the same procedure given[13] for compound [III], except using the compound[VIII] instead of compound[II], recrystallized from acetone ,color dark brawn ,yield 70%, m.p > 295 oC. Synthesis of 2-(4`-Oxyethylacetate phenyl azo)-4-[4``-(4```-oxyethylacetate phenyl azo)] phenyl -1,3-thiazole [X] This compound was synthesized by using the same procedure given for compound [IV], except using the compound [IX] instead of compound[III] and used (0.002mol),( 0.492g ,0.006mol) from ethyl α -chloroacetate , fused sodium acetate respectively . The resulting was filter and purified by ethanol to give brown solid, yield 65%,m.p > 295 oC. Synthesis of 2-(4`-Oxy acid hydrazide phenyl azo)-4-[4``-(4```-oxy acid hydrazide phenyl azo)] phenyl -1,3-thiazole [XI] This compound was synthesized by using the same procedure given[15] for compound [V], except using the compound[X] instead of compound[IV] and used 3mL instead of 1.5 mL hydrazine hydrate. Recrystallized from dichloromethane to yield brown product 82%, m.p= 109-111 oC. Synthesis of 2-[4`-(4``- Substutied benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````- substutied benzaledineamino)-oxy acetamide phenyl azo] phenyl -1,3-thiazole [XII]n These compounds were synthesized using the same procedure given for compounds [VI]n , except using the compound[XI] instead of compound [V] and used (0.002 mol) from different aromatic aldehyde, recrystallized from ethanol. The physical data are given in Table 3. Synthesis of Thiazolidin-4-one derivatives [XIII]n These compounds were synthesized by using the same procedure given for compounds [VII]n, except using the compounds[XII]n instead of compounds [VI]n and used (0.02 mol) from thioglycolic acid, recrystallized from acetone .The physical data are given in Table 4. Results and Discussion The compound [I] was synthesized from fusion 4-hydroxy acetophenone with thiourea in iodine (I2). The suggested mechanism of this reaction may be as follows, Scheme 3. 302 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 OH C CH2 O H OH C CH2I O S NOH NH2 OH C CH2 O I NH2 NH SH OH C CH2 O NH2S NH .. OH C CH H NH2S OH N II+ + HI HI -H2O -+ .. _ Scheme 3 The compound [I] was characterized by melting point ,FTIR and 1HNMR. The characteristic FTIR absorption bands of compound [I] showed the disappearance absorption bands at 1662 cm-1 due to C=O stretching of 4-hydroxy acetophenone with the appearance of three a stretching bands at 3450 cm-1,3302 cm-1and 3199 cm-1 due to ʋ NH, NH2 bonds and appearance of a stretching band at 1622 cm-1 due to ʋ C=N for thiazole ring moiety. The 1HNMR spectrum (in DMSO as a solvent) showed the following signals: a single at signal at δ 9.53 ppm for one proton could be attributed to the OH group, two doublet pairs in regain δ (6.75-7.82) ppm due to four aromatic protons, a broad signal at δ 7. 57 ppm for two protons of NH2 group[16]. The signals δ6.78 ppm for one proton of thiazole ring[17] . The compound[II] was synthesized by the reaction of compound [I] with pentoxy bromide in alkaline media.The FTIR spectrum of compound [II] showed disappearance of a band of ʋ OH group and appearance of new absorption stretching bands of the aliphatic ʋ C-H group in the region 2945-2860 cm-1 for alkyl groups. Elemental analysis result of compound[II] is in good agreement with the theoretical data Elemental analysis of compound[II] : Calc. : C% = 65.11 , H% = 6.97 , N% = 10.85 , S% = 12.40 Found : C% =64.84 , H% = 6.64 , N% = 10.55 , S% = 12.61 The azo compound [III] was synthesized by coupling between diazonium salt of the amino thiazole [II] with phenol at 0-4 ̊ C . Diazonium coupling reactions are typical electrophilic aromatic substitutions in which the positively charged diazonium ion in the electrophile that reacts with the electron-rich ring of a phenol. Theis reaction usually occurs at the para position.The characteristic FTIR absorption bands of compound[III] showed the disappearance of two absorption bands due to NH2 stretching of amine compound together with the appearance of a stretching broad band around 3381 cm-1 due to the intermolecular hydrogen bonding of ʋ O-H band. It also shows a band at 1537 cm-1 which is due to the ʋ N=N group. The new compound[IV] was synthesized by the reaction of compounds[III] with ethyl α - chloroacetate in fused sodium acetate . The FTIR spectrum of compound [IV] showed a significant band at 1732 cm-1 which could be attributed to stretching vibration of the carbonyl of ester group. They also showed the disappearance of absorption band due to ʋ O-H of compound [III]. 303 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 The compound [V] was synthesized by the reaction of ester compound [IV] with hydrazine hydrate in ethanol.The FTIR spectrum of compound [V] showed a shift in the carbonyl stretching band to ester group of compound [IV] to 1666 cm-1 for amide group of compound [V], also showed three bands in the range (3421-3043) cm-1 which is assigned to asymmetric and symmetric bands of NH and NH2groups. The Schiff bases of compounds[VI]n were synthesized by the refluxing of compound [V] with different aromatic aldehydes in ethanol. The new Schiff bases compounds were characterized by melting points , C.H.N.S analysis , FTIR , 1HNMR and Mass spectroscopy for compound[VI]1.The characteristic FTIR absorption bands of series [VI]n showed the disappearance of two absorption bands due to NH2 stretching of acid hydrazide together with the appearance of a stretching bands in the range at(1647-1655) cm-1 assignable to ʋ C=N. The Characteristics FTIR absorption bands of new Schiff bases[VI]n are listed in Table( 5). Elemental analysis of compound [VI]6: Calc. : C% = 66.98 , H% = 6.53 , N% = 11.16 , S% = 5.10 Found : C% = 67.12 , H% = 6.94 , N% = 11.32 , S% = 5.02 The above values are consistent with their proposed structure . The1HNMR spectrum(in CDCl3 as a solvent) for compound[VI]3 showed the following signals: : a sharp singlet signal at δ8.60 ppm that could be attributed to the azomethaine proton. Two doublets in the region δ (6.93-7.77) ppm due to twelve aromatic protons of phenyl rings and the one proton of thiazole ring overlap with aromatic protons of benzene rings , signal at δ (3.95-3.99)ppm is assigned for four protons of two OCH2 groups and proton of NH group ,multiplate signal in region δ(1.77-1.89) ppm due to eight protons of CH2 groups and two protons of -CH2C=O group appear at δ 2.16 ppm ,triplate signal at δ( 1.02- 1.07) ppm for six protons of two CH3 groups. The mass spectrum of compound [VI]1(M.Wt=557) showed several peaks attributed to the presence of thiazole derivative as in Figure 1, showed two interesting peaks at m/z =269 (base peak) and m/z =393.Also showed most characteristic fragment at m/z =309 due to the cleavage of thaizole ring (HN=CH-Ar) , this is a good evidence for the presence of thaizole ring[18]. In addition showed another fragments at m/z=383 and m/z=369 ,this is another evidence for the presence of thaizole ring [19]. The thiazolidin-4-ones derivatives [VII]n were synthesized by refluxing equimolar amounts of the Schiff bases [VI]n with thioglycolic acid in dry benzene. These compounds were characterized by their melting points, C.H.N.S. analysis ,FTIR and 1HNMR spectroscopy.The FTIR spectra of compounds [VII]n showed the disappearance of a stretching band of imine group and appearance of stretching band due to a carbonyl group of thiazolidinone around (1710-1705) cm-1 and the FTIR spectra showed a band in (904-898) cm-1 for C-S stretching. This was the most characteristic evidence for the success of cyclization step. The FTIR spectral data for these compounds are listed in Table 6. Elemental analysis of compound[VII]6 : Calc. : C% = 63.33 , H% = 6.13 , N% = 9.98 , S% = 9.12 Found : C% = 63.36 , H% = 6.18 , N% = 10.20 , S% = 9.71 This result is consistent with its proposed structure. 1HNMR spectrum of compound[VII]5 (in DMSO as a solvent) showed the following characteristics chemical shifts : a signal at δ 8.12 ppm for proton of NH group ,multiplet signal in region δ (6.90-7.70) ppm for twelve aromatic protons of the benzene rings, signal at δ 6.55 ppm for proton of thiazole ring , a singlet was observed at δ5.70 ppm that could be assigned to the proton of H-2 thiazolidinone , another singlet signal appeared at δ 5.60 ppm due to proton of H-5 thiazolidinone. Also the 1HNMR spectrum show signal observed 304 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 between δ (3.73-3.95) ppm was assigned to four protons of two methylene groups (O-CH2) ,multiplet at δ(0.87-1.69) ppm could be attributed to eighteen protons of two (CH2)3CH3 groups .Finally a sharp singlet signal appears at δ 4.40 ppm for two protons of -CH2C=O group . The compound [VIII] was synthesized from fusion 4-aminoacetophenone with thiourea in iodine (I2) .This compound was characterized by melting point and FTIR. The FTIR spectrum of compound [VIII] showed the disappearance absorption stretching bands of carbonyl group C=O and C=S of 4-aminoacetophenone and thiourea with the appearance of a stretching bands in reign( 3304- 3182 ) cm-1 due to ʋ NH ,NH2 groups and appearance a new stretching band at 1624 cm-1 due to ʋ C=N for thiazole ring moiety. While, the compound [IX] was synthesized by the reaction of one mole of compound [VIII] with HNO2 at 0-4 ̊ C to get diazonium salt, which was reacted with two mole of phenol at the same temperature . The FTIR spectrum of this compound[IX] showed the disappearance of two absorption bands due to NH2 stretching of amine compound [VIII] together with the appearance of a stretching two broad bands at 3404 cm-1and 3340 cm-1 due to the intermolecular hydrogen bonding of ʋ O-H bond. It also shows a band at 1516 cm-1 which is due to the ʋ N=N group. The reaction of compound[IX] with two moles from ethyl α-chloroacetate in basic medium yielded a new compound[X]. This compound identified by melting point and FTIR spectroscopy. The FTIR spectrum of compound [X] showed a significant band at 1730 cm-1 which could be attributed to stretching vibration of the carbonyl of ester groups, they also showed the disappearance absorption band due to ʋ O-H group for compound [XI]. The acid hydrazide [XI] is produced from the condensation of ester compound [X] with two moles hydrazine hydrate in ethanol. This compound is identified by melting point and FTIR spectroscopy.The FTIR spectrum of this compound showed the disappearance of absorption band of carbonyl for ester group and the appearance of a new band at 1666 cm-1 due to stretching vibration carbonyl for amide group, also showed three bands in the region (3387-3188) cm-1 due to asymmetric and symmetric of NH and NH2 groups. The new Schiff bases [XII]n were synthesized by refluxing one mole of compound [XI] with two moles of n-4-alkoxy benzaldehyde in absolute ethanol. The new Schiff bases compounds were characterized by melting points , FTIR spectroscopy. The characteristic FTIR absorption bands showed the disappearance of two absorption bands due to NH2 group together with the appearance of a stretching bands in region (1656- 1650) cm-1 assignable to ʋ C=N group.The Characteristics FTIR absorption bands of these compounds[XII]n are given in Table(7).The compounds[XIII]n were synthesized by the reaction of two moles of thioglycolic acid with one mole of Schiff bases [XII]n in dry benzene. The compounds were characterized by their melting points and FTIR spectroscopy. The FTIR spectra showed the disappearance of a stretching band of imine groups and the appearance of a stretching band of carbonyl group of thiazolidinone moiety around (1712-1716) cm-1 and C-S groups around ( 902- 906) cm-1. The FTIR spectral data for these compounds are listed in Table (8). References 1. 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Res, 27:1099-1105. 5. Gursoy, A. and Glu,N.T.I. (2005) “Synthesis and Isolation of New Regioisomeric 4- Thiazolidinones and Their Anticovulsant ”, Activity. Turk. J.Chem,29:247-254. 6. Pareek, D.; Chaudhary , M .; Pareek , P. K. ; Kant, R.; Ojha , K. G. ; Pareeka, R. and Pareeka, A. (2011) “ Synthesis and biological evaluation of 4-thiazolidinone derivatives incorporating benzothiazole moiety”, Der Pharmacia Sinica , 2 (1) : 170-181. 7. Brown ,F. C. (1961)“ Thiaz olidin-4-ones” . Chem. Revs. 61 :463-521. 8. Newcome, G. R. and Nayak, A. (1961), “Thiazolidin-4-ones ”. adv. Hetero cycl. Chem. 25 : 83-112. 9. Fuloria,N.K. ; Singh, V. ; Yar M.S. and Ali, M. (2009 )“ Synthesis, Characterization And Antimicrobial Evaluation of Novel Imines And Thiazolidinones”, Acta Poloniae Pharmaceutica- Drug Research, 66( 2) : 141-146 . 10. Patel,D. ; Kumari , P. and Patel, N. (2010) “Synthesis and characterization of some new thiazolidinones containing coumarin moiety and their antimicrobial study”, Archives of Applied Science Research, 2 (6) :68-75. 11. Vinay, V.; Shikha, M. ; Ashish, P. ; Mukesh ,G. and Anurag,B.( 2011)“Synthesis And Antimicrobial Evaluation of 4-Thiazolidinone Derivatives”, IJRAP, 2(1) :281-288. 12. Kumar, D. ; Bux,F. B. ; Parmar ,V. and Singh,A. (2012) “Thiazolidinone: Synthesis and biological studies”, Der Pharma Chemica, 4 (1) :538-543. 13. Rou'il, I.H. (2006), Ph.D.Thesis,College of Education Ibn-Al-Haitham, University of Baghdad. 14. King ,L. C. and Hlavacek, R.J. (1950) “The Reaction of Ketones with Iodine and Thiourea”, J. Am. Chem. Soc.,72(8) :3722–3725. 15. Jumbad, H.T; Nasreen,H.K and Amar, H.A.D(2006) “Synthesis a New Series of Compounds Containing Oxadiazole Rings”,National Journal of Chemistry,21:63-72. 16. Yen ,M. S. and Wang,I.J.( 2004 ) “ A facile syntheses and absorption characteristics of some monoazo dyes in bis –heterocyclic aromatic systems part II: syntheses of 4-(p- substituted) phenyl-2-(2-pyrido-5-yl and 5-pyrazolo-4-yl) azo-thiazole derivatives”, Dyes and Pigments ,63: 1-9. 17. Potewar, T. M. ; Ingale ,S. A. and Srinivasan,K. V. (2008) “ Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature”, Tetrahedron ,64: 5019–5022. 18. Katritzky ,A. and Pozharskii, A. F.(2000)“Handbook of Heterocyclic Chemistry”, second Edition. 19. Parmar, J. M. and Joshi, N. K.( 2012) “Mass Spectral Fragmentation Modes of Pyrimidine Derivatives”, International Journal of Chem Tech Research, 4 (2) : 834-841. 306 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Table( 1):the physical properties for the compounds[VI]n Com p. No. Nomenclature Structural formula Molecular formula M. P 0C Yield % Color [VI]1 2-[4`-(4``-methoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OCH2CONHN CH S N N N CH3O C5H11O C30H31O4N 5S 159- 160 88 Pal yellow [VI]3 2-[4`-(4``-propoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OC3H7OCH2CONHN CH S N N N C5H11O C32H35O4N 5S 143- 145 79 Pal yellow [VI]4 2-[4`-(4``-butoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OCH2CONHN CH S N N N OC4H9 C5H11O C33H37O4N 5S 132- 134 85 Yellow [VI]5 2-[4`-(4``-pentoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OCH2CONHN CH S N N N OC5H11 C5H11O C34H39O4N 5S 120- 121 75 Pal yellow [VI]6 2-[4`-(4``-hexoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OC6H13OCH2CONHN CH S N N N C5H11O C35H41O4N 5S 117- 118 80 Pal yellow [VI]7 2-[4`-(4``-heptoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OC7H15OCH2CONHN CH S N N N C5H11O C36H43O4N 5S > 295 70 Pal yellow [VI]8 2-[4`-(4``-octoxy benzaledine amino)- oxyacetamide] phenyl azo-4- (4```-n-pentoxyphenyl)-1,3- thiazole OCH2CONHN CH S N N N OC8H17 C5H11O C37H45O4N 5S 99- 101 83 Pal yellow 307 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Table (2):The physical properties for the compounds[VII]n Comp . No. Nomenclature Structural formula Molecular formula M. P 0C Yiel d % Color [VII]1 2-{4`-[2-(4``- methoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl} azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O OCHN O S CH3 C32H33O5N5 S2 230- 232 64 Off white [VII]3 2-{4`-[2-(4``- propoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl} azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O CHN O S OC3H7 C34H37O5N5 S2 gummy 70 Off white [VII]4 2-{4`-[2-(4``- butoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl} azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O OC4H9CHN O S C35H39O5N5 S2 gummy 74 Off white [VII]5 2-{4`-[2-(4``- pentoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl} azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O OC5H11CHN O S C36H41O5N5 S2 gummy 70 pink [VII]6 2-{4`-[2-(4``- hexoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl }azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O OC6H13CHN O S C37H43O5N5 S2 gummy 65 Off white [VII]7 2-{4`-[2-(4``- heptoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl }azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O OC7H15CHN O S C38H45O5N5 S2 gummy 63 Pal brow n [VII]8 2-{4`-[2-(4``- octoxyphenyl)-3- (oxyacetamide)thiozoliden- 4-one]phenyl }azo-4-(4```- pentoxyphenyl)-1,3-thiazole OCH2CONH S N N N C5H11O CHN O S OC8H17 C39H47O5N5 S2 > 290 68 pink 308 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Table(3):The physical properties of compounds[XII]n Comp. No. Nomenclature Structural formula Molecular formula M. P 0C Yiel d % Color [XII]1 2-[4`-(4``-methoxy benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````-methoxy benzaledineamino)-oxy acetamide phenyl azo] phenyl - 1,3-thiazole S N N N N N OCH2CONHN CH CH NNHCOCH2O OCH3 CH3O C41H35O6N9 S 160- 162 83 yellow [XII]3 2-[4`-(4``- propoxy benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````-propoxy benzaledineamino)-oxy acetamide phenyl azo] phenyl - 1,3-thiazole S N N N N N OCH2CONHN CH CH NNHCOCH2O OC3H7 C3H7O C45H43O6N9 S 140- 141 79 pal brown [XII]4 2-[4`-(4``- butoxy benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````-butoxy benzaledineamino)-oxy acetamide phenyl azo] phenyl - 1,3-thiazole S N N N N N OCH2CONHN CH CH NNHCOCH2O OC4H9 C4H9O C47H47O6N9 S 120- 122 80 pal brown [XII]6 2-[4`-(4``- hexoxy benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````-hexoxy benzaledineamino)-oxy acetamide phenyl azo] phenyl - 1,3-thiazole S N N N N N OCH2CONHN CH CH NNHCOCH2O OC6H13 C6H13O C51H55O6N9 S 90- 92 75 yellow 309 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Table(4):The physical properties of compounds[XIII]n Comp. No. Nomenclature Structural formula Molecular formula M. P 0C Yield % Color [XIII]1 2-{4`-[2-(4``-methoxy phenyl)-3- oxyacetamide)thiozoliden-4- one]phenyl }azo-4-{4```-[2- (4````- methoxy phenyl)-3- (oxyacetamide) thiozoliden-4- one]phenyl azo }phenyl-1,3- thiazole CHN O SS N N N N NNHCOCH2O OCH2CONH S O NCH OCH3 CH3O C45H39O8N9S2 gummy 70 pal yellow [XIII]3 2-{4`-[2-(4``-propoxy phenyl)-3- oxyacetamide)thiozoliden-4- one]phenyl }azo-4-{4```-[2- (4````- propoxy phenyl)-3- (oxyacetamide) thiozoliden-4- one]phenyl azo }phenyl-1,3- thiazole CHN O SS N N N N NNHCOCH2O OCH2CONH S O NCH OC3H7 C3H7O C49H47O8N9S2 gummy 67 pal yellow [XIII]4 2-{4`-[2-(4``-butoxy phenyl)-3- oxyacetamide)thiozoliden-4- one]phenyl }azo-4-{4```-[2- (4````- butoxy phenyl)-3- (oxyacetamide) thiozoliden-4- one]phenyl azo }phenyl-1,3- thiazole CHN O SS N N N N NNHCOCH2O OCH2CONH S O NCH OC4H9 C4H9O C51H51O8N9S2 gummy 64 pal yellow [XIII]6 2-{4`-[2-(4``-hexoxy phenyl)-3- oxyacetamide)thiozoliden-4- one]phenyl}azo-4-{4```-[2-(4````- hexoxy phenyl)-3- (oxyacetamide)thiozoliden-4- one]phenyl azo}phenyl-1,3- thiazole CHN O SS N N N N NNHCOCH2O OCH2CONH S O NCH OC6H13 C6H13O C55H59O8N9S2 gummy 72 pal yellow Table (5) : Characteristics FTIR absorption bands of compounds[VI]n Comp. No. Characteristic bands FTIR spectra(cm-1) ƲNH Ʋ(C-H) aromatic Ʋ(C-H) aliphatic Ʋ(C=O) amide Ʋ(C=N) exocyclic Ʋ(C=N) endocyclic Ʋ (C=C) aromatic [VI]1 3309 3030 2904-2839 1683 1647 1625 1602 [VI]3 3377 3040 2964-2877 1668 1650 1624 1600 [VI]4 3300 3039 2960-2841 1683 1654 1624 1602 [VI]5 3365 3035 2953-2868 1650 1645 1624 1602 [VI]6 3375 3049 2993-2858 1685 1660 1620 1606 [VI]7 3300 3035 2940-2860 1675 1660 1622 1604 [VI]8 3315 3072 2924-2854 1670 1655 1622 1604 310 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Table (6) : Characteristics FTIR absorption bands of thiazoldin-4-ones[VII]n Comp No. Characteristic bands FTIR spectra(cm-1) Ʋ (N-H) Ʋ(C-H) benzylic Ʋ(C- H) aliphatic Ʋ(C=O) thiazoldinone Ʋ(C=O) amide Ʋ(C=C) aromatic Ʋ(C-S) [VII]1 3332 3251 2958-2854 1705 1674 1604 898 [VII]3 3325 3178 2962-2854 1718 1676 1608 902 [VII]4 3242 3190 2956-2854 1714 1678 1605 904 [VII]5 3280 3190 2954-2870 1720 1668 1608 906 [VII]6 3240 3190 2954-2858 1712 1670 1608 902 [VII]7 3350 3155 2956-2854 1716 1670 1603 898 [VII]8 3329 3182 2954-2854 1710 1676 1602 904 Table( 7):Characteristics FTIR absorption bands of compounds [XII]n Comp. No. Characteristic bands FTIR spectra(cm-1) ƲNH Ʋ(C-H) aromatic Ʋ(C-H) aliphatic Ʋ(C=O) Amide Ʋ(C=N) exocyclic Ʋ(C=N) endocyclic Ʋ(C=C) aromatic [XII]1 3310 3012 2985-2839 1665 1656 1625 1602 [XII]3 3331 3010 2964-2877 1664 1641 1624 1602 [XII]4 3317 3037 2980-2875 1656 1645 1624 1602 [XII]6 3313 3049 2945-2860 1678 1650 1622 1606 Table( 8) : Characteristics FTIR absorption bands of thiazoldin-4-one [XIII]n Comp No. Characteristic bands FTIR spectra(cm-1) Ʋ(N-H) Ʋ(C-H) aromatic Ʋ(C- H) aliphatic Ʋ(C=O) thiazoldinone Ʋ(C=O) amide Ʋ(C=C) aromatic Ʋ(C-S) [XIII]1 3346 3007 2970-2837 1712 1670 1583 902 [XIII]3 3410 3028 2968-2875 1712 1680 1608 904 [XIII]4 3310 3040 2958-2875 1716 1650 1610 898 [XIII]6 3390 3030 2931-2821 1716 1670 1602 906 Figure No.(1): Mass spectrum of compound [VI]1 311 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 أمینو – 4ھیدروكسي و -4تحضیر مركبات حلقیة غیر متجانسة مشتقة من أسیتوفینون وتشخیصھا نسرین حسین كرم جمبد ھرمز توما عمار ھاني الدجیلي بغداد جامعة / )الھیثم ابنللعلوم الصرفة (– التربیة كلیة /الكیمیاء قسم 2013 آب 26، قبل البحث في : 2013حزیران 23استلم البحث في : الخالصة وذالك بعدد من الخطوات n[VII]ون 4--ومشتقات الثایوزولدین n[VI]تم في ھذا البحث تحضیر سلسلتین قواعد شف الذي یتفاعل مع بنتوكسي [I] ثایوزول3,1- ھیدروكسي أسیتوفینون مع الثایویورایا والیود لینتج المركب – 4تبدأ بتفاعل وھذا یتفاعل مع الفینول لینتج مركب [II]بروماید وكاربونات البوتاسیوم الالمائیة في االسیتون لینتج المركب والذي تمت [IV] .والذي بدوره یتفاعل مع اثیل كلورواسیتیت في وسط قاعدي لینتج مركب استري جدید[III]االزو . والمركب االخیر یتكاثف مع نورمل الكوكسي بنزالدیھاید لیعطي [V]ض الھیدرازایدمفاعلتھ مع الھیدرازین لینتج حام -.ومجموعة االیمین تدخل اضافة حلقة مع حامض الثایوكالیكولك لتعطي مركبات الثایوزولدین n[VI]قواعد شف جدیدة وذلك بعدد n[XIII]ون 4--ینومشتقات الثایوزولد n[XII]وكذالك حضیرت سلسلتین جدیدة من قواعد شف n[VII]ون-4 أمینو أسیتوفینون – 4عدا استعمال n[VII]ون 4--والثایوزولدین n[VI]من الخطوات المشابھة لتحضیر قواعد شف شخصت جمیع المركبات المحضرة بوساطة درجات انصھارھا، ، تحلیل العناصر ، .ھیدروكسي أسیتوفینون – 4بدل وطیف الكتلة لبعض منھا. 1HNMR، طیف FTIR طیف قواعد شف مركبات حلقیة غیر متجانسة ، الثایوزول ،الثایوزولدینون، :الكلمات المفتاحیة 312 | Chemistry @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@ÚÓ‘Ój�n€a@Î@Úœäñ€a@‚Ï‹»‹€@·rÓ:a@Âig@Ú‹©@Ü‹1a26@@ÖÜ»€a@I3@‚b«@H2013 Ibn Al-Haitham Jour. for Pure & Appl. Sci. Vol. 26 (3) 2013 Synthesis of 4-n-Alkoxybenzaldehyde Synthesis of 2-Amino 4-(4`-hydroxylphenyl)-1,3-thiazole[I] Synthesis of 2-Amino 4-(4`-n- pentoxyphenyl)-1,3-thiazole [II] Synthesis of Thiazolidin-4-one derivatives[VII]n Synthesis of 2- Amino 4-(4`-amino phenyl)-1,3-thiazole [VIII] Synthesis of 2-(4`-Hydroxyphenyl azo)-4-[4``(4```- hydroxy phenyl azo) phenyl ]-1,3-thiazole [IX] Synthesis of 2-(4`-Oxyethylacetate phenyl azo)-4-[4``-(4```-oxyethylacetate phenyl azo)] phenyl -1,3-thiazole [X] Synthesis of 2-(4`-Oxy acid hydrazide phenyl azo)-4-[4``-(4```-oxy acid hydrazide phenyl azo)] phenyl -1,3-thiazole [XI] Synthesis of 2-[4`-(4``- Substutied benzaledine amino)-oxy acetamide] phenyl azo-4-[4```-(4````- substutied benzaledineamino)-oxy acetamide phenyl azo] phenyl -1,3-thiazole [XII]n Synthesis of Thiazolidin-4-one derivatives [XIII]n Table (2):The physical properties for the compounds[VII]n