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Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives
Synthesis, Fastness and Spectral Properties of Some New Azo Pyrazole and Pyrazolotriazole Derivatives
Journal of the Korean Chemical Society. 2010. Dec, 54(6): 737-743
Copyright © 2010, The Korean Chemical Society
  • Received : April 05, 2010
  • Accepted : June 28, 2010
  • Published : December 20, 2010
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Hala F. Rizk
Mahmoud A. El-Badawi
Seham A. Ibrahim
Mohamed A. El-Borai

Abstract
Coupling of 5-amino-1,3-diaryl-pyrazoles 1a - c with diazonium salts of different aryl amines gave a series of novel 1,3-diaryl-5-amino-4-arylazopyrazoles 3a - l . Such compounds could be also obtained by reaction of 5-amino-1,3-diaryl-4-nitroso-1 H -pyrazoles 2a - c with different aryl amines in alkaline medium. Oxidation of azo derivatives 3a - l with cupric acetate, in dimethyl formamide and stream of air, gave 2,4,6-triaryl-2,4-dihydropyrazolo [4,3- d ]-1,2,3-triazoles 4a - l . and the fluorescence properties of the cyclic triazoles were studied. Diazotization of 5-amino-1,3-diaryl-1 H -pyrazoles 1a - c by sodium nitrite in ortho-phosphoric acid followed by coupling with some aryl amines gave o -aminoazo compounds 5a - f . Cyclisation of compounds 5a - f in pyridine and cupric acetate gave the corresponding triazoles 6a - f . The coupling of compounds 6a - f with different aryl diazonium salts gave compounds 7a - j . The synthesized dyes were applied to polyesters as disperse dyes and the fastness properties were evaluated.
Keywords
INTRODUCTION
Pyrazoles are an interesting group of compounds because they have a broad spectrum pharmacologically properties such as antibacterial, 1 antihyperglycemice analgesic, 2 antiparasitic, 3 antimicrobial 4 and antischistosomal activities. 5 The pyrazole synthesis of particular use because there are themselves building block for a variety of pyrazole containing structure such as pyrazoloisoquinolines, 6 pyrazolopyrimidines, 7 pyrazolopyridines, 8 pyrazolopyrazines 9 and pyrazolotriazoles. 10 Some azopyrazole derivatives have many applications in dyes. 11 As a part of our continuing interest in heterocyclic chemistry, we now report the successful synthesis of some new pyrazolotriazoles and fused pyrazolotriazole derivatives.
RESULTS AND DISCUSSION
The nitrosation of the 5-amino-1,3-diaryl-1 H -pyrazoles 1a - c was carried out according to the previously reported methods to give compounds 2a - c . 12 The reaction of 2a - c with aromatic amines gave the corresponding o -amino azo compounds 3a - l in good yield. Also, 5-amino-1,3-diaryl-1 H -pyrazoles 1a - c coupled with aryl diazonium salts to yield 5-amino-4-arylazo-1,3-diaryl-1 H -pyrazoles 3a - l which on oxidation with cupric acetate in the presence of air gave 2,4,6-triaryl-6 H -pyrazolo[3,4- d ]-1,2,3-triazoles 4a - l ( 1 ) in good yield ( 1 ). The 1 H NMR and IR spectra of 4a - l showed the absence of an exchangeable singlet band and the vibrational frequency for the amino groups. The absorption and fluorescence emission spectra of compounds 4a - l have been measured in DMF as a solvent, and the spectral data were collected in ( 2 ). As can be seen the absorption spectra display strong bands (log ε max range from 4.08 to 5.36) in the range from 330 to 390 nm, depending on the nature of substituent at the phenyl rings. Such behavior is characteristic for an allowed π-π* transition over the whole skeleton of the molecule. The fluorescence emission characteristics of the mentioned compounds 4a - l have been also investigated. The spectra reveal blue to green emission (λ ex = 330 - 490 nm) depending on the substituent group. The shift of the emission maximum shows no general trend, however, the emission maximum is red shifted on changing the substituent from Cl or COOH to OCH 3 or OH group in the case of monosubstituted compounds 4a - l which is in agreement with the π-π* nature of the excited single state. The fluorescence quantum yield is also depending on the nature of substituent where Φ f increases by introduction of an electron withdrawing group as can be seen from the value of 4a and 4d . In fact the Φ f -value was markedly decreased when additional substituent was introduced on the co-axial phenyl groups. These results are in agreement with the previously reported data. 13
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Synthesis of substituted 2,4,6-triaryl-2,4-dihydropyrazole[4,3-d][1,2,3] triazoles4a-l
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Synthesis of substituted 2,4,6-triaryl-2,4-dihydropyrazole[4,3-d][1,2,3] triazoles 4a-l
Absorption and fluorescence emission spectral data of the compounds4a-l
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Absorption and fluorescence emission spectral data of the compounds 4a-l
The diazotization of compounds 1a - c followed by coupling with aryl amines gave the corresponding dyes 5a - f in good yield ( 3 ). The IR spectra of 5a - f showed the azo groups (N=N) vibration frequencies at 1662 - 1675 cm -1 region, stretching vibrations for the amino group at 3275 - 3423 cm -1 region. The oxidation of o -aminoazo dyes gave 5-triazoly-1,3-diarylpyrazole derivatives 6a - f in good yield ( 4 ). The 1 H NMR spectra of compounds 6a - f showed singlets within the region of 6.7 - 7.2 ppm due to CH proton of the pyrazole ring, a sharp singlets at δ = 2.1 - 2.3 ppm corresponding to CH 3 groups. Coupling of 6a - f with aryl diazonium salts in ethanol, buffered with sodium acetate solution at pH = 6, gave the corresponding 7a - j in good yield ( 5 ). IR spectra of 7a - j showed the azo groups (N=N) vibration frequencies at 1496 - 1596 cm -1 region. The 1 H NMR spectra of 7a - j showed the absence of singlet signals at 6.6 - 6.8 ppm region corresponding for the CH proton of the pyrazole ring ( 2 ).
Synthesis of substitutedo-amino azo dyes5a-f
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Synthesis of substituted o-amino azo dyes 5a-f
Synthesis of substituted 5-triazoly-1,3-diarylpyrazole derivatives6a-f
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Synthesis of substituted 5-triazoly-1,3-diarylpyrazole derivatives 6a-f
Synthesis of substituted 5-triazol-1,3-diaryl-4-arylazo pyrazole derivatives7a-j
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Synthesis of substituted 5-triazol-1,3-diaryl-4-arylazo pyrazole derivatives 7a-j
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It is worthy to mention that compounds 4a - l have fluorescent properties due to the fused triazole ring to the pyrazole moiety, while compounds 6a - f and 7a - j have no fluorescent properties.
EXPERIMENTAL
Melting points were uncorrected. IR spectra were recorded on a Perkin-Elmer1430 spectrophotometer using KBr disk technique. 1 H-NMR spectra were measured on a Bruker AC spectrometer (300 MHz) in DMSO, in deuterated dimethylsulphoxide (DMSO- d 6 ) using tetramethylsilane (TMS) as the internal reference; chemical shifts were expressed in (δ) ppm. Standard electron impact mass spectra (EI) were obtained using a Finnigan MAT 8222 spectrometer at 70 eV. The electronic absorption spectra of the compounds 4a - l have been measured by using Shimadzu 1301-PC spectrophotometer while their fluorescence spectra have been recorded on Perkin-Elmer L550B spectroflurometer. The measurements were done at room temperature using two matched quartz cuvettes. The fluorescence yield was measured relative to quinine bisulphate with an absorption maximum. Progress of reactions was monitored by the thin-layer chromatography (TLC) using benzene/ethyl acetate (9:1) as eluent.
- Synthesis of 4-Arylazo-5-amino-1,3-diaryl-1H-pyrazoles (3a-l)
Method A : A mixture of 5-amino-1,3-diaryl-4-nitroso-1 H -pyrazoles 2a - c (1.5 mmol) and aromatic amines (1.9 mmol) in NaOH (50%; 1.8 mL) was refluxed for 5 h. The mixture was allowed to cool to room temperature and then, poured into crushed ice with vigorous stirring. The solid formed was filtered, washed with water several times and then dried.
Method B : The conversation of amino pyrazoles 1a - c to 4-arylazo-5-amino-1,3-diaryl-1 H -pyrazoles 3a - l was carried out according to the previously reported method. 14
- General procedure of synthesis 2,4,6-triaryl-2,4-dihydro-pyrazole [4, 3-d] [1,2,3]triazoles (4a-l)
A solution of compounds 3a - l (1.3 mmol) in 2.6 mL of pyridine was added to 0.14 g of cupric acetate (0.17 mmol) and the reaction mixture was refluxed for 7 h while a stream of air was bubbled in the reaction mixture. The reaction mixture was kept for 12 h at room temperature. The separated product was filtered, washed with ethanol, dried and recrystallizated from EtOH to give compounds 4a - l .
2-(4-Methoxyphenyl)-4,6-diphenyl-2,4-dihydropyrazolo [4,3-d] [1,2,3]triazole (4a): IR (KBr) (ν max , cm -1 ): 3052, 2924; 1 H NMR; δ H (ppm): 3.8 (s, 3H, OCH 3 ), 7.2-8.2 (m, 14H, ArH); Ms: 368 (M + ).
2-(4-Chlorophenyl)-4,6-diphenyl-2,4-dihydropyrazolo [4,3-d] [1,2,3] triazole (4b): IR (KBr) (ν max , cm -1 ): 3057, 2923; 1 H NMR; δ H (ppm): 7.2-8.2 (m, 14H, ArH); Ms: 373 (M + +2).
4-(4,6-Diphenylpyrazolo [4,3-d] [1,2,3] triazol-2(4H)-yl) benzoic acid (4c): IR (KBr) (ν max , cm -1 ): 3051, 2923, 1695; 1 H NMR; δ H (ppm): 7.05-8.5 (m, 14H, ArH), 13 (s, 1H, COOH); Ms: 381 (M + ).
4-(4,6-Diphenylpyrazolo [4,3-d] [1,2,3] triazol-2(4H)-yl) phenol (4d): IR (KBr) (ν max , cm -1 ): 3054, 2925; 1 H NMR; δ H (ppm): 5.8 (s, 1H, OH), 7.2-8 (m, 14H, ArH); Ms: 353 (M + ).
6-(4-Dichlorophenyl)-2-(4-methoxyphenyl)-4-phenyl-2,4-dihydropyrazolo[4,3-d] [1,2,3] triazole (4e): IR (KBr) (ν max , cm -1 ): 3058, 2928; 1 H NMR; δ H (ppm): 3.8 (s, 3H, OCH 3 ), δ 7.1-7.8 (m, 13H, ArH); Ms: 403 (M + +2).
2,6-Bis(4-chlorophenyl)-4-phenyl-2,4-dihydropyrazolo [4,3-d] [1,2,3] triazole (4f): IR (KBr) (ν max , cm -1 ): 3058, 2928; 1 H NMR; δ H (ppm): 6.9-8.1 (m, 13H, ArH); Ms: 408 (M + +2).
4-[6-(4-Chlorophenyl)-4-phenylpyrazolo [4,3-d][1,2,3] triazol-2(4H)-yl]benzoic acid (4g): IR (KBr) (ν max , cm -1 ): 3060, 2924), 1600; 1 H NMR; δ H (ppm): 7.05-8.5 (m, 13H, ArH), 12.5 (s, 1H, COOH); Ms: 417 (M + +2).
4-[6-(4-Chlorophenyl)-4-phenylpyrazolo [4,3-d][1,2,3] triazol-2(4H)-yl]phenol (4h): IR (KBr) (ν max , cm -1 ): 3059, 2922; 1 H NMR; δ H (ppm): 5.8 ( s , 1H, OH), 7.1-8.2 (m, 13H, Ar-H); Ms: 388 (M + +2).
2-(4-Methoxyphenyl)-4-phenyl-6-p-tolyl-2,4-dihydropyrazolo[4,3-d][1,2,3]triazole (4i): IR (KBr) (ν max , cm -1 ): 3056, 2919. 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 3.8 (s, 3H, OCH 3 ), 6.9-8.1 (m, 13H, ArH); Ms: 381 (M + ).
2-(4-Chlorophenyl)-4-phenyl-6-p-tolyl-2,4-dihydropyrazolo[4,3-d][1,2,3]triazole (4j): IR (KBr) (ν max , cm -1 ): 3048, 2920; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 6.7-8 (m, 13H, ArH); Ms: 387 (M + +2).
4-(4-Phenyl-6-p-tolylpyrazolo[4,3-d][1,2,3]triazole-2 (4H)-yl)benzoic acid (4k): IR (KBr) (ν max , cm -1 ): 3055, 2920, 1599; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 6.7-8.05 (m, 13H, ArH), 12.3 (s, 1H, COOH); Ms: 396 (M + ).
4-(4-Phenyl-6-p-tolylpyrazolo [4,3-d][1,2,3]triazole-2 (4H)-yl) phenol (4l): IR (KBr) (ν max , cm -1 ): 3056, 2920; 1 H NMR; δ H (ppm): 2.3(s, 3H, CH 3 ), 5.8 (s, 1H, OH), 6.7-8 (m, 13H, ArH); Ms: 367 (M + ).
- General procedure for synthesis of 5-triazoly-1,3-diarylpyrazole derivatives (6a-f)
- Preparation of o-amino azo dye.
The appropriate 5-amino-1,3-diaryl-pyrazoles 1a - c (4.3 mmol) was dissolved in 4.25 mL of phosphoric acid and then, cooled (0 ℃). 0.85 mL of concentrated nitric acid was slowly added in portions (over 15 - 20 min). The reaction mixture was stirred for 30 - 40 min at 0 - 5 ℃, and then, 0.64 g of sodium nitrite as a solid (9.3 mmol) was added slowly (over 30 - 45 min). The mixture was stirred for 1 h, at 0 - 5 ℃ and excess sodium nitrite was decomposed by addition of urea. The diazonium salt prepared was added to the appropriate aromatic amine (4.3 mmol) which dissolved in 2.5 mL of NaHCO 3 (25%), cooled to 0 - 5 ℃ and the pH was kept at 5 - 6 by the addition of sodium acetate. The reaction mixture was stirred for a further period of 3 - 3.5 h and the solid separated was filtered, washed with water and dried to give the o -amino azo dyes 5a - f .
2-[(1,3-Diphenyl-1H-pyrazol-5-yl) diazenyl]-5-methylbenenamine (5a): IR (KBr) (ν max , cm -1 ): 1663, 3396, 3057, 2928; Ms: 353 (M + ).
1-[(1,3-Diphenyl-1H-pyrazol-5-yl) diazenyl] naphthalene-2-amine (5b): IR (KBr) (ν max , cm -1 ): 1666, 3400, 3058, 2928; Ms: 390 (M + +1).
2-[(3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)diazenyl]-5-methyl benzenamine (5c): IR (KBr) (ν max , cm -1 ): 1662, 3423, 3062, 2931; Ms: 389 (M + +2).
1-[(3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-5-yl)diazenyl] naphthalene-2-amine (5d): IR (KBr) (ν max , cm -1 ): 1666, 3427, 3059, 2928; Ms: 425 (M + +2).
5-Methyl-2-[(1-phenyl-3-p-tolyl-1H-pyrazol-5-yl)diazenyl] benzenamine (5e): IR (KBr) (ν max , cm -1 ): 1675, 3275, 3027, 2926; Ms: 367 (M + ).
1-[(1-Phenyl-3-p-tolyl-1H-pyrazol-5-yl) diazenyl] naphthalene- 2-amine (5f): IR (KBr) (ν max , cm -1 ): 1674, 3423, 3055, 2925, 3055; Ms: 403 (M + ).
- Triazolyzation
A mixture of the appropriate o-amino azo dyes 5a - f (4.3 mmol) and 0.28 g of cupric acetate (4.3 mmol) in 7 mL of pyridine was heated under reflux for 4 - 5 h, till the color of the dyes had disappeared. The reaction mixture was cooled to 0 - 5 ℃ and 28.3 mL of HCl (5%) was added with constant stirring. The solid formed was filtered, washed with water and dried. The solid was then dissolved in acetic acid (10 - 15 mL) and a small amount of Zn dust (4.3 mmol) was added, and the mixture was refluxed for 1 h. The reaction mixture was filtered while hot, and the filtrate was cooled and then added to ice-water mixture. The solid formed was filtered, washed with water, dried and recrystallized from ethanol to give compounds 6a - f .
2-(1,3-Diphenyl-1H-pyrazol-5-yl)-5-methyl-2H-benzo [d][1,2,3]triazole (6a): IR (KBr) (ν max , cm -1 ): 3056, 2929; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 6.8 (s, 1H, CH), 7.2-8.5 (m, 13H, ArH); Ms: 351 (M + ).
2-(1,3-Diphenyl-1H-pyrazol-5-yl)-2H-naphtho [2, 3-d] [1,2,3]triazole (6b): IR (KBr) (ν max , cm -1 ): 3056, 2929; 1 H NMR; δ H (ppm): 6.8 (s, 1H, CH), 7.1-8.3 (m, 16H, ArH); Ms: 386 (M + -1).
2-[3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-5-yl]-5-methyl-2H-benz [d][1,2,3] triazole (6c): IR (KBr) (ν max , cm -1 ): 3057, 2935; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 6.8 (s, 1H, CH), 7-8.7 (m, 12H, ArH); Ms: 387 (M + +2).
2-[3-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-5-yl]-2H-naphtho[2,3-d [1,2,3] triazole (6d): IR (KBr) (ν max , cm -1 ): 3057, 2927; 1 H NMR; δ H (ppm): 6.7 (s, 1H, CH), 7.1-8.5 (m, 15H, ArH); Ms: 423 (M + +2).
5-Methyl-2-(1-phenyl-3-p-tolyl-1H-pyrazol-5-yl)-2H-benzo [d][1,2,3]triazole (6e): IR (KBr) (ν max , cm -1 ): 3060, 2928; 1 H NMR; δ H (ppm): 2.1 (s, 3H, CH 3 ), 2.3 (s, 3H, CH 3 ) 7 (s, 1H, CH), 7.1-8.7 (m, 12H, ArH); Ms: 365 (M + ).
2-(1-Phenyl-3-p-tolyl-1H-pyrazol-5-yl)-2H-naphtho[2, 3-d][1,2,3]triazole (6f): IR (KBr) (ν max , cm -1 ): 3055, 2924; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ) 6.8 (s, 1H, CH), 7.1-8.7 (m, 15H, ArH); Ms: 401 (M + ).
- General procedure for synthesis of 5-triazol-1,3-diaryl-4-arylazopyrazole derivatives 7a-j
A solution of 0.11 g of sodium nitrite (1.6 mmol) was gradually added to a cold solution of an aromatic amine (1.6 mmol) in 0.5 mL of conc. HCl. The diazonium salt obtained was added with continuous stirring to a cold of compounds 6a - f (1 mmol) in 4.9 mL of ethanol containing sodium acetate. The reaction mixture was stirred at 0 ℃ for 2 h. The solid obtained was filtered, washed with water and crystallized from ethanol to give compounds 7a - j .
1-(4-Methoxyphenyl)-2-(5-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)-1,3-diphenyl-1H-pyrazol-4-yl) diazene (7a): IR (KBr) (ν max , cm -1 ): 3058, 2927, 1600; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 3.7 (s, 3H, OCH 3 ), 6.1-8.2 (m, 17H, ArH); Ms: 485 (M + ).
1-(5-(2H-naphtho[2,3-d][1,2,3]triazol-2-yl)-1,3-diphenyl-1H-pyrazol-4-yl)-2-(4-methoxyphenyl)diazene (7b): IR (KBr) (ν max , cm -1 ): 3060, 2927, 1600; 1 H NMR; δ H (ppm): 3.8 (s, 3H, OCH 3 ), 6.6-8.8 (m, 20H, ArH); Ms: 521 (M + ).
1-(4-Chlorophenyl)-2-[5-(5-methyl-2H-benzo[d][1,2,3] triazol-2-yl]-1,3-diphenyl-1H-pyrazol-4-yl)diazene (7c): IR (KBr) (ν max , cm -1 ): 3059, 2925, 1597; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 7-8.9 (m, 17H, ArH); Ms: 491 (M + +2).
1-[3-(4-Chlorophenyl)-5-(5-methyl-2H-benzo[d][1,2,3] triazol-2-yl]-1-phenyl-1H-pyrazol-4-yl)-2-(4-methoxyphenyl) diazene (7d): IR (KBr) (ν max , cm -1 ): 3058, 2928, 1598; 1 H NMR; δ H (ppm): 2 (s, 3H, CH 3 ), 3.8 (s, 3H, OCH 3 ), 7-8 (m, 16H, ArH); Ms: 521 (M + +2).
1-[3-(4-Chlorophenyl)-5-(2H-naphtho[2,3-d][1,2,3]triazol-2-yl]-1-phenyl-1H-pyrazol-4-yl)-2-(4-methoxyphenyl) diazene (7e): IR (KBr) (ν max , cm -1 ): 3056, 2928, 1597; 1 H NMR; δ H (ppm): 3.79 ( s , 3H, OCH 3 ), 7.5-8 ( m , 19H, Ar-H); Ms: 558 (M + +2).
1-(4-Chlorophenyl)-2-(3-(4-chlorophenyl)-5-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)-1-phenyl-1H-pyrazol-4-yl)diazene (7f): IR (KBr) (ν max , cm -1 ): 3060, 2926, 1599; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 7-8.7 (m, 16H, Ar-H); Ms: 526 (M + +2).
1-(4-Chlorophenyl)-2-(3-(4-chlorophenyl)-5-(2H-naphtho[2,3-d][1,2,3]triazol-2-yl)-1-phenyl-1H-pyrazol-4-yl) diazene (7g): IR (KBr) (ν max , cm -1 ): 3059, 2928, 1698; 1 H NMR; δ H (ppm): 7-8.35 (m, 19H, Ar-H); Ms: 562 (M + +2).
1-(4-Methoxyphenyl)-2-[5-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)-1-phenyl-3-p-tolyl-1H-pyrazol-4-yl]diazene (7h): IR (KBr) (ν max , cm -1 ): 3024, 2925, 1598; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 3.7 (s, 3H, OCH 3 ), 7-8.35 (m, 16H, Ar-H); Ms: 489 (M + ).
1-[5-(2H-Naphtho[2,3-d][1,2,3]triazol-2-yl)-1-phenyl-3-p-tolyl-1H-pyrazol-4-yl]-2-(4-methoxyphenyl)diazene (7i): IR (KBr) (ν max , cm -1 ): 3055, 2924, 1598; 1 H NMR; δ H (ppm): 2.3 (s, 3H, CH 3 ), 3.7 (s, 3H, OCH 3 ), 6.6-7.9 (m, 19H, ArH); Ms: 535 (M + ).
1-[5-(2H-Naphtho[2,3-d][1,2,3]triazol-2-yl)-1-phenyl-3-p-tolyl-1H-pyrazol-4-yl]-2-(4-chlorophenyl)diazene (7j): IR (KBr) (ν max , cm -1 ): 3056, 2925, 1598; 1 H NMR; δ H (ppm): 2.2 (s, 3H, CH 3 ), 6.6-8.4 (m, 19H, ArH); Ms: 542 (M + +2).
- Dyeing of Polyester Fabrics and Dyeing Properties
Fastness propertiesaof dyes7a-jon polyester fabricsb
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aRate for light fastness: 4-5 (acceptable), 1-3 (not acceptable); rate for different fastness: 3-4 (acceptable), 1-2 (not acceptable). bPES: Polyester
The prepared azo dyes 7a - j was applied to polyester fiber. The dyeing procedure 14 , 15 and color fastness to light, washing, perspiration, and rubbing of the prepared dyes on fibers were studied using standard methods for the assessment of color fastness of textile (the grey scale). 16 The results obtained are shown in ( 6 ). The results revealed that these dyes have good fastness properties. In conclusion, a set of ten useful disperse dyes 7a - j were synthesized by azo coupling. The dyes were investigated for their dyeing characteristics on polyester and showed moderate to good (3-4) washing, perspiration, sublimation and rubbing fastness dry and wet. The light fastness of dyed exhibit good (4-5) fastness properties.
References
Ho Y. W. 2005 Dyes and Pigments 64 223 -    DOI : 10.1016/j.dyepig.2004.06.007
Bazgir A. , Khanaposhtani M. , Maryam M. , Soorki A. A. 2008 Bioorg. Med. Chem. Lett. 18 5800 -    DOI : 10.1016/j.bmcl.2008.09.057
Dias L. R. S. , Alvim M. J , Freitas A. C. C. , Barreiro E. J. , Miranda A. L. P. 1994 Pharmaceutica Acta Helvetiae 69 163 -    DOI : 10.1016/0031-6865(94)90019-1
El-Kashef H. S. , El-Emary T. I. , Gasquet M. , Timon-David P. , Maldonado J. , Vanelle P. 2000 Pharmazie. 55 572 -
El-Emary T. I. , Al-Muaikel N. , Moustafa O. S. 2001 Phosphorus, Sulfur, Silicon 177 195 -    DOI : 10.1080/10426500210238
Abramov A. M. , Ceulemans E. , Jacker C. , Auweraer M. V. , Dehaen W. 2001 Tetrahedron 57 9123 -    DOI : 10.1016/S0040-4020(01)00917-6
Karci F. , Demircah A. 2006 Dyes and Pigments 71 97 -    DOI : 10.1016/j.dyepig.2005.08.004
Wu Y.-C. , Chen Y.-J. , Li H.-J. , Zou X.-M. , Hu F.-Z. , Yang H.-Z. 2006 J. Fluorine Chem. 127 409 -    DOI : 10.1016/j.jfluchem.2006.02.001
El-Emary T. I. 2006 J. Chin. Chem. Soc. 533 91 -
Rangnekar D. W. , Dhamnaskar S. V. 1988 J. Heterocycl. Chem. 25 1663 -    DOI : 10.1002/jhet.5570250611
Vicentini C. , Manfredini S. , Manfrini M. , Bazzanini R. , Musiu C. , Putzolu M. , Perra G. , Marongiu M. E. 1998 Archiv der pharmazie. 331 269 -
Benjamam E. B. , Srivastava A. , Coburn K. R. , Faulkner A. L. , Seibel W. L. 2003 Tetrahedron Lett. 44 3009 -    DOI : 10.1016/S0040-4039(03)00398-8
Rangnekar D. V. , Dhamnaskar S. V. 1988 J. Heterocyclic. Chem. 25 1 -    DOI : 10.1002/jhet.5570250101
Rizk H. F. , El-Badawi M. A. , Ibrahim S. A. , El-Borai M. A. 2010 Arab. J. Chem. 4 xx -
Rizk H. F , El-Badawi M. A. , Ibrahim S. A. , El-Borai M. A. 2008 Org. Chem. An. indian J. 4 115 -
1990 Anon Standard Methods for the Determination of the Color Fastness of Textiles and Leather 5th edn Society of Dyes and Colorists Publication Bradford, England