AlCl3-Catalyzed diazocoupling of 1-(aryl/hetaryl)-3-phenyl-1H-pyrazol-2-in-5-ones in aqueous medium. Synthesis of hetaryl-azopyrazolones and their application as disperse dyes

Basaif, Salem A.; Hassan, Mohamed A.; Gobouri, Adil A.

doi:10.1016/j.dyepig.2005.09.025

Cited by 24 publications

(18 citation statements)

References 22 publications

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“…5‐Pyrazolones and their azo and bisazo derivatives can show different tautomeric structures as has been shown by many researchers [4, 14]. To understand the tautomeric equilibrium in the acidic and basic medium, MeOH + 0.01 M HCl and MeOH + 0.01 M KOH, respectively, were also used (Table ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, and Dyeing Properties of New Azo and Bisazo Dyes Derived from 5‐Pyrazolones

Bağdatlı

Öcal

2012

Journal of Heterocyclic Chem

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This study is in continuation of our work related to 5-pyrazolones aimed at synthesizing new heterocycles with dyeing and anticipated biological properties. Compounds 1 and 2; 1-methyl-or 1-(2,4-dimethylphenyl)-3-phenyl-1H-pyrazol-5(4H)-one, 3; 1-methyl-5-oxo-3-phenyl-4,5-dihydro-1H-pyrazole-4-carbaldehyde and 4; 2-(1-methyl-5-oxo-3-phenyl-1H-pyrazol-4(5H)-ylidene)-3-phenylthiazolidin-5-one were prepared and subjected to diazotation with aromatic amines and diamines. New azo (1a-c, 2a, b, 3a, b, 4a, c) and bisazo dyes (2c, d, 4b) were obtained, and their structures were confirmed by spectroscopic and analytical methods. In addition, UV-vis measurements, dyeing performance, and fastness tests were carried out for all compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, and Dyeing Properties of New Azo and Bisazo Dyes Derived from 5‐Pyrazolones

Bağdatlı

Öcal

2012

Journal of Heterocyclic Chem

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“…For the diverse biological activities of pyrazolone compounds, see: Guckian et al (2010); Fan et al (2006); Castagnolo et al (2008); Idrees et al (2009); Abdel-Aziz et al (2009); Manojkumar et al (2009); Shete et al (2011); Sujatha et al (2009); El-Hawash et al (2006); Kawai et al (1997); Wu et al (20026). For industrial applications of pyrazolones, see: Basaif et al (2007); Ho (2005); Kirschke et al (1984); Chande et al (1993); El-Saraf & El-Sayed (2003). For graph-set motif notation, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…The pyrazolone-like edaravone has been developed as a drug for brain ischemia (Kawai et al, 1997) and has also been reported to be effective for myocardial ischemia (Wu et al, 2002). Additionally, pyrazolones have been reported to be the key starting materials for the synthesis of commercial aryl/heteroaropyrazolone dyes (Basaif et al, 2007;Ho, 2005). Halogenated pyrazolones are also useful synthetic intermediates for synthesis of diazo-dyes (Kirschke et al, 1984), fused (Chande et al, 1993) and spiroheterocyclic compounds (El-Saraf & El-Sayed 2003).…”

Section: S1 Commentmentioning

confidence: 99%

3-Oxo-N′,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide

et al. 2014

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In the title compound, C16H14N4O2, the pyrazole ring makes a dihedral angle of 10.49 (8)° with its N-bound phenyl group, while it is nearly perpendicular to the other phenyl ring [dihedral angle = 88.47 (5)°]. The molecular conformation is stabilized by intramolecular C—H⋯O and N—H⋯O hydrogen bonds. In the crystal, the packing involves sheets of molecules parallel to (100) linked by N—H⋯O hydrogen bonds. A C—H⋯O interaction is also observed.

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“…The growing interest in heterocyclic azo dye chemistry is focused on designing new synthetic approaches to these materials, theoretical calculations, and applications in various industrial fields. Besides having important-applications as textile colorants [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ], they find increasing accessibility in photo-responsive biomaterials [ 9 ], optical sensing of metal ions [ 10 , 11 , 12 ], non-linear optics (NLO) and photoelectronics [ 11 , 13 , 14 , 15 , 16 ]. Functional dyes with special finishing capabilities is currently an area of active research [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

et al. 2011

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A series of novel polyfunctionalized acyclic and heterocyclic dye precursors and their respective azo (hydrazone) counterpart dyes and dye precursors based on conjugate enaminones and/or enaminonitrile moieties were synthesized. The dyes and their precursors are based on 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide, 2-ethoxycarbonyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide or 2-phenylcarbamoyl-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide systems as precursors. The latter compounds were used to synthesize polyfunctional thiophene-, thiazole-, pyrazole, pyridine-, pyrimidine-, oxazine-, as well as acyclic moieties. The dyes and dye precursors were characterized by elemental analysis and spectral methods. All dyes and their precursors were screened in vitro and evaluated for both their antibacterial and antifungal activities. MIC data of the novel dye systems and their respective precursors showed significant antimicrobial activity against most tested organisms. Some compounds exhibited comparable or even higher efficiency than selected standards. Dyes were applied at 5% depth for disperse dyeing of nylon, acetate and polyester fabrics. Their spectral characteristics and fastness properties were measured and evaluated.

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AlCl3-Catalyzed diazocoupling of 1-(aryl/hetaryl)-3-phenyl-1H-pyrazol-2-in-5-ones in aqueous medium. Synthesis of hetaryl-azopyrazolones and their application as disperse dyes

Cited by 24 publications

References 22 publications

Synthesis, Spectroscopic, and Dyeing Properties of New Azo and Bisazo Dyes Derived from 5‐Pyrazolones

Synthesis, Spectroscopic, and Dyeing Properties of New Azo and Bisazo Dyes Derived from 5‐Pyrazolones

3-Oxo-N′,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide

Design and Synthesis of Novel Antimicrobial Acyclic and Heterocyclic Dyes and Their Precursors for Dyeing and/or Textile Finishing Based on 2-N-Acylamino-4,5,6,7-tetrahydro-benzo[b]thiophene Systems

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