Synthesis of some new azo dyes derived from 4-hydroxy coumarin and spectrometric determination of their acidic dissociation constants

Yazdanbakhsh, Mohammad; Ghanadzadeh, A.; Moradi, Ehsan

doi:10.1016/j.molliq.2007.03.005

Cited by 56 publications

(17 citation statements)

References 7 publications

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“…25,26 Treatment of 2a-f with phenyl hydrazine in ethanol under reux afforded the respective 4-(2-arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones 4a-f in good yields (Scheme 1). The structures of the latter derivatives 4a-f Experimental).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones

Metwally¹,

Bondock²,

El-Desouky³

et al. 2012

Journal of the Korean Chemical Society

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ABSTRACT. Novel azopyrazolin-5-one dyes 4a-f were synthesized by the regioselective reaction of phenylhydrazine with 2,3,4-chromantrione-3-arylhydrazones 2a-f. The acid dissociation constants pKa for the series prepared were determined and correlated by the Hammett equation. The results of such correlation together with the spectral data indicated that the studied compounds exist predominantly in the hydrazone keto structure, (D) as the Z-configuration. The dyes were applied to polyester fabrics, affording orange-yellow shades and assessments of their dyeing performance are considered. Further, the compounds 4a-f were screened for their antimicrobial activity against various microorganisms.

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Section: Resultsmentioning

confidence: 99%

“…4-hydroxycoumarin (1), 24 2,3,4-chromantrione-3-arylhydrazones 2a-f, 25,26 and 1-phenyl-3-(2-hydroxyphenyl)-2-pyrazolin-5-one (3) 16 were prepared according to literature procedure.…”

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confidence: 99%

Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones

Metwally¹,

Bondock²,

El-Desouky³

et al. 2012

Journal of the Korean Chemical Society

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“…General procedure for the synthesis of antipyrinyl azo analogues 4(a-f) 16 The novel antipyrinyl azo molecules are synthesized by the method mentioned with little modification. A cold solution of 2.5 mL of sodium nitrite (0.206 g, 3 mmol) was added drop wise to ice-cold solution of 4-aminoantipyrin in conc.…”

Section: Chemicals and Analysismentioning

confidence: 99%

A Study on Antimicrobial Evaluation of Newly Synthesized Antipyrin Analogues

Sahoo¹,

Paidesetty²

2017

IJPER

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The antipyrinyl derived molecules are a versatile building blocker organic compounds and used in medicinal drug research. A versatile range of hybrid molecules have been synthesized by diazotization of 4-aminoantipyrin and further substituted with six different coupling components. The structures of the synthesized compounds have been confirmed by different spectral techniques. The antimicrobial activity of the synthesized molecules is investigated by agar well diffusion method against a wide range of microbial strains. The results of the antimicrobial activities of the novel synthesized molecules are statistically interpreted by dunnet post hoc test. It is found to be observed that the compound 4 -[(4-Hydroxy-2-oxo-2H-chromen-3-yl)diazenyl]-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (4a) showed significant antimicrobial activity against S. flexneri, K. pneumonia, M. luteus, S. mitis, B. subtilis and S. aureus in comparison to standard ampicillin. The solvatochromic study of the synthesized compounds revealed that the compound 4-((2, 4-dihydroxyphenyl) diazenyl)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (4d) 4-((2-hydroxynaphthalen-1-yl) diazenyl)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one(4e) showed good bathochromic shift in comparison to other solvents used. These novel synthesized azo molecules may be suggested for new establishment chemical class of antimicrobial agents and to create an opportunity in new drug discovery and medicinal research.

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“…They were originally regarded as azo-structure (A) [7,8], but others workers [9][10][11] tended to the view that they were keto-hydrazone structure (D). Recently, two groups of workers [12,13] proposed that compounds exist as a mixture of tautomeric forms(A) and (D) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure Elucidation and Application of Some New Azo Disperse Dyes Derived from 4-Hydroxycoumarin for Dyeing Polyester Fabrics

Metwally¹,

Bondock²,

El-Desouky³

et al. 2013

CHEMISTRY

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As a part of our ongoing interest in disperse dyes and task specific azo dyes with better dyeing properties, we synthesized a series of 3-aryl(hetaryl)hydrazono-2,4-chromandiones 4a-k via Coupling of 4-hydroxycoumarin with diazotized aniline derivatives. Structures of the synthesized compounds have been investigated by means of UV, IR, 1 H-NMR and mass spectroscopy in order to elucidate their tautomeric and isomeric structures. The results of such spectral data indicated that compounds 4a-k exist predominantly in the hydrazo structure (D) as a mixture of Z and E-isomer with ratio ~ 84.5:15.5. Finally, the prepared dyestuffs 4a-k were applied as disperse dyes for dyeing polyester fabrics and their fastness properties were evaluated. Also, the position of color in CIELAB coordinates

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Synthesis of some new azo dyes derived from 4-hydroxy coumarin and spectrometric determination of their acidic dissociation constants

Cited by 56 publications

References 7 publications

Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones

Synthesis, Tautomeric Structure, Dyeing Characteristics, and Antimicrobial Activity of Novel 4-(2-Arylazophenyl)-3-(2-hydroxyphenyl)-1-phenyl-2-pyrazolin-5-ones

A Study on Antimicrobial Evaluation of Newly Synthesized Antipyrin Analogues

Synthesis, Structure Elucidation and Application of Some New Azo Disperse Dyes Derived from 4-Hydroxycoumarin for Dyeing Polyester Fabrics

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