Structural analysis of substituted 3-arylazo-2-hydroxy-6-pyridones

Cee, A.; Horáková, B.; Lyčka, Antonı́n

doi:10.1016/0143-7208(88)80005-6

Cited by 33 publications

(13 citation statements)

References 8 publications

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“…[19] concluded from 13 C NMR studies of some N-alkyl derivatives of azopyridones that pyridone azo dyes in CDCl 3 and DMSO-d 6 exist in the hydrazone form. Our results are in agreement with these results.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

Alimmari

Mijin

Vukićević

et al. 2012

Chemistry Central Journal

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BackgroundA series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds.ResultsThe structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents.ConclusionsThe azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.

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Section: Resultsmentioning

confidence: 99%

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

Alimmari

Mijin

Vukićević

et al. 2012

Chemistry Central Journal

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“…[1][2][3][4][5][6] The success of azo colorants is due to the simplicity of their synthesis by diazotization and azo coupling, to the almost innumerable possibilities presented by variation on the diazo compounds and coupling components, to the generally high molar extinction coefficient and to the medium to high light and wet fastness properties. 8 The physico-chemical properties of arylazo pyri-done dyes are closely related to their tautomerism. The azo pyridone dyes give bright hues and are suitable for the dyeing of polyester fabrics.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones

Alimmari¹,

Marinković²,

Mijin³

et al. 2010

JSCS

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A series of some new pyridone arylazo dyes was synthesized from the corresponding diazonium salts and 3-cyano-4,6-diphenyl-2-pyridone using the classical reaction for the synthesis of the azo compounds. The structures of these dyes were confirmed by UV-Vis, FT-IR and 1 H-NMR spectroscopic techniques. The solvatochromism of the dyes was evaluated with respect to visible absorption properties in various solvents. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The 2-pyridone/2-hydroxypiridine tautomeric equilibration was found to depend on the substituents as well as on the solvents.

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“…These dyes exist in the hydrazone tautomeric form in the solid state and in solvent DMSO-d 6 . Synthesis from ethyl 3-oxo-2--(substituted phenylazo)butanoates in acetone gave products in low to moderate yields.…”

Section: Discussionmentioning

confidence: 99%

Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3- cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenyldiazenyl)butanoates

Dostanić

Valentić²,

Ušćumlić³

et al. 2011

J Serb Chem Soc

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A new procedure for the synthesis of known azo pyridone dyes is presented. A series of 5-(substituted arylazo)-6-hydroxy-4-methyl-3-cyano-2--pyridones were prepared from ethyl 3-oxo-2-(substituted phenylazo)butanoates and cyanoacetamide in acetone using potassium hydroxide as a catalyst by simple refluxing the reaction mixture. The structure of these dyes was confirmed by FT-IR, NMR and UV-Vis spectroscopy.

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Structural analysis of substituted 3-arylazo-2-hydroxy-6-pyridones

Cited by 33 publications

References 8 publications

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes

Synthesis, structure and solvatochromic properties of 5-(3- and 4-substituted phenylazo)-4,6-diphenyl-3-cyano-2-pyridones

Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3- cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenyldiazenyl)butanoates

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