Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives

Karcı, Fati

doi:10.1016/j.dyepig.2006.07.029

Cited by 67 publications

(31 citation statements)

References 27 publications

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“…The IR and UV spectra of some of the products have been recorded in acidic and basic solvents [102,103]. No successful intramolecular heterocyclization of pyrazolylazo compounds 34 and 35 has been reported.…”

Section: Reactions With Conservation Of Diazo Groupmentioning

confidence: 99%

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Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Ledenyova

Didenko

Shikhaliev

2014

Chem Heterocycl Comp

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The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.More than one hundred years have passed since α-diazo derivatives of pyrazole were discovered. A substantial amount of knowledge has been accumulated over this time regarding the stability, structure, and transformations of these compounds. However, the chemistry of pyrazole-3(5)-diazonium salts developed rapidly only in the second half of the 20th century, with many studies performed in various countries, in particular Germany, Egypt, Russia, and Japan. Unfortunately, no systematic review has been compiled for the wide range of data about pyrazole-3(5)-diazonium salts. Some aspects regarding the properties of these compounds have been discussed in reviews and monographs on other topics [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17].

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Section: Reactions With Conservation Of Diazo Groupmentioning

confidence: 99%

“…Examples were found for azo coupling of diazonium salts 1 with 4-alkyl-3-cyano-6-hydroxypyridin-2-one [102,103,107], 8-hydroxyquinoline [92], 1,2,3,4-tetrahydroquinolines [43,94,97], 4-hydroxy-2-pyrone [102], and [1,3]thiazolo[3,2-a]benzimidazol-3-one [108].…”

Section: Reactions With Conservation Of Diazo Groupmentioning

confidence: 99%

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Ledenyova

Didenko

Shikhaliev

2014

Chem Heterocycl Comp

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“…Previously, we established that the tautomeric structure of pyrazole dyes in the solid state and solution medium using FT-IR and 1 H NMR. The spectral data generally lead to the conclusion that the tautomeric equilibrium of these dyes was in favour of the hydrazo form [28][29][30]. These suggest that these dyes are predominantly in triazo-hydrazo form (T2), (T3) or dihydrazodiazo form (T4), (T5) and (T6) in the solid state and DMSO.…”

Section: Spectral Characteristics and Tautomerismmentioning

confidence: 99%

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

Patel

2012

Eur. J. Chem.

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KEYWORDSAniline derivatives were diazotized and coupled with 3-aminocrotononitrile to give the corresponding 2-arylhydrazono-3-ketiminobutyronitriles. Cyclization of these arylhydrazono derivatives with hydrazine monohydrate afforded 5-amino-4-arylazo-3-methyl-1H-pyrazoles which were subsequently diazotized and coupled with malononitrile to yield a series of pyrazolylhydrazonomalononitriles. These compounds were then reacted with hydrazine monohydrate to provide, heterocyclic dyes, which were further diazotized and coupled with 4-hexylbenzene-1,3-diol to produce novel heterocyclic tetraazo dyes which were characterized by elemental analysis and spectral methods. The antimicrobial activity and absorption characteristics of the dyes were also examined in detail.Pyrazole Solvatochromism Heterocyclic dyes Antimicrobial activity 3-Aminocrotononitrile 4-Hexylbenzene-1,3-diol

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“…It is well known that λmax values relate to the strength of the electronic power in the benzenoid system [17]. Since electronic transition in these compounds involves a general migration of electron density from the donor group towards the azo group, the greatest effect in terms of longer wavelength is achieved by placing the substituent in the position ortho or para to the azo group for effective conjugation [18].…”

Section: Absorption Spectral Characteristicsmentioning

confidence: 99%

Synthesis, characterization and antimicrobial activity, and applications of new azo pyridone disperse dyes on polyester fabric

et al. 2014

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KEYWORDSThree components; ethyl cyanoacetate, ethyl amines, and methyl propionylacetate were condensed using solid supports in microwave to give 1,4-diethyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile (9) that was then coupled with aromatic diazonium salts to give the corresponding arylhydrazono-1,4-diethyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile disperse dyes, 10a-g. Structures of the afforded compounds were confirmed by (IR, NMR, EI/MS) and one of them was further confirmed by X-ray crystallography (10g). Fastness properties of the reported dyes were intensively examined against light, perspiration and washing fastness, exhibiting moderate, very good and excellent fastness levels, respectively. The antimicrobial activity of the dyes were tested against different bacterial strains of Gram positive and Gram negative characteristics, and yeast, at where most of them showed promising activities against such test organisms.

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Synthesis and absorption spectra of some novel heterocyclic disazo dyes derived from pyridone and pyrazolone derivatives

Cited by 67 publications

References 27 publications

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

Synthesis, antimicrobial activity and absorption studies of some novel heterocyclic dyes based on 4-hexylbenzene-1,3-diol

Synthesis, characterization and antimicrobial activity, and applications of new azo pyridone disperse dyes on polyester fabric

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