Diazotization of 2-amino-6-methoxybenzothiazole at elevated temperature

Penchev, A.; Simov, D.; Gadjev, Nikolai

doi:10.1016/0143-7208(91)87022-f

Cited by 27 publications

(10 citation statements)

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“…IR spectra were recorded in KBr pellets on a Nicolet 760D spectrophotometer (Vaibhav Laboratory, Ahmedabad, India). 1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance DPX 400 spectrometer in DMSO-d 6 (Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, India). Absorption spectra were recorded on a Shimadzu UV-1601 spectrophotometer (Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, India) in various solvents.…”

Section: Methodsmentioning

confidence: 99%

“…In the beaker, 2-pyridone derivatives (0.01 mol) 2a-c as a coupling component were dissolved in water and added solid sodium acetate until solution became clear. It was cooled at 0-5 • C, and then the above-mentioned diazonium salt solution was added into the 2-pyridone solution by dropwise with 13 13…”

Section: Preparation Of Bishetroaryl Monoazo Dyes 3a-cmentioning

confidence: 99%

“…The progress of the reaction was monitored by TLC using a DMSO:water mixture (5:2 by volume) as a developing solvent and silica gel TLC plates as the stationary phase. 13 13 13 13 13 13…”

Section: Synthesis Of Bisheteroaryl Bisazo Dyes 5a-h 6a-h and 7a-hmentioning

confidence: 99%

“…mp: 229 • C. IR (KBr, cm −1 ): 1613 ( C C), 2217 ( CN), 1642 and 1686 ( CO), 3440 ( NH-hydrazo), 1638 ( N N), 3060 ( C H), 837 (p-sub.Ph), 1566 (s, NO 2 ). 1 H NMR (400 MHz, DMSO-d 6 , δ/ppm): 2.52 (s, 3H, CH 3 ), 3.79 (t, J = 7.3 Hz, 2H, CH 2 ), 2.12 (m, 2H, CH 2 ), 4.89 (t, J = 7.3 Hz, 2H, CH 2 ), 3.45 (s, 3H, OCH 3 ), 7.45-8.10 (m, 9H, Ar-H), 15.17 (s, 1H, N H hydrazone form) 13. C NMR: 9.31 ( CH 3 ), 56.36 ( OCH 3 ), 74.53 ( CH 2 ), 117.54 ( CN), 123.42 ( CH 2 , 2C), δ (Ar-C): 74.17, 115.36, 124.13 (2C), 126.52 (2C), 127.62 (2C), 128.40, 129.30 (2C), 133.32, 135.08, 146.53, 148.07, 156.76, 159.27, 163.25, 163.83, 166.82.…”

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Synthesis, Characterization of Novel Bisheteroaryl Bisazo Dyes, and Their Dyeing and Solvatochromic Behavior

Modi

Patel

2013

Heteroatom Chemistry

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4‐Phenyl‐2‐aminothaizole was diazotized and coupled with N‐(alkyl)‐2‐oxo‐3‐cyano‐4‐methyl‐6‐hydroxypyridine (2‐pyridone). The resultant dyes were named as N‐(alkyl)‐6‐hydroxy‐4‐methyl‐2‐oxo‐5‐((4‐phenylthiazole‐2‐yl)diazenyl)‐1,2‐dihydro pyridine‐3‐carbonitrite and duly characterized. The diazotized aryl amines were then coupled to a moiety of above‐mentioned dyes at 5‐position of thiazole. The obtained bisheteroaryl azo dyes were characterized by elemental analysis and spectral studies. Solvent effects on the visible absorption spectra of the dyes were evaluated. The color of the dyes is discussed with respect to the nature of the heterocyclic ring, aromatic amines, and substituents present therein. All these dyes were applied as disperse dyes on to polyester fabrics, and their fastness properties were evaluated. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:208–220, 2013; View this article online at http://wileyonlinelibrary.com. DOI 10.1002/hc.21085

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Section: Methodsmentioning

confidence: 99%

Section: Preparation Of Bishetroaryl Monoazo Dyes 3a-cmentioning

confidence: 99%

“…The progress of the reaction was monitored by TLC using a DMSO:water mixture (5:2 by volume) as a developing solvent and silica gel TLC plates as the stationary phase. 13 13 13 13 13 13…”

Section: Synthesis Of Bisheteroaryl Bisazo Dyes 5a-h 6a-h and 7a-hmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis, Characterization of Novel Bisheteroaryl Bisazo Dyes, and Their Dyeing and Solvatochromic Behavior

Modi

Patel

2013

Heteroatom Chemistry

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“…The use of heterocyclic intermediates in the synthesis of azo disperse dyes is well established and the resultant dyes exhibit good tinctorial strength and brighter dyeing than those derived from aniline-based diazo components. For instance, aminosubstituted thiazole, benzothiazole [19,20] and benzoisothiazole [21] compounds afford highly electronegative diazo components and consequently, provide a pronounced bathochromic effect compared to the corresponding benzoid compounds. Moreover, azo disperse dyes containing 3-methyl-1H-pyrazole-5-one and 4-hexylbenzene-1,3-diol as coupling component have also been described as having red-violet colours in the literature [22][23][24][25].…”

Section: Introductionmentioning

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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DNA Binding, Molecular Docking and Antimicrobial Evaluation of Novel Azo Dye Ligand and Their Metal Complexes

Venugopal

Krishnamurthy

Naik

et al. 2019

J Inorg Organomet Polym

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Diazotization of 2-amino-6-methoxybenzothiazole at elevated temperature

Cited by 27 publications

References 0 publications

Synthesis, Characterization of Novel Bisheteroaryl Bisazo Dyes, and Their Dyeing and Solvatochromic Behavior

Synthesis, Characterization of Novel Bisheteroaryl Bisazo Dyes, and Their Dyeing and Solvatochromic Behavior

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

DNA Binding, Molecular Docking and Antimicrobial Evaluation of Novel Azo Dye Ligand and Their Metal Complexes

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