Nermin Ertan

Hetarylazo disperse dyes derived from 3-methyl-1-(3′,5′-dipiperidino-s-triazinyl)-5-pyrazolone as coupling component

Abstract The synthesis of some novel, hetarylazopyrazolone dyes was achieved by diazotisation of five heterocyclic amines using nitrosyl sulphuric acid, coupling with 3-methyl-1-(3′,5′-dipiperidino- s -triazinyl)-5-pyrazolone. Visible absorption spectra of the dyes were examined in various solvents and the compounds in solution exhibited several equilibria. The hetarylazopyrazolones readily undergo acidic dissociation into the respective common anion in both DMF and DMSO. The absorption maxima of the dyes showed large bathochromic effects in comparison with analogue dyes containing carbocyclic amine residues and N -phenylpyrazolone derivatives. The colour of the dyes is discussed with respect to the nature of the heterocyclic ring and substituents therein. The affects of temperature, concentration as well as acid and base on the visible absorption maxima of the dyes are also reported.

Synthesis and properties of some azo pyridone dyes and their Cu(II) complexes

Abstract A series of azo pyridone dyes derived by the coupling of 3-cyano-6-hydroxy-4-methyl 2 (IH) pyridone with diazotized para and meta substituted anilines, and the Cu(II) complex of the dyes, have been synthesized. The azo dyes and complexes have been characterized by elemental analysis, IR, 1H NMR and UV-visible spectra. The acid dissociation constants of the dyes and formation constants of the complexes have been determined spectrophotometrically. Substituent effects on these parameters have been discussed.

Synthesis, characterization and spectroscopic properties of some new phenylazo-6-aminouracil

In this study, a series of new 5-phenylazo-6-aminouracil dyes were prepared by linking m-,p-nitroaniline, m-,p-chloroaniline, m-,p-anisidine, m-,p-toluidine, m-,p-cyanoaniline, p-ethoxyaniline, p-phenoxyaniline, p-ethylaniline, p-acetamidoaniline, p-acetylaniline, p-carboxyaniline and aniline to 6-aminouracil. The prepared dyes were characterized by UV-vis, FT-IR, 1H NMR spectroscopic techniques and elemental analysis. The effect of acid and base upon the UV-vis spectra of these dyes were investigated. In addition, the solvatochromic behaviors and substituent effects in various solvents were evaluated.

Synthesis and spectral properties of new hetarylazo indole dyes

A series of new hetarylazo indole dyes were synthesized by azo coupling of 2-phenyl-, 2-methyl-, and 1-methyl-1-phenyl-1H-indole with diazonium salts derived from 5-methylsulfanyl-1H-1,2,4-triazol-3-amine, 1H-1,2,4-triazol-3-amine, 5-methylisoxazol-3-amine, and 5-amino-1,3,4-thiadiazole-2-thiol. The dyes were characterized by the IR spectra, electronic absorption spectra in the UV and visible regions, and 1H NMR and mass spectra. The effects of solvent nature, acidity of the medium, temperature, and concentration on the electronic absorption spectra in the visible region and the dependence of the color of the dyes on the nature of heterocyclic fragment were examined.

Synthesis of new hetarylazoindole dyes from some 2-aminothiazole derivatives

A new series of heterocyclic disperse dyes were prepared by diazotization of some 2-aminothiazole derivatives and subsequent coupling with indole compounds. The dyes were characterized by UV-Vis, FT-IR, 1H NMR, and mass spectra (LC-MS). Solvent effects on their visible absorption spectra were estimated. The color of the dyes is discussed with respect to the substituent therein. The effects of acids and bases on the visible absorption maxima of the dyes are also reported. Replacement of methyl group in the 4-position of the thiazole ring by phenyl group leads to red shift of the absorption maximum due to π-electron-donating properties of the phenyl group, while weak electron-withdrawing chlorine or bromine atom in the para-position of the phenyl group in the 2-amino-4-phenylthiazole fragment induce a small blue shift relative to 2-amino-4-phenylthiazole derivatives. Introduction of an electron-withdrawing 4-nitrophenylsulfonyl group into the thiazole ring produces bathochromic shift of the absorption maximum in all solvents.

Hetarylazoindoles 1. Synthesis, Characterization, and Spectroscopic Properties of New Hetarylazoindole Dyes

Synthesis of some new hetarylazoindole dyes have been carried out by diazotization of 5-substituted 2-aminothiazoles in nitrosylsulphuric acid and coupling with various 2- and 1,2-disubstituted indole derivatives. The structures of the dyes were confirmed by UV-VIS, FT-IR, and 1 H NMR spectroscopy as well as by LC-MS or MS spectrometry and elemental analyses. The solvatochromism of the dyes was evaluated with respect to the absorption properties in various solvents. Absorption maxima of the dyes generally did not changed with the polarity of the solvent. The color of the dyes is discussed in relation to the substituents in the thiazole ring. The effects of an acid or a base on the visible absorption maxima of the dyes are also reported. In addition, the absorption spectra of the dyes were compared with those of corresponding model compounds, which do not exhibit azo-hydrazone tautomerism.

Crystal structure of hydrazone form of 1-butyl-3-cyano-6-hydroxy-4-methyl-5-(2-nitrothiazolylazo)-2(1H)-pyridone

Abstract The structural results clearly indicate that 1-butyl-3-cyano-6-hydroxy-4-methyl-5-(2-thiazolylazo)-2(1H)-pyridone, (C 14 H 15 N 5 O 2 S), exists primarily as the hydrazone tautomer in the solid state. The molecule is nearly planar not regarding the butyl group. Some of the bond lengths and angles are distorted due to π-electron delocalization and strain. A strong intramolecular N-H … O hydrogen bond was found [N…O =2.53(1)A]. The crystallographic parameters are as follows: triclinic P1, a=5.972(4)A, b=7.732(5)A, c=17.348(9)A, α=85.62(5) 0 , β=79.24(6) 0 , γ=78.41(7) 0 , V=770.4(9)A 3 , Z=2, D c =1.37 g cm −3 , μ(MoK α )=2.1 cm −1 , R=0.045, G.O.F.=1.78.

1‐Methyl‐2‐phenyl‐1H‐indole

In the structure of the title compound, C15H13N, the dihedral angle between the five- and the six-membered rings of the indole system is 1.19 (5)° and the phenyl ring makes a dihedral angle of 46.09 (5)° with the indole ring system.