Synthesis of new hetarylazoindole dyes from some 2-aminothiazole derivatives |
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Authors: | A Saylam Z Seferoglu N Ertan |
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Institution: | 1.Fen-Edebiyat Fakültesi, Kimya B?lumü,Gazi üniversitesi,Teknikokullar, Ankara,Turkiye |
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Abstract: | 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.
Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 592–599.
The text was submitted by the authors in English. |
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