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بیست و نهمین کنفرانس شیمی آلی ایران
6,8dimethyl-4-hydroxyquinolin-2(1H)-one as a versatile coupling component for the synthesis of some new heterocyclic azo dyes
نویسندگان :
سارا فتوتی ( دانشگاه محقق اردبیلی ) , عنایت الله مرادی روفچاهی ( دانشگاه آزاد اسلامی واحد لاهیجان ) , اسیه یحیی زاده ( دانشگاه گیلان ) , غلامحسن ایمانزاده ( دانشگاه محقق اردبیلی )
کلید واژه ها :
4Hydroxyquinolin-2(1H)-one،Azo dyes،Enol-type coupling component،Benzothiazole
چکیده مقاله :
-4hydroxyquinoline-2(1H)-ones have been investigated as heterocyclic backbones to produce some of the early examples of azo disperse dyes [1]. For example, 4-Hydroxyquinolin-2(1H)- one (2,4-dihydroxyquinoline) and N-butyl-4-hydroxyquinolin-2(1H)-one were respectively employed for the synthesis of C.I. Pigment Yellow 7 and C.I. Mordant Yellow 30 [2, 3]. Inspired by aforementioned results, herein a series of 2-aminobenzothiazoles have been diazotized and coupled with 6, 8-dimethyl-4-hydroxyquinoline-2(1H)-one in basic solution at 0-5°C. The structures of these newly synthesized azo dyes were assigned by IR, 1H NMR and Mass spectroscopic analyses. The visible absorption spectra along with 1H NMR findings of all the 4-hydroxyquinolin-2-one based azo dyes revealed that there is a mixture of tautomeric forms in the solution state in solvents with different polarities. The effects of acid and base on the visible absorption spectra of the of the dyes in ethanol were also studied and showed that the spectral changes are clearly dependent upon the protonation-deprotonation of the dye molecules
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