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Molecules 2014, 19(3), 2993-3003; doi:10.3390/molecules19032993

Synthesis and Spectroscopic Properties of New Azo Dyes Derived from 3-Ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole

1, 1, 2 and 1,2,*
1 Department of Chemistry, Faculty of Science for Girls, King Abdulaziz University, Jeddah, P.O. Box 50918, Jeddah 21533, Saudi Arabia 2 Department of Chemistry, Faculty of Science, El-Minia University, El-Minia 61519, Egypt
* Author to whom correspondence should be addressed.
Received: 31 December 2013 / Revised: 10 February 2014 / Accepted: 10 February 2014 / Published: 7 March 2014
(This article belongs to the Section Organic Synthesis)
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New 1,2,4-triazole colorants were obtained, in high yields, by coupling 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole (1) with diazotized aniline derivatives 2, 4 and 6. The azo dyes prepared in this work may exist in three tautomeric forms. We found that the tautomerism is influenced mainly by the nature of substituent at the para position of the aniline coupling component. This tautomerisation was observed in the NMR spectra of the dyes. The dyes were characterized by IR, 1H-NMR, 13C-NMR and MS spectroscopic techniques.
Keywords: synthesis; azo-hydrazone tautomerism; coupling reaction; diazotization synthesis; azo-hydrazone tautomerism; coupling reaction; diazotization
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Al-Sheikh, M.; Medrasi, H.Y.; Usef Sadek, K.; Mekheimer, R.A. Synthesis and Spectroscopic Properties of New Azo Dyes Derived from 3-Ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole. Molecules 2014, 19, 2993-3003.

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