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Molecules 2012, 17(8), 8822-8831; doi:10.3390/molecules17088822

Synthesis of Some Novel Biologically Active Disperse Dyes Derived from 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as Coupling Component and Their Colour Assessment on Polyester Fabrics

1
Department of Chemistry, Faculty of Science, University of Aleppo, P.O. Box 10229, Aleppo, Syria
2
Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, Dokki, Giza 12622, Egypt
3
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
*
Author to whom correspondence should be addressed.
Received: 7 June 2012 / Revised: 14 July 2012 / Accepted: 21 July 2012 / Published: 25 July 2012
(This article belongs to the Section Organic Synthesis)
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Abstract

A series of novel azo-disperse dyes containing alkylhydrazonopyridinone structures were synthesized. 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitrile (8) is synthesized by one-pot synthesis using ethyl cyanoacetate, propylamine, and ethyl acetoacetate. Compound 8 is then coupled with aromatic and heteroaromatic diazonium salts to afford the corresponding aryl- and heteroaryl-4-methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydropyridine-3-carbonitriles 12a,b and 13a–c. Structural assignments to the dyes were made using NMR spectroscopic methods. A high temperature dyeing method was employed to apply these dyes to polyester fabrics. Most of the dyed fabrics tested displayed very good light fastness levels and good wash fastness. Finally, the biological activity of the prepared dyes against Gram positive bacteria and Gram negative bacteria were evaluated.
Keywords: arylhydrazonopyridinones; biological activity; disperse dyes; polyester fabrics arylhydrazonopyridinones; biological activity; disperse dyes; polyester fabrics
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Ashkar, S.M.; El-Apasery, M.A.; Touma, M.M.; Elnagdi, M.H. Synthesis of Some Novel Biologically Active Disperse Dyes Derived from 4-Methyl-2,6-dioxo-1-propyl-1,2,5,6-tetrahydro-pyridine-3-carbonitrile as Coupling Component and Their Colour Assessment on Polyester Fabrics. Molecules 2012, 17, 8822-8831.

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