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

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, 2,* , 1 and 3
Received: 7 June 2012; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

Ashkar SM, El-Apasery MA, Touma MM, Elnagdi MH. 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(8):8822-8831.

Chicago/Turabian Style

Ashkar, Samar M.; El-Apasery, Morsy A.; Touma, Marwan M.; Elnagdi, Mohamed H. 2012. "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 17, no. 8: 8822-8831.


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