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

Samar M. Ashkar²  Morsy A. El-Apasery¹  Marwan M. Touma² 

[1] Dyeing, Printing and Textile Auxiliaries Department, Textile Research Division, National Research Centre, Dokki, Giza 12622, Egypt;Department of Chemistry, Faculty of Science, University of Aleppo, P.O. Box 10229, Aleppo, Syria

关键词: arylhydrazonopyridinones;    biological activity;    disperse dyes;    polyester fabrics;   

DOI  :  10.3390/molecules17088822

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.