Department of Chemistry, University of Aleppo, Aleppo, Syria.
Molecules. 2012 Jul 25;17(8):8822-31. doi: 10.3390/molecules17088822.
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.
一系列含有烷基亚肼基吡啶酮结构的新型偶氮分散染料被合成出来。4-甲基-2,6-二氧代-1-丙基-1,2,5,6-四氢嘧啶-3-甲腈（8）通过一锅法合成，使用氰基乙酸乙酯、丙胺和乙酰乙酸乙酯。然后，化合物 8 与芳香族和杂环族重氮盐偶联，得到相应的芳基和杂芳基-4-甲基-2,6-二氧代-1-丙基-1,2,5,6-四氢嘧啶-3-甲腈 12a,b 和 13a-c。通过 NMR 光谱方法对染料进行了结构鉴定。采用高温染色法将这些染料应用于聚酯纤维织物。测试的大多数染色织物显示出非常好的耐光牢度和良好的耐洗牢度。最后，评估了所制备的染料对革兰氏阳性菌和革兰氏阴性菌的生物活性。
