基于Ugi四组分反应合成结构多样的新型分散染料

Facile Synthesis of Novel,Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

以Ugi四组分反应为关键步骤,建立了一种合成结构多样、色牢度性能优异新型分散染料的新方法.从简单易得的原料出发,经过4-氧代丁酸衍生物合成,酸、苯胺、苯甲醛和环己基异氰的Ugi四组分反应以及Ugi产物与重氮盐偶合等步骤合成了15个新颖的分散染料.用1H NMR、^(13)C NMR、红外光谱、质谱和高分辨质谱对Ugi产物和新染料的结构进行了表征,并测试了他们的可见光吸收和摩尔消光系数.在聚酰胺和聚酯纤维上色牢度的研究发现,新型分散染料的色牢度比已知分散染料红1和红13有了很大提高.色牢度的提高与分散染料中引入的两个酰胺基和一个酯基以及染料分子量/体积的适当提高相关.这是一个合成新型高性能分散染料分子库的有效方法.

A novel approach has been established for synthesizing novel structurally diverse azo disperse dyes with good fastness properties by employing Ugi four-component reaction as the key step.15 new disperse azo dyes were synthesized efficiently from readily available starting materials with simple operations through a sequence of generation of 4-(2-(ethyl(phenyl)amino)ethoxy)-4-oxobutanoic acid,the Ugi four-component reactions of the acid with anilines,benzaldehydes and cyclohexyl isocyanide,and the coupling of the Ugi adducts with aryl diazonium salts.The structures of Ugi adducts and the new dyes were fully characterized with 1H NMR,^(13)C NMR,IR,MS,and HRMS.Visible absorption measurements and molar extinction coefficients were also carried out.It was found that the obtained dyes exhibited improved fastness properties on both polyamide(PA)and poly(ethylene terephthalate)(PET)fabrics as compared with C.I.Disperse Red 1 and C.I.Disperse Red 13.The improvement of fastness properties should be attributed to the introduced two amides and one ester functionalities,and the appropriately increased molecular weight/size.It is an attractive approach for accessing a library of novel azo disperse dyes with good fastness properties.