Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1703-1711.DOI: 10.6023/cjoc202010033 Previous Articles     Next Articles



郭小燕a, 方帅军b, 钱红飞b, 冯高峰a,*()   

  1. a 绍兴文理学院 浙江省精细化学品传统工艺替代技术研究重点实验室 浙江绍兴 312000
    b 绍兴文理学院纺织服装学院 浙江绍兴 312000
  • 收稿日期:2020-10-22 修回日期:2020-11-13 发布日期:2020-12-05
  • 通讯作者: 冯高峰
  • 基金资助:

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

Xiaoyan Guoa, Shuaijun Fangb, Hongfei Qianb, Gaofeng Fenga,*()   

  1. a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang 312000
    b College of Textile and Garment, Shaoxing University, Shaoxing, Zhejiang 312000
  • Received:2020-10-22 Revised:2020-11-13 Published:2020-12-05
  • Contact: Gaofeng Feng
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21676166)

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, 13C 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.

Key words: azo disperse dye, Ugi four-component reaction, diversity-oriented synthesis, fastness property, hydrogen-bonding interaction