Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (01): 59-64. Previous Articles     Next Articles

Original Articles

聚苯乙烯基N,O-二酰基磺酰羟胺树脂: 一种双酰基转移试剂在合成酰胺库中的应用

李树锋,杨新林,黄文强*   

  1. (南开大学吸附分离功能高分子材料国家重点实验室高分子化学研究所 天津 300071)
  • 收稿日期:2004-03-01 修回日期:2004-07-01 发布日期:2004-12-30
  • 通讯作者: 黄文强

Polystyrene N,O-Diacyl-N-sulfonyl Hydroxyamine. A New Double- Acyl Transfer Reagent for Synthesis of the Amide Library

LI Shu-Feng , YANG Xin-Lin , HUANG Wen-Qiang*   

  1. (State Key Laboratory of Functional Polymer Materials for Adsorption and Separation,
    Institute of Polymer Chemistry, Nankai University, Tianjin 300071)
  • Received:2004-03-01 Revised:2004-07-01 Published:2004-12-30
  • Contact: HUANG Wen-Qiang

A new double-acyl transfer reagent, polystyrene N,O-diacyl-N-sulfonyl hydroxylamine resin 3, was prepared and used in solution-phase synthesis of an amide library. Polystyrene N-hydroxyl sulfonyl amide resin 1 reacted with acid chloride 2 to form polystyrene N,O-diacyl sulfonyl hydroxamate 3, which was cleaved by amine 4 to form amide 5. The results showed that the double p-nitrobenzoyl resin 3a possessed the highest activity. Cleavage of double-acylated resin 3 by aliphatic amines gave the higher amide yields than by aromatic amines. In this way, a library with 24 amides was synthesized. When double-acylated resin 3 was cleaved by the reagent containing both amino and hydroxyl groups, only amino group was selectively acylated but the hydroxyl group remained unacylated. The reusability of resin 3a was also studied.

Key words: polystyrene N-hydroxyl sulfonamide, acyl transfer reagent, amide library, polystyrene N,O-diacyl sulfonyl hydroxamate