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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 59-64. 上一篇    下一篇

研究论文

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

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用聚苯乙烯基磺酰羟胺树脂1与酰氯2反应合成了聚苯乙烯基N,O-二酰基磺酰羟胺树脂3. 树脂3作为一种新的双酰基转移试剂可与胺4发生酰基转移反应, 合成了含有24个结构类似的酰胺化合物库. 改变酰氯的种类, 结果发现双对硝基苯甲酰树脂3a的活性较高. 双酰基树脂3胺解结果表明, 由脂肪族胺得到的酰胺收率较芳香族胺高. 当解脱试剂同时含有羟基和氨基时, 双酰基树脂3能选择性地在氨基端发生酰基转移, 而羟基端不受影响.

关键词: 聚苯乙烯基磺酰羟胺, 聚苯乙烯基N,O-二酰基磺酰羟胺, 酰胺库, 酰基转移剂

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