Polystyrene N,O-Diacyl-N-sulfonyl Hydroxyamine. A New Double-Acyl Transfer Reagent for synthesis of the Amide Library
writer：Shufeng Li, Xinlin Yang, Wenqiang Huang*
keywords：polystyrene N-hydroxyl sulfonamide; polystyrene N,O-diacyl sulfonyl hydroxamate; acyl
source：期刊
specific source：Chin. J. Org. Chem，25 (1), 59-64 (2005).
Issue time：2005年
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.