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2-聚苯乙烯磺酰基乙醇树脂的合成及其在海因和脲固相成中的应用
引用本文:程绍玲,黄文强.2-聚苯乙烯磺酰基乙醇树脂的合成及其在海因和脲固相成中的应用[J].高等学校化学学报,2002,23(9):1809-1813.
作者姓名:程绍玲  黄文强
作者单位: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
基金项目:中国科学院资助项目,20074017,
摘    要:合成了一种新型的聚合物载体—2-聚苯乙烯磺酰基乙醇,并研究其在固相有机合成中应用,聚苯乙烯亚磺酸钠树脂(1)在相转移催化剂BU4NI和助催化KI的作用下,与氯乙进行砜化反应,得到含羟基功能基的2-聚苯乙烯磺酰基乙醇树脂2。树脂2用Boc保护的氨基酯化,封闭树脂上未反应的羟基,用酸脱保护并用三乙胺中和,再与异(硫)氰酸苯酯反应生成聚合生物支载的脲树脂6树脂6用酸解脱得到海因和硫代海因化合物,用碱处理树脂6是得到取代的脲和硫脲,优化了合成反应的全过程,探讨了树脂在酸性和碱性条件下的解脱方法,结果表明,2-聚苯乙烯磺酰基乙醇树脂易与羧基形成含酯键的连接桥,连接桥在强酸性和碱性条件下均可解脱得到产物。

关 键 词:2-聚苯乙烯磺酰基乙醇  固相合成海因  硫代海因    硫脲
文章编号:0251-0790(2002)09-1809-05
修稿时间:2001年6月8日

Synthesis of 2-Polystyrylsulfonylethanol and Its Application in Solid-phase Organic Synthesis of Hydantoins and Ureas
CHENG Shao\|Ling,HUANG Wen\|Qiang\.Synthesis of 2-Polystyrylsulfonylethanol and Its Application in Solid-phase Organic Synthesis of Hydantoins and Ureas[J].Chemical Research In Chinese Universities,2002,23(9):1809-1813.
Authors:CHENG Shao\|Ling  HUANG Wen\|Qiang\
Institution:CHENG Shao\|Ling,HUANG Wen\|Qiang\+*
Abstract:In this article a new kind of polymer\|support: 2\|polystyrylsulfonylethanol was prepared and used in solid\|phase organic synthesis. Sodium polystyrylsulfinate resin 1 reacted with chloroethanol in the presence of phase transfer catalyst Bu\-4NI and KI as a cocatalyst to give 2\|polystyrylsulfonylethanol resin 2. After the esterification of resin 2 with Boc\|Gly, deprotection of Boc group with HCl, neutralization by Et\-3N, conversion of the free amino group with phenyl isocyanate or phenyl isothiocanate to urea to give urea resin 6. The urea resins 6a and 6b were cleaved with \{6 mol/L\} HCl to obtain the hydantoin derivatives 7a and 7b in an overall yields of 29%\_30%. While the resin 6 was treated with 4 mol/L NaOH then HCl to give the urea derivatives 8a and 8b in an overall yields of 20%\_21%. The whole synthesis processes were optimized by the trace of the reactions by using IR spectra. The results show that resin 2 can easily form a stable ester linker with carboxylic acids and this kind of linker can be cleaved by the use of both strong acid or dilute base.
Keywords:Polystyrylsulfonylethanol  Solid\|phase synthesis  Hydantoin  Thiohydantoin  Urea  Thiourea
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