Fluorous parallel synthesis of a hydantoin/thiohydantoin library.
Fluorous parallel synthesis of a hydantoin/thiohydantoin library.
复制标题
乙内酰脲/硫代乙内酰脲文库的氟平行合成。
DOI：
10.1007/s11030-005-1293-y
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发表时间：
2005
影响因子：
3.8
通讯作者：
Zhang,Wei
中科院分区：
文献类型：
--
作者：
Lu,Yimin;Zhang,Wei
将荧光标记策略应用于含有乙内酰脲和硫代乙内酰脲类似物的文库的液相平行合成。两个全氟烷基（Rf）标记的α-氨基酯各自在还原胺化条件下与六个芳香醛反应。然后12个氨基酯各自与10个异氰酸酯和异硫氰酸酯平行反应。所得的脲和硫脲进行自发环化以形成相应的乙内酰脲和乙内酰硫脲。中间体和最终产品纯化采用FluoroFlashTM固相萃取（SPE）柱进行，无需色谱法。使用标准仪器和简单的SPE技术，一位化学家在不到五个工作日内完成了120个成员的库合成，包括起始材料合成和产物分析。
Fluorous tagging strategy is applied to solution-phase parallel synthesis of a library containing hydantoin and thiohydantoin analogs. Two perfluoroalkyl (Rf)-tagged α-amino esters each react with six aromatic aldehydes under reductive amination conditions. Twelve amino esters then each react with 10 isocyanates and isothiocyanates in parallel. The resulting 120 ureas and thioureas undergo spontaneous cyclization to form the corresponding hydantoins and thiohydantoins. The intermediate and final product purifications are performed with solid-phase extraction (SPE) over FluoroFlashTMcartridges, no chromatography is required. Using standard instruments and straightforward SPE technique, one chemist accomplished the 120-member library synthesis in less than five working days, including starting material synthesis and product analysis.