Fluorous Mixture Synthesis of Two Libraries with Hydantoin-, and Benzodiazepinedione-Fused Heterocyclic Scaffolds

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• 作者：Wei Zhang ; Yimin Lu ; Christine Hiu-Tung Chen ; Lu Zeng ; Daniel B. Kassel
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2006
• 出版时间：September 2006
• 年：2006
• 卷：8
• 期：5
• 页码：687 - 695
• 全文大小：487K
• 年卷期：v.8,no.5(September 2006)
• ISSN：1520-4774

文摘

Diversity-oriented synthesis (DOS) and fluorous mixture synthesis (FMS) are two aspects of combinatorialchemistry. DOS generates library scaffolds with skeletal, substitution, and stereochemistry variations, whereasFMS is a highly efficient tool for library production. The combination of these two aspects in solution-phase synthesis of two novel heterocyclic compound libraries is presented in this paper. Mixtures of differentfluorous amino acids undergo [3 + 2] cycloadditions followed by postcondensation reactions. The mixturesare then demixed by fluorous HPLC. Fluorous tags are removed by cyclization to afford hydantoin- andbenzodiazepinedione-fused heterocyclic compounds as individual, pure, and structurally defined molecules.The application of MS-directed HPLC purification and parallel four-channel LC/MS analysis further increasesthe efficiency of FMS.