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    Title: 含硼一級胺類化合物之合成及其應用
    Other Titles: Synthesis of boron-containing primary amines and their applications
    Authors: 鍾勝烜;Chung, Sheng-Hsuan
    Contributors: 淡江大學化學學系碩士班
    潘伯申
    Keywords: ;一級胺;boron;peptoid;primary amine;Ugi-4CR;Suzuki reaction;Gabriel reaction
    Date: 2013
    Issue Date: 2014-01-23 13:46:30 (UTC+8)
    Abstract: 本研究成功利用優化之Gabriel reaction合成六個含硼之一級胺類化合物 (Fig. 1)。由於這六個含硼一級胺類化合物皆在溫和的條件下予以合成,因此所得產率皆高於50%以上 (Scheme 1,2)。
    以含硼一級胺產物為Ugi多組成反應(Ugi-4CR)之起始物並藉由微波輔助條件,本研究成功合成含硼之peptoid衍生物。而這些含硼之peptoid衍生物可藉由一鍋化水解反應,將其轉變為相對應之硼酸化合物 (Fig. 2)。最後,這些Ugi-4CR之peptoids化合物可藉由Suzuki coupling reaction更進一步修飾以達到將結構複雜化的目的 (Fig. 3)。
    In this study, the modified Gabriel synthetic condition was developed to build six boron-containing primary amines in good to excellent yields (Fig. 1). This modified condition allowed the synthesis to carry out in mild synthetic processes (Scheme 1,2).
    Further, the desired boron-containing primary amines were further utilized to construct the peptoid analogs via microwave assisted Ugi four component reaction (Ugi-4CR) (Fig. 2). In addition, these Ugi-4CR boronate esters were converted to the corresponding boronic acids by a one-pot hydration reaction. Finally, the peptoid structures can be further modified by incorporating aryl/heteroaryl component via palladium mediated Suzuki coupling reaction (Fig. 3).
    Appears in Collections:[化學學系暨研究所] 學位論文

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