含硼一級胺類化合物之合成及其應用

Synthesis of Boron-containing Primary Amines and Their Applications

鍾勝烜(Sheng-Hsuan Chung)

指導教授 ： 潘伯申

淡江大學/理學院/化學學系碩士班/碩士(2013年)

https://doi.org/10.6846/TKU.2013.00251

摘要

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)。

關鍵字

硼 ； peptoid ； 一級胺 ； Ugi-4CR ； Suzuki reaction ； Gabriel reaction

並列摘要

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).

並列關鍵字

boron ； peptoid ； primary amine ； Ugi-4CR ； Suzuki reaction ； Gabriel reaction

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