铁催化8-氨基喹啉酰胺远程碳-氢键苄基化反应

发布时间：2018-10-12 17:16

【摘要】：喹啉是一类重要的N-杂环化合物,它具有广谱抗菌、抗疟、抗真菌和抗肿瘤活性,而且也可以作为导向基或配体,因此,取代的8-氨基喹啉衍生物合成方法的发展受到了极大的研究兴趣,理想的方法是通过导向碳-氢键活化反应,但由于喹啉基团的电子性质,通常是不容易控制它的区域选择性。前人成功的反应主要集中在C2位置上,在C=N键的影响下内在反应的官能化,选择性在C3和C8位置的喹啉化合物合成方法也有被报道过,然而,较少有课题组能高区域选择性在喹啉衍生物C5位置上反应。作为我们组内之前工作的延续,在本文中我们报告了首例铁催化喹啉远程C5苄基化反应。该反应的条件温和,具有良好的区域选择性,和良好的官能团兼容性,N-苄基磺胺类化合物能顺利的与脂肪酰胺以及芳香酰胺反应得到良好的收率的目标产物。因此本文提供了一种合成官能团化氨基喹啉衍生物的方法。
[Abstract]:Quinoline is an important class of N-heterocyclic compounds with broad-spectrum antimicrobial, antimalarial, antifungal and antitumor activities, and can also serve as a guiding group or ligand. The development of synthesis methods of substituted 8-aminoquinoline derivatives has attracted great interest. The ideal method is to activate the quinoline derivatives by directed carbon-hydrogen bond. However, due to the electronic properties of the quinoline group, it is not easy to control its regioselectivity. Previous successful reactions were mainly focused on C2 sites. The functionalization of the internal reactions under the influence of Con N bond and the synthesis of quinoline compounds with selectivity at C3 and C8 sites have also been reported. However, Few groups can react with high regioselectivity on the C _ 5 position of quinoline derivatives. As a continuation of previous work in our group, we report the first iron catalyzed long range C 5 benzylation of quinoline. The reaction conditions are mild, with good regioselectivity and good functional compatibility. N-benzyl sulfonamides can be successfully reacted with aliphatic amide and aromatic amide to obtain a good yield target product. Therefore, a method for synthesizing functional groups of aminoquinoline derivatives is presented.
【学位授予单位】：中国科学技术大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.251

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