无金属催化的亚甲基吲哚酮的C-H键酰胺化反应研究

发布时间：2018-07-09 21:34

  本文选题：亚甲基吲哚酮 + N-甲氧基苯甲酰胺　； 参考：《东北师范大学》2017年硕士论文

【摘要】：含氮化合物因良好的生物活性和药物活性而被广泛应用于医药、农药、化工等相关领域。C-N键的构建是合成含氮化合物的有效方法之一,而C-H键的直接官能团化反应,尤其是sp~2C-H键的直接胺化反应无需底物的预活化,可直接将胺基经济高效的引入到指定位点而受到广泛的关注。近年来,芳烃C-H键的胺化反应已取得较好的研究成果。然而关于烯烃C-H键的胺化反应的报道相对较少,传统的烯烃胺化反应需要外加氧化剂、过渡金属催化剂和配体等,通常存在着金属催化剂价格昂贵、有毒、残留等问题,限制了其在有机合成、制药工业等领域的进一步应用。因此发展一种无金属催化、氧化还原中性、条件温和的烯基C-H的胺化反应很有意义。本论文以亚甲基吲哚酮为底物,N-甲氧基苯甲酰胺为氮源,四甲基胍为催化剂,在100℃的条件下,实现了无金属催化的烯基C-H键的酰胺化反应。反应过程中不需要外加氧化剂,也无需底物的预活化就能实现C-H键的直接官能化反应。因此,我们发展了一种无金属参与的、条件温和的,操作简单的烯基C-H键的胺化反应,该反应为合成多取代的烯胺类化合物提供了一种有效的合成途径。
[Abstract]:Nitrogen-containing compounds are widely used in pharmaceutical, pesticide, chemical and other related fields because of their good biological activity and drug activity. The construction of C-N bond is one of the effective methods for the synthesis of nitrogen-containing compounds. In particular, the direct amination reaction of sph2C-H bond without substrate pre-activation can directly introduce the amine group to the designated site economically and efficiently, so it has attracted wide attention. In recent years, the amination reaction of aromatic C-H bond has achieved good results. However, there are relatively few reports on the amination of C-H bonds of olefins. Traditional olefin amination reactions require the addition of oxidants, transition metal catalysts and ligands, etc. It limits its further application in organic synthesis, pharmaceutical industry and other fields. Therefore, it is significant to develop a metal-free, redox neutral, mild amination reaction of alkenyl C-H. In this paper, N-methoxy benzoamide was used as nitrogen source and tetramethylguanidine as catalyst. The amidation of alkenyl C-H bond without metal was realized at 100 鈩，

本文编号：2110735