Diverse privileged N-polycyclic skeletons accessed from a metal-free cascade cyclization reaction
Diverse privileged N-polycyclic skeletons accessed from a metal-free cascade cyclization reaction
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通过无金属级联环化反应获得多种优先的 N-多环骨架
DOI：
10.1039/d1ob01206a
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发表时间：
2021
影响因子：
3.2
通讯作者：
Wang Wei-Li
中科院分区：
文献类型：
--
作者：
Li Wenzhong;Wang Yu;Qi Huijing;Shi Ran;Li Jiazhu;Chen Si;Xu Xin-Ming;Wang Wei-Li
建立了2-酰基苯甲酸与胺的无金属级联环化反应，为一锅法合成各种异吲哚、异喹啉和苯并吲哚类化合物提供了强有力的方法。该方法避免了金属催化剂的使用，反应效率高，底物范围广。这些产物可以在LiAlH4/AlCl3的还原下转化为叔胺，然后经过Hofmann消除，以极高的产率提供了大量的含氮九元环化合物。所有含有融合N-多环骨架的合成产物都很难用传统方法构建，它们在医药领域有着广泛的应用。
An exquisite metal-free cascade cyclization reaction of 2-acylbenzoic acids with amines was developed, which provided a powerful method for the one-pot synthesis of diverse isoindoloisoquinoline and benzoindolizinoindole derivatives. This protocol avoided the use of metal catalysts, proceeded with high efficiency and had broad substrate scope. These resulting products could be transformed into tertiary amines under the reduction of LiAlH4/AlCl3, followed by the Hofmann elimination offering lots of nitrogen-containing nine-membered ring compounds in excellent yields. All synthesized products containing fused N-polycyclic skeletons were difficult to be constructed using traditional methods and they have a wide range of applications in the pharmaceutical area.