α-芳基吲哚醇的自由基加成-重排反应研究

Radical difunctionalization reaction of C=C bond is an important method for the construction of complex organic compounds bearing multifunctionalities, while olefin-based radical addition-rearrangement reaction provides efficient strategy on the synthesis of compounds with multi-functional groups and potent functional organic molecules..In this project, research work mainly focus on the α-aryl indolyl alcohol-based radical addition-rearrangement reaction. Sysmtematic study comprise following points: regioselectivity about the radical addition to the indole ring, structure and property demand for the migrative groups in the rearrangement, distance demand between the indole and migrative groups, driving force in the rearrangement reaction, radical addition-transannular rearrangement, and so on. By this project, a common protocol for the indoline synthesis from indole, which has the advantage of simutanious functionalization of three sites in indole ring and its side-arm, will be established. It will provide an efficient and facile synthetic strategy for the access to the indolines bearing multi-functional groups..About 10 SCI papers will be published and 1 invent patent will be applied at the end of the project. 5-8 graducate students will be trained.

碳碳双键的自由基型双官能化反应是构筑结构较为复杂的多官能团化合物的重要方法。而基于烯烃的自由基加成-重排反应则为构建多官能团化合物和潜在功能有机分子提供了有效手段。.本项目选择以α-芳基吲哚醇为研究对象，以该类化合物的自由基加成-重排反应为主要研究内容，对不同类型的自由基加成吲哚骨架的区位选择性、迁移基团在重排中必须满足的性质和结构特点、迁移基团与吲哚之间的距离要求、重排反应的驱动力、自由基加成-跨环重排等问题进行系统研究，开发出从吲哚合成吲哚啉化合物的一般方法，体现吲哚环系和侧链三位点同时官能化的优势，为多官能团吲哚啉类化合物的高效率简便合成提供参考。.项目预计发表SCI源期刊论文10篇，申请发明专利1项，培养研究生6-8人。

吲哚及吲哚啉骨架是众多天然产物和生物活性分子的核心骨架，含有这些骨架的有机物时常显示重要的生物活性，其合成方法也备受关注。传统直接从吲哚出发构建多官能团或者结构复杂的吲哚及吲哚啉化合物的方法效率低下，产物结构多样性缺乏。本项目从侧链官能化的吲哚出发，设计了吲哚醇、色胺异腈等底物，通过自由基型和离子型反应及其接力转化，探索了底物结构、反应条件、试剂性质等对反应途径的影响，发现了吲哚醇的若干反应规律，色胺异腈的一些新颖反应，为构建含有吲哚骨架的结构复杂性和多样性产物提供了新的参考。同时，借助于本项目的经费，拓展研究了数类新型的吲哚的合成反应、扩环反应、环加成反应以及异腈的相关反应，取得了系列研究成果。