基于有机催化的两可性离子的多组分domino反应构建某些杂(芳)环体系研究

项目名称： 基于有机催化的两可性离子的多组分domino反应构建某些杂(芳)环体系研究

项目编号： No.20872074

项目类型： 面上项目

立项/批准年度： 2009

项目学科： 金属学与金属工艺

项目作者： 李明

作者单位： 青岛科技大学

项目金额： 32万元

中文摘要： 有机合成的基础是各种碳-碳(杂)键的形成及官能团的转化反应。多组分反应因其固有的会聚性、选择性、原子经济性、多样性和产生复杂化合物的能力而备受关注，已成为组合化学、自动合成和药物筛选的首选方法。近年来兴起的多样性导向合成在建立分子库、筛选各类药物等方面已被证明行之有效。基于三苯基膦-DMAD、吡啶-DMAD、咪唑-DMAD和异腈-DMAD产生的两可性离子所诱发的多组分反应提供了一种建立串联反应的合成模式。本课题紧跟学科前沿，基于有机催化的两可性离子的反应性能，从底物设计出发，利用多样性导向合成和多米诺规则，重点研究原位产生上述两可性离子的后续反应，巧妙利用底物化学差异性，组配反应中的各组分及依次产生中间体的活性，精心设计和发现新型多组分反应(重点是4CR)，构建多种碳-碳(杂)键的形成和多种杂(芳)环体系的合成方法，为创造分子多样性、丰富杂(芳)环分子库和满足高通量筛选奠定基础。

中文关键词： 有机合成方法学；多组分反应；两可性离子；杂环；催化

英文摘要： Organic synthetic methodology is aimed at finding or developing novel multicomponent reactions and new synthetic routes for creating new organic molecules.This study consists of four achievements as follows: 1. Based on the reactivity of zwitterions or 1,3-dipoles, some novel multicomponent domino reactions have been developed from in situ produced zwitterions induced by amino acid, pyridine, phenanthridine and DABCO; 2. Based on the concept of substrate-design, some synthetic methods for new complicated heterocycles have been achieved though in situ produced zwitterions induced by isocyanides and phenanthridine,isocyanides and arylidenemalononitriles; 3. The multicomponent reactions using novel thioamides as synthons for the construction of chromeno[2,3-b]quinolines,thiochromeno[2,3-b]pyridine derivatives, imidazo[1,2-a]pyridine derivatives and pyrazolo[5,1-a]isoquinolines have been successfully established; 4. A convenient and unexpected synthesis of new penta-substituted dipyrrole disulfides has been developed by employing αcyl thioformanilides as a synthon. These studies focused on the C-C(hetero) bond-forming for the construction of some active frameworks have provided fundament for creating diversity-oritented molecule library and high-through screening of biologically active compounds. During our investigation, we found that three classes of products synthesized by us exhibited strong fluorescence, one of them was a novel unreported fluorescent core framework with large Stokes shift. We expect these small organic fluorophores after modified in structures, in future, could be applied as fluorescent probes, sensors, organic luminescent materials and so on.

英文关键词： Organic synthetic methodology; Mulicomponent reaction; Zwitterion; Heterocycle; Catalysis