Tetrahedron Letters ( IF 1.5 ) Pub Date : 2023-04-11 , DOI: 10.1016/j.tetlet.2023.154504 Dang Van Do , Ha Nam Do , Ngoc Khanh Nguyen , Tuan Anh Le , Tra My Le , Ban Van Phuc , Thanh Son Le , Quoc Anh Ngo , Hien Nguyen , Tran Quang Hung , Tuan Thanh Dang
Fluorescent active small compounds containing 5H-pyrido[2′,1:2,3]imidazo[4,5-b]indole core could be successfully synthesized by double CN coupling reaction from 3-iodo-2-(2-bromophenyl)imidazo[1,2-a]pyridine with different amines in high yields under air atmosphere. HKUST-1 was found to be the most suitable heterogeneous catalyst for this transformation. Interestingly, HKUST-1 catalyst (∼12 mol% Cu loading for each reaction) showed highly active, robust, and recyclable properties with the tolerance of broad substrate scope. Remarkably, the mechanism for the CN coupling reaction undergoing Cu1+/ Cu3+ catalytic cycle was proposed from several observed important evidence. Cu2+ sites in the node of HKUST-1 structure could be reduced to Cu1+ which initiated the formation of radical amine species. This method may give potential applications in the pharmaceutical and fine chemical industries.
中文翻译:
以HKUST-1为可回收非均相催化剂在空气下通过双CN偶联反应高效合成5-aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles
3-碘-2-(2-溴苯基)双C -N偶联反应成功合成了以5H-吡啶并[2′,1:2,3]咪唑并[4,5- b ]吲哚为核心的荧光活性小分子化合物)咪唑并[1,2- a ]吡啶与不同的胺在空气气氛下高收率。HKUST-1 被发现是最适合这种转化的非均相催化剂。有趣的是,HKUST-1 催化剂(每个反应的 Cu 负载量约为 12 mol%)显示出高活性、稳健和可回收的特性,并且具有广泛的底物范围耐受性。值得注意的是,从几个观察到的重要证据中提出了经历Cu 1+ / Cu 3+催化循环的C N 偶联反应的机理。铜HKUST-1结构节点中的2+位点可被还原为Cu 1+,从而引发自由基胺类物质的形成。该方法可能在制药和精细化工行业具有潜在的应用价值。