N-Methyl Transfer Induced Copper-Mediated Oxidative Diamination of Alkynes
N-Methyl Transfer Induced Copper-Mediated Oxidative Diamination of Alkynes
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DOI：
10.1021/acs.orglett.6b01067
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发表时间：
2016-05-20
期刊：
影响因子：
5.2
通讯作者：
Jin, Tienan
中科院分区：
文献类型：
--
作者：
Ho, Hon Eong;Oniwa, Kazuaki;Jin, Tienan
在Cu(Hfacac)(2)/O-2氧化体系下，利用双(2-氨基苯基)乙炔的分子内氧化缩合反应合成了结构新颖的非共轭多杂环支架5，10-二氢吲哚[3，2-b]吲哚(DHII)。同时含有N，N-二甲胺和伯胺基团的双(2-氨基苯基)乙炔的结构设计是构建相应的DHII支架的关键。值得注意的是，发生了从N，N-二甲胺的氮原子到伯胺的分子间N-甲基转移，这是成功实施本环化过程的关键步骤。
A novel intramolecular oxidative diamination of bis(2-aminophenyl)acetylene for the synthesis of the structurally intriguing irconjugated polyheterocyclic scaffold, 5,10-dihydroindolo[3,2-b]indole (DHII), has been developed under Cu(hfacac)(2)/O-2 oxidation systems. The structure design of bis(2-aminophenyl)acetylene bearing both N,N-dimethylamine and primary amine groups is crucial for constructing the corresponding DHII scaffold. Notably, an intermolecular N -methyl transfer from the nitrogen atom of N,N-dimethylamine to the primary amine takes place, which is a critical step for the successful implementation of the present annulation process.