Cleavage of the C=N bond in carbodiimides via release of high ring strain: a new strategy for the selective synthesis of 2-aminoaryl alkynyl imines.
Cleavage of the C=N bond in carbodiimides via release of high ring strain: a new strategy for the selective synthesis of 2-aminoaryl alkynyl imines.
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DOI：
10.1002/chem.201304701
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发表时间：
2014-02
期刊：
影响因子：
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通讯作者：
Yi Zhou;Yue Chi;F. Zhao;Wen‐Xiong Zhang;Z. Xi
中科院分区：
文献类型：
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作者：
Yi Zhou;Yue Chi;F. Zhao;Wen‐Xiong Zhang;Z. Xi
在端炔或卤代炔、N-酰亚胺和苯炔的多组分反应（MCR）中，首次发现了C=N键断裂和重组的新模式，有效地合成了2-氨基芳基炔基亚胺.具有高环张力的氮杂环丁烷中间体的选择性形成和开环对于该反应是必不可少的。探索了2-氨基芳基炔基亚胺通过Cu催化的环化异构化的进一步转化，以立体选择性地提供双环、三环和四环稠合吡咯啉。
A novel pattern of the cleavage and reorganization of C=N bond in the multicomponent reaction (MCR) of terminal alkynes or haloalkynes, carbodiimides, and benzynes is achieved for the first time to construct efficiently 2-aminoaryl alkynyl imines. The selective formation and ring-opening of the azetine intermediate with the high ring strain is essential for this reaction. Further transformation of 2-aminoaryl alkynyl imines via the Cu-catalyzed cycloisomerization is explored to provide steroselectively the bi-, tri-, and tetracyclic fused pyrrolines.