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可见光诱导的还原氮杂-6π电环化反应合成菲啶类化合物。

Visible light-induced reductive aza-6π electrocyclization access to phenanthridines.

作者信息

Wang Er-Bin, Fan Qingtian, Lu Xuelian, Sun Bing, Zhang Fang-Lin

机构信息

School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. China.

Shenzhen Research Institute, Wuhan University of Technology, Shenzhen 518057, P. R. China.

出版信息

Org Biomol Chem. 2024 Jun 19;22(24):4968-4972. doi: 10.1039/d4ob00656a.

Abstract

Visible light-induced aza-6π electrocyclization was developed for the synthesis of aza-arenes from nitroarenes with diverse aldehydes. This protocol allows the reduction of nitroarenes by Bnep and subsequent 6π-electrocyclization of the formed imine under visible light. An array of 6- and multi-substituted phenanthridines were constructed in moderate to good yields under purple LEDs at room temperature. A wide scope of substrates with diverse functional groups were well tolerated. In addition, the synthetic utility of this methodology was further demonstrated in the late-stage functionalization of celecoxib.

摘要

可见光诱导的氮杂-6π电环化反应被用于从硝基芳烃与多种醛合成氮杂芳烃。该方法允许通过Bnep还原硝基芳烃,并随后在可见光下使生成的亚胺进行6π电环化反应。在室温下紫色发光二极管照射下,一系列6-取代和多取代菲啶以中等至良好的产率被构建出来。具有各种官能团的广泛底物都能很好地兼容。此外,该方法的合成实用性在塞来昔布的后期官能团化中得到了进一步证明。

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