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通过TiCl-DABCO辅助的戊省醌还原胺化一锅法合成双（芳基氨基）戊省

One-Pot Synthesis of Bis(arylamino)pentiptycenes by TiCl-DABCO Assisted Reductive Amination of Pentiptycene Quinone.

作者信息

Zhang Zhe-Jie, Hsu Ying-Feng, Kao Chia-Chien, Yang Jye-Shane

机构信息

Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan.

出版信息

Org Lett. 2024 May 3;26(17):3547-3551. doi: 10.1021/acs.orglett.4c00939. Epub 2024 Apr 24.

DOI:10.1021/acs.orglett.4c00939
PMID:38656102
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11077485/
Abstract

The previously eight-step synthesis of bis(arylamino)pentiptycenes () from pentiptycene quinone () can now be achieved in a single step with 18-90% yields through TiCl-DABCO assisted reductive amination with anilines. Both the dual amination of and the reduction of quinone diimines are unprecedented. The π system of can be further expanded, including the formation of bis(diarylamino)pentiptycenes. This work also provides mechanistic insights into the challenges encountered in the dual reductive amination of with other amines.

摘要

以前从戊蒂烯醌（）合成双（芳基氨基）戊蒂烯（）的八步反应，现在可以通过TiCl-DABCO辅助的苯胺还原胺化反应一步完成，产率为18-90%。和醌二亚胺的双重胺化以及醌二亚胺的还原都是前所未有的。的π体系可以进一步扩展，包括双（二芳基氨基）戊蒂烯的形成。这项工作还为与其他胺的双重还原胺化过程中遇到的挑战提供了机理见解。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/27338b6f946a/ol4c00939_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/71a0f1329ac0/ol4c00939_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/343e793f2034/ol4c00939_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/27338b6f946a/ol4c00939_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/71a0f1329ac0/ol4c00939_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/343e793f2034/ol4c00939_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0411/11077485/27338b6f946a/ol4c00939_0003.jpg

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