A 6π Azaelectrocyclization Strategy towards the 1,5,9‐Triazacoronenes,Advanced Synthesis & Catalysis

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A 6π Azaelectrocyclization Strategy towards the 1,5,9‐Triazacoronenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-01-16 , DOI: 10.1002/adsc.201901433
Yi‐Xun Sun ₁ , Xiao‐Gang Wang ₁ , Guo‐Dong Shen ₁ , Tian Yang ₁ , Yi‐Hui Yang ₁ , Jing Li ₁ , Ming‐Yu Yang ₁ , Hua‐Ming Sun ₁ , Jun‐Fa Wei ₁

Affiliation

We present the instance of two aromatic double bonds and an imine double bond involved thermal 6π‐azaelectrocyclization and, on this basis, a one‐step synthesis of triazacoronenes (TACs) from triphenylene‐1,5,9‐triamines and aldehydes under nonacidic conditions. This method has several advantages such as simplicity, high yields, and extensive substrate scope. A plausible reaction mechanism has been proposed with several experimental supports. A typical derivative shows a unique dimer holding together via a π‐π interaction and six H‐bonds and a zigzag superstructure stabilized by three centered H‐bonds and Br ⋅⋅⋅ π interaction between the adjacent dimers.

中文翻译：

针对1,5,9-三氮唑酮的6π氮杂电环化策略

我们介绍了两个芳族双键和一个亚胺双键涉及热6π-氮杂电环化的实例，在此基础上，在非酸性条件下由三亚苯基-1,5,9-三胺和醛一步合成三氮唑烷酮（TAC）。该方法具有几个优点，例如简单，高产量和广泛的基板范围。已经提出了一种可行的反应机理，并提供了一些实验支持。一个典型的导数显示一个独特的二聚体通过π-π相互作用和六个H键结合在一起，并通过三个居中的H键和相邻二聚体之间的Br⋅⋅⋅π相互作用稳定的锯齿形上层结构。

更新日期：2020-04-21

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