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A 6π Azaelectrocyclization Strategy towards the 1,5,9‐Triazacoronenes
Author(s) -
Sun YiXun,
Wang XiaoGang,
Shen GuoDong,
Yang Tian,
Yang YiHui,
Li Jing,
Yang MingYu,
Sun HuaMing,
Wei JunFa
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901433
Subject(s) - chemistry , triphenylene , zigzag , dimer , imine , double bond , derivative (finance) , superstructure , stereochemistry , computational chemistry , combinatorial chemistry , organic chemistry , catalysis , molecule , oceanography , geometry , mathematics , financial economics , economics , geology
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.
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