Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes

A highly diastereoselective multicomponent dearomative multifunctionalization of N-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2021-01, Vol.8 (2), p.204-211
Main Authors: Miao, Hongjie, Bai, Xuguan, Wang, Lele, Yu, Junhui, Bu, Zhanwei, Wang, Qilin
Format: Article
Language:English
Subjects:
Aromatic compounds
Cages
Crystallography
NMR
Nuclear magnetic resonance
Organic chemistry
Salts
Stereoselectivity
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Summary:A highly diastereoselective multicomponent dearomative multifunctionalization of N-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites of azaarenes, but also provided a convenient and robust approach to access structurally rigid and synthetically challenging cage-like and bridged azaheterocycles. As an important complement, we also realized the dearomative multi-functionalization of N-aryl azaarenes through an in situ activation strategy. Moreover, the workup-directed selective tri- and bi-functionalization of isoquinolinium salts have been accomplished.
ISSN:2052-4110
2052-4110
DOI:10.1039/d0qo01196g