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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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Published in: | Organic chemistry frontiers an international journal of organic chemistry 2021-01, Vol.8 (2), p.204-211 |
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container_title | Organic chemistry frontiers an international journal of organic chemistry |
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creator | Miao, Hongjie Bai, Xuguan Wang, Lele Yu, Junhui Bu, Zhanwei Wang, Qilin |
description | 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. |
doi_str_mv | 10.1039/d0qo01196g |
format | article |
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subjects | Aromatic compounds Cages Crystallography NMR Nuclear magnetic resonance Organic chemistry Salts Stereoselectivity |
title | Diastereoselective construction of cage-like and bridged azaheterocycles through dearomative maximization of the reactive sites of azaarenes |
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