Construction of Cationic Azahelicenes: Regioselective Three‐Component Annulation Using In Situ Activation Strategy | Zendy

Wang Zhishuo | Zendy; Jiang Linfeng | Zendy; Ji Jinwen | Zendy; Zhou Fulin | Zendy; Lan Jingbo | Zendy; You Jingsong | Zendy

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Construction of Cationic Azahelicenes: Regioselective Three‐Component Annulation Using In Situ Activation Strategy

Author(s) -

Wang Zhishuo,

Jiang Linfeng,

Ji Jinwen,

Zhou Fulin,

Lan Jingbo,

You Jingsong

Publication year - 2020

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.202010051

Subject(s) - isoquinoline , annulation , regioselectivity , cationic polymerization , chemistry , in situ , combinatorial chemistry , solvent , stereochemistry , organic chemistry , catalysis

Described herein is a strategy to construct cationic azahelicenes through the three‐component annulation reaction of isoquinoline, indole, and 1,2‐dichloroethane (DCE), in which DCE serves as an in situ activating agent for C1−H activation of isoquinoline, a vinyl equivalent, and a solvent. This in situ activation annulation reaction features a facile one‐step synthesis and complete regioselectivity. The complete regioselectivity of C1 over C3 for the isoquinoline ring paves a path to the helical structure in a highly ordered sequence. One of the synthesized ionic [5]azahelicenium fluorophores exhibits the potential to serve as a mitochondria‐targeted biomarker with good photostability and low cytotoxicity.

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