Related Experiment Video
Updated: Dec 9, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Construction of Cationic Azahelicenes: Regioselective Three-Component Annulation Using In Situ Activation Strategy
Zhishuo Wang1, Linfeng Jiang1, Jinwen Ji1
1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, People's Republic of China.
Abstract:
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.
More Related Videos
11:45Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Nucleophilic Aromatic Substitution: Elimination–Addition