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Build-up of Cationic Azahelicenes via Regioselective Three-Component Annulation Using in Situ Activation Strategy.

Described herein is a build-up strategy of cationic azahelicenes through the three-component annulation reaction of isoquinoline, indole and 1,2-dichloroethane (DCE), in which DCE serves as in situ activating agent for C1-H activation of isoquinoline, vinyl equivalent and 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. As a representative example, the ionic [5]azahelicenium fluorophore 3h exhibits the potential as a mitochondria-targeted biomarker with good photostability and low cytotoxicity.