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Rapid Access to 3-(Aminomethyl)isoquinoline-Fused Polycyclic Compounds by Copper-Catalyzed Four-Component Coupling, Cascade Cyclization, and Oxidation

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Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan
Cite this: J. Org. Chem. 2009, 74, 16, 6299–6302
Publication Date (Web):July 2, 2009
Copyright © 2009 American Chemical Society

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    A novel copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline-fused polycyclic compounds, through four-component coupling, cyclization, and oxidation, has been developed. A Mannich-type reaction of 2-ethynylbenzaldehyde with paraformaldehyde and a secondary amine followed by treatment with a diamine component gave tricyclic isoquinolines through cascade cyclization and oxidation. Construction of fused isoquinolines of various ring sizes is also presented.

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    Experimental procedures, full characterization, and 1H and 13C NMR charts of the 2-ethynylbenzaldehydes and cyclization products and a crystallographic information file for 12a. This material is available free of charge via the Internet at

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