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Copper-Catalyzed Multi-Component Reactions pp 9–45Cite as

Construction of 2-(Aminomethyl)indoles Through Copper-Catalyzed Domino Three-Component Coupling and Cyclization

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Abstract

A direct approach to 2-(aminomethyl)indoles by copper-catalyzed domino three-component coupling–cyclization of 2-ethynylanilines with a secondary amine and aldehyde has been developed. By use of a cyclic or acyclic secondary amine and aldehyde (paraformaldehyde, aliphatic or aromatic aldehydes) in the presence of 1 mol.% CuBr, 2-ethynylanilines were converted to a variety of substituted 2-(aminomethyl)indoles in good to excellent yields. Utilizing this domino reaction and C–H functionalization at the indole C-3 position, polycyclic indoles were readily synthesized. Construction of benzo[e][1,2]thiazine and indene motifs by the reaction of sulfonamide and malonate congeners is also presented.

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Notes

  1. 1.

    The author considered decreasing of the amount of amine component is important and economical especially when using more valuable amines such as 11 (Scheme 4).

  2. 2.

    When benzylamine was used instead of a secondary amine, dimeric compound 18 was produced in 82% yield (100 °C, 3 h, then reflux, 1 h).

  3. 3.

    When acetone was used instead of an aldehyde, Mannich-type reaction did not proceed and compound 19 was produced.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Science, Kyoto University, Yoshidashimoadachicho 26ΓÇô29, Kyoto, 606-8501, Japan

    Yusuke Ohta

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  1. Yusuke Ohta
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Correspondence to Yusuke Ohta .

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Ohta, Y. (2011). Construction of 2-(Aminomethyl)indoles Through Copper-Catalyzed Domino Three-Component Coupling and Cyclization. In: Copper-Catalyzed Multi-Component Reactions. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-15473-7_2

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