Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three-Component Coupling Reaction

Authors

  • Dmitri Chernyak,

    1. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA, Fax: (+1)-312-355-0836; phone: (+1)-312-355-3579
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  • Natalia Chernyak,

    1. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA, Fax: (+1)-312-355-0836; phone: (+1)-312-355-3579
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  • Vladimir Gevorgyan

    1. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA, Fax: (+1)-312-355-0836; phone: (+1)-312-355-3579
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Abstract

An efficient three-component coupling (TCC) reaction toward a variety of 3-aminoindoline and 3-aminoindole derivatives has been developed. This cascade transformation proceeds via the copper-catalyzed coupling reaction between 2-aminobenzaldehyde, a secondary amine, and an alkyne leading to a propargylamine intermediate which, under the reaction conditions, undergoes cyclization into the indoline core. The latter, upon treatment with a base, smoothly isomerizes into the indole. Alternatively, the indole can directly be synthesized in a one-pot sequential reaction.

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