Efficient and general synthesis of 3-aminoindolines and 3-aminoindoles via copper-catalyzed three-component coupling reaction

Dmitri Chernyak, Natalia Chernyak, Vladimir Gevorgyan

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)961-966
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume352
Issue number6
DOIs
StatePublished - Apr 19 2010
Externally publishedYes

Keywords

  • 3-aminoindoles
  • 3-aminoindolines
  • Copper
  • Synthetic methods
  • Three-component coupling

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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