Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

Chan Sik Cho, Jin Hwang Kim, Tae Jeong Kim, Sang Chul Shim

Research output: Contribution to journalArticlepeer-review

70 Scopus citations

Abstract

Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2·2H2O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process.

Original languageEnglish
Pages (from-to)3321-3329
Number of pages9
JournalTetrahedron
Volume57
Issue number16
DOIs
StatePublished - 16 Apr 2001

Keywords

  • Amine exchange reaction
  • Aqueous medium
  • Catalyst
  • Heteroannulation
  • Indoles
  • Ruthenium

Fingerprint

Dive into the research topics of 'Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles'. Together they form a unique fingerprint.

Cite this