Synthesis of 2-Aryl-Substituted Indole-3-acetic Acid Derivatives via Intramolecular Imino-Stetter Reaction of Aldimines with Cyanide

Seong Jong Lee, Hong Ahn Seo, Cheol Hong Cheon

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A general method to generate umpolung of aldimines with cyanide was developed via the addition of cyanide to aldimines followed by a proton transfer from the carbon atom to the nitrogen atom in the resulting cyanide adducts. This novel method was successfully applied to the first imino-Stetter reaction of aldimines obtained from 2-aminocinnamic acid derivatives and aromatic aldehydes with cyanide, affording 2-aryl-substituted indole-3-acetic acid derivatives. Furthermore, the usefulness of this method was successfully demonstrated by the synthesis of an FPTase inhibitor, one of the biologically important 2-arylindole-3-acetic acid derivatives. (Figure presented.).

Original languageEnglish
Pages (from-to)1566-1570
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume358
Issue number10
DOIs
Publication statusPublished - 2016 May 19

Keywords

  • 2-arylindole-3-acetic acid derivatives
  • aldimines
  • cyanide
  • imino-Stetter reaction
  • umpolung

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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