Synthesis of azocino[5,4-b]indoles via gold-catalyzed intramolecular alkyne hydroarylation

Vsevolod A. Peshkov, Olga P. Pereshivko, Erik V.Van Der Eycken

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

An efficient procedure for the synthesis of the azocinoACHTUNGTRENUNG[5,4- b]indole framework is presented, relying on a cationic gold-catalyzed intramolecular alkyne hydroarylation of propargylic amides derived from various tryptamines and 3-substituted 2- propynoic acids. The triphenylphosphinegold(I) chloride/silver(I) triflate catalytic system was found to be superior to our previously described mercury( II) triflate catalyst, and hence the substrate scope of the process was significantly expanded.

Original languageEnglish
Pages (from-to)2841-2848
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number14-15
DOIs
Publication statusPublished - Oct 8 2012
Externally publishedYes

Keywords

  • C-C coupling
  • Cyclization
  • Gold catalysis
  • Medium-ring compounds
  • Nitrogen heterocycles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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