Gold-catalyzed domino cycloisomerization/Pictet-Spengler reaction of 2-(4-aminobut-1-yn-1-yl)anilines with aldehydes: synthesis of tetrahydropyrido[4,3-b]indole scaffolds

J Org Chem. 2012 Dec 21;77(24):11355-61. doi: 10.1021/jo302068e. Epub 2012 Dec 13.

Abstract

A domino cycloisomerization/Pictet-Spengler reaction of 2-(4-aminobut-1-yn-1-yl)aniline with aldehydes has been achieved using a AuIPrCl (5 mol %)/AgSbF(6) (10 mol %) catalytic system to produce the corresponding 1-aryl-N-tosyl-2,3,4,5-tetrahydropyrido[4,3-b] indole derivatives in good yields. This is the first report on the synthesis of tetrahydro pyrido[4,3-b]indole scaffolds through as tandem 5-endo-dig cyclization and Pictect-Spengler reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Aniline Compounds / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Gold / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Isomerism

Substances

  • Aldehydes
  • Aniline Compounds
  • Indoles
  • Gold
  • aniline