Thionium-based one-pot construction of homo-/heterodimeric pyrroloindoline from tryptamine

Org Lett. 2014 Jul 18;16(14):3613-5. doi: 10.1021/ol5012373. Epub 2014 Jul 2.

Abstract

We report a one-pot procedure for forming a dimeric pyrroloindoline framework with a thionium reagent. The cyclization of tryptamine with DMSO and Tf(2)O, followed by substitution with indole derivatives, produced racemic 3a-indolylpyrroloindolines. The method enables rapid access to heterodimeric pyrroloindolines as well as to homodimeric pyrroloindolines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Dimethyl Sulfoxide / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Quaternary Ammonium Compounds / chemistry*
  • Tryptamines / chemistry*

Substances

  • Indoles
  • Pyrroles
  • Quaternary Ammonium Compounds
  • Tryptamines
  • tryptamine
  • indoline
  • thionium
  • Dimethyl Sulfoxide