Highly N2-selective coupling of 1,2,3-triazoles with indole and pyrrole

Chemistry. 2014 Jan 20;20(4):974-8. doi: 10.1002/chem.201302761. Epub 2013 Dec 16.

Abstract

Hydrogen-bond mediated coupling of 1,2,3-triazoles to indoles and pyrroles results in N2 selective functionalization of the triazole moiety in moderate to excellent yields. The reaction was tolerant of un-, mono- and disubstituted triazoles and was applied to synthesize tryptophan derived fluorescent amino acids.

Keywords: 1,2,3-triazole; heterocycles; indole-triazole conjugates; iodination mediated reaction; pyrrole-triazole conjugates; regioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemical synthesis
  • Catalysis
  • Halogenation
  • Indoles / chemistry*
  • Pyrroles / chemistry*
  • Stereoisomerism
  • Triazoles / chemistry*

Substances

  • Amino Acids
  • Indoles
  • Pyrroles
  • Triazoles
  • indole