Synthesis of 4-aryl-1H-1,2,3-triazoles through TBAF-catalyzed [3 + 2] cycloaddition of 2-aryl-1-nitroethenes with TMSN3 under solvent-free conditions

J Org Chem. 2005 Aug 5;70(16):6526-9. doi: 10.1021/jo0507845.

Abstract

TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Catalysis
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Solvents
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry*

Substances

  • Anti-Infective Agents
  • Nitro Compounds
  • Solvents
  • Triazoles