Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: application to amino acid mimetics with a C-terminal imidazole

Org Lett. 2005 Feb 17;7(4):609-11. doi: 10.1021/ol047628p.

Abstract

1-Benzyl-4-methylimidazoles with a range of substituents at the 2-position are prepared from O-pentafluorobenzoylamidoximes on treatment with catalytic amounts of Pd(PPh3)4 and triethylamine. The sequence provides access to optically active amino acid mimetics with a C-terminal imidazole. [structure: see text]

MeSH terms

  • Amino Acids / chemical synthesis*
  • Catalysis
  • Cyclization
  • Imidazoles / chemical synthesis*
  • Models, Molecular
  • Oximes / chemistry*
  • Palladium

Substances

  • Amino Acids
  • Imidazoles
  • Oximes
  • Palladium