Synthesis of Trisubstituted Imidazoles by Palladium-Catalyzed Cyclization of O-Pentafluorobenzoylamidoximes: Application to Amino Acid Mimetics with a C-Terminal Imidazole

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]