Synthesis of trisubstituted imidazoles by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes: application to amino acid mimetics with a C-terminal imidazole.
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]
Zaman
Shazia
S
Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand.
Mitsuru
Kitamura
K
Abell
Andrew D
AD
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis*; D008958:Models, Molecular; D010091:Oximes / Q000737:chemistry*; D010165:Palladium
D000596:Amino Acids; D007093:Imidazoles; D010091:Oximes; D010165:Palladium