161670-78-6Relevant articles and documents
AN EFFICIENT SYNTHESIS OF 4-TRIFLUOROMETHYLATED AND 4-PERFLUOROALKYLATED IMIDAZOLES FROM MESOIONIC 1,3-OXAZOLIUM-5-OLATES
Kawase, Masami,Saito, Setsuo,Kurihara, Teruo
, p. 1617 - 1620 (1995)
4-Trifluoromethyl- and 4-perfluoroalkylimidazoles (4) were conveniently synthesized from mesoionic 4-trifluoroacetyl- or 4-perfluoroacyl-1,3-oxazolium-5-olate (1) via 2-imidazolines (3), which were formed through the regioselective attack of ammonia on the C(2) position of 1.
Convenient synthesis of 5-trifluoroacetylated imidazoles by ring transformation of mesoionic 1,3-oxazolium-5-olates
Kawase, Masami,Saito, Setsuo
, p. 410 - 414 (2007/10/03)
Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with amidines to give 5-trifluoroacetylimidazoles (3) in moderate yield. The novel ring transformations of 1 into 3 occur via an initial attack of amidines on the C-2 position of the ring.