161670-75-3

Upstream product

• 6313-33-3 formamidine hydrochloride 
• 14119-99-4 4-trifluoroacetyl-3-methyl-2-phenyl-1,3-oxazol-3-ium-5-olate 
• 143-37-3 acetamidine 
• 2568-34-5 N-benzoyl-N-methylglycine 
• 407-25-0 trifluoroacetic anhydride 
• 1670-14-0 benzamidine monohydrochloride 
• 124-42-5 acetamidine hydrochloride 
• 3473-63-0 formamidine acetic acid 
• 618-39-3 benzamidin 

Downstream Products

• 63875-06-9 1-N-methyl-3-trifluoromethyl-2-phenylimidazole 

Relevant academic research and scientific papers

Convenient synthesis of 4-trifluoromethyl-substituted imidazole derivatives

Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with ammonia to give 4-trifluoromethyl-3,4-dihydroimidazoles (3) in high yields. Dehydration of 3 gives

Convenient synthesis of 5-trifluoroacetylated imidazoles by ring transformation of mesoionic 1,3-oxazolium-5-olates

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.

AN EFFICIENT SYNTHESIS OF 4-TRIFLUOROMETHYLATED AND 4-PERFLUOROALKYLATED IMIDAZOLES FROM MESOIONIC 1,3-OXAZOLIUM-5-OLATES

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.

A Novel Ring Transformation of Mesoionic 1,3-Oxazolium-5-olates into 5-Trifluoroacetylated and 5-Perfluoroacylated Imidazoles by Reaction with Amidines

Treatment of mesoionic 1,3-oxazolium-5-olates with amidines causes a novel ring transformation affording 5-trifluoroacetyl- and 5-perfluoroacyl-imidazoles in moderate yields.