111269-50-2

Upstream product

• 111269-40-0 3-(Dimethyl-hydrazono)-1,1,1-trifluoro-3-p-tolyl-propan-2-one 
• 111269-40-0 3-(p-tolyl)-1,1,1-trifluoropropane-2,3-dione 3-dimethylhydrazone 

Downstream Products

• 129249-37-2 2,2,2-Trifluoro-1-(3-methyl-5-p-tolyl-6-trifluoromethyl-2,3-dihydro-[1,3,4]oxadiazin-4-yl)-ethanone 
• 118110-45-5 3,3,3-trifluoro-2-hydroxy-1-(4-methylphenyl)-propan-1-one 

Relevant academic research and scientific papers

4- and 5-Trifluoromethylimidazoles. Novel Cyclization of Trifluoroacetylated Aldehyde Dimethylhydrazones

Thermally induced cyclization reaction of trifluoroacetylated arylaldehyde dimethylhydrazones 1 in refluxing toluene afforded 1-methyl-4-aryl-5-trifluoromethylimidazoles 2 in good yields.In contrast thermal cyclization of 1 in the presence of silica gel gave regioisomeric 1-methyl-4-trifluoromethyl-5-aryl-imidazoles 5 as major products.These reactions could be extended to the synthesis of related several 1,4,5-trisubstituted imidazoles.

Electrophilic Substitution at Azomethine Carbon Atoms. Reaction of Aromatic Aldehyde Hydrazones with Trifluoroacetic Anhydride

Reaction of dimethylhydrazones of aromatic aldehydes with trifluoroacetic anhydride at room temperature affords high yields of products bearing trifluoroacetyl groups.These electrophilic substitution reactions generally occur on the azomethine carbon, although competitive N-acylation is observed in highly electron-rich systems.Use of diisopropylhydrazones suppressed this N-acylation completely, leading to high yields of C-acylated products.The trifluoroacetyl hydrazones can be cyclized thermally to imidazole and oxadiazine derivatives and can be converted into 1-trifluoromethyl 1,2-diketones by acid hydrolysis.