14119-98-3

Upstream product

• 579-98-6 N-acetyl-N-phenylglycine 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 161670-76-4 4-hydroxy-2-methyl-1-phenyl-4-trifluoromethyl-4,5-dihydroimidazole 
• 1039176-12-9 6-trifluoromethyl-1,4,5,6-tetrahydro-3-methyl-1,4-diphenyl-1,2,4-triazin-6-ol 
• 1253394-15-8 4-trifluoromethyl-2-methyl-1-phenyl-1H-pyrrole 
• 1426231-13-1 6-trifluoromethyl-5,6-dihydro-3-methyl-4-phenyl-4H-1,2,4-oxadiazin-6-ol 
• 1448021-99-5 6-methyl-5-[(4-methylphenyl)sulfonyl]-1-phenylpyrazin-2(1H)-one 
• 1373155-62-4 C₁₃H₁₂F₃NS 

Relevant academic research and scientific papers

Synthesis and Cycloaddition Reactions of Stabilized Münchnones

A family of stabilized münchnones bearing an acyl group at C4 have been prepared and studied in alkyne cycloaddition reactions. These reactions are highly regioselective, and the method represents a rapid and straightforward route to densely substituted pyrroles. Finally, the C4-stabilizing units can be further manipulated to furnish carboxylic acid and amide groups, or removed altogether to provide unsubstituted pyrroles.

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.

Synthesis and structures of stable phosphorus zwitterions derived from mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates

Trialkyl phosphites were evaluated as phosphorus nucleophiles for addition to mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), thereby producing tetravalent phosphorus zwitterions (2) in good yields. The structure of 2 was determined to be a tetrav

Facile synthesis of imidazo[1,5-a]pyrazin-8(7H)-ones from mesoionic 1,3-oxazolium-5-olates via a multistep one-pot transformation

A novel one-pot conversion of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates into imidazo[1,5-a]pyrazin-8(7H)-ones by the reaction with TosMIC is described. The structure of the product was determined by single-crystal X-ray analysis.

Cyclocondensation reaction of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5- olates with hydroxylamine affording 6-trifluoromethyl-5,6-dihydro-4h-1,2,4- oxadiazin-6-ols

Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) undergo tandem addition of hydroxylamine to afford 6-trifluoromethyl-1,2,4-oxadiazin-6-ols (3) in high yields.

New synthesis of 3-trifluoromethylpyrroles by condensation of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates with phosphorus ylides

Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines with trifluoroacetic anhydride, react with phosphorus ylides to give β-trifluoromethylpyrroles (2) in good yields. The novel ring transformations

Synthesis of trifluoromethyl-substituted pyrazoles and 1,2,4-triazines by ring transformation of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates with phenylhydrazine

Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates 1 were easily prepared by the cyclodehydration reaction of N-acyl-N-alkyl-α-amino acids with trifluoroacetic anhydride. Due to the presence of the trifluoromethyl ketone and the mesoionic five-membered oxazole, there are three reaction sites to be attacked by the nucleophiles at C-2, C-5 and the trifluoroacetyl group in 1. Based on this model, three modes of regioselective attack by phenylhydrazine were found to provide three different products, i.e., 6-trifluoromethyl-1,2,4- triazines 3, 3-trifluoromethyl-5-pyrazolones 5 and 5-trifluoromethyl-3- hydroxypyrazoles 4, in good yields, respectively, depending on the nature of the solvent and reaction temperature. These three types of different reactions may be explained by the polarity of the reaction solvent and the mesoionic oxazole-ketene tautomerism.

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

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.