161670-80-0

Upstream product

• 75-03-6 ethyl iodide 
• 161670-65-1 1-methyl-2-phenyl-5-trifluoroacetylimidazole 
• 2568-34-5 N-benzoyl-N-methylglycine 
• 14119-99-4 4-trifluoroacetyl-3-methyl-2-phenyl-1,3-oxazol-3-ium-5-olate 

Downstream Products

• 161670-81-1 (1-methyl-2-phenyl-1H-imidazol-5-yl)methanol 
• 94938-03-1 1-methyl-2-phenyl-1H-imidazole-5-carboxaldehyde 
• 86119-60-0 N-methyl-2-phenyl-4-carbethoxyimidazole 
• 147591-67-1 1-methyl-2-phenylimidazole-5-carboxylic acid 

Relevant academic research and scientific papers

CARBOXYLIC ACID DERIVATIVES AND DRUGS CONTAINING THE SAME

The present invention provides a novel carboxylic acid compound, a salt thereof or a hydrate of them useful as an insulin-resistant improver, and a medicament comprising the compound as an active ingredient. That is, the present invention provides a carboxylic acid compound represented by the following formula (I), a salt thereof, an ester thereof or a hydrate of them. In the formula, R1 represents hydrogen atom, hydroxyl group or a C1-6 alkyl group etc. which may have one or more substituents; L represents a single or double bond or a C1-6 alkylene group etc. which may have one or more substituents; M represents a single bond or a C1-6 alkylene group etc. which may have one or more substituents; T represents a single bond or a C1-3 alkylene group which may have one or more substituents; W represents carboxyl group or a group represented by the formula -CON(Rw1)Rw2 (wherein Rw1 and Rw2 are the same as or different from each other and each represents hydrogen atom, formyl group etc.) etc.; represents a single or double bond; X represents oxygen atom or a C2-6 alkenylene group etc. which may have one or more substituents; Y represents a C5-12 aromatic hydrocarbon group etc. which may have one or more substituents and which may have one or more heteroatoms; and ring Z represents a C5-6 aromatic hydrocarbon group which may have 0 to 4 substituents and which may have one or more heteroatoms.

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.

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.