SYNTHESIS AND TRANSFORMATION OF 4-(1Н-BENZIMIDAZOL-2-YL)-1-[3-(TRIFLUOROMETHYLPHENYL)]-2-PYRROLIDINONE
DOI:
https://doi.org/10.5755/j01.ct.60.2.1949Abstract
Study of chemical transformations of 4-(1Н-benzimidazol-2-yl)-1-[3-(trifluoromethylphenyl)]-2-pyrrolidinone was carried out. N-Substituted benzimidazole derivative was synthesized by alkylation of 1-(3-fluoromethylphenyl)-3-(1H-benzimidazol-2-yl)-5-oxopyrrolidine with ethyl chloroacetate in toluene in the presence of potassium carbonate, potassium hydroxide and a catalytic amount of tetrabutylammonium iodide. Carbohydrazide was obtained by reaction of the ester with hydrazine hydrate in refluxing 2-propanol. The hydrazones were synthesized by condensation of hydrazide with aromatic aldehydes were carried out. In the reaction with acetone and ethylmethylketone corresponding hydrazones were obtained. In analogous reactions with diketones – 2,4-pentanedione and 2,5-hexandiones – cyclic compounds with pyrrole and pyrazole moieties were synthesized.
The results of this work have pointed to the possibility of synthesis of a wide range of 1,2-disubstituted benzimidazoles, containing 5-оxо-1-(3-trifluoromethylphenyl)pyrrolidine and hydrazone, pyrrole, pyrazole, benzimidazole, or triazine fragments.
