Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives

摘要

Condensation of 1-(3-(fluoromethyl and trifluo-romethyl)phenyl)-5-oxopyrrolidine-3-carbohydrazides with aromatic aldehydes and acetone gave the corresponding hydrazones. Most of the reaction products are able to form isomers, because of the amide and azomethine structural units. The reactions of 1-aryl-4-hydrazinocarbonyl-2-pyrro-lidinones with 2,4-pentanedione gave 3,5-dimethylpyrazole compounds and those with 2,5-hexanedione provided 1-substituted 2,5-dimethylpyrroles. Several oxadiazole derivatives were synthesized. The structures of the synthesized compounds were confirmed on the basis of their MS, IR, ~1H, and ~(13)C NMR spectra and by analytical methods. ~(13)C APT, ~1H/~(13)C 2D (HETCOR), and NOE (~1H) NMR techniques and molecular modeling were used for detailed structure examination. Complete NMR spectral assignment of the studied compounds was performed in order to evaluate their conformation, configuration, and substituent effects.