Monatshefte für Chemie - Chemical Monthly

, Volume 140, Issue 12, pp 1513–1522 | Cite as

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

  • Vytautas Mickevičius
  • Rita Vaickelionienė
  • Ilona Jonuškienė
  • Gema Mikulskienė
  • Kristina Kantminienė
Original Paper
First Online:
Received:
Accepted:

Abstract

Condensation of 1-(3-(fluoromethyl and trifluoromethyl)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-pyrrolidinones 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 13C NMR spectra and by analytical methods. 13C APT, 1H/13C 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.

Graphical Abstract

Keywords

Hydrazides–hydrazones Condensation Rotamers NMR spectroscopy Molecular modeling 
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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Vytautas Mickevičius
    • 1
  • Rita Vaickelionienė
    • 1
  • Ilona Jonuškienė
    • 1
  • Gema Mikulskienė
    • 2
  • Kristina Kantminienė
    • 3
  1. 1.Department of Organic ChemistryKaunas University of TechnologyKaunasLithuania
  2. 2.Department of Bioorganic Compounds ChemistryInstitute of BiochemistryVilniusLithuania
  3. 3.Department of General ChemistryKaunas University of TechnologyKaunasLithuania

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