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

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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.

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Authors and Affiliations

  1. Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Vytautas Mickevičius, Rita Vaickelionienė & Ilona Jonuškienė

  2. Department of Bioorganic Compounds Chemistry, Institute of Biochemistry, Mokslininkų str.12, 08662, Vilnius, Lithuania

    Gema Mikulskienė

  3. Department of General Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Kristina Kantminienė

Authors
  1. Vytautas Mickevičius
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  2. Rita Vaickelionienė
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  3. Ilona Jonuškienė
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  4. Gema Mikulskienė
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  5. Kristina Kantminienė
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Correspondence to Vytautas Mickevičius.

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Mickevičius, V., Vaickelionienė, R., Jonuškienė, I. et al. Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives. Monatsh Chem 140, 1513–1522 (2009). https://doi.org/10.1007/s00706-009-0201-z

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  • DOI: https://doi.org/10.1007/s00706-009-0201-z

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