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Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives

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Abstract

2-[3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (I) was prepared by a three-step synthesis. Its reaction with phosphorus sulfide rendered thione II which was methylated to 2-[3-(Trifluoromethyl)phenyl]-4-methylsulfanylfuro[3,2-c]pyridine (III). 5-Methyl-2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (IV) was obtained by the reaction of I with methyl iodide in PTC conditions. The chlorine atom in derivate V was replaced with heterocyclic secondary amines via nucleophilic substitution and 4-substituted furopyridines VIa and VIb were thus prepared. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, SK-917 01, Trnava, Slovakia

    Ivana Bradiaková, Tatiana Ďurčeková & Alžbeta Krutošíková

  2. Department of NMR and MS Spectroscopy, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

    Naďa Prónayová

  3. Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-812 37, Bratislava, Slovakia

    Anton Gatial

Authors
  1. Ivana Bradiaková
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  2. Tatiana Ďurčeková
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  3. Naďa Prónayová
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  4. Anton Gatial
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  5. Alžbeta Krutošíková
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Correspondence to Alžbeta Krutošíková.

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Bradiaková, I., Ďurčeková, T., Prónayová, N. et al. Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives. Chem. Pap. 63, 586–591 (2009). https://doi.org/10.2478/s11696-009-0052-4

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  • DOI: https://doi.org/10.2478/s11696-009-0052-4

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