Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-<Emphasis Type="Italic">c</Emphasis>]pyridine derivatives |
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| Authors: | Ivana Bradiaková Tatiana ?ur?eková Na?a Prónayová Anton Gatial Al?beta Kruto?íková |
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| Institution: | (1) Department of Chemistry, Faculty of Natural Sciences, University of St. Cyril and Methodius, SK-917 01 Trnava, Slovakia;(2) Department of NMR and MS Spectroscopy, Slovak University of Technology, SK-812 37 Bratislava, Slovakia;(3) Institute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-812 37 Bratislava, Slovakia |
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| Abstract: | 2-3-(Trifluoromethyl)phenyl]-4,5-dihydrofuro3,2-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-methylsulfanylfuro3,2-c]pyridine (III). 5-Methyl-2-3-(trifluoromethyl)phenyl]-4,5-dihydrofuro3,2-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]furo3,2-c]pyridine-4-carboxylic acid (VII) was obtained by hydrolysis of the corresponding carbonitrile Va. |
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| Keywords: | 4-substituted 2-[3-(trifluoromethyl)phenyl]furo[3 2-c]pyridines nucleophilic substitution |
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