Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives |
| |
| Authors: | Ivana Bradiaková Tatiana Ďurčeková Naďa Prónayová Anton Gatial Alžbeta Krutošíková |
| |
| Affiliation: | (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 |
| |
| 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. |
| |
| Keywords: | 4-substituted 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridines nucleophilic substitution |
| 本文献已被 SpringerLink 等数据库收录！ |
|
