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Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
Bradiaková, Ivana, Ďurčeková, Tatiana, Prónayová, Naďa, Gatial, Anton and Krutošíková, Alžbeta Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives Chemical Papers, Vol.63, No. 5, 2009, 586-591
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Author(s) |
Bradiaková, Ivana
Ďurčeková, Tatiana
Prónayová, Naďa
Gatial, Anton
Krutošíková, Alžbeta
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| Title |
Synthesis of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine derivatives
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| Journal name |
Chemical Papers
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| Publication date |
2009
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| Year available |
2009
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| Volume number |
63
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| Issue number |
5
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| ISSN |
0366-6352
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| Start page |
586
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| End page |
591
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2009
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| Language |
english
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| Subject |
250000 Chemical Sciences
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| Abstract/Summary |
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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