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Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
Bradiaková, Ivana, Prónayová, Naďa, Gatial, Anton and Krutošíková, Alžbeta Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine Chemical Papers, Vol.62, No. 4, 2008, 428-434
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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
Prónayová, Naďa
Gatial, Anton
Krutošíková, Alžbeta
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| Title |
Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
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| Journal name |
Chemical Papers
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| Publication date |
2008
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| Year available |
2008
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| Volume number |
62
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| Issue number |
4
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| ISSN |
0366-6352
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| Start page |
428
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| End page |
434
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2008
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| Abstract/Summary |
(E)-3-{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}propenoic acid (I) was prepared from 5-[3-(tri-fluoromethyl)phenyl]furan-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to 2-[3-(trifluoromethyl)phenyl]-4,5-dihydrofuro[3,2-c]pyridin-4-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with H2NNH2-Pd/C to the title compound V. 2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. On treatment of VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction), corresponding 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine-1-carbonitrile (VII) resulted. 5-Amino-2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridin-5-ium-4-methylbenzene sulfonate (VIII) was prepared by direct N-amination of the title compound V with 1-[(aminooxy)sulfonyl]-4-methylbenzene in dichloromethane. Then, VIII was transformed to a non-isolated zwitterionic N-imid IX which afforded the corresponding furo[3,2-c]pyrazolo[1,5-a]pyridine carboxylic acid esters X, XI by 1,3-dipolar cycloaddition reactions with dimethyl but-2-ynedionate (DBD) or ethyl propiolate. The structures of all compounds were confirmed by their IR and NMR spectra.
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