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

Document type: Článok z časopisu / Journal Article
Collection: Chemical papers  

Author(s) Bradiaková, Ivana
Prónayová, Naďa
Gatial, Anton
Krutošíková, Alžbeta
Title Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
Journal name Chemical Papers
Publication date 2008
Year available 2008
Volume number 62
Issue number 4
ISSN 0366-6352
Start page 428
End page 434
Place of publication Poland
Publisher Versita
Collection year 2008
Language english
Subject 250000 Chemical Sciences
250300 Organic Chemistry
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.
Related Links
Link Description   fulltext  
User Comments
Access Statistics: 0 Abstract Views Detailed Statistics
Created: Thu, 18 Mar 2010, 11:52:52 CET by Iveta Drtilová . Detailed History