Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
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Ivana Bradiaková
,
Naďa Prónayová
Abstract
(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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© 2008 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- Square-wave adsorptive stripping voltammetric determination of an antihistamine drug astemizole
- Flow injection spectrophotometric determination of iron(III) using diphenylamine-4-sulfonic acid sodium salt
- Sensitive determination of nitrogenous hydrochloride drugs via their reaction with ammonium molybdate
- Effect of different Fe(III) compounds on photosynthetic electron transport in spinach chloroplasts and on iron accumulation in maize plants
- Comparison of different technologies for alginate beads production
- Design and economics of industrial production of fructooligosaccharides
- Preparation of nanocrystalline anatase TiO2 using basic sol-gel method
- 3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazole based ligands — protonation and metal complex formation
- Synthesis, characterization, fluorescence and redox features of new vic-dioxime ligand bearing pyrene and its metal complexes
- Synthesis and characterization of diaminomaleonitrile-functionalized polystyrene grafts for application in pervaporation separation
- Synthesis and magnetic properties of polymeric complexes containing ruthenium(II)-ruthenium(III) tetracarboxylato units linked by cyanato, thiocyanato, and selenocyanato ligands
- Preparation and modification of collagen-based porous scaffold for tissue engineering
- Synthesis, crystal structure, and magnetic properties of a cobalt(II) complex with (3,5-dichloropyridin-4-yl)(pyridin-4-yl)methanol
- Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
- Alkalimetric determination of hydrophobic pharmaceuticals using stabilized o/w emulsions
- Extraction and analysis of ellagic acid from novel complex sources
