Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
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M. Búdová
,
K. Fojtíková
Abstract
Substituted furopropenoic acids were prepared from appropriate aldehyde under the Doebner’s conditions. Obtained acids were converted to the corresponding azides, which were cyclized by heating in Dowtherm to furopyridones. These compounds were aromatized with phosphorus oxychloride to chloro derivatives of furo[3,2-c]pyridine (Va, Vb). Chloro derivative Vb was reduced with hydrazine hydrate to 2-(4-aminophenyl)furo[3,2-c]pyridine in ethanol and Pd/C as a catalyst. Chloro derivative Va was converted to 4-amino-2-(3-pyridyl)furo[3,2-c]pyridine under the same conditions. The chlorine atom in other chloro derivatives (VIIa, VIIb) was replaced by nucleophilic substitution with alkoxides (sodium ethoxide, propoxide, and isopropoxide) and the corresponding alkoxy derivatives were formed. By reaction of VII with cyclic secondary amines (morpholine, piperidine, and pyrrolidine) 4-substituted furopyridines were prepared.
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© 2006 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- Calibrationless determination of electroactive species using chronoamperograms at collector segment of interdigitated microelectrode array
- The β-carotene dilemma: ESR study with coordinated peroxyl radicals
- Determination of 5-hydroxymethylfurfural after Winkler and by the HPLC method for authentication of honey
- A simple linear sweep voltammetric method for the determination of double-stranded DNA with malachite green
- Spectral and electrochemical study of coordination molecules Cu4OX6L4: 3-Pyridylmethanol and 4-pyridylmethanol Cu4OBrnCl(6−n)(pm)4 complexes
- Magnetic, spectral, and thermal behaviour of 2-chloro-4-nitrobenzoates of Co(II), Ni(II), and Cu(II)
- Synthesis, characterization, and biological activities of some transition metal(II) complexes with the thiosemicarbazone derived from 4-[1-(4-methylphenylsulfonyl)-1H-indol-3-yl]but-3-en-2-one
- Crystal structure and thermal chemical properties of 2-(2,4-dimethylanilino)-3-methyl-6-diethylaminofluorane
- Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins
- Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines
- Synthetic approaches towards bisspiro[naphthalene-2(1H),3′-(3H)pyrazol]-1-one-containing compounds
- Mild Pfitzner—Moffat oxidation of the (1→3)-β-D-glucan from Saccharomyces cerevisiae
- Limited sample recovery in coupled methods of high-performance liquid chromatography of synthetic polymers
