Synthesis and reactions of 2-[3-(trifluoromethyl)phenyl]furo[3,2-c]pyridine
-
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.
[1] Abramovitch, R. A., Deeb, A., Kishore, D., Mpango, G. B. W., & Shinkai, I. (1988). The reaction of 4-chloropyridine 1-oxide with activated acetylenes. A convenient one-step synthesis of furo[3,2-c]pyridines. Gazzetta Chimica Italiana, 118, 167–171. 10.1002/chin.198830212Suche in Google Scholar
[2] Baran, P., Boča, M., Boča, R., Krutošíková, A., Miklovič, J., Pe-likán, J., & Titiš, J. (2005). Structural characterization, spectral and magnetic properties of isothiocyanate nickel(II) complexes with furopyridine derivatives. Polyhedron, 24, 1510–1516. DOI: 10.1016/j.poly.2005.03.103. http://dx.doi.org/10.1016/j.poly.2005.03.10310.1016/j.poly.2005.03.103Suche in Google Scholar
[3] Bátori, S., Hajós, G., Sándor, P., & Messmer, A. (1989). Selective dimerizations of substituted N-aminopyridinium salts and their benzologs. Journal of Organic Chemistry, 54, 3062–3068. DOI: 10.1021/jo00274a020. http://dx.doi.org/10.1021/jo00274a02010.1021/jo00274a020Suche in Google Scholar
[4] Bencková, M., & Krutošíková, A. (1995). Synthesis of pyrrolo[2′, 3′:4,5]furo[3,2-c]pyridines. Monatshefte für Chemie, 126, 753–758. DOI: 10.1007/BF00807166. http://dx.doi.org/10.1007/BF0080716610.1007/BF00807166Suche in Google Scholar
[5] Bencková, M., & Krutošíková, A. (1997). Synthesis of pyrrolo[2′, 3′:4,5]furo[3,2-c]pyridine-2-carboxylic acids. Molecules, 1, 163–165. http://www.springerlink.com/content/w9a9bpg0arrva439/fulltext.pdf http://dx.doi.org/10.1007/s00783005003210.1007/s007830050032Suche in Google Scholar
[6] Bencková, M., & Krutošíková, A. (1999). 5-Aminofuro[3,2-c]pyridinium tosylates and substituted furo[3,2-c]pyridine N-oxides: Synthesis and reactions. Collection of Czechoslovak Chemical Communications, 64, 539–547. DOI: 10.1135/ cccc19990539. http://dx.doi.org/10.1135/cccc1999053910.1135/cccc19990539Suche in Google Scholar
[7] Bencková, M., Krutošíková, A., Pullman, J., & Prónayová, N. (1999). Pyrrolo[2′,3′:4,5]furo[3,2-c]pyridine derivatives reactions in the pyridine and pyrrole ring. Chemical Papers, 53, 118–122. Suche in Google Scholar
[8] Bobošík, V., Krutošíková, A., & Jordis, U. (1995). Synthesis and reactions of 2,3-dimethylfuro[3,2-c]pyridines. Monat-shefte für Chemie, 126, 747–752. DOI: 10.1007/BF00807165. http://dx.doi.org/10.1007/BF0080716510.1007/BF00807165Suche in Google Scholar
[9] Búdová, M., Fojtíková, K., Miklovič, J., Mrázová, V., Horváth, B., & Krutošíková, A. (2006). Synthesis and reactions of 2-and 4-substituted furo[3,2-c]pyridines. Chemical Papers, 60, 231-236. DOI: 10.2478/s11696-006-0041-9. 10.2478/s11696-006-0041-9Suche in Google Scholar
[10] Cyrański, M. K., Krygowski, T. M., Krutošíková, A., & Sleziak, R. (2001). Aromaticity of dihetero analogues of pentalene dianion. X-Ray and ab initio studies of eight methyl furo[3,2-b]pyrrole-5-carboxylate derivatives and five methyl furo[2,3-b]pyrrole-5-carboxylate derivatives. Tetrahedron, 57, 8867–8873. DOI: 10.1016/S0040-4020(01)00854-7. http://dx.doi.org/10.1016/S0040-4020(01)00854-710.1016/S0040-4020(01)00854-7Suche in Google Scholar
[11] Gajdoš, P., Miklovič, J., & Krutošíková, A. (2006). Reactions of 5-[3-(trifluoromethyl)phenyl]furan-2-carbaldehyde. Khimiya Geterotsiklicheskikh Soedinenii, 825–831. (Available also in Chemistry of Heterocyclic Compounds, 42, 719–725. DOI: 10.1007/s10593-006-0151-x). Suche in Google Scholar
[12] Hörlein, G., Kübel, B., Studeneer, A., & Salbeck, A. (1979). Heterocyclen durch Anellierung an 4-Pyridinole, I Furo[3,2-c]pyridin-3-ole und Furo[3,2-c]pyridin-3(2H)-one. Liebigs An-nalen der Chemie, 1979, 371–386. DOI: 10.1002/jlac. 197919790309. http://dx.doi.org/10.1002/jlac.19791979030910.1002/jlac.197919790309Suche in Google Scholar
[13] Howard, A. S. (1996). Bicyclic 5–6 systems with one ring junction nitrogen atom: one extra heteroatom 1:0. In G. Jones (Ed.), Comprehensive heterocyclic chemistry II, Volume 8: Fused five-and six-membered rings with ring junction heteroatoms (pp. 249–286, chapter 8.10). Oxford: Pergamon Press Inc. Suche in Google Scholar
[14] Janda, Ľ., & Votický, Z. (1984). Semisynthetic cephalosporines. I. An improved synthesis of 5-aryl-2-furancarboxylic acids. Chemické Zvesti, 38, 507–513. Suche in Google Scholar
[15] Krischke, R., Grashey, R., & Huisgen, R. (1977). 1,3-Dipolare Cycloadditionen, 83. Pyridinium-N-imid als additionsbereites Azomethinimin. Justus Liebigs Annalen der Chemie, 1977, 498–505. DOI: 10.1002/jlac.197719770315. http://dx.doi.org/10.1002/jlac.19771977031510.1002/jlac.197719770315Suche in Google Scholar
[16] Krutošíková, A. (1995). Synthesis of substituted and fused furo[3,2-c]pyridines. Chemistry of Heterocyclic Compounds, 31, 1219–1221. DOI: 10.1007/BF01185596. http://dx.doi.org/10.1007/BF0118559610.1007/BF01185596Suche in Google Scholar
[17] Krutošíková, A. (1996). Bicyclic 5-5 systems: two heteroatoms 1:1. In C. A. Ramsden (Ed.), Comprehensive heterocyclic chemistry II, Volume 7: Fused five-and six-membered rings without ring junction heteroatoms (pp. 1–47, chapter 7.01). Oxford: Pergamon Press Inc. Suche in Google Scholar
[18] Krutošíková, A., Dandárová, M., & Alföldi, J. (1994). Substituted vinyl azides in the synthesis of condensed nitrogen heterocycles. Chemical Papers, 48, 268–273. Suche in Google Scholar
[19] Krutošíková, A., Dandárová, M., Chylová, J., & Végh, D. (1992). Condensed O-, N-heterocycles by the transformation of azidoacrylates. Monatshefte für Chemie, 123, 807–815. DOI: 10.1007/BF00812330. http://dx.doi.org/10.1007/BF0081233010.1007/BF00812330Suche in Google Scholar
[20] Krutošíková, A., Mitasová, B., Jóna, E., & Bobošíková, M. (2001). Synthesis, thermal and spectral properties of Cu(II) and Ni(II) complexes with furopyridines or quinoline. Chemical Papers, 55, 290–293. Suche in Google Scholar
[21] Krutošíková, A., & Sleziak, R. (1996). Synthesis of 2-arylfuro [3,2-c]pyridines and their derivatives. Collection of Czechoslovak Chemical Communications, 61, 1627–1636. DOI: 10.1135/cccc19961627. http://dx.doi.org/10.1135/cccc1996162710.1135/cccc19961627Suche in Google Scholar
[22] Miklovič, J., Krutošíková, A., & Baran, P. (2004). Two furopyridine complexes of nickel(II) isothiocyanate. Acta Crystallographica Section C, C60, m227–m230 (2004). DOI: 10.1107/S0108270104007796. Suche in Google Scholar
[23] Mojumdar, S. C., Miklovič, J., Krutošíková, A, Valigura, D., & Stewart, J. M. (2005). Furopyridines and furopyridine-Ni(II) complexes: Synthesis, thermal and spectral characterization. Journal of Thermal Analysis and Calorimetry, 81, 211–215, (2005). DOI: 10.1007/s10973-005-6999-7. http://dx.doi.org/10.1007/s10973-005-0769-4Suche in Google Scholar
[24] Molina, P., Fresneda, P. M., & Hurtado, F. (1987). An efficient iminophosphorane-mediated synthesis of thieno[3,2-c] pyridine, thieno [2,3-c] pyridine and furo[3,2-]-pyridine derivatives. Synthesis, 1987, 45–48. DOI: 10.1055/s-1987-27837. http://dx.doi.org/10.1055/s-1987-2783710.1055/s-1987-27837Suche in Google Scholar
[25] New, J. S., Christopher, W. L., Yevich, J. P., Butler, R., Schlemmer, R. F., Van der Maelen, C. P., & Cipollina, J. A. (1989). The thieno[3,2-c]pyridine and furo[3,2-c]pyridine rings: new pharmacophores with potential antipsychotic activity. Journal of Medical Chemistry, 32, 1147–1156. DOI: 10.1021/jm00126a002. http://dx.doi.org/10.1021/jm00126a00210.1021/jm00126a002Suche in Google Scholar
[26] Potts, K. T. (1984). Synthesis of five-membered rings with two or more heteroatoms. In K. T. Potts (Ed.), Comprehensive heterocyclic chemistry I, Vol. 5, Part 4A: Five membered rings with two or more nitrogen atoms (pp. 111–166, chapter 4.03). Oxford: Pergamon Press Inc. Suche in Google Scholar
[27] Sherman, A. R. (1996). Bicyclic 5–6 systems: two heteroatoms 1:1. In C. A. Ramsden (Ed.), Comprehensive heterocyclic chemistry II, Volume 7: Fused five-and six-membered rings without ring junction heteroatoms (pp. 167–227, chapter 7.06). Oxford: Pergamon Press Inc. Suche in Google Scholar
[28] Shiotani, S., Taniguchi, K., Ishida, T., & In, Y. (1996). Furopyridines. XIX [1]. Reaction of furo[2,3-b]-,-[3,2-b]-,-[2,3-c]-and-[3,2-c]pyridine with acetic anhydride. Journal of Heterocyclic Chemistry, 33, 647–654. http://dx.doi.org/10.1002/jhet.557033032110.1002/jhet.5570330321Suche in Google Scholar
[29] Tamura, Y., & Ikeda M. (1981). Advances in the chemistry of heteroaromatic N-imines and N-aminoazonium salts. Advances in Heterocyclic Chemistry, 29, 71–139. http://dx.doi.org/10.1016/S0065-2725(08)60786-210.1016/S0065-2725(08)60786-2Suche in Google Scholar
[30] Titiš, J., Boča, R., Dlháò, L., Ďurčeková, T, Fuess, H., Ivaniková, R., Mrázová, V., Papánková, B., & Svoboda, I. (2007). Magnetostructural correlations in heteroleptic nickel(II) complexes. Polyhedron, 26, 1523–1530. DOI: 10. 1016/j.poly.2006.11.054. http://dx.doi.org/10.1016/j.poly.2006.11.05410.1016/j.poly.2006.11.054Suche in Google Scholar
[31] Voznyi, I. V., Novikov, M. S., & Khlebnikov, A. F. (2005). Synthesis of 6,6-difluorocyclopropa[b]furo[2,3-c]pyrrole and 7-fluorofuro[3,2-c]pyridine derivatives via 1,5-electrocyclization of carbene-derived azomethine ylides. Synlett, 1006–1008. DOI: 10.1055/s-2005-864820. 10.1055/s-2005-864820Suche in Google Scholar
[32] Vrábel, V., Švorc, Ľ., Juristová, N., Miklovič, J., & Kožíšek, J. (2007a). Tetra-µ-acetato-bis[(benzofuro[3,2-c]pyridine)cop-per(II)]. Acta Crystallographica Section E, E63, m2112–m2113. DOI: 10.1107/S1600536807032242. 10.1107/S1600536807032242Suche in Google Scholar
[33] Vrábel, V., Švorc, Ľ, Juristová, N., Miklovič, J., & Kožíšek, J. (2007b). Bis(1-benzofuro[3,2-c]pyridine-κN)dichloridocobalt (II). Acta Crystallographica Section E, E63, m2427–m2428. DOI: 10.1107/S160053680704161X. http://dx.doi.org/10.1107/S160053680704161X10.1107/S160053680704161XSuche in Google Scholar
© 2008 Institute of Chemistry, Slovak Academy of Sciences
Artikel in diesem Heft
- 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
Artikel in diesem Heft
- 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
