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.
[1] New, J. S., Christopher, W. L., Yevich, J. P., Butler, R., Schlemmer, R. S., Jr., Van der Maelen, C. P., and Cipollina, J. A., J. Med. Chem. 32, 1147 (1989). http://dx.doi.org/10.1021/jm00126a00210.1021/jm00126a002Search in Google Scholar PubMed
[2] Sherman, A. R., in Comprehensive Heterocyclic Chemistry II (Ramsden, C. A., Editor), Vol. 7, p. 167. Pergamon Press, Oxford, 1996. 10.1016/B978-008096518-5.00150-7Search in Google Scholar
[3] Lhommet, G., Sliwa, H., and Maitte, P., Bull. Soc. Chim. Fr. 1972, 1442. Search in Google Scholar
[4] Bisagni, E., Civier, A., and Marquet, J.-P., J. Heterocycl. Chem. 12, 461 (1975). Search in Google Scholar
[5] Abramovitch, R. A., Deeb, A., Kishore, D., and Mpango, G. B. W., Gazz. Chim. Ital. 118, 167 (1988). Search in Google Scholar
[6] Hörlein, G., Kübel, B., Studeneer, A., and Salbeck, A., Justus Liebigs Ann. Chem. 371 (1979). 10.1002/jlac.197919790310Search in Google Scholar
[7] Eloy, F. and Deryckere, A., J. Heterocycl. Chem. 8, 57 (1975). http://dx.doi.org/10.1002/jhet.557008011210.1002/jhet.5570080112Search in Google Scholar
[8] Bouzart, J. D. and Bisagni, E., Bull. Soc. Chim. Fr. 1971, 1727. Search in Google Scholar
[9] Molina, P., Fresneda, P. M., and Hurtado, F., Synthesis 1987, 45. 10.1055/s-1987-27837Search in Google Scholar
[10] Krutošíková, A., Dandárová, M., Chylová, J., and Végh, D., Monatsh. Chem. 123, 807 (1992). http://dx.doi.org/10.1007/BF0081233010.1007/BF00812330Search in Google Scholar
[11] Krutošíková, A., Dandárová, M., and Alföldi, J., Chem. Pap. 48, 268 (1994). Search in Google Scholar
[12] Bobošík, V., Krutošíková, A., and Jordis, U., Monatsh. Chem. 126, 747 (1995). http://dx.doi.org/10.1007/BF0080716510.1007/BF00807165Search in Google Scholar
[13] Bencková, M. and Krutošíková, A., Monatsh. Chem. 126, 753 (1995). http://dx.doi.org/10.1007/BF0080716610.1007/BF00807166Search in Google Scholar
[14] Krutošíková, A. and Sleziak, R., Collect. Czech. Chem. Commun. 61, 1627 (1996). http://dx.doi.org/10.1135/cccc1996162710.1135/cccc19961627Search in Google Scholar
[15] Bencková, M. and Krutošíková, A., Molecules 1, 163 (1996). http://dx.doi.org/10.1007/s00783005003210.1007/s007830050032Search in Google Scholar
[16] Bencková, M. and Krutošíková, A., Collect. Czech. Chem. Commun. 64, 539 (1999). http://dx.doi.org/10.1135/cccc1999053910.1135/cccc19990539Search in Google Scholar
[17] Bencková, M., Krutošíková, A., Pullman, J., and Prónayová, N., Chem. Pap. 53, 118 (1999). Search in Google Scholar
[18] Krutošíková, A., Mitasová, B., Jóna, E., and Bobošíková, M., Chem. Pap. 55, 290 (2001). Search in Google Scholar
[19] Miklovič, J., Krutošíková, A., and Baran, P., Acta Crystallogr., C 60, m227 (2004). 10.1107/S0108270104007796Search in Google Scholar PubMed
[20] Baran, P., Boča, M., Boča, R., Krutošíková, A., Miklovič, J., Pelikán, J., and Titiš, J., Polyhedron 24, 1510 (2005). http://dx.doi.org/10.1016/j.poly.2005.03.10310.1016/j.poly.2005.03.103Search in Google Scholar
[21] Bailey, D. M., U.S. 3890335 (1975); Ref. Zh. Khim. 1976, 70124 P. Search in Google Scholar
[22] Pong, S. F., Pelosi, S. S., Wessels, F. L., Yu, C. N., Burns, R. H., White, R. E., Anthony, D. R., Ellis, K. O., Wright, G. C., and White, R. L., Arzneim.-Forsch. 33, 1411 (1983). Search in Google Scholar
© 2006 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- 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
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