Abstract:
(Chemical Equation Presented) We report the synthesis of some furanose and pyranose acylhydrazones and their heterocyclization products. The new compounds were characterized physically and spectroscopically and the syn-anti and (R)-(S) configuration was determined by NOESY experiments. We discuss the influence of the nucleophile, the temperature and the precursor structure on the heterocyclization products.
Registro:
Documento: |
Artículo
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Título: | Synthesis and NMR analysis of spiranic heterocycles from carbohydrate derivatives |
Autor: | Martins Alho, M.A.; D'Accorso, N.B. |
Filiación: | CIHIDECAR (CONICET), Departamento de Química Orgánica, Ciudad Universitaria, Intendente Güiraldes 2160, C1428EGA Buenos Aires, Argentina
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Palabras clave: | carbohydrate derivative; furanose acylhydrazone; heterocyclic compound; hydrazone derivative; pyranose acylhydrazone; unclassified drug; article; carbon nuclear magnetic resonance; chemical structure; cyclization; nuclear Overhauser effect; proton nuclear magnetic resonance; reaction analysis; synthesis |
Año: | 2007
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Volumen: | 44
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Número: | 4
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Página de inicio: | 901
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Página de fin: | 907
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Título revista: | Journal of Heterocyclic Chemistry
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Título revista abreviado: | J. Heterocycl. Chem.
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ISSN: | 0022152X
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CODEN: | JHTCA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v44_n4_p901_MartinsAlho |
Referencias:
- Martins Alho, M.A., D'Accorso, N.B., (2002) J. Heterocycl. Chem, 39, pp. 137-140
- Brousse, B.N., Moglioni, A.G., Martins Alho, M.A., Alvarez Larena, A., Moltrasio, G.Y., D'Accorso, N.B., (2002) Arkivoc, 10, pp. 14-23. , online ed
- García, C.C., Brousse, B.N., Carlucci, M.I., Moglioni, A.G., Martins Alho, M.A., Moltrasio, G.Y., D'Accorso, N.B., Damonte, E.B., (2003) Antiviral Chemistry & Chemotherapy, 14, pp. 99-105
- Brousse, B.N., Massa, R., Moglioni, A.G., Martins Alho, M.A., D'Accorso, N.B., Gutkind, G., Moltrasio, G.Y., (2003) J. Chil. Chem. Soc, 49, pp. 45-49
- Syn, isomer has the -NHR group placed on the same side than the anomeric carbon
- Martins Alho, M.A., D'Accorso, N.B., (1997) J. Heterocycl. Chem, 34, pp. 1415-1419
- Martins Alho, M.A., D'Accorso, N.B., (2000) J. Heterocycl. Chem, 37, pp. 811-814
- Somogyi, L., (1979) Carbohydr. Res, 75, pp. 325-330
- Karabatsos, G.J., Taller, R.A., (1968) Tetrahedron, 24, pp. 3347-3360
- Palmer, A.G., Cavanagh, J., Wright, P.E., Ranee, M., (1991) J. Magn. Reson, 93, pp. 151-170
- Kay, L.E., Keifer, P., Saarinen, T., (1992) J. Am. Chem. Soc, 114, pp. 10663-10665
- Schleucher, J., Schwendinger, M., Sattler, M., Schmidt, P., Schedletzky, O., Glaser, S.J., Sorensen, O.W., Griesinger, C., (1994) J. Biomol. NMR, 4, pp. 301-306
Citas:
---------- APA ----------
Martins Alho, M.A. & D'Accorso, N.B.
(2007)
. Synthesis and NMR analysis of spiranic heterocycles from carbohydrate derivatives. Journal of Heterocyclic Chemistry, 44(4), 901-907.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v44_n4_p901_MartinsAlho [ ]
---------- CHICAGO ----------
Martins Alho, M.A., D'Accorso, N.B.
"Synthesis and NMR analysis of spiranic heterocycles from carbohydrate derivatives"
. Journal of Heterocyclic Chemistry 44, no. 4
(2007) : 901-907.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v44_n4_p901_MartinsAlho [ ]
---------- MLA ----------
Martins Alho, M.A., D'Accorso, N.B.
"Synthesis and NMR analysis of spiranic heterocycles from carbohydrate derivatives"
. Journal of Heterocyclic Chemistry, vol. 44, no. 4, 2007, pp. 901-907.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v44_n4_p901_MartinsAlho [ ]
---------- VANCOUVER ----------
Martins Alho, M.A., D'Accorso, N.B. Synthesis and NMR analysis of spiranic heterocycles from carbohydrate derivatives. J. Heterocycl. Chem. 2007;44(4):901-907.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022152X_v44_n4_p901_MartinsAlho [ ]