Abstract:
Three isoxazoline tetracycles were obtained enantiomerically pure by intramolecular 1,3-dipolar cycloaddition. The characterization of the new compounds was performed by high-resolution 1H and 13C NMR spectroscopy. The relative configuration of the new chiral centers was determined by NOESY experiments and confirmed by single-crystal X-ray structural analysis. © 2002 Elsevier Science Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles |
Autor: | Fascio, M.L.; Alvarez-Larena, A.; D'Accorso, N.B. |
Filiación: | CIHIDECAR, Departamento de Quimica Organica, Universidad de Buenos Aires, C.P. 1428, Buenos Aires, Argentina Unitat de Cristallografia, Universitat Autonoma de Barcelona, 08193 Bellaterra, Barcelona, Spain
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Palabras clave: | Intramolecular 1,3-dipolar cycloaddition; Isoxazolines; Stereocontrol, NMR spectroscopy; X-Ray crystallography; Addition reactions; Nuclear magnetic resonance spectroscopy; Stereochemistry; Synthesis (chemical); X ray diffraction analysis; Chiral centers; Carbohydrates; isoxazoline derivative; fused heterocyclic rings; isoxazole derivative; article; carbon nuclear magnetic resonance; crystal structure; cycloaddition; drug synthesis; nuclear Overhauser effect; priority journal; proton nuclear magnetic resonance; X ray diffraction; chemistry; nuclear magnetic resonance; stereoisomerism; synthesis; X ray crystallography; Crystallography, X-Ray; Heterocyclic Compounds with 4 or More Rings; Isoxazoles; Nuclear Magnetic Resonance, Biomolecular; Stereoisomerism |
Año: | 2002
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Volumen: | 337
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Número: | 24
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Página de inicio: | 2419
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Página de fin: | 2425
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DOI: |
http://dx.doi.org/10.1016/S0008-6215(02)00258-6 |
Título revista: | Carbohydrate Research
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Título revista abreviado: | Carbohydr. Res.
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ISSN: | 00086215
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CODEN: | CRBRA
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CAS: | Heterocyclic Compounds with 4 or More Rings; Isoxazoles
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v337_n24_p2419_Fascio |
Referencias:
- Padwa, A., (1984) 1,3-Dipolar Cycloaddition Chemistry, 1. , New York: John Wiley & Sons. and references cited therein
- Gothelf, K.V., Jorgensen, K.A., (1998) Chem. Rev., 98, pp. 863-909
- Casiraghi, G., Zanardi, F., Rassu, G., Spanu, P., (1995) Chem. Rev., 95, pp. 1677-1716
- Kwon, T., Heiman, A.S., Oriaku, E.T., Yoon, K., Lee, H.J., (1995) J. Med. Chem., 38, pp. 1048-1051
- Gordaliza, M., Faircloth, G.T., Castro, M.A., Miguel del Corral, J.M., Lopez-Vazquez, M.L., San Feliciano, A., (1996) J. Med. Chem., 39, pp. 2865-2868
- Saha, A., Bhattacharjya, A., (1997) Chem. Commun. (Cambridge), pp. 495-496
- Mukhopadhyay, R., Datta, S., Chattopadhyay, P., Bhattacharjya, A., (1996) Indian J. Chem. Sect. B, 35, pp. 1190-1193
- Wolfrom, M.L., Thomas, G.H.S., (1963) Methods Carbohydr. Chem., 2, pp. 320-322
- Sheldrick, G.M., (1985) Crystallographic Computing 3, pp. 175-189. , G.M. Sheldrick, C. Kruger, & R. Goddard. Oxford: Oxford University Press
- Sheldrick, G.M., (1997) SHELX97. Program for Crystal Structure Analysis (Release 97-2), , University of Göttingen, Germany
- Sowden, J.C., (1951) J. Am. Chem. Soc., 73, pp. 5496-5497
Citas:
---------- APA ----------
Fascio, M.L., Alvarez-Larena, A. & D'Accorso, N.B.
(2002)
. Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles. Carbohydrate Research, 337(24), 2419-2425.
http://dx.doi.org/10.1016/S0008-6215(02)00258-6---------- CHICAGO ----------
Fascio, M.L., Alvarez-Larena, A., D'Accorso, N.B.
"Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles"
. Carbohydrate Research 337, no. 24
(2002) : 2419-2425.
http://dx.doi.org/10.1016/S0008-6215(02)00258-6---------- MLA ----------
Fascio, M.L., Alvarez-Larena, A., D'Accorso, N.B.
"Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles"
. Carbohydrate Research, vol. 337, no. 24, 2002, pp. 2419-2425.
http://dx.doi.org/10.1016/S0008-6215(02)00258-6---------- VANCOUVER ----------
Fascio, M.L., Alvarez-Larena, A., D'Accorso, N.B. Synthesis, high-resolution NMR spectroscopic analysis, and single-crystal X-ray diffraction of isoxazoline tetracycles. Carbohydr. Res. 2002;337(24):2419-2425.
http://dx.doi.org/10.1016/S0008-6215(02)00258-6