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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
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
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
Volumen:337
Número:24
Página de inicio:2419
Página de fin:2425
DOI: http://dx.doi.org/10.1016/S0008-6215(02)00258-6
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Heterocyclic Compounds with 4 or More Rings; Isoxazoles
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
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  • Casiraghi, G., Zanardi, F., Rassu, G., Spanu, P., (1995) Chem. Rev., 95, pp. 1677-1716
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  • Saha, A., Bhattacharjya, A., (1997) Chem. Commun. (Cambridge), pp. 495-496
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  • 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