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Abstract:

The 1,3-dipolar cycloaddition reaction between a 2-deoxy-D-aldose oxime (D-gluco or D-ribo) and an alkyne as dipolarophile (phenylacetylene, 2-propyn-1-o1, 3-chloro-1-propyne, or 3-bromo-1-propyne) is described. The new 3-glycosyl-5-substituted-2-isoxazoles are characterized physically and spectroscopically.

Registro:

Documento: Artículo
Título:A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles
Autor:Fascio, M.L.; D'Accorso, N.B.
Filiación:Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C. P. 1428, Buenos Aires, Argentina
Palabras clave:2 isoxazole derivative; alkyne; isoxazole derivative; oxime; unclassified drug; article; cyclization; drug synthesis; reaction analysis; spectroscopy; stereochemistry
Año:2001
Volumen:31
Número:12
Página de inicio:1913
Página de fin:1920
DOI: http://dx.doi.org/10.1081/SCC-100104343
Título revista:Synthetic Communications
Título revista abreviado:Synth. Commun.
ISSN:00397911
CODEN:SYNCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397911_v31_n12_p1913_Fascio

Referencias:

  • Mitsui Toatsu Chemicals, Mitsui Seiyaku Kogyoo KK, Toyama Chemical Co. Ltd.; Jpn. Kokai 1994, 06 116 146; Marquis, E.T., Sanderson, J.R., (1994) Chem. Abstr., 120, p. 217. , US Pat., 1994, 52833356
  • Lang, S.A., Lin, Y.-I., (1984) Comp. Heterocycl. Chem. Ist edn, 2 (1), p. 222
  • Padwa, A., (1984) 1,3-Dipolar Cycloadditions Chemistry, 1, p. 337. , ed. by J. Wiley & Sons, Chapter 3, New York
  • Kozikowski, A.P., Goldstein, S., (1983) J. Org. Chem., 48, p. 1139
  • Fascio, M.L., D'Accorso, N.B., (1996) J. Heterocyclic Chem., 33, p. 1573
  • Hassner, A., Lokanatha Rai, K.M., (1989) Synthesis, p. 57
  • Lokanatha Rai, K.M., Hassner, A., (1990) Heterocycles, 30, p. 817

Citas:

---------- APA ----------
Fascio, M.L. & D'Accorso, N.B. (2001) . A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles. Synthetic Communications, 31(12), 1913-1920.
http://dx.doi.org/10.1081/SCC-100104343
---------- CHICAGO ----------
Fascio, M.L., D'Accorso, N.B. "A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles" . Synthetic Communications 31, no. 12 (2001) : 1913-1920.
http://dx.doi.org/10.1081/SCC-100104343
---------- MLA ----------
Fascio, M.L., D'Accorso, N.B. "A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles" . Synthetic Communications, vol. 31, no. 12, 2001, pp. 1913-1920.
http://dx.doi.org/10.1081/SCC-100104343
---------- VANCOUVER ----------
Fascio, M.L., D'Accorso, N.B. A facile synthesis of 3-glycosyl-5-substituted-2-isoxazoles. Synth. Commun. 2001;31(12):1913-1920.
http://dx.doi.org/10.1081/SCC-100104343