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Synthesis of isoxazoles
Recent Literature

A 1,3-dipolar cycloaddition of phenyl vinylic selenide to nitrile oxides and
subsequent oxidation-elimination furnished 3-substituted isoxazoles with
good yields in a one-pot, two-step transformation.
S.-R. Sheng, X.-L. Liu, Q. Xu, C.-S. Song, Synthesis, 2003, 2763-2764.

The dehydration of primary nitro compounds can be performed by bases in the
presence of dipolarophiles. Among the organic bases examined, DABCO gave the
best results. The reaction is applicable to activated nitro compounds and to
phenylnitromethane and affords isoxazoline derivatives in higher yields
compared with those of other methods. The reaction, however, is not
compatible with nitroalkanes.
L. Cecchi, F. De Sarlo, F. Machetti, Eur. J. Org. Chem., 2006,
4852-4860.

3,5-Disubstituted isoxazoles are regioselectively obtained in good yields by
a mild and convenient one-pot, three-step procedure utilizing a
copper(I)-catalyzed cycloaddition reaction between in situ generated
nitrile oxides and terminal acetylenes.
T. V. Hansen, P. Wu, V. V. Fokin, J. Org. Chem., 2005, 70, 7761-7764.

Pyrazole or isoxazole derivatives are prepared by a palladium-catalyzed four-component coupling of a terminal alkyne, hydrazine (hydroxylamine),
carbon monoxide under ambient pressure, and an aryl iodide.
M. S. M. Ahmed, K. Kobayashi, A. Mori, Org. Lett.,
2005, 7, 4487-4489.

The reaction of
various 2-alkyn-1-one O-methyl oximes with ICl, I2, Br2, or PhSeBr
provided 3,5-disubstituted 4-halo(seleno)isoxazoles
in good to excellent yields under mild reaction conditions.
J. P. Waldo, R. C. Larock, Org. Lett.,
2005, 7, 5203-5205.

A series of 4-alkyl-5-aminoisoxazoles have been synthesized in high yield by
nucleophilic addition of lithiated alkyl nitriles to (α)-chlorooximes.
M. P. Bourbeau, J. T. Rider, Org. Lett.,
2006, 8, 3679-3680.

3-Acylisoxazoles were synthesized by the reaction of alkenes or alkynes with
ketones (acetone or acetophenone), as both a reagent and the solvent, by
three methods: iron(III) nitrate under reflux, iron(III) salt-nitrogen
dioxide (NO2) at room temperature, and iron(III) nitrate under microwave
irradiation (MW).
K.-I. Itoh, H. Sakamaki, N. Nakazato, A. Horiuchi, E. Horn, C. A. Horiuchi, Synthesis, 2005, 3541-3548.
