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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis and Reactions of Fatty Ester Isoxazole Heterocycles

item Kenar, James
item Wetzel, Amanda - PREV STUDENT, NCAUR

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 8, 2002
Publication Date: N/A

Technical Abstract: Long chain fatty esters, derived from vegetable oils, are of interest as renewable raw materials. These fatty compounds can be functionalized at the ester site to give new long- chain compounds containing the heterocyclic isoxazole ring. Here we report on the successful one-pot condensation of fatty esters, such as methyl oleate, linoleate, stearate, palmitate, and brassylate, with a metallated imine followed by reaction with hydroxylamine and dehydration to give lipid isoxazole heterocycles in good yields. The isoxazole ring represents a versatile synthetic intermediate, and ring opening reactions of the lipid isoxazoles were examined to give fatty compounds containing a beta-aminoenones and beta- diketones. The isoxazoles and their ring-opened compounds may have potentially interesting chemical and physical properties and are not easily accessible by other methods.

Last Modified: 4/22/2015
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