Synthèse d'isoxazoles substitués en α de l'azote par une chaine alkyle ou alcényle

Autor:	Yvette Guichon, Jean-Claude Cherton, Marc Lanson, Jean-Jacques Basselier, Daïf Ladjama
Rok vydání:	1990
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry General Chemistry Medicinal chemistry Catalysis Cycloaddition chemistry.chemical_compound Hydroxylamine chemistry 1 3-Dipolar cycloaddition Vinyl acetate Side chain Isoxazole Isomerization Alkyl
Zdroj:	Canadian Journal of Chemistry. 68:1271-1276
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v90-196
Popis:	Several syntheses of special isoxazoles bearing a long alkyl or alkenyl side chain in the α position of the nitrogen are presented. A very convenient route in the case of an alkyl side chain is the classical 1,3-dipolar cycloaddition of a nitrile-oxide to a vinyl acetate. Although it is a rather long approach, the reaction of hydroxylamine with enone-epoxides represents a new and unequivocal method compatible with alkenyl side chains. The isomerisation of the easily synthesized isoxazoles bearing such substitutents α to the oxygen, by the reaction of their isoxazolium salts with hydroxylamine, is a fast and general method. Another very convenient access to "α-N substituted" isoxazoles is the coupling of magnesium compounds with 3-bromomethyl 5-methyl isoxazole. Keywords: isoxazoles, substitution in the α position of nitrogen.
Databáze:	OpenAIRE
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