2010•Letters in Organic ChemistryRequires access

Synthesis of 2,3 and 4,5-Dihydro-hydroxy-isoxazoles and Isoxazoles Under Different pH Conditions

Virginie Andrzejak, Régis Millet, Jamal El Bakali, A. Guelzim, Sébastien Gluszok, Philippe Chavatte, Jean‐Paul Bonte, Claude Vaccher, Emmanuelle Lipka

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Abstract

Reaction between aryl 1,3-diketoesters 2a-e and hydroxylamine hydrochloride has been investigated under different experimental conditions. Whereas acid conditions gave principally 3,5-isoxazole esters (3a-e), reactions under neutral and basic conditions led to different 4,5 and 2,3-dihydro-hydroxy-isoxazoles 4a-e and 5a-e. Keywords: Isoxazoles, dihydro-hydroxy-isoxazoles, aryl 1,3-diketoesters, hydroxylamine

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Key concepts: Isoxazole, Chemistry, Hydroxylamine Hydrochloride, Hydroxylamine, Aryl, Hydrochloride, Medicinal chemistry, Organic chemistry