Rhodium- and Non-Metal-Catalyzed Approaches for the Conversion of Isoxazol-5-ones to 2,3-Dihydro-6H-1,3-oxazin-6-ones

Autor(es)

Jurberg, Igor D. ^{[1, 2]} ; Davies, Huw M. L. ^[1]

Afiliação do(s) autor(es)

^[1] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 - USA

^[2] Univ Estadual Campinas, Inst Chem, Rua Monteiro Lobato 270, Campinas, SP 13083970 - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC LETTERS; v. 19, n. 19, p. 5158-5161, OCT 6 2017.
• Citações Web of Science: 13

Resumo

Two approaches were developed for the conversion of isoxazol-5-ones to 2,3-dihydro-6H-1,3-oxazin-6-ones. The first involves dirhodium-catalyzed reaction of aryl diazoacetates, leading to rhodium carbene intermediates that undergo insertion into the N-O bond of isoxazol-5-ones. The second approach involves conversion of the aryldiazoacetates to the corresponding tosylates, followed by reaction with the isoxazol-5-one in a metal-free one-pot procedure. These studies illustrate an alternative method to achieve a carbene-like transformation without requiring a metal catalyst. (AU)

• Processo FAPESP: 15/20809-4 - Exploração da Química de Isoxazol-5-onas como Blocos de Construção Versáteis em Síntese Orgânica
• Beneficiário: Igor Dias Jurberg
• Modalidade de apoio: Auxílio à Pesquisa - Regular