Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas

• Ano de defesa: 2003
• Autor(a) principal: Borchhardt, Deise Moreira
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; Brasil; Química; UFSM; Programa de Pós-Graduação em Química; Centro de Ciências Naturais e Exatas
• Palavras-chave em Português: Química orgânica; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/26805

This work presents a three steps synthetic route to obtain 1,3- oxazin-2-ones, from the β-alkoxyvinyl trihalomethyl ketones of general formula X3CC(O)CH=C(R)OR¹, where R = H, CH3, Ph, p-Me-Ph; R¹ = Me, Et. β-alkoxyvinyl trihalomethyl ketones were obtained from the acylation reaction of acetals or enolethers with trifluoracetic anhydride and trichloroacetil chloride. In a first step, the substitution reaction on the C-β of the β- alkoxyvinyl trihalomethyl cetones with ethyl carbamate furnished the corresponding enamino compounds. This compounds, in a second step, underwent reduction reaction with NaBH4, leading to the respective γ- aminoalcohols. In a third step, the γ-aminoalcohols were submitted to cyclization reaction with triphosgene furnishing a new series of 1,3-oxazin-2-ones.