Síntese de 3-trifluoracetilpirróis N-substituídos

• Ano de defesa: 2008
• Autor(a) principal: Wouters, Ana Dionéia
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria; BR; Química; UFSM; Programa de Pós-Graduação em Química
• Palavras-chave em Português: Química; Pirróis; Compostos sintetizados; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/10415

This work presents a new, simple and versatile one-pot strategy for the synthesis of new N-substituted 3-trifluoroacetyl-pyrroles. These compounds were obtained by the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with primary amines (RNH2, where R = H, CH3, CH2CH3, CH(CH3)2, (CH2)2OH, CH2(C5H4N), CH2(C6H5), among others), generating 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-alkylamino-3-buten-2-ones intermediates that in the most cases could not be isolated. Thus, in the same reaction pot they were directly submitted to oxidation reaction with PCC (Corey s Reaction) giving 1,1,1-trifluoro-3-(2-ethanal)-4- alkylamino-3-buten-2-ones, which under reflux underwent intramolecular cyclisation furnishing the desired N-substituted 3-trifluoroacetyl-pyrroles, in moderate yields (20-56%). The pyrroles obtained in this study were identified by NMR 1H, NMR 13C and Mass Espectroscopy.