Síntese de heteroarilazóis trialometilsubstituídos a partir de 2-acetilfurano e 2-acetiltiofeno

• Ano de defesa: 2004
• Autor(a) principal: Brondani, Sergio
• Orientador(a): Martins, Marcos Antonio Pinto
• Banca de defesa: Bonacorso, Helio Gauze , Zanatta, Nilo
• Tipo de documento: Tese
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Santa Maria
• Programa de Pós-Graduação: Programa de Pós-Graduação em Química
• Departamento: Química
• País: BR
• Palavras-chave em Português: Química orgânica; Síntese química; Isoxazois; Pirazois
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/4218

The synthesis of 1,1,1-trihalo-4-methoxy-4-[2-thienyl]-3-buten-2-ones, 1,1,1-trihalo-4-methoxy-4-[2-furyl]-3-buten-2-ones and the respective trihalomethyl 1,3-butanone derivatives by trihaloacylation of dimethoxy acetals derived from 2-acetylthiophene and 2-acetylfuran is reported. This is a convenient method to obtain fluorinated and chlorinated 1,3-dielectrophiles from 2-acetylthiophene and 2-acetylfuran. The halogenated 1,3-dielectrophiles were used to synthesize six new series of 2-thienyl- and 2-furylazoles. Heterocyclization of 1,1,1-trifluoro[trichloro]-4-methoxy-4-[2-tienyl]-3-buten-2-one and 1,1,1-trifluoro[trichloro]-4-methoxy-4-[2-furyl]-3-buten-2-ones in to isoxazoles and pyrazoles derivatives as a new type of trihalomethylated bicyclic heterocycles is reported. The structure of all products were assigned by 1H and 13C NMR and mass spectrometry.