Síntese de 3-haloacetil-4-metilquinolinas utilizando líquido iônico sob irradiação de micro-ondas

• Ano de defesa: 2011
• Autor(a) principal: Prola, Liziê Daniela Tentler
• 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: Irradiação de micro-ondas; Líquidos iônicos; Quinolinas; Enonas; Ciclocondensação; Microwave irradiation; Ionic liquid; Quinoline; Enone; Cyclocondensation; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/10492

The synthesis of a series of 3-haloacetyl-4-methyl-quinolines from the cyclocondensation reaction of 4-alkoxyvinyl ketones [R1C(O)CH=C(R2)(OCH3), where R1 = CF3, CCl3, CHCl2, CF2Cl, CF2CF3 and R2 = Me, Et, Pr, Bu, i-Bu, i- Pent] with 2-aminoacetophenone is reported. The reaction was performed in the presence of p-toluene sulphonic acid (p-TsOH), ionic liquid ([HMIM][TsO]) and under microwave irradiation. The molar ratio of the reactants 4-alkoxyvinyl ketone and 2-aminoacetophenone was of 1:1, respectively, for the quinoline with R1 = CHCl2, while for the other reactions was necessary a molar ratio of 1.2:1, respectively. The results showed that the combination of ionic liquid and microwave irradiation was effective for this synthesis, since the products were obtained with short rteaction times (10-20 min) and high yields (70-91%). In addition, the advantages of using the microwave irradiation method in comparison to the conventional thermal heating were also demonstrated.