Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas

• Ano de defesa: 2011
• Autor(a) principal: Lobo, Marcio Marçal
• 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: Alcoxipiranos; Tetraidropiridinas; Aza-heterocíclos; Alkoxypirans; Tetrahydropirydine; Aza-heterocycles; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
• Link de acesso: http://repositorio.ufsm.br/handle/1/10487

This work presents the synthesis of two novel series of 1-alkyl(aryl)-2-amino- 5-trifluoroacetyl-1,2,3,4-tetrahydropyridine (6, 8), obtained from the reaction of 2- alkoxy-5-trifluoroacetyl-3,4-dihydro-2H-pyrans (alkoxy = OMe (3), EtO (4)) with primary ethylamines, with general formula R1CH2CH2NH2, where R1 = 2-MeO-Ph (5a), 4-MeO-Ph (5b), 3,4-OMe-Ph (5c), 4-F-Ph (5d), 2-Cl-Ph (5e), 3-Cl-Ph (5f), 4-Cl- Ph (5g), 2,4-Cl-Ph (5h), 4-OH-Ph (5i) , 1-(2-cycloexenyl) (5j), 1-(2-N-morpholil) (5k), 1-(2-N-diethylamino) (5l) and 2-(1H-indole-3-yl) (5m), and primary arylamines, of general formula NH2-Ar were Ar = 4-F-Ph (7a), 2-OMe-Ph (7b), 3-OMe-Ph (7c), 2- OH-5-Me-Ph (7d). The cyclic enones 3,4 were obtained by acylation of 2-alkoxy-3,4- dihydro-2H-pyrans with trifluoroacetic anhydride, in chloroform, under catalysis of pyridine (Py), according to the literature. The tetrahydropyridines (6), derived from ethylamines 5a-m was obtained in high yields (90-98%) using methanol or ethanol as solvent at room temperature (r.t.) for a period of 24 hours. For the reaction of cyclic enones 3 and 4 with amines 5i, 5l and 5m the addition of an excess of amines and equimolar amount of triethylamine were need. The second series of tetrahydropyridines (8) was obtained from the reaction of primary arylamines (7a-d) with enones 3 and 4, using methanol or ethanol as solvent at room temperature. The correspondent tetrahydropyridines (8a-d) were obtained with yields ranging from 86 to 98%.