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

• Autor(a) principal: Lobo, Marcio Marçal
• Data de Publicação: 2011
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: Manancial - Repositório Digital da UFSM
• dARK ID: ark:/26339/0013000014r46
• Texto Completo: http://repositorio.ufsm.br/handle/1/10487
• topic: Alcoxipiranos; Tetraidropiridinas; Aza-heterocíclos; Alkoxypirans; Tetrahydropirydine; Aza-heterocycles; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA

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%.