Tesis
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas
Fecha
2011-02-25Registro en:
LOBO, Marcio Marçal. Reactions of 2-alkoxy-5-trifluoroacetyl-3,4-dihydro-2H-pyrans with substituted ethylamines and arylamines . 2011. 128 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011.
Autor
Lobo, Marcio Marçal
Institución
Resumen
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%.