Conselho Nacional de Desenvolvimento Científico e Tecnológico / 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%. / Este trabalho apresenta a síntese de duas séries inéditas de 1-alquil(aril)-2-
amino-5-trifluoracetil-1,2,3,4-tetraidropiridinas (6,8), obtidas a partir da reação de 2-
alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos (alcóxi = MeO (3), EtO (4)) com
etilaminas primárias, de fórmula geral R1CH2CH2NH2, onde 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-cicloexenil) (5j), 1-(2-N-morfolil) (5k), 1-(2-Ndietilamino)
(5l) e 2-(1H-indol-3-il) (5m), e arilaminas primárias, de fórmula geral
NH2-Ar sendo, Ar: 4-F-Ph (7a), 2-OMe-Ph (7b), 3-OMe-Ph (7c), 2-OH-4-Me-Ph (7d).
As enonas cíclicas 3, 4 foram obtidas a partir da acilação do 2-alcóxi-3,4-diidro-2Hpiranos
com anidrido trifluoracético, em clorofórmio sob catálise de piridina (Py), de
acordo com a literatura. As tetraidropiridinas (6), derivadas de etilaminas 5a-m,
foram obtidas em ótimos rendimentos (90 - 98%) empregando metanol ou etanol
como solvente, à temperatura ambiente (t.a.) por um período de 24 horas. Para a
reação das enonas cíclicas 3 e 4 com as aminas 5i, 5l e 5m houve a necessidade de
adição de excesso de amina e de quantidade equimolar de trietilamina.
A segunda série de tetraidropiridinas (8) foi obtida a partir da reação das
arilaminas primárias (7a-d) com as enonas 3 e 4, utilizando metanol ou etanol como
solventes à temperatura ambiente. As tetraidropiridinas correspondentes (8a-d)
foram obtidas com rendimentos que variaram de 86 a 98%.
| Identifer | oai:union.ndltd.org:IBICT/oai:repositorio.ufsm.br:1/10487 |
| Date | 25 February 2011 |
| Creators | Lobo, Marcio Marçal |
| Contributors | Zanatta, Nilo, Flores, Alex Fabiani Claro, Amaral, Simone Schneider |
| Publisher | Universidade Federal de Santa Maria, Programa de Pós-Graduação em Química, UFSM, BR, Química |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Repositório Institucional da UFSM, instname:Universidade Federal de Santa Maria, instacron:UFSM |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 100600000000, 400, 500, 500, 500, 300, 233dc1de-ab03-4f57-9b85-e40dc01a2d4f, c6bd5528-d450-4368-8e98-de23fc46b18d, 4d308e51-3866-4274-9e77-03644c9383df, 75993644-ddaa-4ef7-a552-a70d9b33e9a8 |
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