Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas
Ano de defesa: | 2011 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10487 |
Resumo: | 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%. |
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2011-12-022011-12-022011-02-25LOBO, 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.http://repositorio.ufsm.br/handle/1/10487This 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%.Conselho Nacional de Desenvolvimento Científico e Tecnológicoapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaAlcoxipiranosTetraidropiridinasAza-heterocíclosAlkoxypiransTetrahydropirydineAza-heterocyclesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas Reactions of 2-alkoxy-5-trifluoroacetyl-3,4-dihydro-2H-pyrans with substituted ethylamines and arylamines info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9Flores, Alex Fabiani Clarohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0Amaral, Simone Schneiderhttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4764345U8http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4240255Z6Lobo, Marcio Marçal100600000000400500500500300233dc1de-ab03-4f57-9b85-e40dc01a2d4fc6bd5528-d450-4368-8e98-de23fc46b18d4d308e51-3866-4274-9e77-03644c9383df75993644-ddaa-4ef7-a552-a70d9b33e9a8info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALLOBO, MARCIO MARCAL.pdfapplication/pdf3774601http://repositorio.ufsm.br/bitstream/1/10487/1/LOBO%2c%20MARCIO%20MARCAL.pdf8a5afbe45c847426bf16c27e27eacdd7MD51TEXTLOBO, MARCIO MARCAL.pdf.txtLOBO, MARCIO MARCAL.pdf.txtExtracted texttext/plain143315http://repositorio.ufsm.br/bitstream/1/10487/2/LOBO%2c%20MARCIO%20MARCAL.pdf.txt7cace891cf64abf7fe5cfc8950c5b16eMD52THUMBNAILLOBO, MARCIO MARCAL.pdf.jpgLOBO, MARCIO MARCAL.pdf.jpgIM Thumbnailimage/jpeg6533http://repositorio.ufsm.br/bitstream/1/10487/3/LOBO%2c%20MARCIO%20MARCAL.pdf.jpg997e30fba2436c8ce4021ef603e51a6dMD531/104872017-07-25 12:05:00.8oai:repositorio.ufsm.br:1/10487Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:05Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
dc.title.alternative.eng.fl_str_mv |
Reactions of 2-alkoxy-5-trifluoroacetyl-3,4-dihydro-2H-pyrans with substituted ethylamines and arylamines |
title |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
spellingShingle |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas Lobo, Marcio Marçal Alcoxipiranos Tetraidropiridinas Aza-heterocíclos Alkoxypirans Tetrahydropirydine Aza-heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
title_full |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
title_fullStr |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
title_full_unstemmed |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
title_sort |
Reações de 2-alcóxi-5-trifluoracetil-3,4-diidro-2H-piranos com etilaminas substituídas e arilaminas |
author |
Lobo, Marcio Marçal |
author_facet |
Lobo, Marcio Marçal |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783100P9 |
dc.contributor.referee1.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0 |
dc.contributor.referee2.fl_str_mv |
Amaral, Simone Schneider |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4764345U8 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4240255Z6 |
dc.contributor.author.fl_str_mv |
Lobo, Marcio Marçal |
contributor_str_mv |
Zanatta, Nilo Flores, Alex Fabiani Claro Amaral, Simone Schneider |
dc.subject.por.fl_str_mv |
Alcoxipiranos Tetraidropiridinas Aza-heterocíclos |
topic |
Alcoxipiranos Tetraidropiridinas Aza-heterocíclos Alkoxypirans Tetrahydropirydine Aza-heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Alkoxypirans Tetrahydropirydine Aza-heterocycles |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
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%. |
publishDate |
2011 |
dc.date.accessioned.fl_str_mv |
2011-12-02 |
dc.date.available.fl_str_mv |
2011-12-02 |
dc.date.issued.fl_str_mv |
2011-02-25 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
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. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10487 |
identifier_str_mv |
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. |
url |
http://repositorio.ufsm.br/handle/1/10487 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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400 500 500 500 300 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
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UFSM |
dc.publisher.country.fl_str_mv |
BR |
dc.publisher.department.fl_str_mv |
Química |
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Universidade Federal de Santa Maria |
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