Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC
Ano de defesa: | 2013 |
---|---|
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10548 |
Resumo: | This paper presents a synthetic strategy for the preparation of two series of novel 1,6-disubstituted Ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate from the reaction of the cyclic enone ethyl 2-(6-ethoxy-5 ,6-dihydro-4H-pyran-3-yl)-2-oxoacetate and aryl amines as precursors, following an ANRORC type mechanism. The substituents of the amines are the flowing: C6H5, C6H4-4-Cl, 3-Cl-C6H4,-C6H3 3,4-Cl 2,4-Cl-C6H3 3-F-C6H4, 2-F-C6H4 3-Me-C6H4, 2-OMe-C6H4, 4-Br-C6H4. The ethyl 1-aryl-6-arylamino-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate were synthesized in a simple procedure, using room temperature and 24 h as the reaction condition. The products from this series were obtained with satisfactory yields between 45-93% and the purification thereof was performed by recrystallization. To obtain the Ethyl 1-amino-6-ethoxy-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate the ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate was reacted withan equivalent of primary amine in ethanol and an equivalent of pyridine was required. The reaction was refluxed for 48h. Purification of this series of compounds was accomplished by eluting the compound through a chromatographic column. The products were obtained in good yields ranging from 66-86%. |
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2017-05-182017-05-182013-03-18PRETTO, Leida de Mendonça. ANRORC syntesis of 1,6-disubstituted ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate. 2013. 136 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.http://repositorio.ufsm.br/handle/1/10548This paper presents a synthetic strategy for the preparation of two series of novel 1,6-disubstituted Ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate from the reaction of the cyclic enone ethyl 2-(6-ethoxy-5 ,6-dihydro-4H-pyran-3-yl)-2-oxoacetate and aryl amines as precursors, following an ANRORC type mechanism. The substituents of the amines are the flowing: C6H5, C6H4-4-Cl, 3-Cl-C6H4,-C6H3 3,4-Cl 2,4-Cl-C6H3 3-F-C6H4, 2-F-C6H4 3-Me-C6H4, 2-OMe-C6H4, 4-Br-C6H4. The ethyl 1-aryl-6-arylamino-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate were synthesized in a simple procedure, using room temperature and 24 h as the reaction condition. The products from this series were obtained with satisfactory yields between 45-93% and the purification thereof was performed by recrystallization. To obtain the Ethyl 1-amino-6-ethoxy-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate the ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate was reacted withan equivalent of primary amine in ethanol and an equivalent of pyridine was required. The reaction was refluxed for 48h. Purification of this series of compounds was accomplished by eluting the compound through a chromatographic column. The products were obtained in good yields ranging from 66-86%.Este trabalho apresenta uma estratégia sintética para a preparação de duas séries inéditas de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas à partir da enona cíclica 2-(6-etóxi-5,6-diidro-4H-piran-3-il)-2-oxoacetato de etila e aril aminas como precursores, através de um único passo reacional. Essas aminas possuem diferentes substituintes, sendo eles: C6H5, 4-Cl-C6H4, 3-Cl-C6H4, 3,4-Cl-C6H3, 2,4-Cl-C6H3, 3-F-C6H4, 2-F-C6H4, 3-Me-C6H4, 2-OMe-C6H4, 4-Br-C6H4. As 1-aril-6-arilamino-2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila, foram sintetizadas de maneira simples, utilizando temperatura ambiente e 24h como condição reacional. Os produtos dessa série foram obtidos com rendimentos satisfatórios, entre 45-93% e a purificação dos mesmos foi feita através de recristalização. Para obtenção das 1-aril-6-etóxi-2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila, foi necessário o uso equimolar de piridina como reagente no decorrer de todo o processo reacional, contando ainda com temperatura de refluxo e um período de 48h. A purificação dos compostos desta série foi efetuada de forma eficiente, sendo realizada através da eluição dos compostos através de uma coluna cromatográfica. Os produtos foram obtidos com bons rendimentos, variando entre 66-86%. Todos os produtos sintetizados neste trabalho foram obtidos com alto grau de pureza e identificados por Ressonância Magnética Nuclear de Hidrogênio, Ressonância Magnética Nuclear de Carbono-13, Espectrometria de Massa, Análise elementar e Massa de alta resolução.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaTetraidropiridinasEnona cíclicaAril aminasCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORCANRORC syntesis of 1,6-disubstituted ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetateinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Flores, Alex Fabiani Clarohttp://lattes.cnpq.br/1159954352174167Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397http://lattes.cnpq.br/4376226225043426Pretto, Leida de Mendonça100600000000400500300500500233dc1de-ab03-4f57-9b85-e40dc01a2d4f098c50ac-cd5b-4b49-ae5f-314a1d732d6a4d308e51-3866-4274-9e77-03644c9383df079f4612-cd36-4354-af6f-25f7736dccd2info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALPRETTO, LEIDA DE MENDONCA.pdfapplication/pdf5270234http://repositorio.ufsm.br/bitstream/1/10548/1/PRETTO%2c%20LEIDA%20DE%20MENDONCA.pdf3a81e7e66335d6281701d5268d6162caMD51TEXTPRETTO, LEIDA DE MENDONCA.pdf.txtPRETTO, LEIDA DE MENDONCA.pdf.txtExtracted texttext/plain137751http://repositorio.ufsm.br/bitstream/1/10548/2/PRETTO%2c%20LEIDA%20DE%20MENDONCA.pdf.txt8258746a20a184a7091b3b16477b9c6aMD52THUMBNAILPRETTO, LEIDA DE MENDONCA.pdf.jpgPRETTO, LEIDA DE MENDONCA.pdf.jpgIM Thumbnailimage/jpeg6306http://repositorio.ufsm.br/bitstream/1/10548/3/PRETTO%2c%20LEIDA%20DE%20MENDONCA.pdf.jpg3b6a82643dc8c5a6d86e2fde273b8c4fMD531/105482023-06-20 08:31:32.235oai:repositorio.ufsm.br:1/10548Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-06-20T11:31:32Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
dc.title.alternative.eng.fl_str_mv |
ANRORC syntesis of 1,6-disubstituted ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate |
title |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
spellingShingle |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC Pretto, Leida de Mendonça Tetraidropiridinas Enona cíclica Aril aminas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
title_full |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
title_fullStr |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
title_full_unstemmed |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
title_sort |
Síntese de 2-(1,4,5,6-tetraidropiridin-3-il)-2-oxoacetato de etila 1,6-dissubstituídas via mecanismo ANRORC |
author |
Pretto, Leida de Mendonça |
author_facet |
Pretto, Leida de Mendonça |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/1159954352174167 |
dc.contributor.referee2.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4376226225043426 |
dc.contributor.author.fl_str_mv |
Pretto, Leida de Mendonça |
contributor_str_mv |
Zanatta, Nilo Flores, Alex Fabiani Claro Fantinel, Leonardo |
dc.subject.por.fl_str_mv |
Tetraidropiridinas Enona cíclica Aril aminas |
topic |
Tetraidropiridinas Enona cíclica Aril aminas CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This paper presents a synthetic strategy for the preparation of two series of novel 1,6-disubstituted Ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate from the reaction of the cyclic enone ethyl 2-(6-ethoxy-5 ,6-dihydro-4H-pyran-3-yl)-2-oxoacetate and aryl amines as precursors, following an ANRORC type mechanism. The substituents of the amines are the flowing: C6H5, C6H4-4-Cl, 3-Cl-C6H4,-C6H3 3,4-Cl 2,4-Cl-C6H3 3-F-C6H4, 2-F-C6H4 3-Me-C6H4, 2-OMe-C6H4, 4-Br-C6H4. The ethyl 1-aryl-6-arylamino-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate were synthesized in a simple procedure, using room temperature and 24 h as the reaction condition. The products from this series were obtained with satisfactory yields between 45-93% and the purification thereof was performed by recrystallization. To obtain the Ethyl 1-amino-6-ethoxy-2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate the ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate was reacted withan equivalent of primary amine in ethanol and an equivalent of pyridine was required. The reaction was refluxed for 48h. Purification of this series of compounds was accomplished by eluting the compound through a chromatographic column. The products were obtained in good yields ranging from 66-86%. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-03-18 |
dc.date.accessioned.fl_str_mv |
2017-05-18 |
dc.date.available.fl_str_mv |
2017-05-18 |
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 |
PRETTO, Leida de Mendonça. ANRORC syntesis of 1,6-disubstituted ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate. 2013. 136 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10548 |
identifier_str_mv |
PRETTO, Leida de Mendonça. ANRORC syntesis of 1,6-disubstituted ethyl 2-(1,4,5,6-tetrahydropyridin-3-yl)-2-oxoacetate. 2013. 136 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. |
url |
http://repositorio.ufsm.br/handle/1/10548 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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400 500 300 500 500 |
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Universidade Federal de Santa Maria |
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UFSM |
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Universidade Federal de Santa Maria |
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