Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas
Ano de defesa: | 2003 |
---|---|
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
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/26805 |
Resumo: | This work presents a three steps synthetic route to obtain 1,3- oxazin-2-ones, from the β-alkoxyvinyl trihalomethyl ketones of general formula X3CC(O)CH=C(R)OR¹, where R = H, CH3, Ph, p-Me-Ph; R¹ = Me, Et. β-alkoxyvinyl trihalomethyl ketones were obtained from the acylation reaction of acetals or enolethers with trifluoracetic anhydride and trichloroacetil chloride. In a first step, the substitution reaction on the C-β of the β- alkoxyvinyl trihalomethyl cetones with ethyl carbamate furnished the corresponding enamino compounds. This compounds, in a second step, underwent reduction reaction with NaBH4, leading to the respective γ- aminoalcohols. In a third step, the γ-aminoalcohols were submitted to cyclization reaction with triphosgene furnishing a new series of 1,3-oxazin-2-ones. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2022-11-08T19:17:47Z2022-11-08T19:17:47Z2003-03http://repositorio.ufsm.br/handle/1/26805This work presents a three steps synthetic route to obtain 1,3- oxazin-2-ones, from the β-alkoxyvinyl trihalomethyl ketones of general formula X3CC(O)CH=C(R)OR¹, where R = H, CH3, Ph, p-Me-Ph; R¹ = Me, Et. β-alkoxyvinyl trihalomethyl ketones were obtained from the acylation reaction of acetals or enolethers with trifluoracetic anhydride and trichloroacetil chloride. In a first step, the substitution reaction on the C-β of the β- alkoxyvinyl trihalomethyl cetones with ethyl carbamate furnished the corresponding enamino compounds. This compounds, in a second step, underwent reduction reaction with NaBH4, leading to the respective γ- aminoalcohols. In a third step, the γ-aminoalcohols were submitted to cyclization reaction with triphosgene furnishing a new series of 1,3-oxazin-2-ones.Este trabalho apresenta uma rota sintética em três etapas para obtenção de oito 1,3-oxazin-2-onas 6-trialometil substituídas inéditas a partir de β-alcoxivinil trialometil cetonas de fórmula geral X3CC(O)CH=C(R)OR¹, onde R = H, CH3, Ph, p-Me-Ph; R¹ = Me, Et. As β-alcoxivinil trialometil cetonas utilizadas foram obtidas através de acilação de acetais ou enol éteres com anidrido trifluoracético e cloreto de tricloro acetila. Em uma primeira etapa, a reação de substituição no carbono β das β-alcoxivinil trialometil cetonas com carbamato de etila levaram à obtenção dos correspondentes enamino compostos, os quais, em uma segunda etapa, sofreram reações de redução com NaBH4, obtendo-se os respetivos γ-amino álcoois. Em uma terceira etapa, os γ-amino álcoois foram submetidos à ciclização com trifosgênio fornecendo uma série inédita de 1,3-oxazin-2- onas.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessQuímica orgânicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onasSynthesis of 3-carboxyethyl-6-trihalomethyl–[1,3]-oxazin-2-onesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Bonacorso, Helio GauzeFlores, Alex Fabiani Clarohttp://lattes.cnpq.br/7419859603031477Borchhardt, Deise Moreira100600000000600600600600600233dc1de-ab03-4f57-9b85-e40dc01a2d4f39c1858f-954e-413b-8a85-348d22acdd5cdbcce58b-96b0-4f45-a78d-ca6f339e038d17a00027-8984-4561-9228-46697f540c2breponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUÍMICA_2003_BORCHHARDT_DEISE.pdfDIS_PPGQUÍMICA_2003_BORCHHARDT_DEISE.pdfDissertação de Mestradoapplication/pdf928784http://repositorio.ufsm.br/bitstream/1/26805/1/DIS_PPGQU%c3%8dMICA_2003_BORCHHARDT_DEISE.pdf8f0b8ab86b1c9dafb875331c9be6d04dMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/26805/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/26805/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/268052022-11-08 16:17:47.648oai:repositorio.ufsm.br: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 Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-11-08T19:17:47Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 3-carboxyethyl-6-trihalomethyl–[1,3]-oxazin-2-ones |
title |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
spellingShingle |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas Borchhardt, Deise Moreira Química orgânica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
title_full |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
title_fullStr |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
title_full_unstemmed |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
title_sort |
Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas |
author |
Borchhardt, Deise Moreira |
author_facet |
Borchhardt, Deise Moreira |
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 |
Bonacorso, Helio Gauze |
dc.contributor.referee2.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7419859603031477 |
dc.contributor.author.fl_str_mv |
Borchhardt, Deise Moreira |
contributor_str_mv |
Zanatta, Nilo Bonacorso, Helio Gauze Flores, Alex Fabiani Claro |
dc.subject.por.fl_str_mv |
Química orgânica |
topic |
Química orgânica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work presents a three steps synthetic route to obtain 1,3- oxazin-2-ones, from the β-alkoxyvinyl trihalomethyl ketones of general formula X3CC(O)CH=C(R)OR¹, where R = H, CH3, Ph, p-Me-Ph; R¹ = Me, Et. β-alkoxyvinyl trihalomethyl ketones were obtained from the acylation reaction of acetals or enolethers with trifluoracetic anhydride and trichloroacetil chloride. In a first step, the substitution reaction on the C-β of the β- alkoxyvinyl trihalomethyl cetones with ethyl carbamate furnished the corresponding enamino compounds. This compounds, in a second step, underwent reduction reaction with NaBH4, leading to the respective γ- aminoalcohols. In a third step, the γ-aminoalcohols were submitted to cyclization reaction with triphosgene furnishing a new series of 1,3-oxazin-2-ones. |
publishDate |
2003 |
dc.date.issued.fl_str_mv |
2003-03 |
dc.date.accessioned.fl_str_mv |
2022-11-08T19:17:47Z |
dc.date.available.fl_str_mv |
2022-11-08T19:17:47Z |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/26805 |
url |
http://repositorio.ufsm.br/handle/1/26805 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 |
dc.relation.authority.fl_str_mv |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
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