Síntese de 3-carboxietil-6-trialometil-[1,3]-oxazin-2-onas

Detalhes bibliográficos
Ano de defesa: 2003
Autor(a) principal: Borchhardt, Deise Moreira lattes
Orientador(a): Zanatta, Nilo lattes
Banca de defesa: Bonacorso, Helio Gauze, Flores, Alex Fabiani Claro
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:
Química orgânica
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
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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spelling 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
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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
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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 reponame:Biblioteca Digital de Teses e Dissertações do UFSM
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