Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois

Detalhes bibliográficos
Ano de defesa: 2003
Autor(a) principal: Barichello, Rosemario lattes
Orientador(a): Zanatta, Nilo lattes
Banca de defesa: Zoch, Alana Neto, Siqueira, Geonir Machado, Martins, Marcos Antonio Pinto, Bonacorso, Helio Gauze
Tipo de documento: Tese
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
Síntese orgânica
Química orgânica
Reações químicas
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/26991
Resumo: This work presents the synthesis of α-alkylaminomethylene-γ- lactones 8 (one pot reaction) and α-alkylaminomethylene-δ-lactones 9 (two steps reaction), from the reaction of 3-trichloroacetyl-4,5-dihydrofuran (3) and 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) respectively, with ammonium hydroxide and amines such as methylamine, ethylamine, propylamine, iso-propylamine, allylamine, ethanolamine, dimethylamine, diethylamine, pyrrolidine, piperidine and morpholine in dichloromethane or ethanol at room temperature for 1 hour, in good yields The 1,1,1-trihalo-3-hydroxyalkyl-4-alkylamino-3-buten-2-ones (5-7) were obtained in good yields from the reaction of 3-trihaloacetyl-4,5-dihydrofuran (1, 3) and 5-trihaloacetyl-3,4-dihydro-2H-pyran (2, 4) respectively, whit the same amines, in dichloromethane at room temperature for 1 hour. The reactions of 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) with dimethylamine in the presence of alcohols, as solvent, furnished 3,4-dihydro-2H-piran-5-carboxylic esters 10.
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spelling 2022-11-18T13:11:37Z2022-11-18T13:11:37Z2003-03-21http://repositorio.ufsm.br/handle/1/26991This work presents the synthesis of α-alkylaminomethylene-γ- lactones 8 (one pot reaction) and α-alkylaminomethylene-δ-lactones 9 (two steps reaction), from the reaction of 3-trichloroacetyl-4,5-dihydrofuran (3) and 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) respectively, with ammonium hydroxide and amines such as methylamine, ethylamine, propylamine, iso-propylamine, allylamine, ethanolamine, dimethylamine, diethylamine, pyrrolidine, piperidine and morpholine in dichloromethane or ethanol at room temperature for 1 hour, in good yields The 1,1,1-trihalo-3-hydroxyalkyl-4-alkylamino-3-buten-2-ones (5-7) were obtained in good yields from the reaction of 3-trihaloacetyl-4,5-dihydrofuran (1, 3) and 5-trihaloacetyl-3,4-dihydro-2H-pyran (2, 4) respectively, whit the same amines, in dichloromethane at room temperature for 1 hour. The reactions of 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) with dimethylamine in the presence of alcohols, as solvent, furnished 3,4-dihydro-2H-piran-5-carboxylic esters 10.Este trabalho apresenta a síntese de α-alquil(dialquil)aminometileno-γ- lactonas 8 (um passo reacional) e de α-alquilaminometileno-δ-lactonas 9 (em dois passos reacionais), a partir das reações do 3-tricloroacetil-4,5-diidrofurano (3) e 5- tricloroacetil-3,4-diidro-2H-pirano (4) respectivamente, com hidróxido de amônio e aminas como metilamina, etilamina, propilamina, iso-propilamina, alilamina, etanolamina, dimetilamina, dietilamina, pirrolidina, piperidina e morfolina em diclorometano ou etanol à temperatura ambiente por 1 hora com bons rendimentos. As 1,1,1-trialo-3-hidroxialquil-4-alquilamino-3-buten-2-onas (5-7) foram obtidas com bons rendimentos a partir das reações de 3-trialoacetil-4,5- diidrofurano (1, 3) e 5-trialoacetil-3,4-diidro-2H-pirano (2, 4) respectivamente, com as mesmas aminas acima citadas, em diclorometano a temperatura ambiente por 1 hora. As reações de 5-tricloroacetil-3,4-diidro-2H-pirano (4) com dimetilamina na presença de álcoois, como solvente, forneceu os ésteres 3,4- diidro-2H-pirano-5-carboxílicos 10.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade 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/openAccessQuímicaSíntese orgânicaQuímica orgânicaReações químicasCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAReações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcooisReactions of 3-trihaloacetyl-4,5-dihydrofurans e 5-trihaloacetyl-3,4-dihydro-2H-pyrans with amines and alcohols.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Zoch, Alana NetoSiqueira, Geonir MachadoMartins, Marcos Antonio PintoBonacorso, Helio Gauzehttp://lattes.cnpq.br/8251059080103642Barichello, Rosemario100600000000600600600600600600600233dc1de-ab03-4f57-9b85-e40dc01a2d4f8bc694ad-e02a-4929-88e3-aac4520b61d0a5d677e5-2cb0-4552-a4bb-750f18fc2f0f39dc23ab-ef8b-429d-9c37-d1efcde74a4c61e3f21e-e99f-42f0-88a7-5efcc6352f9448e895f9-11c1-4820-af8e-776681d2fe26reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2003_BARICHELLO_ROSEMARIO.pdfTES_PPGQUÍMICA_2003_BARICHELLO_ROSEMARIO.pdfTese de Doutoradoapplication/pdf2631901http://repositorio.ufsm.br/bitstream/1/26991/1/TES_PPGQU%c3%8dMICA_2003_BARICHELLO_ROSEMARIO.pdfbec87922fb2fcdc2e32bbb32ec0bfb6bMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
dc.title.alternative.eng.fl_str_mv Reactions of 3-trihaloacetyl-4,5-dihydrofurans e 5-trihaloacetyl-3,4-dihydro-2H-pyrans with amines and alcohols.
title Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
spellingShingle Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
Barichello, Rosemario
Química
Síntese orgânica
Química orgânica
Reações químicas
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
title_full Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
title_fullStr Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
title_full_unstemmed Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
title_sort Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
author Barichello, Rosemario
author_facet Barichello, Rosemario
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 Zoch, Alana Neto
dc.contributor.referee2.fl_str_mv Siqueira, Geonir Machado
dc.contributor.referee3.fl_str_mv Martins, Marcos Antonio Pinto
dc.contributor.referee4.fl_str_mv Bonacorso, Helio Gauze
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/8251059080103642
dc.contributor.author.fl_str_mv Barichello, Rosemario
contributor_str_mv Zanatta, Nilo
Zoch, Alana Neto
Siqueira, Geonir Machado
Martins, Marcos Antonio Pinto
Bonacorso, Helio Gauze
dc.subject.por.fl_str_mv Química
Síntese orgânica
Química orgânica
Reações químicas
topic Química
Síntese orgânica
Química orgânica
Reações químicas
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description This work presents the synthesis of α-alkylaminomethylene-γ- lactones 8 (one pot reaction) and α-alkylaminomethylene-δ-lactones 9 (two steps reaction), from the reaction of 3-trichloroacetyl-4,5-dihydrofuran (3) and 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) respectively, with ammonium hydroxide and amines such as methylamine, ethylamine, propylamine, iso-propylamine, allylamine, ethanolamine, dimethylamine, diethylamine, pyrrolidine, piperidine and morpholine in dichloromethane or ethanol at room temperature for 1 hour, in good yields The 1,1,1-trihalo-3-hydroxyalkyl-4-alkylamino-3-buten-2-ones (5-7) were obtained in good yields from the reaction of 3-trihaloacetyl-4,5-dihydrofuran (1, 3) and 5-trihaloacetyl-3,4-dihydro-2H-pyran (2, 4) respectively, whit the same amines, in dichloromethane at room temperature for 1 hour. The reactions of 5- trichloroacetyl-3,4-dihydro-2H-pyran (4) with dimethylamine in the presence of alcohols, as solvent, furnished 3,4-dihydro-2H-piran-5-carboxylic esters 10.
publishDate 2003
dc.date.issued.fl_str_mv 2003-03-21
dc.date.accessioned.fl_str_mv 2022-11-18T13:11:37Z
dc.date.available.fl_str_mv 2022-11-18T13:11:37Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/26991
url http://repositorio.ufsm.br/handle/1/26991
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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:Manancial - Repositório Digital da UFSM
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