Reações de 3-trialoacetil-4,5-diidrofuranos e 5-trialoacetil-3,4-diidro-2H-piranos com aminas e álcoois
Ano de defesa: | 2003 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
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: | |
Área do conhecimento CNPq: | |
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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network_acronym_str |
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network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
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:Biblioteca Digital de Teses e Dissertações do 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 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/26991 |
url |
http://repositorio.ufsm.br/handle/1/26991 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 |
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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