Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina

Detalhes bibliográficos
Ano de defesa: 2019
Autor(a) principal: Dilelio, Marina Cardoso lattes
Orientador(a): Silveira, Claudio da Cruz lattes
Banca de defesa: Lenardao, Eder Joao lattes, Zeni, Gilson Rogério lattes
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:
1,3-oxazinas
1,2,3-triazóis
Cumarina
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/16737
Resumo: In this work we developed a methodology for the synthesis of 1,3-oxazines derived from aminocoumarins by the hydroxymethylation/acetalization reaction with aldehydes catalyzed by H2SO4 in aqueous media. The scope and limitations of this methodology were also studied, presenting good results for different substrates. Twelve compounds were obtained with 34 to 90% yields. Subsequently, N-propargylation of one of the 1,3-oxazines was performed, and then the 1,3-dipolar cycloaddition was carried out with different organic azides, obtaining five 1,4-dissubstituted 1,2,3-triazoles, with 65 to 96% yields. Some selected coumpounds presented antifungal activity against Candida krusei, Candida dublieneses, Candida glabrata and Candida tropicalis. The photophysical properties of the compounds were analyzed, presenting high quantum yields of fluorescence (up to Φf = 0.69) and large Stokes shifts (up to 201 nm).
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spelling 2019-06-04T15:03:38Z2019-06-04T15:03:38Z2019-02-19http://repositorio.ufsm.br/handle/1/16737In this work we developed a methodology for the synthesis of 1,3-oxazines derived from aminocoumarins by the hydroxymethylation/acetalization reaction with aldehydes catalyzed by H2SO4 in aqueous media. The scope and limitations of this methodology were also studied, presenting good results for different substrates. Twelve compounds were obtained with 34 to 90% yields. Subsequently, N-propargylation of one of the 1,3-oxazines was performed, and then the 1,3-dipolar cycloaddition was carried out with different organic azides, obtaining five 1,4-dissubstituted 1,2,3-triazoles, with 65 to 96% yields. Some selected coumpounds presented antifungal activity against Candida krusei, Candida dublieneses, Candida glabrata and Candida tropicalis. The photophysical properties of the compounds were analyzed, presenting high quantum yields of fluorescence (up to Φf = 0.69) and large Stokes shifts (up to 201 nm).Neste trabalho foi desenvolvida uma metodologia para a síntese de 1,3- oxazinas derivadas de aminocumarinas em reação de hidroximetilação/ acetalização com aldeídos, catalisada por H2SO4 em meio aquoso. O alcance e limitações desta metodologia também foram estudados, apresentando bons resultados para diferentes substratos. Foram obtidos 12 compostos, com rendimentos de 34 a 90%. Posteriormente, realizou-se a N-propargilação de uma das 1,3-oxazinas e, em seguida, realizou-se a cicloadição 1,3-dipolar com diferentes azidas orgânicas, obtendo-se cinco 1,2,3-triazóis 1,4-dissubstituídos, com rendimentos de 65 a 96%. Alguns compostos selecionados apresentaram atividade antifúngica contra Candida krusei, Candida dublieneses, Candida glabrata e Candida tropicalis. As propriedades fotofísicas dos compostos foram analisadas, apresentando altos rendimentos quânticos de fluorescência (até Φf = 0,69) e grandes deslocamentos de Stokes (até 201 nm).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccess1,3-oxazinas1,2,3-triazóisCumarinaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarinaSynthesis of 1,3-oxazines and 1,2,3-triazoles derived from coumarininfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisSilveira, Claudio da Cruzhttp://lattes.cnpq.br/6152568411858220Lenardao, Eder Joaohttp://lattes.cnpq.br/9974684005171829Zeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937http://lattes.cnpq.br/4095061144644808Dilelio, Marina Cardoso1006000000006003be6a9b9-f9d9-448f-9487-6074331b34a18e943931-146e-4325-b17c-322eeaa0e93bca9fcc2d-9963-41ad-88e6-0a2521e17c649886a90a-985e-4537-825b-61dc895c650areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdfDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdfDissertação de Mestradoapplication/pdf6969214http://repositorio.ufsm.br/bitstream/1/16737/1/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf7505fdc9ab3448bc2d000b64d5298128MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
dc.title.alternative.eng.fl_str_mv Synthesis of 1,3-oxazines and 1,2,3-triazoles derived from coumarin
title Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
spellingShingle Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
Dilelio, Marina Cardoso
1,3-oxazinas
1,2,3-triazóis
Cumarina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
title_full Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
title_fullStr Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
title_full_unstemmed Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
title_sort Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
author Dilelio, Marina Cardoso
author_facet Dilelio, Marina Cardoso
author_role author
dc.contributor.advisor1.fl_str_mv Silveira, Claudio da Cruz
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/6152568411858220
dc.contributor.referee1.fl_str_mv Lenardao, Eder Joao
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/9974684005171829
dc.contributor.referee2.fl_str_mv Zeni, Gilson Rogério
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/2355575631197937
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/4095061144644808
dc.contributor.author.fl_str_mv Dilelio, Marina Cardoso
contributor_str_mv Silveira, Claudio da Cruz
Lenardao, Eder Joao
Zeni, Gilson Rogério
dc.subject.por.fl_str_mv 1,3-oxazinas
1,2,3-triazóis
Cumarina
topic 1,3-oxazinas
1,2,3-triazóis
Cumarina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In this work we developed a methodology for the synthesis of 1,3-oxazines derived from aminocoumarins by the hydroxymethylation/acetalization reaction with aldehydes catalyzed by H2SO4 in aqueous media. The scope and limitations of this methodology were also studied, presenting good results for different substrates. Twelve compounds were obtained with 34 to 90% yields. Subsequently, N-propargylation of one of the 1,3-oxazines was performed, and then the 1,3-dipolar cycloaddition was carried out with different organic azides, obtaining five 1,4-dissubstituted 1,2,3-triazoles, with 65 to 96% yields. Some selected coumpounds presented antifungal activity against Candida krusei, Candida dublieneses, Candida glabrata and Candida tropicalis. The photophysical properties of the compounds were analyzed, presenting high quantum yields of fluorescence (up to Φf = 0.69) and large Stokes shifts (up to 201 nm).
publishDate 2019
dc.date.accessioned.fl_str_mv 2019-06-04T15:03:38Z
dc.date.available.fl_str_mv 2019-06-04T15:03:38Z
dc.date.issued.fl_str_mv 2019-02-19
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/1/16737
url http://repositorio.ufsm.br/handle/1/16737
dc.language.iso.fl_str_mv por
language por
dc.relation.cnpq.fl_str_mv 100600000000
dc.relation.confidence.fl_str_mv 600
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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
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reponame_str Biblioteca Digital de Teses e Dissertações do UFSM
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