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

Detalhes bibliográficos
Autor(a) principal: Dilelio, Marina Cardoso
Data de Publicação: 2019
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Manancial - Repositório Digital da UFSM
Texto Completo: 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 Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarinaSynthesis of 1,3-oxazines and 1,2,3-triazoles derived from coumarin1,3-oxazinas1,2,3-triazóisCumarinaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn 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).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESNeste 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).Universidade Federal de Santa MariaBrasilQuímicaUFSMPrograma de Pós-Graduação em QuímicaCentro de Ciências Naturais e ExatasSilveira, Claudio da Cruzhttp://lattes.cnpq.br/6152568411858220Lenardao, Eder Joaohttp://lattes.cnpq.br/9974684005171829Zeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Dilelio, Marina Cardoso2019-06-04T15:03:38Z2019-06-04T15:03:38Z2019-02-19info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://repositorio.ufsm.br/handle/1/16737porAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2022-09-05T13:53:45Zoai:repositorio.ufsm.br:1/16737Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2024-07-29T10:48:22.335380Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.none.fl_str_mv Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
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.none.fl_str_mv Silveira, Claudio da Cruz
http://lattes.cnpq.br/6152568411858220
Lenardao, Eder Joao
http://lattes.cnpq.br/9974684005171829
Zeni, Gilson Rogério
http://lattes.cnpq.br/2355575631197937
dc.contributor.author.fl_str_mv Dilelio, Marina Cardoso
dc.subject.por.fl_str_mv 1,3-oxazinas
1,2,3-triazóis
Cumarina
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic 1,3-oxazinas
1,2,3-triazóis
Cumarina
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.none.fl_str_mv 2019-06-04T15:03:38Z
2019-06-04T15:03:38Z
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.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.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Universidade Federal de Santa Maria
Brasil
Química
UFSM
Programa de Pós-Graduação em Química
Centro de Ciências Naturais e Exatas
publisher.none.fl_str_mv Universidade Federal de Santa Maria
Brasil
Química
UFSM
Programa de Pós-Graduação em Química
Centro de Ciências Naturais e Exatas
dc.source.none.fl_str_mv reponame:Manancial - Repositório Digital da UFSM
instname:Universidade Federal de Santa Maria (UFSM)
instacron:UFSM
instname_str Universidade Federal de Santa Maria (UFSM)
instacron_str UFSM
institution UFSM
reponame_str Manancial - Repositório Digital da UFSM
collection Manancial - Repositório Digital da UFSM
repository.name.fl_str_mv Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)
repository.mail.fl_str_mv atendimento.sib@ufsm.br||tedebc@gmail.com
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