Síntese de 1,3-oxazinas e 1,2,3-triazóis derivados de cumarina
Ano de defesa: | 2019 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
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: | |
Área do conhecimento CNPq: | |
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). |
id |
UFSM_757b6eb7bd08780f1ac2e2a43107fcd5 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/16737 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
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; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/16737/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/16737/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53TEXTDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.txtDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.txtExtracted texttext/plain125355http://repositorio.ufsm.br/bitstream/1/16737/4/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.txt4b247a141c9bf7923031324871aa19e9MD54THUMBNAILDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.jpgDIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.jpgIM Thumbnailimage/jpeg5391http://repositorio.ufsm.br/bitstream/1/16737/5/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.jpgee15eb0e7fba053d5c0add2f8951a945MD551/167372022-09-05 10:53:45.426oai: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:2022-09-05T13:53:45Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
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 |
dc.relation.authority.fl_str_mv |
3be6a9b9-f9d9-448f-9487-6074331b34a1 8e943931-146e-4325-b17c-322eeaa0e93b ca9fcc2d-9963-41ad-88e6-0a2521e17c64 9886a90a-985e-4537-825b-61dc895c650a |
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 instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/16737/1/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf http://repositorio.ufsm.br/bitstream/1/16737/2/license_rdf http://repositorio.ufsm.br/bitstream/1/16737/3/license.txt http://repositorio.ufsm.br/bitstream/1/16737/4/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.txt http://repositorio.ufsm.br/bitstream/1/16737/5/DIS_PPGQUIMICA_2019_DILELIO_MARINA.pdf.jpg |
bitstream.checksum.fl_str_mv |
7505fdc9ab3448bc2d000b64d5298128 4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df 4b247a141c9bf7923031324871aa19e9 ee15eb0e7fba053d5c0add2f8951a945 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1793240165162942464 |