Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos
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: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/17202 |
Resumo: | The present work describes the synthesis, structural study and evaluation of the photophysical properties of novel 6-amino-4-(trifluoromethyl)quinolines, as well as their application in obtaining an unpublished series of 2-alkyl(aryl/heteroaryl)-6-(4-alkyl(aryl)-1H- 1,2,3-triazol-1-yl)-4-(trifluoromethyl)quinolines, 2-alkyl = Me; 2-aryl(heteroaryl) = Ph, 4-Me- C6H4, 4-F-C6H4, 4-NO2-C6H4, 2-furyl; 4-alkyl(aryl) = -CH2OH, -(CH2)5CH3, Ph. Structural and electronic properties were investigated by mass spectrometry (GC/MS), 1H-, 13C- and 19F-NMR and by single-crystal X-ray diffraction. The methodology begins with the synthesis of an unprecedented series of precursors namely (Z)-4-alkyl(aryl)-4-(4-aminophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3), obtained from reactions between 4-methoxy-1,1,1-trifluoro-3-alken-2-ones (1) and pphenylenediamine (2) in yields of 71-87%. The enaminoketones 3, on the other hand, were successfully used in regioselective reactions of intramolecular cyclization in sulfuric acid, bringing the corresponding 6-amino-4-(trifluoromethyl)quinolines (4) in yields of 22-87%. In sequence, the 6-aminoquinoline derivatives 4 had their photophysical properties as absorption, emission, fluorescence quantum yield and Stokes displacement evaluated and related to theoretical calculations (TD-DFT). An initial evaluation of thermal stability using DSC/TGA techniques was also obtained in the present study. The quinolines 4 were also converted to an unpublished series of 6-azido-4-(trifluoromethyl)quinolines (5) in 78-87% yields employing diazonium salts and sodium azide. Finally, the azides originating 5 reacted with different terminal alkynes (6-8) under a copper-catalysed 1,3-dipolar cycloaddition reactions (CuAAC - Click Chemistry), to performed the exclusive synthesis of 1,4-disubstituted 1,2,3-triazolylquinoline derivatives (9-11) in yields of 77-95% (12 examples). |
id |
UFSM_27ef9ec22d7f7e4b3abfdb0f6cd1d8ed |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/17202 |
network_acronym_str |
UFSM |
network_name_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
repository_id_str |
|
spelling |
2019-06-28T15:42:32Z2019-06-28T15:42:32Z2019-02-28http://repositorio.ufsm.br/handle/1/17202The present work describes the synthesis, structural study and evaluation of the photophysical properties of novel 6-amino-4-(trifluoromethyl)quinolines, as well as their application in obtaining an unpublished series of 2-alkyl(aryl/heteroaryl)-6-(4-alkyl(aryl)-1H- 1,2,3-triazol-1-yl)-4-(trifluoromethyl)quinolines, 2-alkyl = Me; 2-aryl(heteroaryl) = Ph, 4-Me- C6H4, 4-F-C6H4, 4-NO2-C6H4, 2-furyl; 4-alkyl(aryl) = -CH2OH, -(CH2)5CH3, Ph. Structural and electronic properties were investigated by mass spectrometry (GC/MS), 1H-, 13C- and 19F-NMR and by single-crystal X-ray diffraction. The methodology begins with the synthesis of an unprecedented series of precursors namely (Z)-4-alkyl(aryl)-4-(4-aminophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3), obtained from reactions between 4-methoxy-1,1,1-trifluoro-3-alken-2-ones (1) and pphenylenediamine (2) in yields of 71-87%. The enaminoketones 3, on the other hand, were successfully used in regioselective reactions of intramolecular cyclization in sulfuric acid, bringing the corresponding 6-amino-4-(trifluoromethyl)quinolines (4) in yields of 22-87%. In sequence, the 6-aminoquinoline derivatives 4 had their photophysical properties as absorption, emission, fluorescence quantum yield and Stokes displacement evaluated and related to theoretical calculations (TD-DFT). An initial evaluation of thermal stability using DSC/TGA techniques was also obtained in the present study. The quinolines 4 were also converted to an unpublished series of 6-azido-4-(trifluoromethyl)quinolines (5) in 78-87% yields employing diazonium salts and sodium azide. Finally, the azides originating 5 reacted with different terminal alkynes (6-8) under a copper-catalysed 1,3-dipolar cycloaddition reactions (CuAAC - Click Chemistry), to performed the exclusive synthesis of 1,4-disubstituted 1,2,3-triazolylquinoline derivatives (9-11) in yields of 77-95% (12 examples).O presente trabalho descreve a síntese, o estudo estrutural e a avalição das propriedades fotofísicas de novas 6-amino-2-alquil(aril/heteroaril)-4-(trifluormetil)quinolinas, além da aplicação destas na obtenção de uma série inédita de 2-alquil(aril/heteroaril)-6-(4-alquil(aril)- 1H-1,2,3-triazol-1-il)-4-(trifluormetil)quinolinas, sendo 2-alquil = Me; 2-aril(heteroaril) = Ph, 4-Me-C6H4, 4-F-C6H4, 4-NO2-C6H4, 2-furil; 4-alquil(aril) = -CH2OH, -(CH2)5CH3, Ph. As propriedades estruturais e eletrônicas foram investigadas por espectrometria de massas (CG/EM), RMN de 1H, 13C e 19F e por de difração de raios X em monocristal. A metodologia inicia com a síntese de uma série inédita de precursores, denominados (Z)-4-alquil(aril)-4-(4-aminofenil)amino)-1,1,1-triflúor-3-alquen-2-onas (3), obtidas a partir de reações entre 4-metóxi-1,1,1-triflúor-3-alquen-2-onas (1) e p-fenilenodiamina (2), com rendimentos de 71-87 %. As enaminocetonas 3, por sua vez, foram utilizadas com sucesso em reações regiosseletivas de ciclização intramolecular em ácido sulfúrico, levando aos respectivos heterociclos 6-amino-4-(trifluormetil)quinolinas (4) em rendimentos de 22-87%. Em sequência, as 6-aminoquinolinas derivadas 4 tiveram suas propriedades fotofísicas de absorção, emissão, rendimento quântico de fluorescência e deslocamento Stokes avaliadas e relacionadas a cálculos teóricos (TD-DFT). Uma avaliação inicial da estabilidade térmica via técnicas de DSC/TGA também foi realizada no presente estudo. As quinolinas 4 foram também convertidas a uma série inédita de 6-azido-4-(trifluormetil)quinolinas (5) em rendimentos de 78-87%, via sais de diazônio e azida de sódio. Finalmente, as azidas originadas 5 foram empregadas, na presença de diferentes alcinos terminais (6-8) e em reações de cicloadição 1,3-dipolares regiosseletivas catalisadas por sais de cobre (CuAAC - Click Chemistry) na síntese exclusiva de sistemas 1H-1,2,3-triazolilquinolínicos 1,4-dissubstituídos (9-11) em rendimentos de 77-95%, sendo representada por 12 exemplares sintéticos.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/openAccessAminoquinolinasTriazóisPropriedades fotofísicasAminoquinolinesTriazolesPhotophysical propertiesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicosSynthesis, photophysical properties of 6-amino-4- (trifluoromethyl)quinolines and their application in the construction of triazolyl-quinoline systemsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Andrighetto, Rosáliahttp://lattes.cnpq.br/9569995843681336Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977http://lattes.cnpq.br/0190842021073920Kappenberg, Yúri Giovane10060000000060006c852ad-d805-43c3-99d6-93a6a86f507c6973021c-5f56-4019-b42b-c4b3a82af0668110e58d-41d8-4edc-affc-2b8fb89a55acbef0481f-6297-4683-a6d3-ce04e5d709e3reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdfDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdfDissertação de Mestradoapplication/pdf20348766http://repositorio.ufsm.br/bitstream/1/17202/1/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf36a4e21543a06d154797b94a4a81c9e2MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/17202/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/17202/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52TEXTDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.txtDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.txtExtracted texttext/plain276395http://repositorio.ufsm.br/bitstream/1/17202/4/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.txt0dbb579d5a7022c060e050a2106955e1MD54THUMBNAILDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.jpgDIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.jpgIM Thumbnailimage/jpeg4550http://repositorio.ufsm.br/bitstream/1/17202/5/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.jpg5ba9ca51c62e1814ed77abbdba7d42deMD551/172022019-06-29 03:02:06.145oai: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:2019-06-29T06:02:06Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
dc.title.alternative.eng.fl_str_mv |
Synthesis, photophysical properties of 6-amino-4- (trifluoromethyl)quinolines and their application in the construction of triazolyl-quinoline systems |
title |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
spellingShingle |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos Kappenberg, Yúri Giovane Aminoquinolinas Triazóis Propriedades fotofísicas Aminoquinolines Triazoles Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
title_full |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
title_fullStr |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
title_full_unstemmed |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
title_sort |
Síntese, propriedades fotofísicas de 6-amino-4- (trifluormetil)quinolinas e sua aplicação na construção de sistemas triazolil-quinolínicos |
author |
Kappenberg, Yúri Giovane |
author_facet |
Kappenberg, Yúri Giovane |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Andrighetto, Rosália |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/9569995843681336 |
dc.contributor.referee2.fl_str_mv |
Iglesias, Bernardo Almeida |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0190842021073920 |
dc.contributor.author.fl_str_mv |
Kappenberg, Yúri Giovane |
contributor_str_mv |
Bonacorso, Helio Gauze Andrighetto, Rosália Iglesias, Bernardo Almeida |
dc.subject.por.fl_str_mv |
Aminoquinolinas Triazóis Propriedades fotofísicas |
topic |
Aminoquinolinas Triazóis Propriedades fotofísicas Aminoquinolines Triazoles Photophysical properties CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Aminoquinolines Triazoles Photophysical properties |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The present work describes the synthesis, structural study and evaluation of the photophysical properties of novel 6-amino-4-(trifluoromethyl)quinolines, as well as their application in obtaining an unpublished series of 2-alkyl(aryl/heteroaryl)-6-(4-alkyl(aryl)-1H- 1,2,3-triazol-1-yl)-4-(trifluoromethyl)quinolines, 2-alkyl = Me; 2-aryl(heteroaryl) = Ph, 4-Me- C6H4, 4-F-C6H4, 4-NO2-C6H4, 2-furyl; 4-alkyl(aryl) = -CH2OH, -(CH2)5CH3, Ph. Structural and electronic properties were investigated by mass spectrometry (GC/MS), 1H-, 13C- and 19F-NMR and by single-crystal X-ray diffraction. The methodology begins with the synthesis of an unprecedented series of precursors namely (Z)-4-alkyl(aryl)-4-(4-aminophenyl)amino)-1,1,1-trifluoro-3-alken-2-ones (3), obtained from reactions between 4-methoxy-1,1,1-trifluoro-3-alken-2-ones (1) and pphenylenediamine (2) in yields of 71-87%. The enaminoketones 3, on the other hand, were successfully used in regioselective reactions of intramolecular cyclization in sulfuric acid, bringing the corresponding 6-amino-4-(trifluoromethyl)quinolines (4) in yields of 22-87%. In sequence, the 6-aminoquinoline derivatives 4 had their photophysical properties as absorption, emission, fluorescence quantum yield and Stokes displacement evaluated and related to theoretical calculations (TD-DFT). An initial evaluation of thermal stability using DSC/TGA techniques was also obtained in the present study. The quinolines 4 were also converted to an unpublished series of 6-azido-4-(trifluoromethyl)quinolines (5) in 78-87% yields employing diazonium salts and sodium azide. Finally, the azides originating 5 reacted with different terminal alkynes (6-8) under a copper-catalysed 1,3-dipolar cycloaddition reactions (CuAAC - Click Chemistry), to performed the exclusive synthesis of 1,4-disubstituted 1,2,3-triazolylquinoline derivatives (9-11) in yields of 77-95% (12 examples). |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-06-28T15:42:32Z |
dc.date.available.fl_str_mv |
2019-06-28T15:42:32Z |
dc.date.issued.fl_str_mv |
2019-02-28 |
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/1/17202 |
url |
http://repositorio.ufsm.br/handle/1/17202 |
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 |
06c852ad-d805-43c3-99d6-93a6a86f507c 6973021c-5f56-4019-b42b-c4b3a82af066 8110e58d-41d8-4edc-affc-2b8fb89a55ac bef0481f-6297-4683-a6d3-ce04e5d709e3 |
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/1/17202/1/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf http://repositorio.ufsm.br/bitstream/1/17202/3/license.txt http://repositorio.ufsm.br/bitstream/1/17202/2/license_rdf http://repositorio.ufsm.br/bitstream/1/17202/4/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.txt http://repositorio.ufsm.br/bitstream/1/17202/5/DIS_PPGQUIMICA_2019_KAPPENBERG_YURI.pdf.jpg |
bitstream.checksum.fl_str_mv |
36a4e21543a06d154797b94a4a81c9e2 2f0571ecee68693bd5cd3f17c1e075df 4460e5956bc1d1639be9ae6146a50347 0dbb579d5a7022c060e050a2106955e1 5ba9ca51c62e1814ed77abbdba7d42de |
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_ |
1793240093323952128 |