Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina

Detalhes bibliográficos
Ano de defesa: 2017
Autor(a) principal: Padilha, Gustavo lattes
Orientador(a): Silveira, Claudio da Cruz lattes
Banca de defesa: Mostardeiro, Marco Aurélio lattes, Rodrigues, Oscar Endrigo Dorneles lattes, Silveira, Gustavo Pozza lattes, Gariani, Rogério Aparecido lattes
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:
Química
Seneletos
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/12740
Resumo: This work describes the synthesis of pyrrolo[3,2-c]coumarins from 4-aminophenylcoumarins and nitrostyrenes (17 examples), which were obtained in yelds between 6 and 76 % in a reaction catalised by PTSA.H2O and under solvent-free conditions. These pyrrolocoumarins proved to be suitable substrates for further functionalization toward more complex polycyclic structures. A new derivative was synthesized by annulation reaction with diphenylacetylene and had eletrochemical and photophysical properties evaluated. Subsequently, novel selenocoumarins were prepared from diselenides and 4-tosylcoumarin (33 examples) in mild conditions and short reaction times. Products were obtained mostly in good yelds (22 to 85 %). Some selected examples of these novel selenides showed antioxidant properties on mice brain tissue.
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spelling 2018-03-16T15:26:00Z2018-03-16T15:26:00Z2017-03-08http://repositorio.ufsm.br/handle/1/12740This work describes the synthesis of pyrrolo[3,2-c]coumarins from 4-aminophenylcoumarins and nitrostyrenes (17 examples), which were obtained in yelds between 6 and 76 % in a reaction catalised by PTSA.H2O and under solvent-free conditions. These pyrrolocoumarins proved to be suitable substrates for further functionalization toward more complex polycyclic structures. A new derivative was synthesized by annulation reaction with diphenylacetylene and had eletrochemical and photophysical properties evaluated. Subsequently, novel selenocoumarins were prepared from diselenides and 4-tosylcoumarin (33 examples) in mild conditions and short reaction times. Products were obtained mostly in good yelds (22 to 85 %). Some selected examples of these novel selenides showed antioxidant properties on mice brain tissue.Este trabalho descreve, inicialmente, a síntese de pirrolo[3,2-c]cumarinas a partir de 4-fenilaminocumarinas e nitroestirenos (17 exemplos) que foram obtidos com rendimentos entre 6 e 76 % após uma reação catalisada por PTSA.H2O sem solvente. Essas pirrolocumarinas sintetizadas podem ser utilizados como material de partida para a síntese de estruturas policíclicas de maior complexidade, onde, sintetizou-se um novo derivado após reação de anelação com difenilacetileno que teve suas propriedades eletroquímicas e fotofísicas estudadas. Posteriormente, preparou-se novos selenetos derivados da cumarina a partir de disselenetos e derivados da 4-tosilcumarina (33 exemplos) em condições brandas e curtos tempos reacionais, onde os produtos foram obtidos em sua maioria em bons rendimentos, variando de 22 a 85 %. Alguns exemplos selecionados desses novos selenetos apresentaram atividade antioxidante em tecido cerebral de camundongos.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessQuímicaSeneletosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarinaSynthesis of pyrrolocoumarins from nitrostyrenes and novel selenides derived from coumarininfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisSilveira, Claudio da Cruzhttp://lattes.cnpq.br/6152568411858220Mostardeiro, Marco Auréliohttp://lattes.cnpq.br/6195396264565980Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Silveira, Gustavo Pozzahttp://lattes.cnpq.br/4546630251833765Gariani, Rogério Aparecidohttp://lattes.cnpq.br/7296497637303200http://lattes.cnpq.br/2706309455546776Padilha, Gustavo1006000000006003be6a9b9-f9d9-448f-9487-6074331b34a100e14f94-a103-4a50-a100-d3030af8c6cc259f023a-7aaf-4ad9-a61c-33a96fa11e74f0970438-aab7-4bbe-8d26-13140ae7303ae08dc8bc-dbea-4571-878c-d715f176d98f48ca3883-3fe4-4e29-b2b6-6f6985248499reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2017_PADILHA_GUSTAVO.pdfTES_PPGQUIMICA_2017_PADILHA_GUSTAVO.pdfTese de Doutoradoapplication/pdf10043786http://repositorio.ufsm.br/bitstream/1/12740/1/TES_PPGQUIMICA_2017_PADILHA_GUSTAVO.pdf1e80b025ca73c67f30d4abf155bfb912MD51LICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
dc.title.alternative.eng.fl_str_mv Synthesis of pyrrolocoumarins from nitrostyrenes and novel selenides derived from coumarin
title Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
spellingShingle Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
Padilha, Gustavo
Química
Seneletos
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
title_full Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
title_fullStr Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
title_full_unstemmed Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
title_sort Síntese de pirrolocumarinas via nitroestirenos e de novos selenetos derivados da cumarina
author Padilha, Gustavo
author_facet Padilha, Gustavo
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 Mostardeiro, Marco Aurélio
dc.contributor.referee1Lattes.fl_str_mv http://lattes.cnpq.br/6195396264565980
dc.contributor.referee2.fl_str_mv Rodrigues, Oscar Endrigo Dorneles
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/6536519955416085
dc.contributor.referee3.fl_str_mv Silveira, Gustavo Pozza
dc.contributor.referee3Lattes.fl_str_mv http://lattes.cnpq.br/4546630251833765
dc.contributor.referee4.fl_str_mv Gariani, Rogério Aparecido
dc.contributor.referee4Lattes.fl_str_mv http://lattes.cnpq.br/7296497637303200
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/2706309455546776
dc.contributor.author.fl_str_mv Padilha, Gustavo
contributor_str_mv Silveira, Claudio da Cruz
Mostardeiro, Marco Aurélio
Rodrigues, Oscar Endrigo Dorneles
Silveira, Gustavo Pozza
Gariani, Rogério Aparecido
dc.subject.por.fl_str_mv Química
Seneletos
topic Química
Seneletos
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description This work describes the synthesis of pyrrolo[3,2-c]coumarins from 4-aminophenylcoumarins and nitrostyrenes (17 examples), which were obtained in yelds between 6 and 76 % in a reaction catalised by PTSA.H2O and under solvent-free conditions. These pyrrolocoumarins proved to be suitable substrates for further functionalization toward more complex polycyclic structures. A new derivative was synthesized by annulation reaction with diphenylacetylene and had eletrochemical and photophysical properties evaluated. Subsequently, novel selenocoumarins were prepared from diselenides and 4-tosylcoumarin (33 examples) in mild conditions and short reaction times. Products were obtained mostly in good yelds (22 to 85 %). Some selected examples of these novel selenides showed antioxidant properties on mice brain tissue.
publishDate 2017
dc.date.issued.fl_str_mv 2017-03-08
dc.date.accessioned.fl_str_mv 2018-03-16T15:26:00Z
dc.date.available.fl_str_mv 2018-03-16T15:26:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/doctoralThesis
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dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/12740
url http://repositorio.ufsm.br/handle/1/12740
dc.language.iso.fl_str_mv por
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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/
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rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 International
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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
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reponame_str Biblioteca Digital de Teses e Dissertações do UFSM
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