Síntese de novos pirróis derivados de aminocumarinas

Detalhes bibliográficos
Ano de defesa: 2018
Autor(a) principal: Brites, Nathan Pinto lattes
Orientador(a): Silveira, Claudio da Cruz lattes
Banca de defesa: Lenardao, Eder Joao lattes, Schumacher, Ricardo Frederico 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:
Clauson-Kaas
Paal-Knorr
Aminocumarina
Pirróis e tiocianação
Palavras-chave em Inglês:
Aminocoumarines
Pyrroles and thiocyanation
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/16272
Resumo: In this work, the synthesis of new pyrroles derived from aminocoumarins was developed. First, the synthesis of pyrroles derived from 4-amino-2H-chromen-2-one was carried out by the Paal-Knorr and Clauson-Kaas reactions, using anhydrous cerium chloride and PTSA.H2O as catalysts. The reaction was carried out under conventional heating and microwave irradiation, using 2,5-hexanedione (1.2 equiv.) and 2,5-dimethoxy-THF (3 equiv.) in toluene and acetonitrile as solvents, respectively. A novel methodology for synthesizing pyrroles from 6-amino-2H-chromen-2-one was also explored. In this synthesis, anhydrous cerium chloride as catalyst and acetonitrile was used as solvent at reflux temperature. Finally, it was evaluated the functionalization of this class of compounds, performing the thiocyanation of selected pyrroles.
id UFSM_0f5c43affebaba7ddcaba47f03a8ee83
oai_identifier_str oai:repositorio.ufsm.br:1/16272
network_acronym_str UFSM
network_name_str Biblioteca Digital de Teses e Dissertações do UFSM
repository_id_str
spelling 2019-04-22T12:05:29Z2019-04-22T12:05:29Z2018-07-19http://repositorio.ufsm.br/handle/1/16272In this work, the synthesis of new pyrroles derived from aminocoumarins was developed. First, the synthesis of pyrroles derived from 4-amino-2H-chromen-2-one was carried out by the Paal-Knorr and Clauson-Kaas reactions, using anhydrous cerium chloride and PTSA.H2O as catalysts. The reaction was carried out under conventional heating and microwave irradiation, using 2,5-hexanedione (1.2 equiv.) and 2,5-dimethoxy-THF (3 equiv.) in toluene and acetonitrile as solvents, respectively. A novel methodology for synthesizing pyrroles from 6-amino-2H-chromen-2-one was also explored. In this synthesis, anhydrous cerium chloride as catalyst and acetonitrile was used as solvent at reflux temperature. Finally, it was evaluated the functionalization of this class of compounds, performing the thiocyanation of selected pyrroles.Neste trabalho desenvolveu-se a síntese de novos pirróis derivados de aminocumarinas. Primeiramente, realizou-se, a síntese de pirróis derivados de 4- amino-2H-cromen-2-onas através das reações de Paal-Knorr e Clauson-Kaas, empregando cloreto de cério anidro e PTSA.H2O como catalisadores. A reação foi realizada sob aquecimento convencional e sob irradiação de micro-ondas, utilizandose 2,5-hexanodiona (1,2 equiv.) e 2,5-dimetóxi-THF (3 equiv.) em tolueno e acetonitrila como solventes, respectivamente. Explorou-se, também, uma nova metodologia para a síntese de pirróis a partir da 6- amino-2H-cromen-2-ona. Nesta síntese, utilizou-se cloreto de cério anidro como catalisador e acetonitrila como solvente, á temperatura de refluxo. Por fim, foi realizada a funcionalização dos compostos preparados, realizando-se a tiocianação de pirróis selecionados.porUniversidade 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/openAccessClauson-KaasPaal-KnorrAminocumarinaPirróis e tiocianaçãoAminocoumarinesPyrroles and thiocyanationCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de novos pirróis derivados de aminocumarinasSynthesis of new pyrroles derived from aminocumarinsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisSilveira, Claudio da Cruzhttp://lattes.cnpq.br/6152568411858220Lenardao, Eder Joaohttp://lattes.cnpq.br/9974684005171829Schumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135http://lattes.cnpq.br/8468135456169967Brites, Nathan Pinto1006000000006003be6a9b9-f9d9-448f-9487-6074331b34a1f693f370-52ca-470d-87a4-5ee7a71a21f2ca9fcc2d-9963-41ad-88e6-0a2521e17c646a26f817-0d52-41d8-9183-c785c92d110areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdfDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdfDissertação de Mestradoapplication/pdf6669561http://repositorio.ufsm.br/bitstream/1/16272/1/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf898b3772191ceb2d30fbceccf2d9025bMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/16272/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/16272/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD53TEXTDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.txtDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.txtExtracted texttext/plain108414http://repositorio.ufsm.br/bitstream/1/16272/4/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.txte43c07220b8c8eda5ba7fbe91f573f30MD54THUMBNAILDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.jpgDIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.jpgIM Thumbnailimage/jpeg4148http://repositorio.ufsm.br/bitstream/1/16272/5/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.jpg5c1e4c2943035402a53d29f5779e811bMD551/162722019-04-23 03:02:14.195oai: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:2019-04-23T06:02:14Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese de novos pirróis derivados de aminocumarinas
dc.title.alternative.eng.fl_str_mv Synthesis of new pyrroles derived from aminocumarins
title Síntese de novos pirróis derivados de aminocumarinas
spellingShingle Síntese de novos pirróis derivados de aminocumarinas
Brites, Nathan Pinto
Clauson-Kaas
Paal-Knorr
Aminocumarina
Pirróis e tiocianação
Aminocoumarines
Pyrroles and thiocyanation
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de novos pirróis derivados de aminocumarinas
title_full Síntese de novos pirróis derivados de aminocumarinas
title_fullStr Síntese de novos pirróis derivados de aminocumarinas
title_full_unstemmed Síntese de novos pirróis derivados de aminocumarinas
title_sort Síntese de novos pirróis derivados de aminocumarinas
author Brites, Nathan Pinto
author_facet Brites, Nathan Pinto
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 Schumacher, Ricardo Frederico
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/7856034546434135
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/8468135456169967
dc.contributor.author.fl_str_mv Brites, Nathan Pinto
contributor_str_mv Silveira, Claudio da Cruz
Lenardao, Eder Joao
Schumacher, Ricardo Frederico
dc.subject.por.fl_str_mv Clauson-Kaas
Paal-Knorr
Aminocumarina
Pirróis e tiocianação
topic Clauson-Kaas
Paal-Knorr
Aminocumarina
Pirróis e tiocianação
Aminocoumarines
Pyrroles and thiocyanation
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Aminocoumarines
Pyrroles and thiocyanation
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In this work, the synthesis of new pyrroles derived from aminocoumarins was developed. First, the synthesis of pyrroles derived from 4-amino-2H-chromen-2-one was carried out by the Paal-Knorr and Clauson-Kaas reactions, using anhydrous cerium chloride and PTSA.H2O as catalysts. The reaction was carried out under conventional heating and microwave irradiation, using 2,5-hexanedione (1.2 equiv.) and 2,5-dimethoxy-THF (3 equiv.) in toluene and acetonitrile as solvents, respectively. A novel methodology for synthesizing pyrroles from 6-amino-2H-chromen-2-one was also explored. In this synthesis, anhydrous cerium chloride as catalyst and acetonitrile was used as solvent at reflux temperature. Finally, it was evaluated the functionalization of this class of compounds, performing the thiocyanation of selected pyrroles.
publishDate 2018
dc.date.issued.fl_str_mv 2018-07-19
dc.date.accessioned.fl_str_mv 2019-04-22T12:05:29Z
dc.date.available.fl_str_mv 2019-04-22T12:05:29Z
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/1/16272
url http://repositorio.ufsm.br/handle/1/16272
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
f693f370-52ca-470d-87a4-5ee7a71a21f2
ca9fcc2d-9963-41ad-88e6-0a2521e17c64
6a26f817-0d52-41d8-9183-c785c92d110a
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/1/16272/1/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf
http://repositorio.ufsm.br/bitstream/1/16272/2/license_rdf
http://repositorio.ufsm.br/bitstream/1/16272/3/license.txt
http://repositorio.ufsm.br/bitstream/1/16272/4/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.txt
http://repositorio.ufsm.br/bitstream/1/16272/5/DIS_PPGQUIMICA_2018_BRITES_NATHAN.pdf.jpg
bitstream.checksum.fl_str_mv 898b3772191ceb2d30fbceccf2d9025b
4460e5956bc1d1639be9ae6146a50347
2f0571ecee68693bd5cd3f17c1e075df
e43c07220b8c8eda5ba7fbe91f573f30
5c1e4c2943035402a53d29f5779e811b
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_ 1793240020679655424

Registros relacionados