Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime

Detalhes bibliográficos
Autor(a) principal: Bueno Broterson, Yoisel
Data de Publicação: 2020
Tipo de documento: Dissertação
Idioma: eng
Título da fonte: Repositório Institucional da UFSCAR
Texto Completo: https://repositorio.ufscar.br/handle/ufscar/12959
Resumo: Sustainable chemistry has gained relevance in recent years, not only in the fine chemical industry, but also in organic synthesis. This new conception of chemistry allows the development of environmentally friendly processes, by minimizing waste generation as well as in reducing the handling of hazardous chemical reagents. However, this approach encourages the use of "sustainable or green" substrates and solvents. In this context, the use of continuous flow has been extended at an exponential rate in organic synthesis, due to the various applications to the synthesis of derivatives of natural products of interest to the pharmaceutical industry. In order to contribute in the area, this project aimed to develop a new stereoselective methodology for the synthesis of tetrasubstituted cyclopentenes through sustainable approach. Combination of organocatalysis and multicomponent reactions as synthesis tools was chosen. Both methodologies allowed the use of green solvents, as well as the incorporation of continuous flow techniques in the substitution of batch methods. The multicomponent stage represented significant advances in the development of a more sustainable methodology. Finally, the designed methodology can be considered as a sustainable protocol for the synthesis of analogues of natural products, enantiomerically enriched, quick and efficiently.
id SCAR_882c8aad8125fa43b49f86b214225237
oai_identifier_str oai:repositorio.ufscar.br:ufscar/12959
network_acronym_str SCAR
network_name_str Repositório Institucional da UFSCAR
repository_id_str 4322
spelling Bueno Broterson, YoiselPaixão, Márcio Weberhttp://lattes.cnpq.br/3773908504964104http://lattes.cnpq.br/55887875347222857f6cd869-7b06-4ab9-a1f8-bf1d891ba5e12020-06-23T21:01:34Z2020-06-23T21:01:34Z2020-03-25BUENO BROTERSON, Yoisel. Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime. 2020. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2020. Disponível em: https://repositorio.ufscar.br/handle/ufscar/12959.https://repositorio.ufscar.br/handle/ufscar/12959Sustainable chemistry has gained relevance in recent years, not only in the fine chemical industry, but also in organic synthesis. This new conception of chemistry allows the development of environmentally friendly processes, by minimizing waste generation as well as in reducing the handling of hazardous chemical reagents. However, this approach encourages the use of "sustainable or green" substrates and solvents. In this context, the use of continuous flow has been extended at an exponential rate in organic synthesis, due to the various applications to the synthesis of derivatives of natural products of interest to the pharmaceutical industry. In order to contribute in the area, this project aimed to develop a new stereoselective methodology for the synthesis of tetrasubstituted cyclopentenes through sustainable approach. Combination of organocatalysis and multicomponent reactions as synthesis tools was chosen. Both methodologies allowed the use of green solvents, as well as the incorporation of continuous flow techniques in the substitution of batch methods. The multicomponent stage represented significant advances in the development of a more sustainable methodology. Finally, the designed methodology can be considered as a sustainable protocol for the synthesis of analogues of natural products, enantiomerically enriched, quick and efficiently.A química sustentável ganhou relevância nos últimos anos, não apenas na indústria de química fina, mas também, em síntese orgânica. Essa nova concepção da química, permite o desenvolvimento de processos de maneira ambientalmente mais amigáveis, através da minimização na geração resíduos, reduzindo a manipulação de reagentes químicos perigosos – no entanto, essa abordagem estimula o uso de substratos e solventes “sustentáveis ou verdes”. Nesse contexto, o uso de fluxo contínuo em síntese orgânica foi estendido a uma taxa exponencial, devido as várias aplicações na síntese de derivados de produtos naturais de interesse para indústria farmacêutica. De forma a contribuir com a área, esse projeto tem por objetivo desenvolver uma nova metodologia estereosseletiva para síntese de ciclopentenos tetrasubstituídos através de uma abordagem mais sustentável. Nesse sentido, elegemos a combinação de organocatálise e reações multicomponentes como ferramentas de síntese. Ambas metodologias permitem o emprego de solventes verdes, bem como, a incorporação de técnicas de fluxo contínuo na substituição dos métodos em batelada. A etapa multicomponente representou avanços significativos no desenvolvimento de uma metodologia mais sustentável. Finalmente, a metodologia desenhada pode ser considerada como um protocolo sustentável para a síntese de análogos de produtos naturais, enantiomericamente enriquecidos, de maneira rápida e eficiente.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)CNPq: 133691/2018-7engUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarAttribution-NonCommercial-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nc-nd/3.0/br/info:eu-repo/semantics/openAccessSustainable chemistryOrganocatalysisMulticomponent reactionsContinuous flow chemistryCiclopentene derivativesCIENCIAS EXATAS E DA TERRA::QUIMICACIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICACIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICASustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regimeSíntese sustentável de derivados de ciclopenteno através de reações multicomponentes em regime de fluxo contínuoinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesis600c9d783c2-174c-4a51-9643-0e44f6fc9ac9reponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALDissertação_Yoisel Bueno Broterson 2020.pdfDissertação_Yoisel Bueno Broterson 2020.pdfDissertação_Yoisel Bueno Broterson 2020application/pdf7575454https://repositorio.ufscar.br/bitstream/ufscar/12959/1/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf168905bd00910c13e2686ceec3106306MD51Carta de Homoloção Dissertação Yoisel Bueno Broterson.pdfCarta de Homoloção Dissertação Yoisel Bueno Broterson.pdfapplication/pdf1145496https://repositorio.ufscar.br/bitstream/ufscar/12959/3/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdfb3bcc12bbc4d1992980cf78d55805e26MD53CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8811https://repositorio.ufscar.br/bitstream/ufscar/12959/4/license_rdfe39d27027a6cc9cb039ad269a5db8e34MD54TEXTDissertação_Yoisel Bueno Broterson 2020.pdf.txtDissertação_Yoisel Bueno Broterson 2020.pdf.txtExtracted texttext/plain123969https://repositorio.ufscar.br/bitstream/ufscar/12959/5/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf.txta80b5b4942a14626d52a10c0d502bd52MD55Carta de Homoloção Dissertação Yoisel Bueno Broterson.pdf.txtCarta de Homoloção Dissertação Yoisel Bueno Broterson.pdf.txtExtracted texttext/plain1https://repositorio.ufscar.br/bitstream/ufscar/12959/7/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdf.txt68b329da9893e34099c7d8ad5cb9c940MD57THUMBNAILDissertação_Yoisel Bueno Broterson 2020.pdf.jpgDissertação_Yoisel Bueno Broterson 2020.pdf.jpgIM Thumbnailimage/jpeg9469https://repositorio.ufscar.br/bitstream/ufscar/12959/6/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf.jpg8b48e2811b6ea489dcb1a3f396e4b1a4MD56Carta de Homoloção Dissertação Yoisel Bueno Broterson.pdf.jpgCarta de Homoloção Dissertação Yoisel Bueno Broterson.pdf.jpgIM Thumbnailimage/jpeg10242https://repositorio.ufscar.br/bitstream/ufscar/12959/8/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdf.jpgaf003123d48cbae43f5cb44363684885MD58ufscar/129592023-09-18 18:31:57.154oai:repositorio.ufscar.br:ufscar/12959Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:57Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false
dc.title.eng.fl_str_mv Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
dc.title.alternative.por.fl_str_mv Síntese sustentável de derivados de ciclopenteno através de reações multicomponentes em regime de fluxo contínuo
title Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
spellingShingle Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
Bueno Broterson, Yoisel
Sustainable chemistry
Organocatalysis
Multicomponent reactions
Continuous flow chemistry
Ciclopentene derivatives
CIENCIAS EXATAS E DA TERRA::QUIMICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
title_short Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
title_full Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
title_fullStr Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
title_full_unstemmed Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
title_sort Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime
author Bueno Broterson, Yoisel
author_facet Bueno Broterson, Yoisel
author_role author
dc.contributor.authorlattes.por.fl_str_mv http://lattes.cnpq.br/5588787534722285
dc.contributor.author.fl_str_mv Bueno Broterson, Yoisel
dc.contributor.advisor1.fl_str_mv Paixão, Márcio Weber
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/3773908504964104
dc.contributor.authorID.fl_str_mv 7f6cd869-7b06-4ab9-a1f8-bf1d891ba5e1
contributor_str_mv Paixão, Márcio Weber
dc.subject.eng.fl_str_mv Sustainable chemistry
Organocatalysis
Multicomponent reactions
Continuous flow chemistry
Ciclopentene derivatives
topic Sustainable chemistry
Organocatalysis
Multicomponent reactions
Continuous flow chemistry
Ciclopentene derivatives
CIENCIAS EXATAS E DA TERRA::QUIMICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
dc.subject.cnpq.fl_str_mv CIENCIAS EXATAS E DA TERRA::QUIMICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
description Sustainable chemistry has gained relevance in recent years, not only in the fine chemical industry, but also in organic synthesis. This new conception of chemistry allows the development of environmentally friendly processes, by minimizing waste generation as well as in reducing the handling of hazardous chemical reagents. However, this approach encourages the use of "sustainable or green" substrates and solvents. In this context, the use of continuous flow has been extended at an exponential rate in organic synthesis, due to the various applications to the synthesis of derivatives of natural products of interest to the pharmaceutical industry. In order to contribute in the area, this project aimed to develop a new stereoselective methodology for the synthesis of tetrasubstituted cyclopentenes through sustainable approach. Combination of organocatalysis and multicomponent reactions as synthesis tools was chosen. Both methodologies allowed the use of green solvents, as well as the incorporation of continuous flow techniques in the substitution of batch methods. The multicomponent stage represented significant advances in the development of a more sustainable methodology. Finally, the designed methodology can be considered as a sustainable protocol for the synthesis of analogues of natural products, enantiomerically enriched, quick and efficiently.
publishDate 2020
dc.date.accessioned.fl_str_mv 2020-06-23T21:01:34Z
dc.date.available.fl_str_mv 2020-06-23T21:01:34Z
dc.date.issued.fl_str_mv 2020-03-25
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.citation.fl_str_mv BUENO BROTERSON, Yoisel. Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime. 2020. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2020. Disponível em: https://repositorio.ufscar.br/handle/ufscar/12959.
dc.identifier.uri.fl_str_mv https://repositorio.ufscar.br/handle/ufscar/12959
identifier_str_mv BUENO BROTERSON, Yoisel. Sustainable synthesis of ciclopentene derivatives through multicomponent reactions in continuous flow regime. 2020. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2020. Disponível em: https://repositorio.ufscar.br/handle/ufscar/12959.
url https://repositorio.ufscar.br/handle/ufscar/12959
dc.language.iso.fl_str_mv eng
language eng
dc.relation.confidence.fl_str_mv 600
dc.relation.authority.fl_str_mv c9d783c2-174c-4a51-9643-0e44f6fc9ac9
dc.rights.driver.fl_str_mv Attribution-NonCommercial-NoDerivs 3.0 Brazil
http://creativecommons.org/licenses/by-nc-nd/3.0/br/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 3.0 Brazil
http://creativecommons.org/licenses/by-nc-nd/3.0/br/
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Universidade Federal de São Carlos
Câmpus São Carlos
dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química - PPGQ
dc.publisher.initials.fl_str_mv UFSCar
publisher.none.fl_str_mv Universidade Federal de São Carlos
Câmpus São Carlos
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFSCAR
instname:Universidade Federal de São Carlos (UFSCAR)
instacron:UFSCAR
instname_str Universidade Federal de São Carlos (UFSCAR)
instacron_str UFSCAR
institution UFSCAR
reponame_str Repositório Institucional da UFSCAR
collection Repositório Institucional da UFSCAR
bitstream.url.fl_str_mv https://repositorio.ufscar.br/bitstream/ufscar/12959/1/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf
https://repositorio.ufscar.br/bitstream/ufscar/12959/3/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdf
https://repositorio.ufscar.br/bitstream/ufscar/12959/4/license_rdf
https://repositorio.ufscar.br/bitstream/ufscar/12959/5/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf.txt
https://repositorio.ufscar.br/bitstream/ufscar/12959/7/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdf.txt
https://repositorio.ufscar.br/bitstream/ufscar/12959/6/Disserta%c3%a7%c3%a3o_Yoisel%20Bueno%20Broterson%202020.pdf.jpg
https://repositorio.ufscar.br/bitstream/ufscar/12959/8/Carta%20de%20Homolo%c3%a7%c3%a3o%20Disserta%c3%a7%c3%a3o%20Yoisel%20Bueno%20Broterson.pdf.jpg
bitstream.checksum.fl_str_mv 168905bd00910c13e2686ceec3106306
b3bcc12bbc4d1992980cf78d55805e26
e39d27027a6cc9cb039ad269a5db8e34
a80b5b4942a14626d52a10c0d502bd52
68b329da9893e34099c7d8ad5cb9c940
8b48e2811b6ea489dcb1a3f396e4b1a4
af003123d48cbae43f5cb44363684885
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
MD5
MD5
MD5
repository.name.fl_str_mv Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)
repository.mail.fl_str_mv
_version_ 1802136376727044096