Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor®
Ano de defesa: | 2021 |
---|---|
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/1/23937 |
Resumo: | This paper reports the development of an effective synthetic protocol between 1,3- organo-propynones 1 and different diorganoyl dicalcogenides 2 mediated by Selectfluor® and employing acetonitrile as a solvent, at room temperature and open atmosphere for a time of 20 h to obtain a series of 2-organo-3-organoselenyl-chromen-4-ones 3. Through the developed methodology, it was possible to synthesize different chromenones (21 compounds) with yields ranging from 27% to 89%, which 8 of these are unpublished examples. The method is also suitable for the formation of several classes of heterocycles such as thiochromenone and isochromenone. The proposed mechanism for the reaction is based on the cleavage of diorganoyl dichalcogenide promoted by Selectfluor®, which generates electrophilic chalcogenium species capable to activate the triple bond of propynone to promote the intramolecular cyclization. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2022-03-25T13:56:51Z2022-03-25T13:56:51Z2021-09-30http://repositorio.ufsm.br/handle/1/23937This paper reports the development of an effective synthetic protocol between 1,3- organo-propynones 1 and different diorganoyl dicalcogenides 2 mediated by Selectfluor® and employing acetonitrile as a solvent, at room temperature and open atmosphere for a time of 20 h to obtain a series of 2-organo-3-organoselenyl-chromen-4-ones 3. Through the developed methodology, it was possible to synthesize different chromenones (21 compounds) with yields ranging from 27% to 89%, which 8 of these are unpublished examples. The method is also suitable for the formation of several classes of heterocycles such as thiochromenone and isochromenone. The proposed mechanism for the reaction is based on the cleavage of diorganoyl dichalcogenide promoted by Selectfluor®, which generates electrophilic chalcogenium species capable to activate the triple bond of propynone to promote the intramolecular cyclization.Este trabalho relata o desenvolvimento de um protocolo sintético eficaz entre 1,3- organo-propinonas 1 e diferentes dicalcogenetos de diorganoíla 2 mediada por Selectfluor® e empregando acetonitrila como solvente, à temperatura e atmosfera ambiente por um período de 20 h para a formação de uma série de 2-organo-3-organoselenil-cromen-4-onas 3. Mediante a metodologia desenvolvida, foi possível a obtenção de diferentes cromenonas (21 exemplos) com rendimentos que variam entre 27% a 89%, sendo 8 destes exemplos inéditos. O método também se mostrou funcional para a formação de outras classes de heterociclos tais como tiocromenona e isocromenona. O mecanismo proposto para a reação baseia-se na clivagem do dicalcogeneto de diorganoíla promovida pelo Selectfluor®, a qual gera espécies eletrofílicas do organocalcogênio capazes de ativar a ligação tripla da propinona para promover a ciclização intramolecular.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/openAccessDicalcogeneto de diorganoílaCromen-4-onaReação de ciclização intramolecularSelectfluor®Diorganoyl dicalcogenideIntramolecular cyclization reactionCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor®Synthesis of 3-organochalcogenyl-2-organo-chromenones via selectfluor-mediated intramolecular cycling reactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisSchumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135Cargnelutti, RobertaBarancelli, Daniela AlineOliveira, Daniela Hartwig dehttp://lattes.cnpq.br/9974833238603991Ribeiro, Thiago dos Anjos100600000000600600600600c0f45597-54e3-490c-9f9d-6888803e1a2a1f45154b-e07d-49c8-9308-95aee92a383959d5d1ee-dfd5-40de-b551-f8f3ecc4670e5d3faa3c-c7d2-40c6-a2a2-8848f99e523e46067263-3e2c-49c5-8562-59a4f9a2b690reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 3-organochalcogenyl-2-organo-chromenones via selectfluor-mediated intramolecular cycling reactions |
title |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
spellingShingle |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® Ribeiro, Thiago dos Anjos Dicalcogeneto de diorganoíla Cromen-4-ona Reação de ciclização intramolecular Selectfluor® Diorganoyl dicalcogenide Intramolecular cyclization reaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
title_full |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
title_fullStr |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
title_full_unstemmed |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
title_sort |
Síntese de 3-organocalcogenil-2-organo-cromenonas via reações de ciclização intramolecular mediada por selectfluor® |
author |
Ribeiro, Thiago dos Anjos |
author_facet |
Ribeiro, Thiago dos Anjos |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Schumacher, Ricardo Frederico |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7856034546434135 |
dc.contributor.advisor-co1.fl_str_mv |
Cargnelutti, Roberta |
dc.contributor.referee1.fl_str_mv |
Barancelli, Daniela Aline |
dc.contributor.referee2.fl_str_mv |
Oliveira, Daniela Hartwig de |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9974833238603991 |
dc.contributor.author.fl_str_mv |
Ribeiro, Thiago dos Anjos |
contributor_str_mv |
Schumacher, Ricardo Frederico Cargnelutti, Roberta Barancelli, Daniela Aline Oliveira, Daniela Hartwig de |
dc.subject.por.fl_str_mv |
Dicalcogeneto de diorganoíla Cromen-4-ona Reação de ciclização intramolecular Selectfluor® |
topic |
Dicalcogeneto de diorganoíla Cromen-4-ona Reação de ciclização intramolecular Selectfluor® Diorganoyl dicalcogenide Intramolecular cyclization reaction CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Diorganoyl dicalcogenide Intramolecular cyclization reaction |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This paper reports the development of an effective synthetic protocol between 1,3- organo-propynones 1 and different diorganoyl dicalcogenides 2 mediated by Selectfluor® and employing acetonitrile as a solvent, at room temperature and open atmosphere for a time of 20 h to obtain a series of 2-organo-3-organoselenyl-chromen-4-ones 3. Through the developed methodology, it was possible to synthesize different chromenones (21 compounds) with yields ranging from 27% to 89%, which 8 of these are unpublished examples. The method is also suitable for the formation of several classes of heterocycles such as thiochromenone and isochromenone. The proposed mechanism for the reaction is based on the cleavage of diorganoyl dichalcogenide promoted by Selectfluor®, which generates electrophilic chalcogenium species capable to activate the triple bond of propynone to promote the intramolecular cyclization. |
publishDate |
2021 |
dc.date.issued.fl_str_mv |
2021-09-30 |
dc.date.accessioned.fl_str_mv |
2022-03-25T13:56:51Z |
dc.date.available.fl_str_mv |
2022-03-25T13:56:51Z |
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/1/23937 |
url |
http://repositorio.ufsm.br/handle/1/23937 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 |
dc.relation.authority.fl_str_mv |
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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/ info:eu-repo/semantics/openAccess |
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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 |
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