Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos

Detalhes bibliográficos
Ano de defesa: 2020
Autor(a) principal: Maroneze, Adriano lattes
Orientador(a): Zeni, Gilson Rogério lattes
Banca de defesa: Rhoden, Cristiano Rodrigues Bohn, Frizon, Tiago Elias Allievi
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:
Selênio
Isocromenos
Heterociclos
Organolítio
Isômeros
Palavras-chave em Inglês:
Selenium
Isochromene
Heterocycles
Organolithium
Isomers
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/23938
Resumo: In the present work, we developed the synthesis of 1H-isocalcogenochromene via a nucleophilic addition of Na2Se to enynes. The reaction parameters were studied and the results indicated that the reaction of enynes (0.25 mmol) with elemental selenium (2.0 equiv) and NaBH4 (3 equiv), under 75 ◦C, using DMF and EtOH as the solvent, was the best reaction condition, providing the products in 52-81% yield. In order to demonstrate the versatility of the synthesized products, they were subjected to reactions with different boronic acids in the presence of SeO2 and against organolithium compounds.
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spelling 2022-03-25T14:35:00Z2022-03-25T14:35:00Z2020-02-21http://repositorio.ufsm.br/handle/1/23938In the present work, we developed the synthesis of 1H-isocalcogenochromene via a nucleophilic addition of Na2Se to enynes. The reaction parameters were studied and the results indicated that the reaction of enynes (0.25 mmol) with elemental selenium (2.0 equiv) and NaBH4 (3 equiv), under 75 ◦C, using DMF and EtOH as the solvent, was the best reaction condition, providing the products in 52-81% yield. In order to demonstrate the versatility of the synthesized products, they were subjected to reactions with different boronic acids in the presence of SeO2 and against organolithium compounds.No presente trabalho desenvolveu-se a síntese 1H-isocalcogenocromenos a partir da adição nucleofílica de Na2Se a diínos. Os parâmetros reacionais foram estudados e os resultados indicaram que a reação dos eninos (0,25 mmol) com Selênio elementar (2,0 equiv) e NaBH4 (3 equiv), sob 75 ◦C em uma mistura de solventes DMF e EtOH, foi a melhor condição reacional, fornecendo os produtos em 52-81% de rendimento. Afim de demostrar a versatilidade dos produtos sintetizados submeteu-se os mesmos a reações com diferentes ácidos borônicos em presença de SeO2 e frente a compostos organolítio.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/openAccessSelênioIsocromenosHeterociclosOrganolítioIsômerosSeleniumIsochromeneHeterocyclesOrganolithiumIsomersCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninosSynthesis of 1H-isocalcogênocromenos via NA2SE from enyne derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Rhoden, Cristiano Rodrigues BohnFrizon, Tiago Elias Allievihttp://lattes.cnpq.br/1755218781781135Maroneze, Adriano100600000000600600600600600b21a898a-0ab0-4f33-b980-2b55ef590b94199957ee-b70b-4ef4-ba46-16326c22da7c45ee51a5-5bc6-4ac0-8edf-bbbb0661df754b40b41e-3539-488c-af73-ee974f3b10ebreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUÍMICA_2020_MARONEZE_ADRIANO.pdfDIS_PPGQUÍMICA_2020_MARONEZE_ADRIANO.pdfDissertação de mestradoapplication/pdf5337946http://repositorio.ufsm.br/bitstream/1/23938/1/DIS_PPGQU%c3%8dMICA_2020_MARONEZE_ADRIANO.pdf601d2c0fb9ac4c5d11ef09fc276fe5c5MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/23938/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/23938/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/239382022-03-25 11:38:59.171oai: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:2022-03-25T14:38:59Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
dc.title.alternative.eng.fl_str_mv Synthesis of 1H-isocalcogênocromenos via NA2SE from enyne derivatives
title Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
spellingShingle Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
Maroneze, Adriano
Selênio
Isocromenos
Heterociclos
Organolítio
Isômeros
Selenium
Isochromene
Heterocycles
Organolithium
Isomers
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
title_full Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
title_fullStr Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
title_full_unstemmed Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
title_sort Síntese de 1H-isocalcogênocromenos via NA2SE a partir de derivados de eninos
author Maroneze, Adriano
author_facet Maroneze, Adriano
author_role author
dc.contributor.advisor1.fl_str_mv Zeni, Gilson Rogério
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/2355575631197937
dc.contributor.referee1.fl_str_mv Rhoden, Cristiano Rodrigues Bohn
dc.contributor.referee2.fl_str_mv Frizon, Tiago Elias Allievi
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/1755218781781135
dc.contributor.author.fl_str_mv Maroneze, Adriano
contributor_str_mv Zeni, Gilson Rogério
Rhoden, Cristiano Rodrigues Bohn
Frizon, Tiago Elias Allievi
dc.subject.por.fl_str_mv Selênio
Isocromenos
Heterociclos
Organolítio
Isômeros
topic Selênio
Isocromenos
Heterociclos
Organolítio
Isômeros
Selenium
Isochromene
Heterocycles
Organolithium
Isomers
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv Selenium
Isochromene
Heterocycles
Organolithium
Isomers
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description In the present work, we developed the synthesis of 1H-isocalcogenochromene via a nucleophilic addition of Na2Se to enynes. The reaction parameters were studied and the results indicated that the reaction of enynes (0.25 mmol) with elemental selenium (2.0 equiv) and NaBH4 (3 equiv), under 75 ◦C, using DMF and EtOH as the solvent, was the best reaction condition, providing the products in 52-81% yield. In order to demonstrate the versatility of the synthesized products, they were subjected to reactions with different boronic acids in the presence of SeO2 and against organolithium compounds.
publishDate 2020
dc.date.issued.fl_str_mv 2020-02-21
dc.date.accessioned.fl_str_mv 2022-03-25T14:35:00Z
dc.date.available.fl_str_mv 2022-03-25T14:35:00Z
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/1/23938
url http://repositorio.ufsm.br/handle/1/23938
dc.language.iso.fl_str_mv por
language 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/
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
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