Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner
Ano de defesa: | 2023 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
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: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/30324 |
Resumo: | This work describes the synthesis of 15 novel vinyl sulfides based on a series of substituted indoles via Wittig-Horner reaction. The synthesized products were obtained in yields ranging from 255 to 93%. Initially, different substituted indole-3-carbaldehydes 1a-f were reacted with arylsulfide-functionalized phosphine oxides 2a-b, employing NaH as base and THF as solvent, at reflux temperature for 3 to 24 h, leading to the obtention of vinyl sulfides 3a-n. On the other hand, this same method was not efficient for obteining vinyl sulfides based on indoles substituted with N-Boc- or N-tosyl-groups, leading to low yields and to byproducts formation. Subsequently, the previously developed protocol was employed for the synthesis of non-symmetrical substituted bisvinyl derivatives 4a-c, employing NaH as base, THF as solvent and HMPA, at reflux temperature, for 5 to 24 h. Under these conditions, four new products were obtained in 70% to 81% yields. The developed procedure furnished the vinyl sulfides as an isomeric mixture, with preferential formation of, respectively, E and E,E geometric isomers. From this result, the same reaction conditions were tested by employing bismethylene sulfide phosphinoxide derivative 2e and two equivalents of indole-3- carbaldehyde 1a as reactants to synthesize a bis-indolyl-vinyl sulfide 5. The reaction was conducted at reflux temperature for 5 h, furnishing the product in 71% yield. Thereafter, a method for the synthesis of alkynyl-functionalized vinyl sulfides 6a-b via Wittig-Horner reaction was developed. In this reaction, an alkynylsulfide- - functionalized phosphinoxide derivative 2f and indole-3-carbaldehydes 1 were employed as reagents. The reactions were conducted in THF, employing NaH as base at reflux temperature for 4 h. The vinyl sulfides were obtained in 78% to 89% yields, with good stereoselectivity. This method furnished two alkyne-functionalized vinyl sulfides as an isomeric mixture, with preferential formation of geometric isomers with E-configuration. N-Benzyl-substituted indole derivative 6a was obtained as a 91:9 E:Z mixture, while N-methyl-substituted indole derivative 6b was obtained as a 70:30 E:Z mixture. |
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2023-10-09T19:12:31Z2023-10-09T19:12:31Z2023-08-25http://repositorio.ufsm.br/handle/1/30324This work describes the synthesis of 15 novel vinyl sulfides based on a series of substituted indoles via Wittig-Horner reaction. The synthesized products were obtained in yields ranging from 255 to 93%. Initially, different substituted indole-3-carbaldehydes 1a-f were reacted with arylsulfide-functionalized phosphine oxides 2a-b, employing NaH as base and THF as solvent, at reflux temperature for 3 to 24 h, leading to the obtention of vinyl sulfides 3a-n. On the other hand, this same method was not efficient for obteining vinyl sulfides based on indoles substituted with N-Boc- or N-tosyl-groups, leading to low yields and to byproducts formation. Subsequently, the previously developed protocol was employed for the synthesis of non-symmetrical substituted bisvinyl derivatives 4a-c, employing NaH as base, THF as solvent and HMPA, at reflux temperature, for 5 to 24 h. Under these conditions, four new products were obtained in 70% to 81% yields. The developed procedure furnished the vinyl sulfides as an isomeric mixture, with preferential formation of, respectively, E and E,E geometric isomers. From this result, the same reaction conditions were tested by employing bismethylene sulfide phosphinoxide derivative 2e and two equivalents of indole-3- carbaldehyde 1a as reactants to synthesize a bis-indolyl-vinyl sulfide 5. The reaction was conducted at reflux temperature for 5 h, furnishing the product in 71% yield. Thereafter, a method for the synthesis of alkynyl-functionalized vinyl sulfides 6a-b via Wittig-Horner reaction was developed. In this reaction, an alkynylsulfide- - functionalized phosphinoxide derivative 2f and indole-3-carbaldehydes 1 were employed as reagents. The reactions were conducted in THF, employing NaH as base at reflux temperature for 4 h. The vinyl sulfides were obtained in 78% to 89% yields, with good stereoselectivity. This method furnished two alkyne-functionalized vinyl sulfides as an isomeric mixture, with preferential formation of geometric isomers with E-configuration. N-Benzyl-substituted indole derivative 6a was obtained as a 91:9 E:Z mixture, while N-methyl-substituted indole derivative 6b was obtained as a 70:30 E:Z mixture.Desenvolveu-se, no presente trabalho, a síntese de 15 novos sulfetos vinílicos derivados de indóis diferentemente substituídos através da reação de Wittig-Horner, obtendo-se rendimentos de 25% a 93%. Primeiramente, reagiu-se 3-carbaldeídoindóis 1a-f diferentemente substituídos com fosfinóxidos funcionalizados com sulfetos arílicos 2a-b, empregando-se NaH como base e THF como solvente, à temperatura de refluxo por um período de 3 a 24 horas de reação, para a síntese dos respectivos sulfetos vinílicos 3a-n. Por outro lado, essa mesma metodologia não foi eficiente para o preparo de sulfetos vinílicos derivados de indóis N-Boc e N-tosil-substituídos, que levaram a baixos rendimentos e formação de subprodutos. Em um segundo momento, o protocolo previamente estabelecido, foi empregado na síntese de compostos bisvínilicos não simétricos 4a-c, utilizando-se NaH como base, THF como solvente e HMPA, à temperatura de refluxo por 5 a 24 horas de reação. Sob essas condições, obteve-se quatro novos produtos com rendimentos entre 70% e 81%. A metodologia desenvolvida forneceu os sulfetos vinílicos como uma mistura isomérica, com formação preferencial dos isômeros geométricos E e E,E, respectivamente. A partir deste resultado, testou-se a reação utilizando-se como reagentes o derivado de fosfinóxido do sulfeto bis-metilênico 2e e dois equivalentes do 3-carbaldeído-indol 1a, para síntese do sulfeto bis-indolil-vinílico 5. A reação foi conduzida a temperatura de refluxo por 5 horas, fornecendo o produto de interesse em um rendimento de 71%. Posteriormente, foi desenvolvida uma metodologia para a síntese de sulfetos vinílicos funcionalizados com alquinos 6a-b através da reação de Wittig-Horner. Nesta reação, empregou-se como materiais de partida um derivado de fosfinóxido 2f funcionalizado com um sulfeto derivado do fenil acetileno e aldeídos derivados de indóis 1. As reações foram realizadas em THF, utilizando-se NaH como base à uma temperatura de refluxo por 4 horas. Os sulfetos vinílicos foram obtidos com rendimentos de 78% a 89%, e com boa estereosseletividade. A metodologia empregada forneceu dois sulfetos vinílicos funcionalizados com alquinos como uma mistura isomérica, com formação preferencial dos isômeros geométricos de configuração E. O sulfeto derivado do indol substituído por N-benzila 6a foi obtido como uma mistura E:Z de 91:9, enquanto o derivado de indol substituído por N-metila 6b, foi obtido como uma mistura E:Z de 70:30.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/openAccessReação de acoplamento3-carbaldeído-indolFosfinóxidosSulfetos vinílicosCoupling reactionIndole-3-carbaldehydePhosphine oxidesVinyl sulfidesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-HornerSynthesis of novel vinyl sulfides based on indole-3- carbaldehyde via Wittig-Horner reactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisSchumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135Rodrigues, Oscar Endrigo DornelesBarancelli, Daniela AlineScaranaro, Filipe Vinicius PenteadoSoares, Letiere CabreiraBandeira, Pamela Taislinehttp://lattes.cnpq.br/8468135456169967Brites, Nathan Pinto100600000000600600600600600600600600c0f45597-54e3-490c-9f9d-6888803e1a2af693f370-52ca-470d-87a4-5ee7a71a21f26721ab73-0457-4ffc-aa9d-bda83c8246ee5d3faa3c-c7d2-40c6-a2a2-8848f99e523ebf5c8c79-13cd-4746-b5f4-6ba088fe95910e272fff-41f5-4b0b-8abd-f268a2ef857215cd7a23-001b-4761-9dcb-a489e00c79cfreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2023_BRITES_NATHAN.pdfTES_PPGQUIMICA_2023_BRITES_NATHAN.pdfTese de doutoradoapplication/pdf5261156http://repositorio.ufsm.br/bitstream/1/30324/1/TES_PPGQUIMICA_2023_BRITES_NATHAN.pdfa6f5c2157b3dc5567d15ec85f38f11faMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805http://repositorio.ufsm.br/bitstream/1/30324/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81956http://repositorio.ufsm.br/bitstream/1/30324/3/license.txt2f0571ecee68693bd5cd3f17c1e075dfMD531/303242023-10-09 16:12:31.394oai: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:2023-10-09T19:12:31Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
dc.title.alternative.eng.fl_str_mv |
Synthesis of novel vinyl sulfides based on indole-3- carbaldehyde via Wittig-Horner reactions |
title |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
spellingShingle |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner Brites, Nathan Pinto Reação de acoplamento 3-carbaldeído-indol Fosfinóxidos Sulfetos vinílicos Coupling reaction Indole-3-carbaldehyde Phosphine oxides Vinyl sulfides CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
title_full |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
title_fullStr |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
title_full_unstemmed |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
title_sort |
Síntese de novos sulfetos vinílicos derivados de 3- carbaldeído indóis via reações de Wittig-Horner |
author |
Brites, Nathan Pinto |
author_facet |
Brites, Nathan Pinto |
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 |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee1.fl_str_mv |
Barancelli, Daniela Aline |
dc.contributor.referee2.fl_str_mv |
Scaranaro, Filipe Vinicius Penteado |
dc.contributor.referee3.fl_str_mv |
Soares, Letiere Cabreira |
dc.contributor.referee4.fl_str_mv |
Bandeira, Pamela Taisline |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8468135456169967 |
dc.contributor.author.fl_str_mv |
Brites, Nathan Pinto |
contributor_str_mv |
Schumacher, Ricardo Frederico Rodrigues, Oscar Endrigo Dorneles Barancelli, Daniela Aline Scaranaro, Filipe Vinicius Penteado Soares, Letiere Cabreira Bandeira, Pamela Taisline |
dc.subject.por.fl_str_mv |
Reação de acoplamento 3-carbaldeído-indol Fosfinóxidos Sulfetos vinílicos |
topic |
Reação de acoplamento 3-carbaldeído-indol Fosfinóxidos Sulfetos vinílicos Coupling reaction Indole-3-carbaldehyde Phosphine oxides Vinyl sulfides CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Coupling reaction Indole-3-carbaldehyde Phosphine oxides Vinyl sulfides |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis of 15 novel vinyl sulfides based on a series of substituted indoles via Wittig-Horner reaction. The synthesized products were obtained in yields ranging from 255 to 93%. Initially, different substituted indole-3-carbaldehydes 1a-f were reacted with arylsulfide-functionalized phosphine oxides 2a-b, employing NaH as base and THF as solvent, at reflux temperature for 3 to 24 h, leading to the obtention of vinyl sulfides 3a-n. On the other hand, this same method was not efficient for obteining vinyl sulfides based on indoles substituted with N-Boc- or N-tosyl-groups, leading to low yields and to byproducts formation. Subsequently, the previously developed protocol was employed for the synthesis of non-symmetrical substituted bisvinyl derivatives 4a-c, employing NaH as base, THF as solvent and HMPA, at reflux temperature, for 5 to 24 h. Under these conditions, four new products were obtained in 70% to 81% yields. The developed procedure furnished the vinyl sulfides as an isomeric mixture, with preferential formation of, respectively, E and E,E geometric isomers. From this result, the same reaction conditions were tested by employing bismethylene sulfide phosphinoxide derivative 2e and two equivalents of indole-3- carbaldehyde 1a as reactants to synthesize a bis-indolyl-vinyl sulfide 5. The reaction was conducted at reflux temperature for 5 h, furnishing the product in 71% yield. Thereafter, a method for the synthesis of alkynyl-functionalized vinyl sulfides 6a-b via Wittig-Horner reaction was developed. In this reaction, an alkynylsulfide- - functionalized phosphinoxide derivative 2f and indole-3-carbaldehydes 1 were employed as reagents. The reactions were conducted in THF, employing NaH as base at reflux temperature for 4 h. The vinyl sulfides were obtained in 78% to 89% yields, with good stereoselectivity. This method furnished two alkyne-functionalized vinyl sulfides as an isomeric mixture, with preferential formation of geometric isomers with E-configuration. N-Benzyl-substituted indole derivative 6a was obtained as a 91:9 E:Z mixture, while N-methyl-substituted indole derivative 6b was obtained as a 70:30 E:Z mixture. |
publishDate |
2023 |
dc.date.accessioned.fl_str_mv |
2023-10-09T19:12:31Z |
dc.date.available.fl_str_mv |
2023-10-09T19:12:31Z |
dc.date.issued.fl_str_mv |
2023-08-25 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/30324 |
url |
http://repositorio.ufsm.br/handle/1/30324 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
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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 |
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