Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/16722 |
Resumo: | This work initially describes a novel and efficient protocol for the synthesis of 3-selenophen-3-yl-1H-indole derivatives via the electrophilic addition of SeCl2 to the conveniently substituted propargyl-indoles. The synthetic route involved an initial migration of the indole group, caused by the electrophilic addition of SeCl2 to the triple bond of propargyl indole, through the 1-seleno-1,3-diene intermediate, followed by cyclization and formation of the respective selenophene nucleus. The reaction occurs at room temperature in very good yields, showing excellent selectivity, broad substrate scope and wide tolerance to functional groups. In a second part, an easy and convenient route was developed for the synthesis of selenofen[2,3-b]indole derivatives via the electrophilic addition of SeCl2 to the appropriately substituted 3-(alkyl-ethynyl)-1H-indoles. The reaction scope was systematically evaluated, and the products containing the selenophenic ring fused to the indole were obtained in moderate to very good yields. The performance of the transformation was affected by steric and electronic properties of the substituent attached to the nitrogen atom of the indole moiety of the starting material and to a lesser extent by the nature and position of the substituents at the aryl moiety. In addition to the synthesis, it was evaluated the antifungal and antibacterial activities of the obtained products. |
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Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2Synthesis of new indolic selenophenes via electrophylic addition of SeCl2SelenofenoAdição eletrofílica de SeCl2CiclizaçãoHeterociclos bioativosSelenopheneElectrophilic addition of SeCl2CyclizationBioactive heterocyclesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThis work initially describes a novel and efficient protocol for the synthesis of 3-selenophen-3-yl-1H-indole derivatives via the electrophilic addition of SeCl2 to the conveniently substituted propargyl-indoles. The synthetic route involved an initial migration of the indole group, caused by the electrophilic addition of SeCl2 to the triple bond of propargyl indole, through the 1-seleno-1,3-diene intermediate, followed by cyclization and formation of the respective selenophene nucleus. The reaction occurs at room temperature in very good yields, showing excellent selectivity, broad substrate scope and wide tolerance to functional groups. In a second part, an easy and convenient route was developed for the synthesis of selenofen[2,3-b]indole derivatives via the electrophilic addition of SeCl2 to the appropriately substituted 3-(alkyl-ethynyl)-1H-indoles. The reaction scope was systematically evaluated, and the products containing the selenophenic ring fused to the indole were obtained in moderate to very good yields. The performance of the transformation was affected by steric and electronic properties of the substituent attached to the nitrogen atom of the indole moiety of the starting material and to a lesser extent by the nature and position of the substituents at the aryl moiety. In addition to the synthesis, it was evaluated the antifungal and antibacterial activities of the obtained products.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqEste trabalho descreve, inicialmente, um novo e eficiente protocolo para a síntese de derivados de 3-selenofen-3-il-1H-indóis via adição eletrofílica de SeCl2 a propargil-indóis, convenientemente substituídos. A rota sintética implicou em uma migração inicial do grupamento indol, provocada pela adição eletrofílica de SeCl2 à ligação tripla do propargil-indol, passando pelo intermediário de 1-seleno-1,3-dieno, seguido pela ciclização e formação do respectivo núcleo de selenofeno. A reação ocorre sob temperatura ambiente em ótimos rendimentos, mostrando excelente seletividade, amplo escopo de substrato e ampla tolerância aos grupos funcionais. Em um segundo momento, desenvolveu-se uma fácil e conveniente rota para síntese de derivados de selenofen[2,3-b]indóis via adição eletrofílica de SeCl2 à 3-(alquil-etinil)-1H-indóis, convenientemente substituídos. O escopo reacional foi sistematicamente avaliado, e os produtos contendo o anel selenofênico fundido ao anel indólico foram obtidos em rendimentos moderados a muito bons. O desempenho da transformação foi afetado pelas propriedades estéricas e eletrônicas do substituinte ligado ao átomo de nitrogênio da porção indólica do material de partida e, em menor grau, pela natureza e posição dos substituintes da porção arílica presente. Além da síntese, também foi avaliada a atividade biológica antifúngica e antibacteriana dos produtos obtidos.Universidade Federal de Santa MariaBrasilQuímicaUFSMPrograma de Pós-Graduação em QuímicaCentro de Ciências Naturais e ExatasSilveira, Claudio da Cruzhttp://lattes.cnpq.br/6152568411858220Lenardao, Eder Joaohttp://lattes.cnpq.br/9974684005171829Perin, Gelsonhttp://lattes.cnpq.br/5962449538872950Rodrigues, Oscar Endrigo Dorneleshttp://lattes.cnpq.br/6536519955416085Schumacher, Ricardo Fredericohttp://lattes.cnpq.br/7856034546434135Martins, Guilherme Ariel Machado2019-06-03T14:08:19Z2019-06-03T14:08:19Z2019-02-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfhttp://repositorio.ufsm.br/handle/1/16722porAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2019-06-04T06:02:32Zoai:repositorio.ufsm.br:1/16722Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2019-06-04T06:02:32Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 Synthesis of new indolic selenophenes via electrophylic addition of SeCl2 |
title |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
spellingShingle |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 Martins, Guilherme Ariel Machado Selenofeno Adição eletrofílica de SeCl2 Ciclização Heterociclos bioativos Selenophene Electrophilic addition of SeCl2 Cyclization Bioactive heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
title_full |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
title_fullStr |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
title_full_unstemmed |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
title_sort |
Síntese de novos selenofenos indólicos via adição eletrofílica de SeCl2 |
author |
Martins, Guilherme Ariel Machado |
author_facet |
Martins, Guilherme Ariel Machado |
author_role |
author |
dc.contributor.none.fl_str_mv |
Silveira, Claudio da Cruz http://lattes.cnpq.br/6152568411858220 Lenardao, Eder Joao http://lattes.cnpq.br/9974684005171829 Perin, Gelson http://lattes.cnpq.br/5962449538872950 Rodrigues, Oscar Endrigo Dorneles http://lattes.cnpq.br/6536519955416085 Schumacher, Ricardo Frederico http://lattes.cnpq.br/7856034546434135 |
dc.contributor.author.fl_str_mv |
Martins, Guilherme Ariel Machado |
dc.subject.por.fl_str_mv |
Selenofeno Adição eletrofílica de SeCl2 Ciclização Heterociclos bioativos Selenophene Electrophilic addition of SeCl2 Cyclization Bioactive heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Selenofeno Adição eletrofílica de SeCl2 Ciclização Heterociclos bioativos Selenophene Electrophilic addition of SeCl2 Cyclization Bioactive heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work initially describes a novel and efficient protocol for the synthesis of 3-selenophen-3-yl-1H-indole derivatives via the electrophilic addition of SeCl2 to the conveniently substituted propargyl-indoles. The synthetic route involved an initial migration of the indole group, caused by the electrophilic addition of SeCl2 to the triple bond of propargyl indole, through the 1-seleno-1,3-diene intermediate, followed by cyclization and formation of the respective selenophene nucleus. The reaction occurs at room temperature in very good yields, showing excellent selectivity, broad substrate scope and wide tolerance to functional groups. In a second part, an easy and convenient route was developed for the synthesis of selenofen[2,3-b]indole derivatives via the electrophilic addition of SeCl2 to the appropriately substituted 3-(alkyl-ethynyl)-1H-indoles. The reaction scope was systematically evaluated, and the products containing the selenophenic ring fused to the indole were obtained in moderate to very good yields. The performance of the transformation was affected by steric and electronic properties of the substituent attached to the nitrogen atom of the indole moiety of the starting material and to a lesser extent by the nature and position of the substituents at the aryl moiety. In addition to the synthesis, it was evaluated the antifungal and antibacterial activities of the obtained products. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-06-03T14:08:19Z 2019-06-03T14:08:19Z 2019-02-01 |
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/1/16722 |
url |
http://repositorio.ufsm.br/handle/1/16722 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da 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 |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922173415587840 |