Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol
Autor(a) principal: | |
---|---|
Data de Publicação: | 2019 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/19158 |
Resumo: | The treatment of alkynyl índoles by using iodine with electrophilic source led to 3-iodo-4H-calcogenophene[3,2-b]indoles derivates. Firstly a series of studies were performed variations to obtain the compounds containing a selenium heteroatom in the structure, thus investigating the reaction parameters such as temperature, solvente and proportion of reagentes. The results indicated the best reaction condition using 2-alkynyl indole (0,25 mmol), THF (5ml) iodine (1,1 equiv) at room temperature. By means this methodology the products were obtained in yelds of 39-89%. A second study were performed reporting the products containing a súlfur heteroatom in the structure. Thus, the best reaction conditions studied used alkynyl indole (0,25 mmol), etanol (5 mL), iodine (3 equiv.), ethyl disulfide ( 3 equiv.) at 70 °C for 3 hours. The use iodine as an electrophilic source in additon to demonstrating efficiency as triple bond activation agente is efficient in the cyclization process, making the metodology more efficient for both other cyclizations and future functionalisations. The insertion of a halogen atom in a strategy position in the molecule allows the synthesis of new heterocycles of greater complexity through coupling reactions with metals such as Ullmann type complings. |
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2019-12-16T15:48:12Z2019-12-16T15:48:12Z2019-07-26http://repositorio.ufsm.br/handle/1/19158The treatment of alkynyl índoles by using iodine with electrophilic source led to 3-iodo-4H-calcogenophene[3,2-b]indoles derivates. Firstly a series of studies were performed variations to obtain the compounds containing a selenium heteroatom in the structure, thus investigating the reaction parameters such as temperature, solvente and proportion of reagentes. The results indicated the best reaction condition using 2-alkynyl indole (0,25 mmol), THF (5ml) iodine (1,1 equiv) at room temperature. By means this methodology the products were obtained in yelds of 39-89%. A second study were performed reporting the products containing a súlfur heteroatom in the structure. Thus, the best reaction conditions studied used alkynyl indole (0,25 mmol), etanol (5 mL), iodine (3 equiv.), ethyl disulfide ( 3 equiv.) at 70 °C for 3 hours. The use iodine as an electrophilic source in additon to demonstrating efficiency as triple bond activation agente is efficient in the cyclization process, making the metodology more efficient for both other cyclizations and future functionalisations. The insertion of a halogen atom in a strategy position in the molecule allows the synthesis of new heterocycles of greater complexity through coupling reactions with metals such as Ullmann type complings.O tratamento de alqunil indóis utilizando iodo como fonte eletrofílica forneceu os derivados de 3-iodo-4H-calcogeno[3,2-b]indol. Primeiramente, uma série de estudos para obtenção dos compostos contendo um heteroátomo de selênio em sua estrutura foi realizada, assim, as variações dos parâmetros reacionais foram investigadas, tais como solvente temperatura e proporção de reagentes. Os resultados indicaram a melhor condição reacional utilizando alquinil indol (0,25 mmol), THF (5 ml), iodo (1,1 equiv) a temperatura ambiente. Por meio dessa metodologia os produtos foram obtidos em rendimentos de 39 a 89%. Um segundo estudo foi realizado relatando a obtenção dos produtos contendo um heteroátomo de enxofre na estrutura. Assim, a melhor condição reacional estudada utilizou alquinil indol (0,25 mmol), etanol (5 mL), iodo (3,0 equiv.), dissulfeto de etila (3 equiv.) a temperatura de 70 ºC por 3 horas. Os produtos ciclizados com enxofre são obtidos em rendimentos de 55 a 90%. A utilização de iodo como fonte eletrofílica além de demostrar eficiência como agente de ativação de triplas ligações é eficiente no processo de ciclização, tornando a metodologia mais eficiente tanto para demais ciclizações como para futuras funcionalizações. A inserção de um átomo de halogênio em posição estratégica na molécula permite a síntese de novos heterocíclos de maior complexidade, através de reações de acoplamento com metais como, por exemplo, os acoplamentos do tipo Ullmann.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessIndóisOrganocalcogêniosCiclização eletrofílicaIodoIndolesOrganochalcogenesElectrophilic cyclizationIodineCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indolSynthesis of 3-iodo-4H-chalcogenepheno[3,2-b]indole via iodine-promoted electrophlic cyclization of alkynyl indol derivatesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Souza, Diego dehttp://lattes.cnpq.br/3561369550388349Barancelli, Daniela Alinehttp://lattes.cnpq.br/4995499872041179http://lattes.cnpq.br/1042388169453183Leonel, Guilherme100600000000600b21a898a-0ab0-4f33-b980-2b55ef590b94dc489a41-c052-426a-8ab9-4b3ee00acec237d0397a-6793-4738-b96d-282ba988a6d32a53111b-b21f-41a1-87af-ac65e8819e9areponame:Manancial - Repositório Digital da 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-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 3-iodo-4H-chalcogenepheno[3,2-b]indole via iodine-promoted electrophlic cyclization of alkynyl indol derivates |
title |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
spellingShingle |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol Leonel, Guilherme Indóis Organocalcogênios Ciclização eletrofílica Iodo Indoles Organochalcogenes Electrophilic cyclization Iodine CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
title_full |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
title_fullStr |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
title_full_unstemmed |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
title_sort |
Síntese de 3-iodo-4H-calcogenofeno[3,2-b]indol via ciclização eletrofílica mediada por iodo de derivados de alquinil indol |
author |
Leonel, Guilherme |
author_facet |
Leonel, Guilherme |
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 |
Souza, Diego de |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3561369550388349 |
dc.contributor.referee2.fl_str_mv |
Barancelli, Daniela Aline |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/4995499872041179 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/1042388169453183 |
dc.contributor.author.fl_str_mv |
Leonel, Guilherme |
contributor_str_mv |
Zeni, Gilson Rogério Souza, Diego de Barancelli, Daniela Aline |
dc.subject.por.fl_str_mv |
Indóis Organocalcogênios Ciclização eletrofílica Iodo |
topic |
Indóis Organocalcogênios Ciclização eletrofílica Iodo Indoles Organochalcogenes Electrophilic cyclization Iodine CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Indoles Organochalcogenes Electrophilic cyclization Iodine |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The treatment of alkynyl índoles by using iodine with electrophilic source led to 3-iodo-4H-calcogenophene[3,2-b]indoles derivates. Firstly a series of studies were performed variations to obtain the compounds containing a selenium heteroatom in the structure, thus investigating the reaction parameters such as temperature, solvente and proportion of reagentes. The results indicated the best reaction condition using 2-alkynyl indole (0,25 mmol), THF (5ml) iodine (1,1 equiv) at room temperature. By means this methodology the products were obtained in yelds of 39-89%. A second study were performed reporting the products containing a súlfur heteroatom in the structure. Thus, the best reaction conditions studied used alkynyl indole (0,25 mmol), etanol (5 mL), iodine (3 equiv.), ethyl disulfide ( 3 equiv.) at 70 °C for 3 hours. The use iodine as an electrophilic source in additon to demonstrating efficiency as triple bond activation agente is efficient in the cyclization process, making the metodology more efficient for both other cyclizations and future functionalisations. The insertion of a halogen atom in a strategy position in the molecule allows the synthesis of new heterocycles of greater complexity through coupling reactions with metals such as Ullmann type complings. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-12-16T15:48:12Z |
dc.date.available.fl_str_mv |
2019-12-16T15:48:12Z |
dc.date.issued.fl_str_mv |
2019-07-26 |
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/1/19158 |
url |
http://repositorio.ufsm.br/handle/1/19158 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
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 |
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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