Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas
Ano de defesa: | 2021 |
---|---|
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/1/23014 |
Resumo: | In the present work, a synthetic route was developed for the preparation of 3- (organochalcogenyl)-azaespiro. The methodology developed involves an ipso cyclization reaction of arylpropynyl amides 1 in the presence of phenyl selenium bromine 2. After a study in search of the best optimization condition, it was found that the use of 1.3 equivalents of the electrophilic species, in nitromethane at 90 ° C for 22 hours guaranteed the best conversion of the starting materials into the desired product. The developed condition was applied to a range of arylpropynyl amides 1 and electrophilic species of organochalcogens 2, leading to the formation of 22 new compounds derived from 3- (organochalcogenyl)-azaspiro. The realization of mechanistic studies indicated that the reaction occurs through an electrophilic cyclization route, and it is possible to observe that halogen (bromine) acts as the base and leads to the aromatization of the system. In a second step, a synthetic protocol was developed for the preparation of 5- (organochalcogenyl)pyrrole[1,2-a] quinolines. The methodology developed involves a cyclization reaction of the type 6-endo-dig of 1- (4-methyl-2- (phenylethynyl) phenyl) -1H-pyrrole and derivatives 7, in the presence of diorganoyl dichalcogenides 8 and ferric chloride. The study of the best reaction condition demonstrated that, in the presence of 1.1 equivalents of diorganoyl dicalcogenide 8, ferric chloride (2.0 equiv.), in dichloromethane at room temperature for 30 minutes, there is a conversion of the starting material in the desired product in a good yield. The developed methodology was applied to different substrates and, in the end, 22 new compounds derived from 5-(organochalcogenyl)pyrrole[1,2-a]quinolines were obtained. It should be noted that, at the end of both developed protocols, some of the compounds obtained were selected and they were subjected to Suzuki-type cross-coupling reactions, leading to the obtaining of 2 new compounds in a yield range of (68-73%). |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2021-11-26T15:33:49Z2021-11-26T15:33:49Z2021-07-28http://repositorio.ufsm.br/handle/1/23014In the present work, a synthetic route was developed for the preparation of 3- (organochalcogenyl)-azaespiro. The methodology developed involves an ipso cyclization reaction of arylpropynyl amides 1 in the presence of phenyl selenium bromine 2. After a study in search of the best optimization condition, it was found that the use of 1.3 equivalents of the electrophilic species, in nitromethane at 90 ° C for 22 hours guaranteed the best conversion of the starting materials into the desired product. The developed condition was applied to a range of arylpropynyl amides 1 and electrophilic species of organochalcogens 2, leading to the formation of 22 new compounds derived from 3- (organochalcogenyl)-azaspiro. The realization of mechanistic studies indicated that the reaction occurs through an electrophilic cyclization route, and it is possible to observe that halogen (bromine) acts as the base and leads to the aromatization of the system. In a second step, a synthetic protocol was developed for the preparation of 5- (organochalcogenyl)pyrrole[1,2-a] quinolines. The methodology developed involves a cyclization reaction of the type 6-endo-dig of 1- (4-methyl-2- (phenylethynyl) phenyl) -1H-pyrrole and derivatives 7, in the presence of diorganoyl dichalcogenides 8 and ferric chloride. The study of the best reaction condition demonstrated that, in the presence of 1.1 equivalents of diorganoyl dicalcogenide 8, ferric chloride (2.0 equiv.), in dichloromethane at room temperature for 30 minutes, there is a conversion of the starting material in the desired product in a good yield. The developed methodology was applied to different substrates and, in the end, 22 new compounds derived from 5-(organochalcogenyl)pyrrole[1,2-a]quinolines were obtained. It should be noted that, at the end of both developed protocols, some of the compounds obtained were selected and they were subjected to Suzuki-type cross-coupling reactions, leading to the obtaining of 2 new compounds in a yield range of (68-73%).No presente trabalho desenvolveu-se uma rota sintética para a preparação de derivados de 3-(organocalcogenil)-azaespiros. A metodologia desenvolvida envolve uma reação de ciclização do tipo ipso de amidas arilpropinílicas 1 na presença de brometo de fenilselenila 2. Após um estudo em busca da melhor condição de otimização, verificou-se que a utilização de 1,3 equivalentes da espécie eletrofílica de brometo de fenilselenila, em nitrometano a 90°C por 22 horas garantiu a melhor conversão dos materiais de partida no produto desejado. A condição desenvolvida foi aplicada a uma gama de arilpropila amidas 1 e espécies eletrofílicas de organocalcogênios 2, levando a formação de 22 novos compostos derivados de 3-(organocalcogenil)-azaespiros. A realização de estudos mecanísticos indicou que a reação se dá por uma rota de ciclização eletrofílica, sendo possível observar que o halogênio (bromo) é quem atua como base e leva a aromatização do sistema. Em um segundo momento, desenvolveu-se um protocolo sintético para a preparação de 5-(organocalcogenil)pirrolo[1,2-a]quinolinas. A metodologia desenvolvida envolve uma reação de ciclização do tipo 6-endo-dig de 1-(4-metil-2-(feniletinil)fenil)-1H-pirrol e derivados 7, na presença de dicalcogenetos de diorganoíla 8 e cloreto férrico. O estudo da melhor condição reacional demonstrou que, na presença de 1,1 equivalentes de dicalcogeneto de diorganoíla 8, cloreto férrico (2,0 equiv.), em diclorometano a temperatura ambiente por 30 minutos, tem-se uma conversão do material de partida no produto desejado em um bom rendimento. A metodologia desenvolvida foi aplicada a diferentes substratos e, ao final, obteve-se 22 novos compostos derivados de 5-(organocalcogenil)pirrolo[1,2-a]quinolinas. Cabe destacar que, ao final de ambos os protocolos desenvolvidos, selecionaram-se alguns dos compostos obtidos e os mesmos foram submetidos a reções de acoplamento do tipo Suzuki, levando a obtenção de 2 novos compostos em uma faixa de rendimento de (68-73%).Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESConselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade 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/openAccessCiclização eletrofílicaDicalcogenetosHeterociclosCloreto férricoElectrophilic cyclizationDichalcogenidesHeterocyclesFerric chlorideCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinasSynthesis of nitrogen heterocyclic compounds via cyclization reactions promoted by electrophilic organocalcogen species: synthesis of azaspiro and pyrroloquinolines derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Santos Neto, José SebastiãoPanatieri, Rodrigo BarrosoRosário, Alisson RodriguesAzeredo, Juliano Braun deRoehrs, Juliano Alexhttp://lattes.cnpq.br/0302295391496951Recchi, Ana Maria Spohr100600000000600600600600600600600600b35c9860-bf5d-4c8a-ab16-02ed6931c067435a47a4-e0a4-474a-84ee-b5fbc324508422d3e4ad-428e-4e25-a694-f681d9a27ee115bc0a6e-861e-407c-a970-9f15a2b63c1209572565-7d90-44a4-ac6a-b4e38ea7e312aabc8dae-7bf3-4fa1-9061-5feca5886968ca509c1e-5e9b-48ae-b180-e852745880d0reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2021_RECCHI_ANA.pdfTES_PPGQUIMICA_2021_RECCHI_ANA.pdfTeseapplication/pdf25257739http://repositorio.ufsm.br/bitstream/1/23014/1/TES_PPGQUIMICA_2021_RECCHI_ANA.pdfa641037dbe92061e1ba5ccf2be1fe6bcMD51LICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of nitrogen heterocyclic compounds via cyclization reactions promoted by electrophilic organocalcogen species: synthesis of azaspiro and pyrroloquinolines derivatives |
title |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
spellingShingle |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas Recchi, Ana Maria Spohr Ciclização eletrofílica Dicalcogenetos Heterociclos Cloreto férrico Electrophilic cyclization Dichalcogenides Heterocycles Ferric chloride CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
title_full |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
title_fullStr |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
title_full_unstemmed |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
title_sort |
Síntese de compostos heterocíclicos nitrogenados via reações de ciclização promovidas por espécies eletrofílicas de organocalcogênios: síntese de derivados de azaespiros e pirroloquinolinas |
author |
Recchi, Ana Maria Spohr |
author_facet |
Recchi, Ana Maria Spohr |
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.advisor-co1.fl_str_mv |
Santos Neto, José Sebastião |
dc.contributor.referee1.fl_str_mv |
Panatieri, Rodrigo Barroso |
dc.contributor.referee2.fl_str_mv |
Rosário, Alisson Rodrigues |
dc.contributor.referee3.fl_str_mv |
Azeredo, Juliano Braun de |
dc.contributor.referee4.fl_str_mv |
Roehrs, Juliano Alex |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0302295391496951 |
dc.contributor.author.fl_str_mv |
Recchi, Ana Maria Spohr |
contributor_str_mv |
Zeni, Gilson Rogério Santos Neto, José Sebastião Panatieri, Rodrigo Barroso Rosário, Alisson Rodrigues Azeredo, Juliano Braun de Roehrs, Juliano Alex |
dc.subject.por.fl_str_mv |
Ciclização eletrofílica Dicalcogenetos Heterociclos Cloreto férrico |
topic |
Ciclização eletrofílica Dicalcogenetos Heterociclos Cloreto férrico Electrophilic cyclization Dichalcogenides Heterocycles Ferric chloride CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Electrophilic cyclization Dichalcogenides Heterocycles Ferric chloride |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In the present work, a synthetic route was developed for the preparation of 3- (organochalcogenyl)-azaespiro. The methodology developed involves an ipso cyclization reaction of arylpropynyl amides 1 in the presence of phenyl selenium bromine 2. After a study in search of the best optimization condition, it was found that the use of 1.3 equivalents of the electrophilic species, in nitromethane at 90 ° C for 22 hours guaranteed the best conversion of the starting materials into the desired product. The developed condition was applied to a range of arylpropynyl amides 1 and electrophilic species of organochalcogens 2, leading to the formation of 22 new compounds derived from 3- (organochalcogenyl)-azaspiro. The realization of mechanistic studies indicated that the reaction occurs through an electrophilic cyclization route, and it is possible to observe that halogen (bromine) acts as the base and leads to the aromatization of the system. In a second step, a synthetic protocol was developed for the preparation of 5- (organochalcogenyl)pyrrole[1,2-a] quinolines. The methodology developed involves a cyclization reaction of the type 6-endo-dig of 1- (4-methyl-2- (phenylethynyl) phenyl) -1H-pyrrole and derivatives 7, in the presence of diorganoyl dichalcogenides 8 and ferric chloride. The study of the best reaction condition demonstrated that, in the presence of 1.1 equivalents of diorganoyl dicalcogenide 8, ferric chloride (2.0 equiv.), in dichloromethane at room temperature for 30 minutes, there is a conversion of the starting material in the desired product in a good yield. The developed methodology was applied to different substrates and, in the end, 22 new compounds derived from 5-(organochalcogenyl)pyrrole[1,2-a]quinolines were obtained. It should be noted that, at the end of both developed protocols, some of the compounds obtained were selected and they were subjected to Suzuki-type cross-coupling reactions, leading to the obtaining of 2 new compounds in a yield range of (68-73%). |
publishDate |
2021 |
dc.date.accessioned.fl_str_mv |
2021-11-26T15:33:49Z |
dc.date.available.fl_str_mv |
2021-11-26T15:33:49Z |
dc.date.issued.fl_str_mv |
2021-07-28 |
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/1/23014 |
url |
http://repositorio.ufsm.br/handle/1/23014 |
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 |
dc.relation.authority.fl_str_mv |
b35c9860-bf5d-4c8a-ab16-02ed6931c067 435a47a4-e0a4-474a-84ee-b5fbc3245084 22d3e4ad-428e-4e25-a694-f681d9a27ee1 15bc0a6e-861e-407c-a970-9f15a2b63c12 09572565-7d90-44a4-ac6a-b4e38ea7e312 aabc8dae-7bf3-4fa1-9061-5feca5886968 ca509c1e-5e9b-48ae-b180-e852745880d0 |
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 instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
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