Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica
Ano de defesa: | 2019 |
---|---|
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/1/19169 |
Resumo: | This work reports the synthesis of a series of selenium heterocyclics containing in it’s core structure. These compounds are obtained through intramolecular electrophilic cyclization reactions of alkynyl substrates and promoted by different electrophilic sources. In the first step, new alternative methods were developed to promote the intramolecular electrophilic cyclization reaction of 2-(selenobutyl)-1- (alkynyl)cyclohexanol in the presence of different electrophilic source. The use of resulted in molecular iodine series of 3-iodoselenofenes (22 examples) in yields 30 to 94% isolated yields. The use of cupper (II) bromide as an electrophilic afforded 10 examples of 3-bromoselenofenes in 50 and 94% yield. When a copper iodide and diphenyl diselenide were employed, 6 novel examples of 3- (phenylselenyl)selenophene were obtained in satisfactory to good yields (29-70%). In addition, we also successfully applied 3-iodoselenophen as a substrate in coupling conditions of the Sonogashira, Suzuki and Ulmmann type, providing the corresponding products in moderate to good (60-84%). In a second step, we developed an alternative method in the regioselective cyclization 6-endo-dig of 2-(2- (selenobutyl)aryl)-4-arylbut-3-yn-2-ol, by employing iron (III) chloride and differently substituted diorganoyl diselenides as promoters for this process. Through this cyclization protocol we obtained a series of (27 examples) 4-methylene-3- (selenoaryl)-4H-selenocromene in 30 to 71% yield. Finally, when the PhSeBr was applied to electrophilic source for 2-(2-(selenobutyl)aryl)-4-arylbut-3-in-2-ol, interestingly two examples of 3- (bromomethyl) benzo[b]selenoar-2-yl)arylmethanone were obtained in satisfactory yields. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2019-12-17T15:23:56Z2019-12-17T15:23:56Z2019-07-26http://repositorio.ufsm.br/handle/1/19169This work reports the synthesis of a series of selenium heterocyclics containing in it’s core structure. These compounds are obtained through intramolecular electrophilic cyclization reactions of alkynyl substrates and promoted by different electrophilic sources. In the first step, new alternative methods were developed to promote the intramolecular electrophilic cyclization reaction of 2-(selenobutyl)-1- (alkynyl)cyclohexanol in the presence of different electrophilic source. The use of resulted in molecular iodine series of 3-iodoselenofenes (22 examples) in yields 30 to 94% isolated yields. The use of cupper (II) bromide as an electrophilic afforded 10 examples of 3-bromoselenofenes in 50 and 94% yield. When a copper iodide and diphenyl diselenide were employed, 6 novel examples of 3- (phenylselenyl)selenophene were obtained in satisfactory to good yields (29-70%). In addition, we also successfully applied 3-iodoselenophen as a substrate in coupling conditions of the Sonogashira, Suzuki and Ulmmann type, providing the corresponding products in moderate to good (60-84%). In a second step, we developed an alternative method in the regioselective cyclization 6-endo-dig of 2-(2- (selenobutyl)aryl)-4-arylbut-3-yn-2-ol, by employing iron (III) chloride and differently substituted diorganoyl diselenides as promoters for this process. Through this cyclization protocol we obtained a series of (27 examples) 4-methylene-3- (selenoaryl)-4H-selenocromene in 30 to 71% yield. Finally, when the PhSeBr was applied to electrophilic source for 2-(2-(selenobutyl)aryl)-4-arylbut-3-in-2-ol, interestingly two examples of 3- (bromomethyl) benzo[b]selenoar-2-yl)arylmethanone were obtained in satisfactory yields.Este trabalho relata a síntese de uma série de heterocíclicos contendo o átomo de selênio em sua estrutura. A obtenção destes compostos se dá através de reações de ciclização eletrofílica intramolecular dos substratos alquinílicos, promovidas por diferentes fontes eletrofílicas. No primeiro momento, desenvolveu-se métodos alternativos para a promoção da reação de ciclização intramolecular de 2- (selenobutil)-1-(alquinil)ciclohexanol, empregando diferentes eletrófilos. A utilização de iodo molecular levou a uma série de 3-iodoselenofenos (22 exemplos) com rendimentos que variaram de 30 a 94%. Já a utilização de brometo de cobre II como fonte eletrofílica, levou a síntese de 10 exemplos dos 3-bromoselenofenos com rendimentos entre 50 e 94%. Quando empregado um sistema de iodeto de cobre I e disseleneto de difenila, pode-se obter 6 novos exemplos de selenofenos substituídos na posição 3 com grupamentos selenofenil com rendimentos satisfatórios (29-70%). A fim de avaliar a versatilidade do composto 3-iodoselenofeno, este foi submetido a reações de acoplamento cruzado do tipo Sonogashira, Suzuki e tipo-Ulmmann, onde foi possível a obtenção de novos selenofenos com diferentes funcionalizações em bons rendimentos (60-84%). Num segundo momento, desenvolveu-se um método alternativo para a ciclização regiosseletiva 6-endo-dig de 2-(2-(selenobutil)aril)-4- arilbut-3-in-2-ol, empregando-se cloreto de ferro III e alguns disselenetos de diorganoíla como agentes promotores da ciclização. Através deste protocolo de ciclização, pode-se sintetizar uma série de 4-metileno-3-(selenoaril)-4Hselenocromeno (27 exemplos) em bons rendimentos os quais variaram de 30 a 71%. Por fim, quando submetidos o substrato 2-(2-(selenobutil)aril)-4-arilbut-3-in-2-ol a presença de PhSeBr como fonte eletrofílica, obteve-se dois exemplos de (3- (bromometil)benzo[b]selenoar-2-il)arilmetanona com rendimentos satisfatórios.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/openAccessSelenofenoSelenocromenoCiclização eletrofílicaSelenopheneSelenochromeneElectrophilic cyclizationCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílicaSynthesis of selenophene and 4H-selenochromene derivatives via electrophilic cyclization reactionsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Iglesias, Bernardo Almeidahttp://lattes.cnpq.br/4402375533322977Rhoden, Cristiano Rodrigo Bohnhttp://lattes.cnpq.br/1501354546180254Machado, Pablohttp://lattes.cnpq.br/3319303431365448Khan, Jamal Rafiquehttp://lattes.cnpq.br/9076951500265924http://lattes.cnpq.br/5300124123728053Casola, Kamila Kayser100600000000600b21a898a-0ab0-4f33-b980-2b55ef590b94a0006981-41d4-4592-bf7a-7d680b7d54b3483d6d0c-e419-454b-b413-1a51673258c33ae04d95-f7ab-4cb0-9f6d-2c48befc185c5947edc6-cc49-4ac6-9e09-1424ae969e89359b711f-bacb-4703-ab4b-a9940aca38a3reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMLICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
dc.title.alternative.eng.fl_str_mv |
Synthesis of selenophene and 4H-selenochromene derivatives via electrophilic cyclization reactions |
title |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
spellingShingle |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica Casola, Kamila Kayser Selenofeno Selenocromeno Ciclização eletrofílica Selenophene Selenochromene Electrophilic cyclization CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
title_full |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
title_fullStr |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
title_full_unstemmed |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
title_sort |
Síntese de derivados de selenofenos e 4H-selenocromeno via reações de ciclização eletrofílica |
author |
Casola, Kamila Kayser |
author_facet |
Casola, Kamila Kayser |
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 |
Iglesias, Bernardo Almeida |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/4402375533322977 |
dc.contributor.referee2.fl_str_mv |
Rhoden, Cristiano Rodrigo Bohn |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/1501354546180254 |
dc.contributor.referee3.fl_str_mv |
Machado, Pablo |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/3319303431365448 |
dc.contributor.referee4.fl_str_mv |
Khan, Jamal Rafique |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/9076951500265924 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5300124123728053 |
dc.contributor.author.fl_str_mv |
Casola, Kamila Kayser |
contributor_str_mv |
Zeni, Gilson Rogério Iglesias, Bernardo Almeida Rhoden, Cristiano Rodrigo Bohn Machado, Pablo Khan, Jamal Rafique |
dc.subject.por.fl_str_mv |
Selenofeno Selenocromeno Ciclização eletrofílica |
topic |
Selenofeno Selenocromeno Ciclização eletrofílica Selenophene Selenochromene Electrophilic cyclization CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Selenophene Selenochromene Electrophilic cyclization |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work reports the synthesis of a series of selenium heterocyclics containing in it’s core structure. These compounds are obtained through intramolecular electrophilic cyclization reactions of alkynyl substrates and promoted by different electrophilic sources. In the first step, new alternative methods were developed to promote the intramolecular electrophilic cyclization reaction of 2-(selenobutyl)-1- (alkynyl)cyclohexanol in the presence of different electrophilic source. The use of resulted in molecular iodine series of 3-iodoselenofenes (22 examples) in yields 30 to 94% isolated yields. The use of cupper (II) bromide as an electrophilic afforded 10 examples of 3-bromoselenofenes in 50 and 94% yield. When a copper iodide and diphenyl diselenide were employed, 6 novel examples of 3- (phenylselenyl)selenophene were obtained in satisfactory to good yields (29-70%). In addition, we also successfully applied 3-iodoselenophen as a substrate in coupling conditions of the Sonogashira, Suzuki and Ulmmann type, providing the corresponding products in moderate to good (60-84%). In a second step, we developed an alternative method in the regioselective cyclization 6-endo-dig of 2-(2- (selenobutyl)aryl)-4-arylbut-3-yn-2-ol, by employing iron (III) chloride and differently substituted diorganoyl diselenides as promoters for this process. Through this cyclization protocol we obtained a series of (27 examples) 4-methylene-3- (selenoaryl)-4H-selenocromene in 30 to 71% yield. Finally, when the PhSeBr was applied to electrophilic source for 2-(2-(selenobutyl)aryl)-4-arylbut-3-in-2-ol, interestingly two examples of 3- (bromomethyl) benzo[b]selenoar-2-yl)arylmethanone were obtained in satisfactory yields. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-12-17T15:23:56Z |
dc.date.available.fl_str_mv |
2019-12-17T15:23:56Z |
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/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/19169 |
url |
http://repositorio.ufsm.br/handle/1/19169 |
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 |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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UFSM |
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