Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/22999 |
Resumo: | In this present work, an unprecedented series of 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21 was synthesized with interest in the potential biological, because to the presence of different heterocyclic nucleus. The 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7 were obtained through a cyclization reaction of benzochalcogenoamides 3 and 4 with 1,3- dichloroacetone 5, with yields of 55% and 80%. For the synthesis reaction of 4-(azidomethyl)-2-phenyl- 1,3-chalcogenazoles 10 and 11, were used 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7, potassium iodide and sodium azide 9, of the yields were 55% and 60%. Through the Click reaction type, catalyzed by copper iodide, between 4-(azidomethyl)-2-phenyl-1,3-chalcogenazoles (10; 11) and propargyl alcohol 12, the formation of (1-((2-phenylchalcogenazo-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14, with yields of 88% and 76%, respectively. Subsequently, the protection of the alcohol function of (1-((2- phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14 was performed with mesyl chloride 15, where yields varied from 67% to 60% in obtaining (1-(((2-phenylchalcogenazol-4-yl)methyl)- 1H-1,2,3-triazol-4-yl) methanesulfonate 16 and 17, respectively. From the nucleophilic substitution reaction, optimized, between (1-(((2-phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazol-4- yl)methanesulfonates (16, 17) and diphenyl dichalcogenides 18 and 19 take to the formation of the products desired, the 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21, with yields of 47% to 94%. |
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Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolarSynthesis of 1,2,3-triazoles-1,4-dissubstitutes containing organochalcogens derived from 4- (azidomethil) -2-phenyl-1,3- chalcogenazoles via 1,3-dipolar cycloaddition reactionOrganocalcogêniosCalcogenazolTriazolOrganochalcogenChalcogenazoleTriazoleCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn this present work, an unprecedented series of 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21 was synthesized with interest in the potential biological, because to the presence of different heterocyclic nucleus. The 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7 were obtained through a cyclization reaction of benzochalcogenoamides 3 and 4 with 1,3- dichloroacetone 5, with yields of 55% and 80%. For the synthesis reaction of 4-(azidomethyl)-2-phenyl- 1,3-chalcogenazoles 10 and 11, were used 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7, potassium iodide and sodium azide 9, of the yields were 55% and 60%. Through the Click reaction type, catalyzed by copper iodide, between 4-(azidomethyl)-2-phenyl-1,3-chalcogenazoles (10; 11) and propargyl alcohol 12, the formation of (1-((2-phenylchalcogenazo-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14, with yields of 88% and 76%, respectively. Subsequently, the protection of the alcohol function of (1-((2- phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14 was performed with mesyl chloride 15, where yields varied from 67% to 60% in obtaining (1-(((2-phenylchalcogenazol-4-yl)methyl)- 1H-1,2,3-triazol-4-yl) methanesulfonate 16 and 17, respectively. From the nucleophilic substitution reaction, optimized, between (1-(((2-phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazol-4- yl)methanesulfonates (16, 17) and diphenyl dichalcogenides 18 and 19 take to the formation of the products desired, the 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21, with yields of 47% to 94%.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSNesse presente trabalho, uma série inédita de 4-((4-((arilcalcogeno)metil)-1H-1,2,3-triazol-1-il)metil)-2- fenilcalcogenazóis 20 e 21 foi sintetizada com interesse no potencial biológico, devido a presença de diferentes núcleos heterocíclicos. Os 4-(clorometil)-2-fenilcalcogenazóis 6 e 7 foram obtidos por meio de uma reação de ciclização das benzocalcogenoamidas 3 e 4 com a 1,3-dicloroacetona 5, com rendimentos de 55% e 80%. Para reação de síntese dos 4-(azidometil)-2-fenil-1,3-calcogenazóis 10 e 11 foram utilizados os 4-(clorometil)-2-fenilcalcogenazóis 6 e 7, o iodeto de potássio e a azida de sódio 9, os rendimentos foram de 55% e 60%. Através da reação tipo Click, catalisada por iodeto de cobre, entre os 4-(azidometil)- 2-fenil-1,3-calcogenazóis (10; 11) e o álcool propargílico 12, levou-se a formação dos (1-((2- fenilcalcogenazol-4-il)metil)-1H-1,2,3-triazol-4-il)metanol 13 e 14, com rendimentos de 88% e 76%. Posteriormente, realizou-se a proteção da função álcool dos (1-((2-fenilcalcogenazo-4-il)metil)-1H-1,2,3- triazo-4-il)metanol 13 e 14 com o cloreto de mesila 15, onde os rendimentos variaram de 67% a 60% na obtenção dos metanossulfonato de (1-((2-fenilcalcogenazol-4-il)metil)-1H-1,2,3-triazol-4-il)metila 16 e 17, respectivamente. A partir da reação de substituição nucleofílica, devidamente otimizada, entre os metanossulfonatos de (1-((2-fenilcalcogenazol-4-il)metil)-1H-1,2,3-triazol-4-il)metila (16, 17) e os dicalcogenetos de difenila 18 e 19 levou-se a formação dos produtos desejados, os 4-((4- ((arilcalcogeno)metil)-1H-1,2,3-triazol-1-il)metil)-2-fenilcalcogenazóis 20 e 21, com rendimentos que variaram de 47% a 94%.Universidade Federal de Santa MariaBrasilQuímicaUFSMPrograma de Pós-Graduação em QuímicaCentro de Ciências Naturais e ExatasDornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Rodrigues, Oscar Endrigo DornelesIglesias, Bernardo AlmeidaAppelt, Helmoz RoseniaimBernardy, Silvia2021-11-26T12:08:24Z2021-11-26T12:08:24Z2020-10-20info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://repositorio.ufsm.br/handle/1/22999porAttribution-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:UFSM2021-11-27T06:03:18Zoai:repositorio.ufsm.br:1/22999Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2021-11-27T06:03:18Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar Synthesis of 1,2,3-triazoles-1,4-dissubstitutes containing organochalcogens derived from 4- (azidomethil) -2-phenyl-1,3- chalcogenazoles via 1,3-dipolar cycloaddition reaction |
title |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
spellingShingle |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar Bernardy, Silvia Organocalcogênios Calcogenazol Triazol Organochalcogen Chalcogenazole Triazole CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
title_full |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
title_fullStr |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
title_full_unstemmed |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
title_sort |
Síntese de 1,2,3-triazóis-1,4-dissubstituídos contendo organocalcogênios derivados de 4-(azidometil)-2-fenil-1,3-calcogenazóis via reação de cicloadição 1,3-dipolar |
author |
Bernardy, Silvia |
author_facet |
Bernardy, Silvia |
author_role |
author |
dc.contributor.none.fl_str_mv |
Dornelles, Luciano http://lattes.cnpq.br/7629319262073140 Rodrigues, Oscar Endrigo Dorneles Iglesias, Bernardo Almeida Appelt, Helmoz Roseniaim |
dc.contributor.author.fl_str_mv |
Bernardy, Silvia |
dc.subject.por.fl_str_mv |
Organocalcogênios Calcogenazol Triazol Organochalcogen Chalcogenazole Triazole CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Organocalcogênios Calcogenazol Triazol Organochalcogen Chalcogenazole Triazole CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this present work, an unprecedented series of 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21 was synthesized with interest in the potential biological, because to the presence of different heterocyclic nucleus. The 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7 were obtained through a cyclization reaction of benzochalcogenoamides 3 and 4 with 1,3- dichloroacetone 5, with yields of 55% and 80%. For the synthesis reaction of 4-(azidomethyl)-2-phenyl- 1,3-chalcogenazoles 10 and 11, were used 4-(chloromethyl)-2-phenylchalcogenazoles 6 and 7, potassium iodide and sodium azide 9, of the yields were 55% and 60%. Through the Click reaction type, catalyzed by copper iodide, between 4-(azidomethyl)-2-phenyl-1,3-chalcogenazoles (10; 11) and propargyl alcohol 12, the formation of (1-((2-phenylchalcogenazo-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14, with yields of 88% and 76%, respectively. Subsequently, the protection of the alcohol function of (1-((2- phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazo-4-yl)methanol 13 and 14 was performed with mesyl chloride 15, where yields varied from 67% to 60% in obtaining (1-(((2-phenylchalcogenazol-4-yl)methyl)- 1H-1,2,3-triazol-4-yl) methanesulfonate 16 and 17, respectively. From the nucleophilic substitution reaction, optimized, between (1-(((2-phenylchalcogenazol-4-yl)methyl)-1H-1,2,3-triazol-4- yl)methanesulfonates (16, 17) and diphenyl dichalcogenides 18 and 19 take to the formation of the products desired, the 4-((4-((arylchalcogen)methyl)-1H-1,2,3-triazol-1-yl) methyl)-2-phenylchalcogenazole 20 and 21, with yields of 47% to 94%. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-10-20 2021-11-26T12:08:24Z 2021-11-26T12:08:24Z |
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/1/22999 |
url |
http://repositorio.ufsm.br/handle/1/22999 |
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 |
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1805922056062107648 |