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dc.creatorMalavolta, Juliana Limana
dc.date.accessioned2019-07-04T18:54:29Z
dc.date.available2019-07-04T18:54:29Z
dc.date.issued2014-12-19
dc.identifier.urihttp://repositorio.ufsm.br/handle/1/17319
dc.description.abstractThis study shows strategies to prepare 1,3,4-oxadiazoles and derivatives from 4-oxopentanoic acid is reported. The compounds 4-(2-(5-substituted-1,3,4-oxadiazol-2-yl)ethyl)-2-(methylthio/phenyl)-6-(trifluoromethyl)pyrimidine; 7aa (5-H, 2-SMe); 7ab (5-Me, 2-SMe); 7ac (5-Ph, 2-SMe); 7ba (5-H, 2-Ph); 7bb (5-Me, 2-Ph); 7bc (5-Ph, 2-Ph); and 2-methyl-5-(2-(5-substituted-1,3,4-oxadiazol-2-yl)ethyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine; 8a (5-H); 8b (5-Me); 8c (5-Ph); were obtained through of reaction between the hydrazides trifluormetilated previously synthesized with orthoesters which lead to obtaining of product in yields of 55-98%. The synthesis of oxadiazoles-2-tiosubstituted through of reaction of hydrazides with carbon disulfide conducted the formation of compounds 5-(2-(methylthio/phenyl-6-(trifluoromethyl)pyrimidin-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol; 9a (2-SMe); 9b (2-Ph); and 5-(2-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)ethyl)-1,3,4-oxadiazole-2-thiol; 10; with yields of 84-97%. This compounds series were reacted with alkylating and acylating agents and derivatized to compounds 1,3,4-oxadiazoles 2-S-alkylated/acylated 5-(2-(methylthio/phenyl)-6-(trifluoromethyl)pyrimidin-4-yl)ethyl)-1,3,4-oxadiazol-2-yl-thiosubstituted; 11aa (2-SMe, 2-S(CO)Me); 11ab (2-SMe, 2-S(CO)CCl3); 11ac (2-SMe, 2-SCH2(CO)Ph); 11ba (2-Ph, 2-S(CO)Me); 11bb (2-Ph, 2-S(CO)CCl3); 11bc (2-Ph, 2-SCH2(CO)Ph); and 5-(2-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)ethyl)-1,3,4-oxadiazol-2-yl-thiosubstituted; 12 (2-S(CO)Me). Series of hydrazones N’-(substituted)-3-(2- (methylthio/phenyl)-6-(trifluoromethyl)pyrimidin-4-yl)propanehydrazide, 13aa (Ph, 2-SMe); 13ab (2-ClPh, 2-SMe); 13ac (4-(N(Me)2)Ph, 2-SMe); 13ad (4-NO2Ph, 2-SMe); 13ae (furano, 2-SMe); 13ba (Ph, 2-Ph); 13bb (2-ClPh, 2-Ph); 13bc (4-(N(Me)2)Ph, 2-Ph); 13be (furan, 2-Ph); and N’-(substituted)-3-(2-methyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl)propanehydrazide; 14a (Ph); 14b (2-ClPh); 14c (4-(N(Me)2)Ph); 14e (furan); were also synthesized to use as precursors for 2,3-dihydro-1,3,4-oxadiazoles synthesis. N-substituted by reaction with acetic anhydride which led to the formation of N-acetyl-3-(2-(methylthio/phenyl)-6-(trifluoromethyl)pyrimidin-4-yl)propanehydrazide; 15a (2-SMe); 15b (2-Ph) with yields of 51-66%. Finally was investigated the oxadative cyclization of N-acyl hydrazones with trichloroisocyanuric acid to obtain 1,3,4-oxadiazoles it allowed to obtain 2-methyl-5-(3-yl-propanoate ethyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine and 2-(methylthio/phenyl)-4-(3-propanoate ethyl-yl)-6-(trifluoromethyl)pyrimidine with yields of 64-79%. All the synthesized compounds are new and their structures were confirmed by 1H, 13C NMR data and two-dimensional NMR techniques as well as mass spectrometry data.eng
dc.description.sponsorshipConselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqpor
dc.languageporpor
dc.publisherUniversidade Federal de Santa Mariapor
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectÁcido 4-oxopentanóicopor
dc.subjectPirimidinaspor
dc.subjectPirazolo[1,5-a]pirimidinas hidrazidaspor
dc.subject1,3,4-oxadiazóispor
dc.subject4-oxopentanoic acideng
dc.subjectPyrimidineseng
dc.subjectPyrazolo[1,5-a]-pyrimidineeng
dc.subjectHydrazideseng
dc.subject1,3,4-oxadiazoleseng
dc.title1,3,4-oxadiazóis: estratégias para síntese e derivatização a partir do ácido 4-oxopentanóicopor
dc.title.alternative1,3,4-oxadiazoles: strategies for synthesis and derivatization from 4-oxopentanoic acideng
dc.typeTesepor
dc.description.resumoEste trabalho descreve um estudo sobre estratégias sintéticas para promover a síntese de 1,3,4-oxadiazóis e seus derivados a partir do ácido 4-oxopentanóico. Os compostos 4-(2-(5-substituído-1,3,4-oxadiazol-2-il)etil)-2-(metiltio/fenil)-6-(trifluormetil)pirimidina; 7aa (5-H, 2-SMe); 7ab (5-Me, 2-SMe); 7ac (5-Ph, 2-SMe); 7ba (5-H, 2-Ph); 7bb (5-Me, 2-Ph); 7bc (5-Ph, 2-Ph); e 2-metil-5-(2-(5-substituído-1,3,4-oxadiazol-2-il)etil)-7-(trifluormetil)pirazolo[1,5-a]pirimidina; 8a (5-H); 8b (5-Me); 8c (5-Ph); foram obtidos através da reação entre hidrazidas trifluormetiladas previamente sintetizadas, com ortoésteres, o que possibilitou a obtenção dos produtos alvo com rendimentos de 55-98%. A síntese de oxadiazóis 2-tiossubstituídos através da reação entre as hidrazidas com dissulfeto de carbono conduziu à formação dos compostos 5-(2-(metiltio/fenil-6-(trifluormetil)pirimidin-4-il)etil)-1,3,4-oxadiazol-2-tiol; 9a (2-SMe); 9b (2-Ph); e 5-(2-metil-7-(trifluormetil)-pirazolo[1,5-a]pirimidin-5-il)etil)-1,3,4-oxadiazol-2-tiol 10; com rendimentos de 84-97%. Esta série de compostos foi levada à reação com agentes alquilantes e acilantes e derivatizadas para os compostos 1,3,4-oxadiazóis 2-S-alquilados/acilados 5-(2-(metiltio/fenil)-6-(trifluormetil)pirimidin-4-il)etil)-1,3,4-oxadiazol-2-il-tiosubstituído; 11aa (2-SMe, 2-S(CO)Me); 11ab (2-SMe, 2-S(CO)CCl3); 11ac (2-SMe, 2-SCH2(CO)Ph); 11ba (2-Ph, 2-S(CO)Me); 11bb (2-Ph, 2-S(CO)CCl3); 11bc (2-Ph, 2-SCH2(CO)Ph); e 5-(2-metil-7-(trifluormetil)pirazolo[1,5-a]pirimidin-5-il)etil)-1,3,4-oxadiazol-2-il-tiosubstituído; 12 (2-S(CO)Me). As séries de hidrazonas N’-(substituído)-3-(2-(metiltio/fenil)-6-(trifluormetil)pirimidin-4-il)propanoidrazida, 13aa (Ph, 2-SMe); 13ab (2-ClPh, 2-SMe); 13ac (4-(N(Me)2)Ph, 2-SMe); 13ad (4-NO2Ph, 2-SMe); 13ae (furano, 2-SMe); 13ba (Ph, 2-Ph); 13bb (2-ClPh, 2-Ph); 13bc (4-(N(Me)2)Ph, 2-Ph); 13be (furano, 2-Ph); e N’-(substituído)-3-(2-metil-7-(trifluormetil)pirazolo[1,5-a]pirimidin-5-il)propanoidrazida; 14a (Ph); 14b (2-ClPh); 14c (4-(N(Me)2)Ph); 14e (furano); também foram sintetizadas a fim de serem utilizadas como precursores para a síntese de 2,3-diidro-1,3,4-oxadiazóis-N-substituídos através da reação com anidrido acético, as quais promoveram a formação das N-acetil-3-(2-(metiltio/fenil)-6-(trifluormetil)pirimidin-4-il)propanohidrazida; 15a (2-SMe); 15b (2-Ph) com rendimentos de 51-66%. Por fim, foi investigada a ciclização oxiadativa das N-acilidrazonas com ácido tricloroisocianúrico para obtenção dos 1,3,4-oxadiazóis, a qual possibilitou obtenção da 2-metil-5-(propanoato-3-il de etila)-7-(trifluormetil)pirazolo[1,5-a]pirimidina 16 e 2-(metiltio/fenil)-4-(propanoato-3-il de etila)-6-(trifluormetil)pirimidina; 17a (2-SMe); 17b (2-Ph); com rendimentos de 64-79%. Todos os compostos sintetizados são inéditos e tiveram suas estruturas confirmadas por dados de RMN 1H, 13C e técnicas bidimensionais além de dados de espectrometria de massas.por
dc.contributor.advisor1Flores, Alex Fabiani Claro
dc.contributor.advisor1Latteshttp://lattes.cnpq.br/1159954352174167por
dc.contributor.referee1Fernandes, Liana da Silva
dc.contributor.referee1Latteshttp://lattes.cnpq.br/0573570242395130por
dc.contributor.referee2Zanatta, Nilo
dc.contributor.referee2Latteshttp://lattes.cnpq.br/0719465062354576por
dc.contributor.referee3Machado, Pablo
dc.contributor.referee3Latteshttp://lattes.cnpq.br/3319303431365448por
dc.contributor.referee4Silva, Sidnei Moura e
dc.contributor.referee4Latteshttp://lattes.cnpq.br/3505301292906591por
dc.creator.Latteshttp://lattes.cnpq.br/8371389172266454por
dc.publisher.countryBrasilpor
dc.publisher.departmentQuímicapor
dc.publisher.initialsUFSMpor
dc.publisher.programPrograma de Pós-Graduação em Químicapor
dc.subject.cnpqCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICApor
dc.publisher.unidadeCentro de Ciências Naturais e Exataspor


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