Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados

Detalhes bibliográficos
Ano de defesa: 2014
Autor(a) principal: Kuhn, Bruna Pereira lattes
Orientador(a): Flores, Alex Fabiani Claro lattes
Banca de defesa: Pizzuti, Lucas lattes, Bresolin, Leandro lattes
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Universidade Federal de Santa Maria
Programa de Pós-Graduação: Programa de Pós-Graduação em Química
Departamento: Química
País: BR
Palavras-chave em Português:
4,5-diidropirazóis
Pirazóis
4,5-diidroisoxazóis
Palavras-chave em Inglês:
4,5-dihydropyrazoles
Pyrazoles
4,5-dihydroisoxazoles
Área do conhecimento CNPq:
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Link de acesso: http://repositorio.ufsm.br/handle/1/10587
Resumo: This work describes the application of the method of trifluoroacetic anhydride acetal acylation to four new functionalized ketones: 6-methyl-5-hepten-2-one, 4-phenyl-4- oxobutanoic acid (3-benzoylpropionic acid), 5-bromo-2-acetylthiophene and 2- propionylthiophene. The acylated products were obtained as β-trifluoromethyl ketones alkoxyvinyl and β-diketones. The product derived from 2-propionylthiophene was obtained as dihydrate, 3,3-dihydroxy-4,4,4-trifluoro-1-(2-thienyl)-2-butanone, its structure was confirmed by X-ray diffraction crystallography. The acylated dielectrophilic precursors were cyclized with dinucleophiles hydroxylamine, hydrazine, semicarbazide and thiosemicarbazide to form the corresponding 5-trifluoromethyl-4,5-dihydroisoxazoles, 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles and trifluoromethyl-1H-pyrazole in good yields (>80%). The molecular structure of the synthesized products were assigned based on the data of 1H NMR, 13C and X-ray diffraction.
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spelling 2017-05-112017-05-112014-03-03KUHN, Bruna Pereira. Synthesis of 1,1,1-trifluoro-4-methoxy-3-alquen-2-ones functionalized and 1,2-azole derivatives. 2014. 180 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014.http://repositorio.ufsm.br/handle/1/10587This work describes the application of the method of trifluoroacetic anhydride acetal acylation to four new functionalized ketones: 6-methyl-5-hepten-2-one, 4-phenyl-4- oxobutanoic acid (3-benzoylpropionic acid), 5-bromo-2-acetylthiophene and 2- propionylthiophene. The acylated products were obtained as β-trifluoromethyl ketones alkoxyvinyl and β-diketones. The product derived from 2-propionylthiophene was obtained as dihydrate, 3,3-dihydroxy-4,4,4-trifluoro-1-(2-thienyl)-2-butanone, its structure was confirmed by X-ray diffraction crystallography. The acylated dielectrophilic precursors were cyclized with dinucleophiles hydroxylamine, hydrazine, semicarbazide and thiosemicarbazide to form the corresponding 5-trifluoromethyl-4,5-dihydroisoxazoles, 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles and trifluoromethyl-1H-pyrazole in good yields (>80%). The molecular structure of the synthesized products were assigned based on the data of 1H NMR, 13C and X-ray diffraction.Este trabalho descreve a aplicação do método de acilação de cetais com anidrido trifluoracético, (CF3CO)2O, a quatro novas cetonas funcionalizadas: 6-metil-5-hepten-2- ona, ácido 4-fenil-4-oxobutanóico (ácido 3-benzoilpropiônico), 5-bromo-2-acetiltiofeno e 2-propioniltiofeno. Foram obtidos os produtos acilados na forma de β-alcoxivinil trifluormetil cetonas e β-dicetonas. O produto derivado do 2-propioniltiofeno foi obtido na forma de hidrato, o 3,3-dihidroxi-4,4,4-trifluor-1-(2-tienil)-2-butanona, sua estrutura foi confirmada por difração de raio-X em monocristal. Os precursores acilados dieletrofílicos foram ciclizados com dinucleofilos hidroxilamina, hidrazina, semicarbazida e tiosemicarbazida formando os respectivos 5-trifluorometil-4,5-diidroisoxazóis, 5- trifluorometil-4,5-diidro-1H-pirazóis e trifluorometil-1H-pirazóis em bons rendimentos (>80%). As estruturas moleculares dos produtos sintetizados foram atribuídas a partir dos dados de RMN 1H, 13C e difração de raios-X.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímica4,5-diidropirazóisPirazóis4,5-diidroisoxazóis4,5-dihydropyrazolesPyrazoles4,5-dihydroisoxazolesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivadosSynthesis of 1,1,1-trifluoro-4-methoxy-3-alquen-2-ones functionalized and 1,2-azole derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisFlores, Alex Fabiani Clarohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0Pizzuti, Lucashttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4759097T8Bresolin, Leandrohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4792250U4http://lattes.cnpq.br/4576069940870025Kuhn, Bruna Pereira1006000000004005003003003008a4555ae-c246-4b1a-adac-bf3b2784da086d35512f-324a-4b85-a5ad-bef9a5f68f1c3194b07f-98a6-400b-b7f4-a3efd3f3810b91c3f2e2-4d94-416b-a0db-90ca6e6906d5info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALKUHN, BRUNA PEREIRA.pdfapplication/pdf7543619http://repositorio.ufsm.br/bitstream/1/10587/1/KUHN%2c%20BRUNA%20PEREIRA.pdf163e073686a6e62b1edbacee0ab3b423MD51TEXTKUHN, BRUNA PEREIRA.pdf.txtKUHN, BRUNA PEREIRA.pdf.txtExtracted texttext/plain159550http://repositorio.ufsm.br/bitstream/1/10587/2/KUHN%2c%20BRUNA%20PEREIRA.pdf.txtc1ee318e312e050a7a0669829b4c341dMD52THUMBNAILKUHN, BRUNA PEREIRA.pdf.jpgKUHN, BRUNA PEREIRA.pdf.jpgIM Thumbnailimage/jpeg5590http://repositorio.ufsm.br/bitstream/1/10587/3/KUHN%2c%20BRUNA%20PEREIRA.pdf.jpgfe0103c387887f0a400e4f142a70021cMD531/105872017-07-25 12:05:02.213oai:repositorio.ufsm.br:1/10587Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:05:02Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false
dc.title.por.fl_str_mv Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
dc.title.alternative.eng.fl_str_mv Synthesis of 1,1,1-trifluoro-4-methoxy-3-alquen-2-ones functionalized and 1,2-azole derivatives
title Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
spellingShingle Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
Kuhn, Bruna Pereira
4,5-diidropirazóis
Pirazóis
4,5-diidroisoxazóis
4,5-dihydropyrazoles
Pyrazoles
4,5-dihydroisoxazoles
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
title_short Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
title_full Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
title_fullStr Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
title_full_unstemmed Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
title_sort Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados
author Kuhn, Bruna Pereira
author_facet Kuhn, Bruna Pereira
author_role author
dc.contributor.advisor1.fl_str_mv Flores, Alex Fabiani Claro
dc.contributor.advisor1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0
dc.contributor.referee1.fl_str_mv Pizzuti, Lucas
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4759097T8
dc.contributor.referee2.fl_str_mv Bresolin, Leandro
dc.contributor.referee2Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4792250U4
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/4576069940870025
dc.contributor.author.fl_str_mv Kuhn, Bruna Pereira
contributor_str_mv Flores, Alex Fabiani Claro
Pizzuti, Lucas
Bresolin, Leandro
dc.subject.por.fl_str_mv 4,5-diidropirazóis
Pirazóis
4,5-diidroisoxazóis
topic 4,5-diidropirazóis
Pirazóis
4,5-diidroisoxazóis
4,5-dihydropyrazoles
Pyrazoles
4,5-dihydroisoxazoles
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
dc.subject.eng.fl_str_mv 4,5-dihydropyrazoles
Pyrazoles
4,5-dihydroisoxazoles
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
description This work describes the application of the method of trifluoroacetic anhydride acetal acylation to four new functionalized ketones: 6-methyl-5-hepten-2-one, 4-phenyl-4- oxobutanoic acid (3-benzoylpropionic acid), 5-bromo-2-acetylthiophene and 2- propionylthiophene. The acylated products were obtained as β-trifluoromethyl ketones alkoxyvinyl and β-diketones. The product derived from 2-propionylthiophene was obtained as dihydrate, 3,3-dihydroxy-4,4,4-trifluoro-1-(2-thienyl)-2-butanone, its structure was confirmed by X-ray diffraction crystallography. The acylated dielectrophilic precursors were cyclized with dinucleophiles hydroxylamine, hydrazine, semicarbazide and thiosemicarbazide to form the corresponding 5-trifluoromethyl-4,5-dihydroisoxazoles, 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles and trifluoromethyl-1H-pyrazole in good yields (>80%). The molecular structure of the synthesized products were assigned based on the data of 1H NMR, 13C and X-ray diffraction.
publishDate 2014
dc.date.issued.fl_str_mv 2014-03-03
dc.date.accessioned.fl_str_mv 2017-05-11
dc.date.available.fl_str_mv 2017-05-11
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.citation.fl_str_mv KUHN, Bruna Pereira. Synthesis of 1,1,1-trifluoro-4-methoxy-3-alquen-2-ones functionalized and 1,2-azole derivatives. 2014. 180 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014.
dc.identifier.uri.fl_str_mv http://repositorio.ufsm.br/handle/1/10587
identifier_str_mv KUHN, Bruna Pereira. Synthesis of 1,1,1-trifluoro-4-methoxy-3-alquen-2-ones functionalized and 1,2-azole derivatives. 2014. 180 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2014.
url http://repositorio.ufsm.br/handle/1/10587
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dc.publisher.program.fl_str_mv Programa de Pós-Graduação em Química
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dc.publisher.country.fl_str_mv BR
dc.publisher.department.fl_str_mv Química
publisher.none.fl_str_mv Universidade Federal de Santa Maria
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