Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / 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. / 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.
| Identifer | oai:union.ndltd.org:IBICT/oai:repositorio.ufsm.br:1/10587 |
| Date | 03 March 2014 |
| Creators | Kuhn, Bruna Pereira |
| Contributors | Flores, Alex Fabiani Claro, Pizzuti, Lucas, Bresolin, Leandro |
| Publisher | Universidade Federal de Santa Maria, Programa de Pós-Graduação em Química, UFSM, BR, Química |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Repositório Institucional da UFSM, instname:Universidade Federal de Santa Maria, instacron:UFSM |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 100600000000, 400, 500, 300, 300, 300, 8a4555ae-c246-4b1a-adac-bf3b2784da08, 6d35512f-324a-4b85-a5ad-bef9a5f68f1c, 3194b07f-98a6-400b-b7f4-a3efd3f3810b, 91c3f2e2-4d94-416b-a0db-90ca6e6906d5 |
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