Synthesis of the omega-brominated alpha-trifluoroacetylcycloalkanones and their isoxazole derivatives



Título del documento: Synthesis of the omega-brominated alpha-trifluoroacetylcycloalkanones and their isoxazole derivatives
Revista: Journal of the Brazilian Chemical Society
Base de datos: PERIÓDICA
Número de sistema: 000311782
ISSN: 0103-5053
Autores: 1




Instituciones: 1Universidade Federal de Santa Maria, Departamento de Quimica, Santa Maria, Rio Grande do Sul. Brasil
Año:
Periodo: Feb
Volumen: 17
Número: 1
Paginación: 79-84
País: Brasil
Idioma: Inglés
Tipo de documento: Artículo
Enfoque: Experimental, aplicado
Resumen en inglés The reactions of a serie of the 2-trifluoroacetyl-1-methoxy-1-cycloalkenes (1a-1e) and 2-trifluoroacetylcycloalkanones (2a-2e) with molecular bromine to obtain omega-bromo-alpha-trifluoroacetylcycloalkanones (3a-3e, 4a) is reported. Was determined that 2-trifluoroacetyl group have established the C-omega as reactive site. The 2-trifluoroacetylcycloalkanones and omega-bromo-alpha-trifluoroacetylcycloalkanones were reacted with hydroxylamine hydrochloride leading to respective 5-trifluoromethyl-5-hydroxy-4,5-dihydro-3,4-polimethyleneisoxazole derivatives (5c-5e and 6c-6e)
Resumen en portugués Este trabalho mostra as reações entre 2-trifluoracetil-1-metoxi-1-cicloalquenos (1a-1e) ou 2-trifluoracetilcicloalcanonas e bromo molecular, para produção de ômega-bromo-2-trifluoracetilcicloalcanonas (3a-3e, 4a). Ficou demonstrado que o grupo 2-trifluoracetil determina o sítio de bromação no C-omega, carbono vizinho à carbonila endocíclica. Os produtos 2-trifluoracetilcicloalcanonas e ômega-bromo-alfa-trifluoracetilcicloalcanonas foram ciclocondensados com cloridrato de hidroxilamina, formando os respectivos 5-trifluormetil-5-hidroxido-3,4-polimetileno-4,5-diidroisoxazóis (5c-5e e 6c-6e)
Disciplinas: Química
Palabras clave: Química orgánica,
Bromo-trifluoroacetilcicloalcanonas,
Reacción de bromación,
Ciclocondensación,
Isoxazoles
Keyword: Chemistry,
Organic chemistry,
Bromo-trifluoroacetylcycloalkanones,
Bromination reaction,
Cyclocondensation,
Isoxazoles
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