Síntese de derivados do bisabolol através de reações de heterociclização intramolecular promovidas por calcogenetos de organoíla

• Autor(a) principal: Melo, Diêgo de
• Data de Publicação: 2017
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: Repositório Institucional da UFG
• dARK ID: ark:/38995/001300000cmxd
• Texto Completo: http://repositorio.bc.ufg.br/tede/handle/tede/7192
• topic: (-)-α-bisabolol, ciclização eletrofílica; (-)-α-bisabolol, electrophilic cyclization; CIENCIAS EXATAS E DA TERRA::QUIMICA

This work describes a practical method for intramolecular heterocyclization of the (-)-α-bisabolol to obtain cyclic arylselenoethers and arylthioethers. The electrophilic cyclization addition is promoted by arylselenenyl bromide (ArSeBr) and arylsulfenyl chloride (ArSCl) through electrophilic addition across the terminally disubstituted double bond of the alfa-bisabolol. The cyclization reaction preceeded cleanly and smoothly under mild reaction conditions and provided the cyclic arylselenoethers and arylthioethers with 71% and 47% of yield respectively, employing pyridine as addictive under inert atmosphere. The methodology showed to be highly regioselective since the tetrahydrofuranes were obtained as unique products, presumably because of electronic and conformational factors. It is well known that cyclic ethers are present in the skeletons of several groups of natural compounds exhibiting important biological activities.