Estudos visando a síntese de isoflavonóides e análogos fluorados

• Autor(a) principal: Pires, Josi Macillo Firmo
• Data de Publicação: 2016
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: Biblioteca Digital de Teses e Dissertações da UERJ
• Texto Completo: http://www.bdtd.uerj.br/handle/1/15816
• topic: Isoflavanones; homo-isoflavanones; carba-analogues; chromanone; tetralone; fluorination; Isoflavanona; homoisoflavonóide; carba-análogo; cromanona; Tetralona; Fluoração; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA

The work presented here has as main goals the preparation of isoflavanones and to study the synthesis of fluorinated analogs of isoflavanones, homo-isoflavanones and its carba-analogues. It is worth to mention that these fluorinated analogs were not previously reported in literature. Four isoflavanones were obteined with different pattern of substituitions at A and C rings, one of them was synthesized through the α-arylation reaction of 4-chromanone with bromo-2,4-dimethoxybenzene, while the others with substitution at the A-ring, prepared in three steps from resorcinol and phenylacetic acids. Global yields were about 70%. One α-aryl-α-tetralones were also obtained through the α-arylation reaction in good yield. The homoisoflavonoids were prepared by reacting chromanone and tetralones with p-methoxybenzaldehyde, under secondary amine and acid catalysis, respectively. The products were obtained in yields ranging from 60-95%. The fluorination reactions were tested by using two fluorinating agents, XtalFluor-M and DAST, and the substrates were the α-aryl-α-tetralone and the homoisoflavonoid derived from 6-methoxy-tetralone. The TLC analysis of the reactions indicated the consumption of the starting materials