Artículo
Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
Scoccia, Jimena
; Castro, Maria Julia
; Faraoni, María Belén; Bouzat, Cecilia Beatriz
; Martín García, Victor Sotero; Gerbino, Darío César
Fecha de publicación:
18/05/2017
Editorial:
Pergamon-Elsevier Science Ltd
Revista:
Tetrahedron
ISSN:
0040-4020
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(INIBIBB)
Articulos de INST.DE INVEST.BIOQUIMICAS BAHIA BLANCA (I)
Articulos de INST.DE INVEST.BIOQUIMICAS BAHIA BLANCA (I)
Articulos(INQUISUR)
Articulos de INST.DE QUIMICA DEL SUR
Articulos de INST.DE QUIMICA DEL SUR
Citación
Scoccia, Jimena; Castro, Maria Julia; Faraoni, María Belén; Bouzat, Cecilia Beatriz; Martín García, Victor Sotero; et al.; Iron(II) promoted direct synthesis of dibenzo[ b,e ]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin; Pergamon-Elsevier Science Ltd; Tetrahedron; 73; 20; 18-5-2017; 2913-2922
Compartir
Altmétricas