INVESTIGADORES
BOUZAT Cecilia Beatriz
artículos
Título:
Iron(II) promoted direct synthesis of dibenzo[b,e]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin
Autor/es:
SCOCCIA J; CASTRO MJ; FARAONI MB; BOUZAT C; MARTIN V; GEBINO D
Revista:
TETRAHEDRON
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Lugar: Amsterdam; Año: 2017 vol. 73 p. 2913 - 2922
ISSN:
0040-4020
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 freeliving nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery