Efficient synthesis and biological evaluation of dibenzo(b,e)oxepin-11(6H)-ones as potential anthelmintic agents)

SCOCCIA, J.; CASTRO, M.J.; FARAONI, M.; BOUZAT, C.; MARTÍN, V.S.; GERBINO, D.C.

Conferencia; 20th International Electronic Conference on Synthetic Organic Chemistry; 2016

The first systematic study for the construction of a small library dibenzo[b,e]oxepin-11(6H)-ones by directintramolecular acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. For thispurpose, a novel and efficient cooperative system consisting of SnCl2 and Cl2CHOCH3 is presented. Thismethodology show be compatible with a wide variety of functional groups in good to excellent yields andhigh regioselectivity. The generality of new protocol was applied to the scalable and reproducible synthesisof tricyclic antidepressant doxepin. The synthesized dibenzo[b,e]oxepins were evaluated for their biologicalactivities using free-living nematode Caenorhabditis elegans as effective and cost-efficient model system for anthelmintic discovery.