Efficient Synthesis And Biological Evaluation Of Dibenzo[B,E] Oxepin-11(6h)-Ones As Potential Anthelmintic Agents

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