Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors.

Abstract

A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.

Cite this paper

@article{Angeli2016IntramolecularOD, title={Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors.}, author={Andrea Angeli and Thomas S. Peat and Gianluca Bartolucci and Alessio Nocentini and Claudiu T. Supuran and Fabrizio Carta}, journal={Organic & biomolecular chemistry}, year={2016}, volume={14 48}, pages={11353-11356} }