Fast and easy conversion of ortho amidoaryldiselenides into the corresponding ebselen-like derivatives driven by theoretical investigations

Abstract

DFT calculations performed on amidoaryldiselenides as electrophilic derivatives evidenced the presence of a prevalent Se⋯O weak interaction when selenium is bonded to a Se atom (diselenides), a Br atom (selenenyl bromide) and an O atom (selenenic acid), while for selenenyl iodide derivatives, a prevalent contribution of the Se⋯N interaction was predicted. This in silico observation has been experimentally exploited for the efficient synthesis of a small library of N-substituted benzoisoselenazol-3(2H)-ones and benzoisothiazol-3(2H)-ones considering the pharmacological relevance of ebselen recently reported also as an antiviral agent against Sars-Cov2.