Features of oxa-bridge cleavage in hexahydro-3a,6-epoxyisoindol-1(4H)-ones: A concise method to access acetylisoindolones possessing anti-viral activity

Unusual stereo- and regioselective methods for epoxy-bridge cleavage in perhydro-3a,6-epoxyisoindolones, under the action of the BF3·Et2O/Ac2O system, were discovered. The reaction pathway strongly depends on the characteristics of the isoindolone ring substituents and allows the synthesis of a wide diversity of isoindole-containing heterocycles. The obtained isoindolinones belong to a new class of anti-viral agents possessing a high activity against influenza virus A/Puerto Rico/8/34 (H1N1) in in vitro experiments. © 2019 Elsevier Ltd