An oxidative expansion mechanism of isatin-derived imines

Sodium borohydride induces the oxidative expansion of the imine derived from isatin and phenylethylamine to form 3-phenethylquinazoline-2,4(1H,3H)-dione. It has been proposed that this transformation occurs by in situ formation of hydroperoxyl anions by a reaction between sodium borohydride and atmospheric oxygen. To contribute to understanding this oxidative expansion, the reaction between the imine derived from isatin and phenylethylamine with hydrogen peroxide was studied in this work. From this reaction, 3-phenethylquinazoline-2,4(1H,3H)-dione was isolated and two by-products were identified: N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. This article analyses the structure of these by-products and proposes a mechanism that explains the reaction.

It was established that the reaction of the imine derived from isatin and phenylethylamine with hydrogen peroxide produces a mixture of three compounds: 3-phenethylquinazoline-2,4(1H,3H)-dione, N-phenethyl-2-(3-phenethyl-ureido)-benzamide and methyl(2-(phenethylcarbamoyl)phenyl)carbamate. A reaction mechanism is proposed that explains this behaviour