A REACTION OF BERBERINE WITH AMIDES IN ALKALINE MEDIA: AN EXPERIMENTAL AND QUANTUM CHEMICAL STUDY

Abstract

The possibility of obtaining electroneutral 8-amido derivatives of dihydroberberines was shown experimentally and with the support of quantum chemical calculations based on the density functional theory (B3LYP/6-311+G(d,p)). In alkaline media, amides deprotonated to form amide anions, which, in turn, could add to the berberine framework at the C-8 position. Competing processes in this case were the reactions of the formation of 8-hydroxy- or 8-alkoxyberberines.