Multicomponent Cyanation of 2-Amino-3-cyano-4H-chromenes in Aqueous Media

Abstract

Chromenes represent a pivotal molecular structure found in a diverse range of biologically active compounds. Specifically, derivatives of 2-amino-3-cyano-4H-chromene have demonstrated pharmacological applications, displaying potential antioxidant and anticancer activities. This has heightened interest in the exploration of new and more efficient methods for their synthesis. In recent years, few examples have emerged, focusing on the organocatalytic and enantioselective synthesis of 2-amino-3-cyano-4H-chromene derivatives, although the overall number of works to date is limited. In this study, we present the results of the synthesis of 2-amino-4H-chromen-3,4-dicarbonitriles through a Michael addition of cyanide to 2-iminochromenes. To achieve this, we utilized a mild source of cyanide (acetone cyanohydrin), green solvents and catalytic conditions at room temperature, via a multicomponent approach. Furthermore, we initiated the enantioselective study of this process using chiral organocatalysts obtaining promising preliminary results.