Synthesis of 3-Substituted 2-Aminonaphtho[2,3-b]furan-4,9-diones from 2-Hydroxy-1,4-Naphthoquinone and Nitroalkenes

The efficient base-catalyzed synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-dione derivatives from readily available precursors such as 2-hydroxy-1,4-naphthoquinone and nitroalkenes under aqueous conditions is described. Interesting features of this methodology are the conversion of a nitro functionality into an amino functionality in the absence of a reducing agent and the development of a three component reaction for accessing the same product from an aldehyde, 2-hydroxy-1,4-naphthoquinone and nitromethane.