Catalyst-free, one-pot four-component synthesis of aryl-linked hydroxy-naphthoquinone fused with imidazolone and 2-hydroxy-1,4-naphthoquinone moiety: naphtho[1,2-d]imidazolyl(aryl)methylnaphthalene-1,4-diones

Abstract

Herein, we report a one-pot four-component reaction of two mol of 2-hydroxy-1,4-naphthoquinone, aromatic aldehydes and guanidine in DMF medium at 80 °C for the easy access of aryl-linked hydroxy-naphthoquinone fused with imidazolone and 2-hydroxy-1,4-naphthoquinone moiety. This domino reaction entails Knoevenagel condensation, Michael addition, intramolecular cyclization, and hydrolysis. Catalyst-free reaction, good yields of the products, easy purification process, formation of four new bonds (two C–C and two C–N) in one-pot, and products having two different bioactive moieties are the notable features of this methodology. All the products were fully characterized by IR, ¹H NMR, ¹³C NMR, and CHN analysis.