An efficient one-pot synthesis of novel 6-hydroxy-14-aryl-8H-dibenzo[a,i]xanthene-8,13(14H)-diones derived from lawsone

An efficient and convenient procedure for the synthesis of novel 6-hydroxy-14-aryl-8H-dibenzoa,i]xanthene-8,13(14H)-dione derivatives has been developed by one-pot, three-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and 2,3-naphthalenediol in glacial acetic acid under reflux conditions. This domino reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. The reaction avoids tedious workup procedure due to the direct precipitation of products from the reaction medium. The notable features of this domino transformation are operational simplicity, clean reaction, easy handling, easy purification process and high yields of the products.

Graphical abstract