Polystyrene-supported GaCl3 as a highly efficient and reusable heterogeneous Lewis acid catalyst for the three-component synthesis of benzoxanthene derivatives

Abstract

Naphthoquinone-based xanthenes, specifically 14-aryl-13H-dibenzo[a,i]xanthene-8,13(14H)-diones and 12-aryl-2,3,4,12-tetrahydro-1H-benzo[b]xanthene-1,6,11-triones, were obtained in good to excellent yields by a simple, mild, and efficient three-component coupling procedure utilizing polystyrene-supported gallium trichloride as a highly active and eco-friendly heterogeneous Lewis acid catalyst. This reaction was also extended to the preparation of 14-aryl-2-hydroxy-13H-dibenzo[a,i]xanthene-8,13(14H)-diones. The experimental and work-up procedure is very simple and the catalyst can be easily separated from the reaction mixture and reused several times in subsequent reactions.