A SIMPLE HIGH-YIELDING APPROACH TO PERYLENEQUINONE FROM THE NOVEL ONE-STEP DOUBLE COUPLING REACTION OF 1,2-NAPHTHOQUINONE

The transformation from 1,2-naphthoquinone to perylenequinone, which usually requires several steps, is stereo-selectively realized via one step in excellent yield by a newly developed, double coupling method. The possible mechanism for this novel reaction and the properties of the resulting perylenequinone are discussed. Moreover, an improved procedure for the preparation of a 5-bromo-1,2-naphthalenediol, a reported coupling precursor to perylenequinone, is also described. These synthetic procedures open convenient ways to perylenequinone structures of significant biological potential.