Synthesis of Eight-, Nine-, and Ten-Membered, Nitrogen-Containing Quinone-Fused Heterocycles

A series of allylamino-, diallylamino-, homoallylamino-and bishomoallylamino naphthoquinones were synthesized. Ruthenium-mediated ring-closing metathesis (RCM) efficiently converted these substrates into novel eight-, nine-, and ten-membered quinone-fused heterocycles. Hydro-derivatives of diazacine, diazonine, and diazecine were isolated and characterized.