Reactions of 9-aroyl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-diones with hydrazine and methylhydrazine produced cinnoline derivatives. A homolytic cleavage of C–C bond in the intermediate product occured in the case of methylhydrazine, leading to the dimeric 4,4'-bis(3-aryl-1,7,7-trimethyl-1,4,5,6,7,8-hexahydrocinnoline-5-ones).