Novel cycloaddition reactions with alkyl substituted nitrogen heterocycles

2-Methylquinoxaline reacted with two molar equivalents of tetrachloro-1,2-benzoquinone to give two products (a) a colored polycyclic heterocycle structurally related to quinoxaline orange and (b) 2-(2-quinoxalino)-4,5,6,7-tetrachlorobenzo-1,3-dioxole. 2,6-Dimethylquinoline, 2-methylquinoline, and 1-methylisoquinoline react with the quinone to give products of type (a) whilst, 2,3-dimethylquinoxaline, 2,3-dibenzylquinoxaline, and 2-benzylpyridine react with the quinone to give products of type (b). Thermal decomposition of 2-quinoxalinylmethyltrimethylammonium hydroxides results in cycloaddition to form the new 5,8,13,16-tetraazadibenz[a,h]anthracene system. Similar thermal decomposition of 2-quinolinylmethyltrimethylammonium hydroxide produced the new 8,16-diazadibenz[a,h]anthracene ring system.