Reactions of benzofurazan oxide with amines—I : Reduction with diethylamine

The reactions of benzofurazan oxide with diethylamine gave a complex mixture from which quinoxaline-1,4-dioxide (10–15%), o-benzoquinone dioxime (5%), benzofurazan (5–10%), 1-hydroxy-2-methyl-benzimidazole-3-oxide (3%), o-nitrosoaniline (5%), o-nitroaniline (<3%), 3-methylbenzotriazine (5%), 3-methyl-benzotriazine-4-oxide (10%), and o-nitrophenyl-N,N-diethyl hydrazine (10%) were isolated.The formation of these products seems to have a common pathway that involves the reduction of benzofurazan oxide and the oxidation of diethylamine.