Reaction of N1,N2-diarylamidines with 3,4,5,6-tetrachloro-1,2-benzoquinone

A synthesis of 5,11b-dihydro-1H-dibenzo[d,f][1,3]diazepin-1-ones was found in the reaction of nitro-substituted N1,N2-diarylamidines with 3,4,5,6-tetrachloro-1,2-benzoquinone. In contrast, 6,7,8,9-tetrachlorodibenzodioxins were obtained from reaction of N1,N2-diphenylpropionamidine and N1,N2-di-(4-tert-butylphenyl)acetamidine with 3,4,5,6-tetrachloro-1,2-benzoquinone.