2, 3, 5, 6-Tetrachloro-1, 4-benzoquinone (2) and 2, 3-dichloro-1, 4-naphthoquinone (3) undergo nucleophilic substitution of one or two chlorine atoms by primary amines [1, 2], amino acids [3, 4], and aziridines [5]. Up to four nitrogen residues are introduced into 2 and 3 in their reaction with pyrazole [6], imidazole [7, 8], and 1, 2, 4-triazole [7, 9]. Amides and thioamides were added to 3 to produce two related heterocyclic diones series in excellent ...