Tandem directed ortho-metallation/metal-halogen exchange reactions between N,N-diethylpyridine-2-carboxamide and 2-bromopyridine-3-carbaldehyde yield 1,8-diazaanthracene-9,10-dione. This compound has been further functionalized to its N-oxide and the corresponding 2,9,10-trione derivative, structurally related to the antibiotic diazaquinomycin A.