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ABSTRACT
3,4-Diethoxycarbonyl-5,6-diphenylpyridazine 1 reacted with hydrazine hydrate to form tetrahydropyridazino [4,5-c]pyridazine 2, which reacted with ethyl bromoacetate to give 6,7-diethoxycarbonylmethyl-3,4-diphenyl-5,8-dioxopyridazino [4,5-c]pyridazine 3. However, acetylation of 2 with acetyl chloride gave three different pyridazino[4,5-c]pyridazines 4–6. The reaction of the starting diester 1 with different amounts of phenylmagnesium bromide gave different products 7–10. The structure of product 8 was elucidated by alkaline hydrolysis and hydrazinolysis to afford 11 and 13, respectively. Treatment of 13 with benzaldehyde in piperidine yielded the starting Grignard product 8 and benzalazine 17.