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A stepwise sequence for the interaction of 3-ethoxycarbonyl(acyl)coumarins with cyanoacetylhydrazine, its N-acetyl and N-isopropylidene derivatives, leading to the formation of 3-cyanocoumarins, is proposed and demonstrated. It was established that the 3-cyanocoumarins formed are also able to participate in further conversions by a type of Michael reaction.