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An efficient general synthesis of hydrazones of 4-(3-oxobutyl)semicarbazones using novel semicarbazone-based amidoalkylation reagents has been developed. The prepared hydrazones were converted under acidic conditions into 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. Plausible pathway and stereochemistry of the macrocyclization are discussed.

Novel Semicarbazone-Based Amidoalkylation Reagents: Preparation and Application to the Stereoselective Synthesis of 14-Membered Hexaaza Macrocycles