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.
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Novel Semicarbazone-Based Amidoalkylation Reagents: Preparation and Application to the Stereoselective Synthesis of 14-Membered Hexaaza Macrocycles
Published: 03 November 2017 by MDPI in The 21st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: Semicarbazones; 4-(Tosylmethyl)semicarbazones; Hydrazones; Azamacrocycles; Amidoalkylation; retro-Claisen reaction; Heterocyclization