Please login first
Novel Semicarbazone-Based Amidoalkylation Reagents: Preparation and Application to the Stereoselective Synthesis of 14-Membered Hexaaza Macrocycles
, , *
1  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation


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.

Keywords: Semicarbazones; 4-(Tosylmethyl)semicarbazones; Hydrazones; Azamacrocycles; Amidoalkylation; retro-Claisen reaction; Heterocyclization