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Novel 14-Membered Hexaaza Macrocycles
* 1 , 1 , 2 , 2 , 3
1  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation
2  M. V. Lomonosov Moscow State University
3  A. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS

Abstract: An efficient method for the stereoselective synthesis of novel 14-membered cyclic bis-semicarbazones based on acid-catalyzed cyclization of the hydrazones of 3-(3-oxobutyl)semicarbazides has been developed. The starting semicarbazides were prepared according to a four-step strategy involving amidoalkylation of the sodium enolate of acetylacetone with N-(α-tosylbenzyl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained N-(3-oxobutyl)carbamates with hydrazine.
Keywords: Amidoalkylation; retro-Claisen reaction; Semicarbazides; Azamacrocycles