Novel 14-Membered Hexaaza Macrocycles

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

Published: 03 November 2014 by MDPI in The 18th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-18-a042

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

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