Events The 18th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 18th International Electronic Conference on Synthetic Organic Chemistry

Published date

03 Nov, 2014

Citation

Anatoly Shutalev, Anastasia Fesenko, Dmitry Albov, Vladimir Chernyshev, Ilia Zamilatskov, Novel 14-Membered Hexaaza Macrocycles, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-a042

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Novel 14-Membered Hexaaza Macrocycles

Anatoly Shutalev ¹

Anastasia Fesenko ¹

Dmitry Albov ²

Vladimir Chernyshev ²

Ilia Zamilatskov 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

Manuscript

Azamacrocycles.pdf

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