EventsThe 21st International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-21-04765
This submission belongs to the session A. General Organic Synthesis of the event The 21st International Electronic Conference on Synthetic Organic Chemistry
Published date
03 Nov, 2017
Citation
Anatoly Shutalev, Anastasia Fesenko, Alexander Yankov, Novel Semicarbazone-Based Amidoalkylation Reagents: Preparation and Application to the Stereoselective Synthesis of 14-Membered Hexaaza Macrocycles, in Proceedings of The 21st International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2017, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-21-04765
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Novel Semicarbazone-Based Amidoalkylation Reagents: Preparation and Application to the Stereoselective Synthesis of 14-Membered Hexaaza Macrocycles

Anastasia Fesenko 1
Alexander Yankov 1
Anatoly Shutalev 1
1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., 119991 Moscow, Russian Federation
Abstract

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
Manuscript
Proceedings_Macrocycles from Semicarbazone-Based Amidoalkylation Reagents.pdf
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