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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Synthesis of Trimacrocyclic Compounds Comprising Diazacrown Ether Moieties via Pd(0)-Catalyzed Amination Reactions

Author(s): Nataliya M. Chernichenko, Alexei D. Averin and Irina P. Beletskaya*

Volume 15, Issue 5, 2018

Page: [425 - 430] Pages: 6

DOI: 10.2174/1570178615666171222151821

Price: $65

Abstract

Macrobicycles comprising a central diazacrown structural unit were modified with two 3-bromobenzyl substituents and the resulting compounds were introduced in Pd(0)-catalyzed macrocyclization reactions with trioxadiamine, to give cryptand-like macrotricycles. In the second approach, diazacrown ethers were substituted with two 3,5-dibromobenzyl groups and their Pd(0)-catalyzed double macrocyclization with a series of oxadiamines produced a new family of trimacrocyclic compounds; the Pd(dba)2/RuPhos catalytic system was found to be the most efficient. The decoration of one trimacrocycle with four dansyl fluorophore groups produced a fluorescent molecular probe for Cu(II) and Al(III) cations.

Keywords: Amination, cryptands, diazacrown ethers, macrocycles, Pd catalysis, polyamines.

Graphical Abstract

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