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

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

Journal Name: Letters in Organic Chemistry

Volume 15 , Issue 5 , 2018

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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.

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Article Details

VOLUME: 15
ISSUE: 5
Year: 2018
Page: [425 - 430]
Pages: 6
DOI: 10.2174/1570178615666171222151821
Price: $58

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