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

[ Vol. 15 , Issue. 5 ]

Author(s):

Nataliya M. Chernichenko, Alexei D. Averin and Irina P. Beletskaya*   Pages 425 - 430 ( 6 )

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.

Affiliation:

Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow

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