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

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

Volume: 15 Issue: 5

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

Affiliation:

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

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

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.

Cite this article as:

Chernichenko M. Nataliya , Averin D. Alexei and Beletskaya P. Irina *, Synthesis of Trimacrocyclic Compounds Comprising Diazacrown Ether Moieties via Pd(0)-Catalyzed Amination Reactions, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178615666171222151821