Pd-Catalyzed Amination in the Synthesis of a New Family of Macropolycyclic Compounds Comprising Diazacrown Ether Moieties

Molecules

Alexei A. Yakushev³  Nataliya M. Chernichenko³  Maxim V. Anokhin³  Alexei D. Averin³  Alexei K. Buryak¹  Franck Denat² 

[1] A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, 31 Leninskii prosp., Moscow 119991, Russia; E-Mail:;Institut de Chimie Moléculaire de l’Université de Bourgogne (ICMUB), UMR CNRS 6302, 9 avenue A. Savary, Dijon Cedex 21078, France; E-Mail:;Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1–3, Moscow 119991, Russia; E-Mails:

关键词: diazacrown ethers;    polyamines;    Pd catalysis;    amination;    macropolycycles;   

DOI  :  10.3390/molecules19010940

来源: mdpi

【 摘 要 】

N,N'-bis(bromobenzyl) and N,N'-bis(halopyridinyl) derivatives of diaza-12-crown-4, diaza-15-crown-5 and diaza-18-crown-6 ethers were synthesized in high yields. The Pd-catalyzed macrocyclization reactions of these compounds were carried out using a variety of polyamines and oxadiamines were carried out to give novel macrobicyclic and macrotricyclic compounds of the cryptand type. The dependence of the yields of macropolycycles on the nature of the starting diazacrown derivatives and polyamines was established. Generally N,N'-bis(3-bromobenzyl)-substituted diazacrown ethers and oxadiamines provided better yields of the target products. The highest yield of the macrobicyclic products reached 57%.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.