Synthesis of Macropolycycles Comprising Diazacrown and Adamantane Moieties via Pd-Catalyzed Amination Reaction

被引:8
|
作者
Yakushev, Alexei A. [1 ,2 ]
Anokhin, Maksim V. [1 ]
Averin, Alexei D. [1 ,2 ]
Maloshitskaya, Olga A. [1 ]
Savelyev, Evgenii N. [3 ]
Butov, Gennadii M. [4 ]
Orlinson, Boris S. [3 ]
Novakov, Ivan A. [3 ]
Beletskaya, Irina P. [1 ,2 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia
[2] AN Frumkin Inst Phys & Electrochem, Moscow 119991, Russia
[3] Volgograd State Tech Univ, Volgograd 400131, Russia
[4] Volgograd State Tech Univ, Volzhsky Polytech Inst Branch, Volzhsky 404131, Russia
来源
MACROHETEROCYCLES | 2013年 / 6卷 / 01期
关键词
Diazacrown ethers; macropolycycles; palladium-catalyzed amination; adamantane; BIS-CROWN ETHERS; COMPLEXING PROPERTIES; CRYPTANDS; COMPLEXATION; LIGANDS; FAMILY; DIHALOBENZENES; CHEMISTRY; ARYLATION;
D O I
10.6060/mhc121214a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N,N'-bis(bromobenzyl) substituted diazacrown ethers were obtained in the reactions of corresponding free diazacrowns with two equivalents of bromobenzyl bromides in high yields. These compounds were introduced in the Pd-catalyzed amination reaction with 1,3-bis(aminomethyl) and 1,3-bis(2-aminoethyl)adamantanes to give macrobicyclic products. The yields were shown to be dependent on the nature of starting diazacrown derivatives and diamines. N, N'-bis(3-bromobenzyl) substituted diazacrown ethers provided better yields of the target macrobicycles than N,N'-bis(4-bromobenzyl) derivatives. In the latter case substantial amounts of cyclic oligomers were formed and isolated.
引用
收藏
页码:40 / 46
页数:7
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