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Molecules 2014, 19(1), 940-965; doi:10.3390/molecules19010940
Article

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

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Received: 5 December 2013 / Revised: 26 December 2013 / Accepted: 27 December 2013 / Published: 15 January 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

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%.
Keywords: diazacrown ethers; polyamines; Pd catalysis; amination; macropolycycles diazacrown ethers; polyamines; Pd catalysis; amination; macropolycycles
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Yakushev, A.A.; Chernichenko, N.M.; Anokhin, M.V.; Averin, A.D.; Buryak, A.K.; Denat, F.; Beletskaya, I.P. Pd-Catalyzed Amination in the Synthesis of a New Family of Macropolycyclic Compounds Comprising Diazacrown Ether Moieties. Molecules 2014, 19, 940-965.

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