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Search Results (3)

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Keywords = oxadiamines

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16 pages, 4154 KiB  
Article
Macrocyclic Compounds Comprising Tris(3-Aminopropyl)Amine Units and Fluorophore Moieties: Synthesis and Spectroscopic Studies in the Presence of Metal Salts
by Daria S. Kuliukhina, Nataliya M. Chernichenko, Alexei D. Averin, Anton S. Abel, Olga A. Maloshitskaya and Irina P. Beletskaya
Chemosensors 2023, 11(3), 186; https://doi.org/10.3390/chemosensors11030186 - 10 Mar 2023
Cited by 3 | Viewed by 2372
Abstract
The synthesis of a variety of polyazamacrocyclic compounds comprising structural units of tris(3-aminopropyl)amine (TRPN) and oxadiamines, decorated with one or two fluorophore groups (dansyl or quinoline) at different nitrogen atoms, was carried out using Pd(0)-catalyzed amination. The dependence of the yields of the [...] Read more.
The synthesis of a variety of polyazamacrocyclic compounds comprising structural units of tris(3-aminopropyl)amine (TRPN) and oxadiamines, decorated with one or two fluorophore groups (dansyl or quinoline) at different nitrogen atoms, was carried out using Pd(0)-catalyzed amination. The dependence of the yields of the macrocycles on the synthetic path was observed. The spectrophotometric and fluorescent properties of the target compounds were studied, and their coordination with metal cations using UV–vis, fluorescence spectra as well as NMR titration was investigated. The stoichiometry and binding constants of several complexes with Cu(II), Zn(II), Cd(II), Pb(II) and Hg(II) were established. Three of the six studied macrocycles can be judged as prospective detectors of Zn(II) cations due to the substantial enhancement of fluorescence. Full article
(This article belongs to the Special Issue Advances in Fluorescence Sensing)
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20 pages, 1912 KiB  
Article
Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency
by Maria S. Lyakhovich, Alexei D. Averin, Olga K. Grigorova, Vitaly A. Roznyatovsky, Olga A. Maloshitskaya and Irina P. Beletskaya
Molecules 2020, 25(5), 1084; https://doi.org/10.3390/molecules25051084 - 28 Feb 2020
Cited by 6 | Viewed by 3048
Abstract
The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents [...] Read more.
The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents and halogen atoms as well as on the structure of oxadiamines was investigated. It was found that the copper-catalyzed reactions were somewhat comparable with the palladium-mediated processes in the majority of cases, especially in the reactions with para-fluorine- and para-(trifluoromethyl)-substituted aryl halides, although the necessity to use aryl iodides in the Cu(I)-catalyzed amination was obvious. Pd catalysis was found inevitable for the successful amination of more sterically hindered ortho-(trifluoromethyl)aryl bromides. Full article
(This article belongs to the Special Issue Fabulous Fluorine in Organic and Medicinal Chemistry)
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26 pages, 484 KiB  
Article
Pd-Catalyzed Amination in the Synthesis of a New Family of Macropolycyclic Compounds Comprising Diazacrown Ether Moieties
by Alexei A. Yakushev, Nataliya M. Chernichenko, Maxim V. Anokhin, Alexei D. Averin, Alexei K. Buryak, Franck Denat and Irina P. Beletskaya
Molecules 2014, 19(1), 940-965; https://doi.org/10.3390/molecules19010940 - 15 Jan 2014
Cited by 15 | Viewed by 6131
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 [...] Read more.
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%. Full article
(This article belongs to the Section Organic Chemistry)
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