54384-47-3Relevant academic research and scientific papers
Synthesis of New Pyridinoazacrown Ethers Containing Aromatic and Heteroaromatic Proton Ionizable Substituents
Bordunov, Andrei V.,Hellier, Paul C.,Bradshaw, Jerald S.,Dalley, N. Kent,Kou, Xiaolan,et al.
, p. 6097 - 6102 (1995)
Methods for the synthesis of pyridinocrowns functionalized with various proton ionizable groups have been elaborated.Sixteen new ligands containing pyridine rings as part of the macrocycle or as a side arm have been prepared.Different interactive abilities of the OH and NH functions of 3,9-dioxa-6-azaundecane-1,11-diol (3) in strong base allowed the synthesis of pyridinoazacrowns 1 and 2 by cyclization with 2,6-bis((tosyloxy)methyl)pyridine (4) and THP-protected 4-hydroxy-2,6-bis((tosyloxy)methyl)pyridine (5).Pyridinoazacrown 1 was functionalized with different proton ionizable side arms by treatment first with formaldehyde in methanol to form the N-methoxymethyl derivative 6 and then treating 6 with 5-chloro-8-hydroxyquinoline or the appropriate substituted phenol.Pyridinoaza-18-crown-6 ligands containing p-methylphenol (7), p-metoxyphenol (8), p-chlorophenol (9), p-fluorophenol (10), p-cyanophenol (11), 2-formyl-4-bromophenol (12), or 5-chloro-8-hydroxyquinoline (13) groups were prepared by this process.Pyridinoazacrowns 1 and 2 were alkylated with 2-hydroxy-5-nitrobenzyl chloride or 5-chloro-8-methoxy-2-(bromomethyl)quinoline followed by removal of the protecting groups to form p-nitrophenol- and 5-chloro-8-hydroxy-2-quinolinyl-substituted ligands (16, 18, and 21).Macrocycles 22 and 23 containing proton ionizable triazole and phenol functions inside the macrocyclic cavity and a pyridine side arm were prepared by cyclization of the appropriate dihalide with 6-(2'-pyridylmethyl)-3,9-dioxa-6-azaundecane-1,11-diol followed by cleavage of the THP or methoxy protecting groups.Preliminary complexation data show that the phenol-substituted pyridinoaza-18-crown-6 ligands form strong complexes with various metal cations and exhibit high selectivity toward Ag(1+).Macrocycle 16 containing a p-nitrophenol substituent formed a complex with benzylamine.The crystal structures for 16 and its benzylamine complex are also given here.
Synthesis and evaluation of novel water-soluble ligands for the complexation of metals during the partitioning of actinides
Iqbal, Mudassir,Huskens, Jurriaan,Sypula, Michal,Modolo, Giuseppe,Verboom, Willem
experimental part, p. 2591 - 2600 (2012/01/04)
Different types of water-soluble ligands were synthesized and their capability was evaluated by solvent extraction studies to complex trivalent actinides and suppress their extraction by a strong lipophilic ligand, such as TODGA. The back extraction efficiency of hydrophilic diglycolamide (DGA) derivatives with a varying number of ethylene glycol groups, or containing sodium acetate moieties on the amidic nitrogen shows a decrease in back-extraction efficiency with increasing number of ethylene glycol units on the amidic nitrogen at various pH values of the aqueous phase. Among the PS donating ligands only the ligand with a malonamide backbone exhibits a high reverse extraction efficiency, although, with no selectivity for americium. Within the water-soluble tripodal ligands, i.e. the amide derivatives of nitrilotriacid with N,N-dimethyl and N,N-bis(hydroxyethyl) moieties, the first one shows a pronounced selectivity for Am(iii) over Eu(iii), with a maximum separation factor of 11.1, while the latter one more efficiently complexes the radionuclides in the aqueous phase with a maximum separation factor of 5. Isothermal microcalorimetry experiments of the complexation of Eu(iii) by a selected series of ligands confirm the observed trend in the back extraction properties.
Synthesis of new multidentate ligands for the coordination of indium(iii), gadolinium(iii) and thorium(iv)
Sun, Yizhen,Martell, Arthur E.,Welch, Michael J.
, p. 8863 - 8868 (2007/10/02)
Efficient syntheses are described for five new multidentate ligands containing 3-hydroxy-6-methyl-2-pyridyl donor groups: 4,7,10-tris(3-hydroxy-6-methyl-2-pyridylmethyl)-1-oxa-4,7, 10-triazacyclododecane, 2; 4,10,13-tris(3-hydroxy-6-methyl-2-pyrildylmethy
SYNTHESIS AND CHARACTERIZATION OF A NEW MACROBICYCLIC (CRYPTAND) SIDEROPHORE CONTAINING THREE ENDOCYCLIC HYDROXAMATE DONOR GROUPS
Sun, Yizhen,Martell, Athur E.
, p. 2725 - 2736 (2007/10/02)
The first trishydroxamate cryptand ligand was synthesized by tripodal coupling of a tris acid chloride and a tris O-benzylhydroxylamine.The spectrophotometric properties of its Fe(III) complex were investigated and compared with those of desferriferrioxamine B.Its 1:1 Ga(III) complex was also prepared and characterized.
Synthesis of Monoaza Crown Ethers from N,N-Diamines and Oligoethylene Glycol Di(p-toluenesulfonates) or Corresponding Dichlorides
Maeda, Hirokazu,Furuyoshi, Shigeo,Nakatsuji, Yohji,Okahara, Mitsuo
, p. 212 - 218 (2007/10/02)
Monoaza crown ethers were prepared in satisfactory yields by the one-step reaction between diethanolamine or N,N-diamines and oligoethylene glycol di(p-toluenesulfonates) or corresponding dichlorides in t-butyl alcohol/dioxane in the presence of sodium or potassium t-butoxide.The reaction conditions in the preparation of monoaza 15- and 18-crown ethers were studied.Various monoaza crown ethers having substituents were also prepared and their properties were investigated.
Macrocyclic compounds having oxa and aza linkages in the ring and containing spirooxetane groups
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, (2008/06/13)
Compound having the formula EQU1 WHEREIN Y is --XCH2 CH2 --X--, --X(CH2 CH2 X)2 or EQU2 p is 1 to 4, and each X is O or NH, N-alkanoyl, N-benzoyl wherein the benzene ring is optionally substituted with --NO2, --NH2, or --CH3, N-alkyl or N-β-hydroxyalkyl each of up to 8 carbons and wherein the total number of N is 1 to 3 are disclosed. The compounds can be polymerized by opening of the oxetane ring in the presence of electrophilic agents, or the oxetane ring can be hydrolyzed to a dihydroxy group and reacted with diacid halides to form polyesters or with diisocyanates to form polyurethanes. Both monomers and polymers complex metal ions and can be used to separate such ions from solutions.
