Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

Siaugue, Jean‐Michel; Ségat-Dioury, Fabienne; Sylvestre, Isabelle; Favre‐Réguillon, Alain; Foos, J.; Madic, C.; Guy, Alain

doi:10.1016/s0040-4020(01)00328-3

Cited by 35 publications

(33 citation statements)

References 24 publications

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“…[8,27,28] Potentiometric Titrations: The electrodes were calibrated to read the pH by a classical method. [29] .The ligand (5 mL, 0.001 ) was titrated with standardized 0.01  sodium hydroxide.…”

Section: Synthesis Of Ligandsmentioning

confidence: 99%

Effect of Mixed Pendant Groups on the Solution Properties of 12‐Membered Azapyridinomacrocycles: Evaluation of the Protonation Constants and the Stability Constants of the Europium(III) Complexes

et al. 2003

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The protonation constants (logK i H ) of new N-acetate or Npropionate substituted azamacrocycles derived from 12-membered pyridinoazamacrocycles were determined by potentiometric methods. The number of coordinated water molecules, determined from the luminescence lifetime of the Eu III complexes, indicates a decreasing degree of hydration upon increasing the ring size of the pendant arms. Each ligand forms a 1:1 complex with Eu III , for which the stability constants (logK therm ) have been measured by time-resolved

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Section: Synthesis Of Ligandsmentioning

confidence: 99%

Effect of Mixed Pendant Groups on the Solution Properties of 12‐Membered Azapyridinomacrocycles: Evaluation of the Protonation Constants and the Stability Constants of the Europium(III) Complexes

et al. 2003

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“…This is followed by deprotection of the amines using thiophenol and potassium hydroxide according to a modified method of the published procedure shown in Scheme 1. 65 The full synthetic details and characterization can be found in the supplemental information.…”

Section: Materials and Measurementsmentioning

confidence: 99%

Chemical characteristics of the products of the complexation reaction between copper(II) and a tetra-aza macrocycle in the presence of chloride ions

Lincoln

Arroyo‐Currás

Johnston

et al. 2015

Journal of Coordination Chemistry

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The reaction of copper(II) perchlorate with the hydrochloride salt of 3, 6,9,15-tetraazabicyclo[9.3.1]penta-deca-1,11,13-triene (L1) in acetonitrile forms two macrocyclic complexes that can be characterized; [L1Cu II Cl][ClO 4 ] (1) and [L1Cu II Cl] 2 [CuCl 4 ] (2). The structural, electronic and redox properties of these complexes were studied using spectroscopy (EPR and UV-visible), and electrochemistry. In addition the solid state structure of 1 was obtained using X-ray diffraction. The copper(II) is five-coordinate; ligated by four N-atoms of the macrocycle and a chloride atom. EPR studies of 1 both DMF and aqueous solution indicate the presence of a single copper(II) species. In contrast, EPR studies of 2 performed in frozen DMF and in the solid-state reveal the presence of two spectroscopically distinct copper(II) complexes assigned as [L1Cu II Cl] + and [Cu II Cl 4 ] 2-. Lastly, electrochemical studies demonstrate that both [L1Cu II Cl] + and [Cu II Cl 4 ] 2-are redox active. Specifically, the [L1Cu II Cl] + undergoes a quasi-reversible Cu(II)/(I) redox reaction in the absence of excess chloride.In the presence of chloride, however, the chemical irreversibility of this couple becomes evident at concentrations of chloride that exceed 50 mM. As a result, the presence of chloride from the chemical equilibrium of this latter species impedes the reversibility of the reduction of [L1Cu II Cl] + to [L1Cu I Cl] 0 .

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“…In the case of the symmetrical substitution, the "naked" macrocycle is prepared in the first step and the pendants are introduced in the second step. This strategy was used for preparation of tri(substituted) ligands with acetate (H 3 PCTA) [340,350], glutarate [351], propionate [352], and acetamide pendant arms [353] as well as for phosphonate derivative (H 6 PCTP) [354,355]. A different strategy can be used for ligands with mixed pendant arms.…”

Section: H 3 Pcta and Related Ligandsmentioning

confidence: 99%

“…The first step is synthesis of a triamine modified on the central nitrogen atom with the corresponding pendant. The modified triamine can be obtained by a selective nosylate diprotection of the terminal amino groups followed by alkylation of the central nitrogen atom [352] is the reaction of the appropriate pendant arm bearing a primary amino group with N-tosylaziridine [356,357] (Scheme 3.62). The modified triamine is used for Richman-Atkins macrocyclization.…”

Section: H 3 Pcta and Related Ligandsmentioning

confidence: 99%

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Kotek¹,

Kubíček²,

Hermann³

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

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Regioselective synthesis of N-functionalized 12-membered azapyridinomacrocycles bearing trialkylcarboxylic acid side chains

Cited by 35 publications

References 24 publications

Effect of Mixed Pendant Groups on the Solution Properties of 12‐Membered Azapyridinomacrocycles: Evaluation of the Protonation Constants and the Stability Constants of the Europium(III) Complexes

Effect of Mixed Pendant Groups on the Solution Properties of 12‐Membered Azapyridinomacrocycles: Evaluation of the Protonation Constants and the Stability Constants of the Europium(III) Complexes

Chemical characteristics of the products of the complexation reaction between copper(II) and a tetra-aza macrocycle in the presence of chloride ions

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

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