Synthesis of platinum, palladium and rhodium complexes of α-aminophosphine ligands

Bálint, Erika; Tajti, Ádám; Tripolszky, Anna; Keglevich, György

doi:10.1039/c8dt00178b

Cited by 30 publications

(18 citation statements)

References 84 publications

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“…2.2 Physical measurements 1 H NMR (400 MHz) and 13 C NMR (100 MHz) spectra were recorded on a Brucker Avance (400 MHz) spectrometer using deuterated dimethyl sulphoxide (DMSO-d 6 ) solvent with chemical shift (𝛿 in ppm) reference to internal TMS. IR Spectra were recorded on an FT-IR ABB Bomen MB-3000 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

“…This ligand (L 1 ) was prepared through the addition of α,β-unsaturated enone (3a) (1.5 mmol) and phenyl hydrazine (123 mg, 1.479 mmol), after 5-6 h re ux; Color: yellowish crystalline solid; Empirical formula: ), 7.133 (1H, dt, H 5" ), 6.893 (4H, d, J = 4.0 Hz, H 2''',3'",5''',6''' ), 6.774 (2H, d, J = 3.6 Hz, H 3,4 ), 5.553 (1H, dd, J 1 = 6.4 Hz, J 2 = 12.4 Hz, H3' ), 3.917 (1H, dd, J 1 = 12 Hz, J 2 = 18.0 Hz, H 4'a ), 3.447 (1H, dd, J 1 = 6.4 Hz, J 2 = 18.0 Hz, H 4'b ) 13 Hz, J2 = 6.8 Hz, H2''',6'''), 7.263 (1H, S, H2"), 7.043 (3H, dt, H4'',5",6''), 6.899 (1H, d, J = 3.6 Hz, H3), 6.779 (1H, d, J = 3.6 Hz, H4), 5.422 (1H, dd, J1 = 6.4 Hz, J2 = 11.6 Hz, H3'), 3.796 (1H, dd, J1 = 11.6 Hz, J2 = 16.8 Hz, H4',a), 3.280 (1H, dd, J1 = 6.4 Hz, J2 = 16.8 Hz, H4'b) 13…”

Section: -(5-(5-bromothiophenmentioning

confidence: 99%

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Heteroleptic C, N- Donor Pd(II) Complexes: Synthesis, Characterization, DNA/BSA Binding Interactions And Biological Studies

Patel

Dhaduk

Dabhi

et al. 2021

Preprint

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A series of trisubstituted pyrazole-based ligands (L1-L6) and corresponding palladium(II) complexes were synthesized and characterized by conductivity measurement, 1H NMR, 13C NMR, Fourier Transform infrared (FT-IR) spectroscopy and liquid chromatography-mass spectrometry (LC-MS). Synthesized compounds were screened for various biological activities. UV-Vis spectroscopy, viscosity measurement, fluorescence spectroscopy and molecular docking studies were used to determine the binding mode between HS-DNA and complexes, which suggest intercalation mode of binding. The protein binding study of complexes was evaluated by UV-visible spectroscopy. Antibacterial study of the complexes was screened against two Gram (+ve) and three Gram (-ve) bacteria and results show that all complexes are more effective against microorganisms than their respective ligands. The cytotoxicity of the synthesized compounds was tested against brine shrimp and MCF-7 Cells. The LC50 values of the ligand and complexes were found in the range of 9.24-4.12 µg/mL and 5.68-7.94 µg/mL, respectively.

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Section: Methodsmentioning

confidence: 99%

Section: -(5-(5-bromothiophenmentioning

confidence: 99%

Heteroleptic C, N- Donor Pd(II) Complexes: Synthesis, Characterization, DNA/BSA Binding Interactions And Biological Studies

Patel

Dhaduk

Dabhi

et al. 2021

Preprint

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“…38,39 Adducts with free N-amino groups, on the other hand, are of interest as they offer easy entry into -aminophosphine ligands showing a plethora of possible coordination modes as demonstrated recently for Pd(II) and Pt(II) complexes. 40 The most straightforward approach towards the required symmetric exo,exo-bicyclo [2.2.2]octenes 4a-d possessing two succinic anhydride moieties starts from the appropriate 2H-pyran-2-ones and maleic anhydride via double stereospecific thermal Diels-Alder cycloaddition. 41,42 Adducts 4 were in the next step transformed into succinimide derivatives 5 via nucleophilic attack of NH 2 group of amines, hydrazines, or hydrazides.…”

Section: Paper Synthesismentioning

confidence: 99%

Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Ekar¹,

Kranjc²

2020

Synthesis

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Efficient and reliable synthesis of substituted hydrazinylpyridines in thick-wall ACE tubes via nucleophilic substitution of a chlorine substituent in different chloropyridines is presented. Hydrazine hydrate and alkylhydrazines were used as nucleophiles and simple alcohols and diethyl ether were the only organic solvents necessary, making the process environmentally and user friendly, potentially reaching 100% atomic efficiency. In the next step, transformations of succinic anhydride moieties fused to the bicyclo[2.2.2]octene framework into succinimide moieties via nucleophilic substitution of oxygens were conducted. As nucleophiles two of the synthesized hydrazinylpyridines (2-hydrazinyl-3-nitropyridine and 2-hydrazinyl-5-nitropyridine) and also hydrazine hydrate, phenylhydrazine, and 4-nitrophenylhydrazine were used. Reactions were again carried out in ACE tubes and only simple alcohols, diethyl ether, and acetone were needed as solvents. One of the prepared bicyclo[2.2.2]octene adducts displayed water solubility thus being a promising candidate for future studies as a novel bidentate ligand for various metal cations in aqueous solutions or acting as an unprecedented halogen bond acceptor.

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“…α-Aminophosphonates and α-aminophosphine oxides containing a reactive group may show special properties as compared to regular derivatives. In case of the closely related α-aminophosphines [3], a -COOH function on the molecule made possible further transformations and ensured a linkage for a polymer support [4,5].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

et al. 2019

Self Cite

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In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-αaminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,NBis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.

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Synthesis of platinum, palladium and rhodium complexes of α-aminophosphine ligands

Cited by 30 publications

References 84 publications

Heteroleptic C, N- Donor Pd(II) Complexes: Synthesis, Characterization, DNA/BSA Binding Interactions And Biological Studies

Heteroleptic C, N- Donor Pd(II) Complexes: Synthesis, Characterization, DNA/BSA Binding Interactions And Biological Studies

Synthesis of Hydrazinylpyridines via Nucleophilic Aromatic Substitution and Further Transformation to Bicyclo[2.2.2]octenes Fused with Two N-Aminosuccinimide Moieties

Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

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