An Efficient Synthesis of 4-Dimethoxyphosphonyl Substituted Pyrazoles and Pyrazoline-5-Ones

Khotinen, A. V.; Polozov, A. M.

doi:10.1080/10426509308034347

Cited by 9 publications

(4 citation statements)

References 13 publications

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“…In addition, a similar procedure in the presence of atmospheric moisture permits the selective production of hydrazonophosphonate derivatives that can be conveniently used for the preparation of interesting dimethyl or diethyl (5-methyl-3-oxo-2,3-dihydro-1 H -4-pyrazolyl)phosphonates and 2-dialkoxyphosphoryl-1,2,3-thiadiazoles …”

Section: Discussionmentioning

confidence: 99%

Solvent-Free Reaction of Some 1,2-Diaza-1,3-butadienes with Phosphites: Environmentally Friendly Access to New Diazaphospholes and E-Hydrazonophosphonates

et al. 2005

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[structures: see text] The present article describes the reaction between 1,2-diaza-1,3-butadienes and trialkyl phosphites, under an atmosphere of nitrogen and under solvent-free conditions, to give alkyl 3,3-dialkoxy-2H-1,2,3lambda5-diazaphosphole-4-carboxylates that, in turn, are converted into corresponding E-hydrazonophosphonates by treatment with THF:water (95:5). These latter compounds are obtained directly by the reaction of 1,2-diaza-1,3-butadienes with trialkyl phosphites in the presence of air. These compounds are useful for the further preparation of dialkyl (5-methyl-3-oxo-2,3-dihydro-1H-4-pyrazolyl)phosphonates and 2-dialkoxyphosphoryl-1,2,3-thiadiazoles.

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Section: Discussionmentioning

confidence: 99%

Solvent-Free Reaction of Some 1,2-Diaza-1,3-butadienes with Phosphites: Environmentally Friendly Access to New Diazaphospholes and E-Hydrazonophosphonates

et al. 2005

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“…1-Phenyl-3-methyl-4-propionyl-5-pyrazolone (H L 1 ) was synthesized according to the reported procedure. , The syntheses of the 4-phosphoryl pyrazolone ligands H L 2 –H L 8 are depicted in Scheme , with those for H L 2 –H L 4 based on literature procedures. − Specifically, the phosphorylated acetates 1a and 1b were prepared from methyl 2-(dichlorophosphoryl)acetate, PCl 5 , and the corresponding phenols to yield, respectively, colorless and pale yellow oils. The β-dicarbonyl-functionalized phosphonates 2a–2c were obtained as yellow oils by the reaction of 1a–1b with the acetyl chlorides.…”

Section: Resultsmentioning

confidence: 99%

“…The syntheses of H L 2 –H L 4 were based on the reported procedure by Khotinen and Polozov . Until the addition of magnesium sulfate, every step was carried out under a nitrogen atmosphere.…”

Section: Methodsmentioning

confidence: 99%

“…The syntheses of HL 2 −HL 4 were based on the reported procedure by Khotinen and Polozov. 41 Until the addition of magnesium sulfate, every step was carried out under a nitrogen atmosphere. To 1.0 equiv of the corresponding 2 compound dissolved in dried acetonitrile, a solution containing 1.0 equiv of the hydrazine derivative in the same solvent was added at once.…”

Section: General Procedures For the Synthesis Of Different Phosphoryl...mentioning

confidence: 99%

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Highly Tunable 4-Phosphoryl Pyrazolone Receptors for Selective Rare-Earth Separation

et al. 2023

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Highly selective rare-earth separation has become increasingly important due to the indispensable role of these elements in various cutting-edge technologies including clean energy. However, the similar physicochemical properties of rare-earth elements (REEs) render their separation very challenging, and the development of new selective receptors for these elements is potentially of very considerable economic and environmental importance. Herein, we report the development of a series of 4-phosphoryl pyrazolone receptors for the selective separation of trivalent lanthanum, europium, and ytterbium as the representatives of light, middle, and heavy REEs, respectively. X-ray crystallography studies were employed to obtain solid-state structures across 11 of the resulting complexes, allowing comparative structure–function relationships to be probed, including the effect of lanthanide contraction that occurs along the series from lanthanum to europium to ytterbium and which potentially provides a basis for REE ion separation. In addition, the influence of ligand structure and lipophilicity on lanthanide binding and selectivity was systematically investigated via n-octanol/water distribution and liquid–liquid extraction (LLE) studies. Corresponding stoichiometry relationships between solid and solution states were well established using slope analyses. The results provide new insights into some fundamental lanthanide coordination chemistry from a separation perspective and establish 4-phosphoryl pyrazolone derivatives as potential practical extraction reagents for the selective separation of REEs in the future.

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Properties and Reactions of Phosphonic and Phosphinic Acids and their Derivatives

Edmundson¹

2009

Patai's Chemistry of Functional Groups

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Introduction The Role of the Phosphoryl ( P  Z )( Z = O , S , Se OR Te )Group Cleavage of the Phosphorus—Carbon Bond Reactions and Properties of the Carbon Ligands: The Functional Groups Reactions and Properties of the Carbon Ligands: The Carbon Skeleton Displacement Reactions of Non‐Carbon Ligands at Phosphorus

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An Efficient Synthesis of 4-Dimethoxyphosphonyl Substituted Pyrazoles and Pyrazoline-5-Ones

Cited by 9 publications

References 13 publications

Solvent-Free Reaction of Some 1,2-Diaza-1,3-butadienes with Phosphites: Environmentally Friendly Access to New Diazaphospholes and E-Hydrazonophosphonates

Solvent-Free Reaction of Some 1,2-Diaza-1,3-butadienes with Phosphites: Environmentally Friendly Access to New Diazaphospholes and E-Hydrazonophosphonates

Highly Tunable 4-Phosphoryl Pyrazolone Receptors for Selective Rare-Earth Separation

Properties and Reactions of Phosphonic and Phosphinic Acids and their Derivatives

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