Synthesis of organophosphates starting from α-hydroxyphosphonates

Kiss, Nóra Zsuzsa; Rádai, Zita; Szabó, Réka; Aichi, Youness; Laasri, Laila; Sebti, Saı̈d M.

doi:10.1080/10426507.2018.1547722

Cited by 4 publications

(2 citation statements)

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“…All the α‐hydroxybenzyl‐diethyl phosphonates 2 yielded the respective phosphates 3 in excellent yields with the exception of the 4‐methyl and 4‐nitro derivatives ( 3 b and 3 e ) which yielded recovered starting material, even when heated at higher temperatures. It is difficult to rationalize these exceptions, [2a,14] however in the case of the 4‐methyl derivative 3 b , the α‐hydroxybenzyl‐dimethyl phosphonate derivative has only been reported to undergo the phospha‐Brook rearrangement at elevated temperatures [12a,19] . The 4‐nitro derivative 3 e has not been prepared using the phospha‐Brook rearrangement and is typically synthesized via a chlorophosphate [20] .…”

Section: Resultsmentioning

confidence: 99%

Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates

et al. 2022

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A series of substituted aryl phosphate esters have been synthesized from their α‐hydroxyphosphonates substrates, using DBN (1,5 diazabicyclo(4.3.0)non‐5‐ene) at room temperature, via a phospha‐Brook rearrangement. The aryl‐substrate dependence of the rearrangement was explored, and excellent yields of the phosphate esters were achieved irrespective of whether the aryl moiety was activated or unactivated. A plausible mechanism for the rearrangement has been proposed. Based on the low temperature 31P‐NMR, the mechanism of the phospha‐Brook rearrangement is proposed to take place via an oxaphosphirane intermediate.

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Section: Resultsmentioning

confidence: 99%

Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates

et al. 2022

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“…The Suzuki–Miyaura carbon coupling for the synthesis of biphenyls, is used in the therapy of disorders caused by atherosclerosis [ 2 ]. The notable Knoevenagel condensation for the preparation of benzylidene malononitrile (BMN) rumored to be powerful inhibitors of tyrosine kinase [ 3 ] and the synthesis of α-hydroxyphosphonates by KF/NP [ 4 ] and the transposition of α-hydroxyphosphonates by K/NP [ 5 ]. These items have organic exercises and drug applications, which had been catalyzed by natural phosphate (NP) [ 6 ] or fluoroapatite (Fap) and fluoroapatite alone or doped with metals, showing extremely very high performance.…”

Section: Introductionmentioning

confidence: 99%

Apatite phosphate doped by cobalt as hight efficient catalyst of multi-component synthesis of therapeutic spiropyrimidine compound

Rhihil

Aichi

Zahouily

et al. 2022

Nat. Prod. Bioprospect.

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Spiropyrimidines vanquish a significant situation in the field of heterocyclic chemistry, they are broadly utilized as an antibacterial, an inhibitor of multidrug opposition, or an antiplatelet and antithrombotic drug. Phosphate, the principal Moroccan mineral wealth occupies a vital spot in the economic sector and its valuation is a goal continually looked for. Among the conceivable outcomes of valorization, its utilization in heterogeneous catalysis which thought about an exceptionally encouraging new way. In this context, the focus on the reaction of the synthesis of spiropyrimidine, catalyzed by natural phosphate (NP) and by fluoroapatite (Fap), are used alone or doped by cobalt. These phosphate catalysts were characterized by XRD, IR and SEM, while the synthesized spiropyrimidine was identified by IR, GC–MS and NMR. The obtained yield with fluorapatite doped by cobalt (Co/Fap), at room temperature in ethanol is very high and shows a high impact performance induced by a synergistic effect compared to that of NP alone. Graphical Abstract

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A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

Rádai

Szabó

Szigetvári

et al. 2020

COC

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The phospha-Brook rearrangement of dialkyl 1-aryl-1-hydroxymethylphosphonates (HPs) to the corresponding benzyl phosphates (BPs) has been elaborated under solid-liquid phase transfer catalytic conditions. The best procedure involved the use of triethylbenzylammonium chloride as the catalyst and Cs2CO3 as the base in acetonitrile as the solvent at room temperature. The substrate dependence of the rearrangement has been studied, and the mechanism of the transformation under discussion was explored by quantum chemical calculations. The key intermediate is an oxaphosphirane. The one-pot version starting with the Pudovik reaction has also been developed. The conditions of this tandem transformation were the same, as those for the one-step HP→BP conversion.

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Synthesis of organophosphates starting from α-hydroxyphosphonates

Cited by 4 publications

References 3 publications

Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates

Room Temperature DBN Initiated Phospha‐Brook Rearrangement of α‐Hydroxyphosphonates to Phosphates

Apatite phosphate doped by cobalt as hight efficient catalyst of multi-component synthesis of therapeutic spiropyrimidine compound

A Study on the Rearrangement of Dialkyl 1-Aryl-1-hydroxymethylphosphonates to Benzyl Phosphates

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