Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst

Kulkarni, Makarand A.; Lad, Uday P.; Desai, Uday V.; Mitragotri, Satish D.; Wadgaonkar, Prakash P.

doi:10.1016/j.crci.2012.10.009

Cited by 35 publications

(16 citation statements)

References 49 publications

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“…The above results drove our decision to study the reactions of paramagnetic aldehydes and ketones with diethyl phosphite to produce α-hydroxyphosphonates because these derivatives have biological importance, i.e., herbicidal, antibacterial, antifungal and antioxidant effects, to mention but a few [27][28][29]. To access paramagnetic α-hydroxyphosphonates among the possible reaction conditions [30,31] tested, we choose the methodology of Kulkarni et al [32], e.g., solvent-free conditions in the presence of 0.05 eq. K 3 PO 4 .…”

Section: Pudovik Hydroxyphosphonate Synthesis and Transformationsmentioning

confidence: 99%

Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

et al. 2020

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Organophosphorus compounds occupy a significant position among the plethora of organic compounds, but a limited number of paramagnetic phosphorus compounds have been reported, including paramagnetic phosphonates. This paper describes the syntheses and further transformations of pyrroline and piperidine nitroxide phosphonates by well-established methods, such as the Pudovik, Arbuzov and Horner-Wadsworth-Emmons (HWE) reactions. The reaction of paramagnetic α-bromoketone produced a vinylphosphonate in the Perkow reaction. Paramagnetic α-hydroxyphosphonates could be subjected to oxidation, elimination and substitution reactions to produce various paramagnetic phosphonates. The synthesized paramagnetic phosphonates proved to be useful synthetic building blocks for carbon-carbon bond-forming reactions in the Horner-Wadsworth-Emmons olefination reactions. The unsaturated compounds achieved could be transformed into various substituted pyrroline nitroxides, proxyl nitroxides and paramagnetic polyaromatics. The Trolox® equivalent antioxidant capacity (TEAC) of new phosphonates was also screened, and tertiary α-hydroxyphosphonatate nitroxides exhibited remarkable antioxidant activity.

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Section: Pudovik Hydroxyphosphonate Synthesis and Transformationsmentioning

confidence: 99%

Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

et al. 2020

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“…A base-catalyzed variation of the Pudovik reaction was carried out in the presence of 5 mol % potassium phosphate as the catalyst ( Table 1 /Entry 1) [ 21 ]. This method has the advantage of using an inexpensive catalyst, requiring short reaction times and an easy work-up procedure that comprises simple extraction, and, in most cases, provides the products in high yields.…”

Section: Synthetic Routes Towards α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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“…Recent articles targeted to perform the addition under mild and solvent‐free reaction conditions. These methods mainly employed simple and inexpensive oxides/bases/salts as catalysts, including aluminum oxide, magnesium oxide, barium hydroxide, sodium carbonate, potassium hydrogen sulfate, and inorganic phosphates, as well as triethylamine or piperazine . In a few cases, the components were activated by grinding or microwave (MW) irradiation .…”

Section: Introductionmentioning

confidence: 99%

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

Rádai

Szeles

Kiss

et al. 2018

Heteroatom Chemistry

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A series of dibenzyl α‐hydroxyphosphonates and the corresponding α‐hydroxyphosphonic acids, mostly new compounds, have been synthesized. The dibenzyl α‐hydroxyphosphonates have been obtained in the Pudovik reaction of substituted benzaldehydes and dibenzyl phosphite in the presence of triethylamine as the catalyst. The amount of the solvent was minimized during the reaction, and the workup involved crystallization from the reaction mixture. A new protocol was developed to transform the dibenzyl 1‐hydroxyphosphonates to the corresponding phosphonic acids by catalytic hydrogenation. The derivatives prepared were screened as potential cytotoxic agents against Mes‐Sa human uterine sarcoma cell line.

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Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst

Cited by 35 publications

References 49 publications

Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

Syntheses and Reactions of Pyrroline, Piperidine Nitroxide Phosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

Green synthesis and cytotoxic activity of dibenzyl α‐hydroxyphosphonates and α‐hydroxyphosphonic acids

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