To date the greenest method for the preparation of α-hydroxyphosphonates from substituted benzaldehydes and dialkyl phosphites

Keglevich, György; Rádai, Zita; Kiss, Nóra Zsuzsa

doi:10.1515/gps-2016-0125

Cited by 26 publications

(21 citation statements)

References 34 publications

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“…Keglevich and co-workers could, however, elaborate a green method, when the hydroxyphosphonate simply crystallized out in a pure form from the reaction mixture. In this case, only a minimal amount of acetone and pentane was necessary as the solvent (Keglevich et al, 2017). A convenient functionalization of -hydroxyphosphonates was also reported recently (Cytlak et al, 2018) en route to the synthesis ofaminophosphonates.…”

Section: Introductionmentioning

confidence: 73%

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

et al. 2019

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The crystal structures of seven -aryl--hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy)(phenyl)methyl]phosphonate, C 9 H 13 O 4 P, dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate, C 11 H 17 O 6 P, dimethyl (1-hydroxy-1-phenylethyl)phosphonate, C 10 H 15 O 4 P, dimethyl [1-hydroxy-1-(4nitrophenyl)ethyl]phosphonate, C 10 H 14 NO 6 P, dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate, C 21 H 20 NO 6 P, dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate, C 21 H 20 ClO 4 P, and dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate, C 22 H 23 O 4 P, were studied to gain a better understanding of the organization in this type of molecule in the solid state. The crystals obtained for this series of compounds show a balance between C-OHÁ Á ÁO P chain-linked packing and the dimeric types of hydrogen-bond bridges of intermolecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (i.e. secondary graph sets of the C-HÁ Á ÁO type) revealed a similarity in the graph-set descriptors, suggesting a fine interplay of substituent-and shape-dependent effects on strong-weak interactions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary C atom, but also by the nature and crowding of the ortho substituents of the -aryl group.

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Section: Introductionmentioning

confidence: 73%

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

et al. 2019

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“…According to our method, the mixture of benzaldehyde derivative and dialkyl phosphite is heated in the presence of 10% of triethylamine as the catalyst in a minimum quantity of acetone as the solvent (Scheme 1, Table 1). [17] After completion of the reaction, the work-up comprised the addition of a small amount of n-pentane, and crystallization on cooling to room temperature. Filtration of the precipitate provided the desired a-hydroxyphosphonates in yields of 78-95%.…”

Section: Resultsmentioning

confidence: 99%

Green syntheses of potentially bioactive α-hydroxyphosphonates and related derivatives

Kiss

Rádai

Keglevich

2019

Phosphorus, Sulfur, and Silicon and the Related Elements

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a-Hydroxyphosphonates have been in the focus of interest for many years due to their potential in biological activity. Not only a-hydroxyphosphonates are of general importance, but also their derivatives. a-Aminophosphonates and a-hydroxyphosphonic acids have already been recognized for their biological effects, while phosphoryloxyphosphonates represent a new family of compounds. In this paper we present alternative syntheses towards a-hydroxyphosphonates and their derivatives.

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“…At first, dibenzyl α‐hydroxyphosphonates ( 1 ) were synthesized from substituted benzaldehydes and dibenzyl phosphite by the extension of our method reported previously . An equimolar mixture of the starting components was stirred at reflux in a minimal amount of acetone (1 mL for 11.0 mmol benzaldehyde) in the presence of 10 mol% triethylamine as the catalyst (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…A new and benign method was developed for the synthesis of α‐hydroxyphosphonates starting from substituted benzaldehyde and dimethyl or diethyl phosphite by us . Our protocol employed triethylamine as an inexpensive catalyst and targeted to minimize the use of organic solvents during the reaction, as well as the work‐up procedure, in contrast to the methods previously described in the literature.…”

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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To date the greenest method for the preparation of α-hydroxyphosphonates from substituted benzaldehydes and dialkyl phosphites

Cited by 26 publications

References 34 publications

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates

Green syntheses of potentially bioactive α-hydroxyphosphonates and related derivatives

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

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