Methods for the synthesis of α-heterocyclic/heteroaryl-α-aminophosphonic acids and their esters

Ali, Tarik E.; Abdel‐Kariem, Somaia M.

doi:10.3998/ark.5550190.p009.112

Cited by 26 publications

(9 citation statements)

References 33 publications

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“…[1][2][3][4] The synthesis of a-aryl-a-aminophosphonates can be carried out in two main routes: by the Kabachnik-Fields condensation, [5][6][7][8][9] or by the Pudovik (aza-Pudovik) reaction. [10][11][12][13] Although, the Pudovik addition, where a >P(O)H reagent, such as a dialkyl phosphite is added to the C ¼ N double-bond of imines, is simpler and widely applied, the Kabachnik-Fields condensation, in which an amine, an aldehyde or ketone and a >P(O)H species react in a one-pot manner, is also of an increased interest. Both reaction types were performed in the presence of a catalyst and/or a solvent.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Hudson

Tajti

Bálint

et al. 2020

Synthetic Communications

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A series of N-benzhydryl protected a-aminophosphonates with a-phenyl, a-(1-naphtyl), a-(9-anthryl) or a-(1-pyrenyl) substituents was synthesized by the Kabachnik-Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these a-aminophosphonates confirmed the presence of unusually short intramolecular C a-H dþ ÁÁÁ dþ H-C peri contacts.

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Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Hudson

Tajti

Bálint

et al. 2020

Synthetic Communications

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“…The organophosphorus compounds have found enormous applications in medicinal chemistry in addition to synthetic chemistry as well as agriculture and plastic industry [1–3]. For example, the α‐hydroxyphosphonates, a common class of organophosphorus derivatives, were explored for various biological activities [4–8], including antibacterial effects.…”

Section: Introductionmentioning

confidence: 99%

Novel 1,2,3‐triazolo phosphonate derivatives as potential antibacterial agents

Telu

Naveen

Kavitha³

et al. 2021

Journal of Heterocyclic Chem

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We describe the synthesis, characterization, and in vitro antibacterial evaluation of a library of novel compounds based on 1,2,3‐triazolo phosphonate framework along with the evaluation of DNA gyrase inhibitory potential of a promising molecule in silico. Preparation of these compounds was carried out via a multistep sequence comprising of the Abramov reaction followed by the Cu(I)‐catalyzed azide–alkyne cycloaddition (CuAAC) as the key steps. Various α‐hydroxyphosphonate derivatives containing either a secondary or tertiary alcohol at the α position were prepared. When screened for their antibacterial activities in vitro using a Gram‐positive (Staphylococcus aureus) and three Gram‐negative (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa) strains, majority of these derivatives exhibited reasonable to good effects with the analogue 5k being active against all the strains. The SAR analysis indicated that the activity was influenced by the position of the α‐hydroxyphosphonate moiety as well as the substituent present on the benzene ring attached to the 1,2,3‐triazole ring. Moreover, the compound 5k showed strong interactions with the DNA active site when docked into the DNA gyrase in silico. Thus, the 1,2,3‐triazolo phosphonate derivative 5k appeared to be a novel and promising hit molecule that deserves further study as a potential antibacterial agent.

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“…21 As a consequence, these family of compounds display diverse biological activities, raising growing interest in medicinal and pharmaceutical science applications. 22 A unique method to build the amino phosphonate framework P(O)-C-N [22][23][24][25][26][27] relies on the threecomponent domino Kabachnik-Fields reaction (KF-3CR). [28][29][30] Also referred to as phospha-Mannich, the reaction involves a hydrophosphoryl compound (e.g., dialkyl phosphite or secondary phosphine oxide), a carbonyl compound (aldehyde or ketone) and a primary or a secondary amine, resulting in the formation of -aminophosphonates (R 3 = OAlkyl) or aminophosphine oxides (R 3 = Ph) (Method A, Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods

Fiore

Sović

Lukin

et al. 2020

ACS Sustainable Chem. Eng.

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-Aminophosphonates are an important class of biologically active compounds, attracting considerable attention in medicinal chemistry, by inhibiting enzymes involved in amino acid metabolism. Herein, the Kabachnik-Fields domino reaction was investigated by mechanochemistry for the first-time preparation of -aminophosphonate derivatives in high yields and with full selectivity, outperforming comparable solution procedures. The reaction is a Lewis acid-catalysed process occurring however without the addition of any external catalyst, but occurring on the surface of the zirconium oxide used as the milling media. The mechanism of the mechanochemical reaction was also investigated by in situ Raman spectroscopy, the kinetic behavior was disclosed. The solid-state structures of two representative compounds have been determined by single-crystal X-ray diffractions.

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Methods for the synthesis of α-heterocyclic/heteroaryl-α-aminophosphonic acids and their esters

Cited by 26 publications

References 33 publications

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Novel 1,2,3‐triazolo phosphonate derivatives as potential antibacterial agents

Kabachnik–Fields Reaction by Mechanochemistry: New Horizons from Old Methods

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