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

Hudson, H. R.; Tajti, Ádám; Bálint, Erika; Czugler, Mátyás; Karaghiosoff, Konstantin; Keglevich, György

doi:10.1080/00397911.2019.1679186

Cited by 10 publications

(12 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structure of the 1,4 regioisomer obtained with an excellent yield is proposed through the analysis of its spectra of the coupled and decoupled 31 P NMR (Fig. 1B), the 1D 1 H and 13 C NMR (Fig. 2 and 3), as well as through the examination of the different correlations from the 2D 1 H-1 H and 1 H- 13 C NMR (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…This wide range of therapeutic and pharmacological activity [9] has led researchers to promote new methods for the preparation of α-amino phosphonic acid [10], whose main routes are the one-pot reaction of Kabachnick field [11]- [13] and the synthesis of chiral products of α-amino phosphonates [14]- [16]. In this case, the synthesis of new heterocyclic phosphonic amino esters continues to bloom in the literature.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Khadir

Boukhssas

Achamlale³

et al. 2021

EJCHEM

View full text Add to dashboard Cite

The biheterocyclic derivative of the phosphonic glycine analogue is prepared selectively by reaction between the α-azidoamino diethyl methylphosphonate and the 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole. The dipolar -1,3 cycloaddition reaction using Click Chemistry was carried out in a solvent water/ethanol mixture in a ratio of 1:1. Copper sulphate pentahydrate and sodium ascorbate are used in the reaction in catalytic amounts. The compound [diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}(benzamido) methyl] phosphonate was isolated pure as a white powder, after chromatography on a silica gel column (ethyl acetate/hexane acetate: 1/1). The yield of pure product is 90%, after recrystallization in an ether/hexane mixture. The structure of the -1,4 isomer is attributed to the compound obtained by means of 1D and 2D NMR and based on data from the literature concerning the cycloaddition reaction via Click Chemistry. Two-dimensional NMR spectroscopy played a major role. The analysis of the different correlations between adjacent hydrogens and carbons, and also between hydrogens and distant carbons, confirmed the proposed structure.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Khadir

Boukhssas

Achamlale³

et al. 2021

EJCHEM

View full text Add to dashboard Cite

show abstract

“…A series of α-aminophosphonates ( 64 , 66 , 68 and 70 ) with sterically demanding α-aryl substituents was synthesized using a MW-assisted catalyst-free and solvent-free protocol ( Scheme 48 ) [ 74 ].…”

Section: Kabachnik–fields Reactions With Dialkyl Phosphites Alkyl H -Phosphinates and Secondary Phosphine Oxidesmentioning

confidence: 99%

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Varga

Keglevich

2021

Molecules

Self Cite

View full text Add to dashboard Cite

The Kabachnik–Fields reaction, comprising the condensation of an amine, oxo compound and a P-reagent (generally a >P(O)H species or trialkyl phosphite), still attracts interest due to the challenging synthetic procedures and the potential biological activity of the resulting α-aminophosphonic derivatives. Following the success of the first part (Molecules 2012, 17, 12821), here we summarize the synthetic developments in this field accumulated in the last decade. The procedures compiled include catalytic accomplishments as well as catalyst-free and/or solvent-free “greener” protocols. The products embrace α-aminophosphonates, α-aminophosphinates, and α-aminophosphine oxides along with different bis derivatives from the double phospha-Mannich approach. The newer developments of the aza-Pudovik reactions are also included.

show abstract

“…Recently, a method of choice was described by Hudson and coworkers [83] under solvent and catalyst‐free conditions by microwave irradiation, for the synthesis aryl‐α‐Aminophosphonates from benzhydrylamine, aromatic aldehydes and dialkyl phosphites. The mixture was irradiated at 100–120 °C for 60–75 min.…”

Section: Microwave As a Green Approachmentioning

confidence: 99%

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

et al. 2021

View full text Add to dashboard Cite

α-Aminophosphonates play an important role across several fields, including organic synthesis and various potential applications. This review paper surveys recent achievements in the synthesis of α-Aminophosphonates, it summarizes the main synthetic routes towards α-Aminophosphonates that are known and it describes their biological proprieties from January2010 till December 2020: Special attention is devoted to green chemical approaches including catalysts, ultrasonic and microwave irradiations. We hope this paper will be a useful resource for researchers and that it will help them to work in this emerging research area.

show abstract

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

Cited by 10 publications

References 34 publications

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Synthesis of α-Aminophosphonates and Related Derivatives; The Last Decade of the Kabachnik–Fields Reaction

Recent Advances in the Synthesis of α‐Aminophosphonates: A Review

Contact Info

Product

Resources

About