Synthesis Of Α-aminophosphonates Research Articles

Synthesis, characterization and application of nitrogen–sulfur-doped carbon spheres as an efficient catalyst for the preparation of novel α-aminophosphonates

Nitrogen–sulfur-doped carbon spheres (NS-CSs) were prepared from sucrose and thiourea through a simple hydrothermal process. NS-CSs were characterized by TEM, FTIR, TGA, XRD, Raman spectroscopy and elemental analyses. The results revealed that the synthesized carbon spheres have an amorphous structure with diameters of 300–500 nm. The microspherical carbon catalyst that is recyclable has been used in the synthesis of α-aminophosphonates derived from 2-aminobenzothiazoles. Three-component reaction was performed between 2-aminobenzothiazoles, aromatic aldehydes and trimethyl phosphite in the presence of NS-CSs as microorganocatalyst at 50 °C under solvent-free conditions in high yield.

An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate

Correction to: An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate PentahydrateSynlett 2007; 2007(05): 0745-0748DOI: 10.1055/s-2007-970762

A novel straightforward synthesis of α-aminophosphonates: one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a catalyst

We report here a novel and straightforward synthesis method for the preparation of α-aminophosphonates in relatively good yield. The method involves the one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a recyclable catalyst. CuO@Fe3O4 nanoparticles were prepared and their structures were confirmed by the FT-IR, TGA, VSM, TEM and X-ray diffraction patterns analyses.

Efficient and Green One-Pot Multi-Component Synthesis of α-Aminophosphonates Catalyzed by Zinc Triflate

Background:α-Aminophosphonates are an important class of compounds in medicinal chemistry with a wide range of biological effects. Despite the numerous synthetic methods for α-aminophosphonates reported in literature, there is still a need for the development of a simpler and greener protocol, for high throughput library synthesis. Keywords: α-Aminophosphonates, Kabachnik-Fields reaction, zinc triflate, green synthesis, multi-component reactions.

A green one-pot three-component synthesis of α-aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe3O4@SiO2-imid-PMAn as magnetic catalyst

GRAPHICAL ABSTRACT

Improved facile synthesis of α-amino phosphonates by the reaction of α-amido sulfones with dialkyl trimethyl silyl phosphites catalyzed by Fe(III) chloride

ABSTRACTAn improved efficient synthesis of α-amino phosphonates has been discovered by the reaction of N-benzyloxycarbonylamino sulfones with dialkyl trimethyl silyl phosphites in the presence of FeCl3 as a catalyst. The products were formed in high yields (86–94%) within 2–4 h. The catalyst is inexpensive, easily available, and highly active. The unreacted dialkyl trimetyl silyl phosphites can easily be removed from the products due to their low boiling points. The sulfones can conveniently be prepared and are generally stable.

Sulfated polyborate catalyzed Kabachnik-Fields reaction: An efficient and eco-friendly protocol for synthesis of α-amino phosphonates

An efficient, and environmentally benign protocol for a three-component Kabachnik-Fields reaction of aldehydes, amines, and diethyl phosphite catalyzed by sulfated polyborate has been described to afford α-amino phosphonates under solvent-free reaction conditions. The major advantages of the present method are high yields, short reaction time, simple work-up procedure, inexpensive, eco-friendly and reusable catalyst and solvent-free reaction conditions and tolerance towards various functional groups present in the substrates.

Synthesis of α-aminophosphonates using solvate ionic liquids

A range of α-aminophosphonates were accessed in high yields and very rapidly, using solvate ionic liquids as the reaction media.

One-pot synthesis of α-aminophosphonates via a cascade sequence of allylamine isomerization/hydrophosphonylation.

A Rh/Ni-catalyzed cascade sequence of allylamine isomerization and hydrophosphonylation to synthesize α-aminophosphonates has been disclosed. The reaction, which not only allows the generation of widespread valuable α-aminophosphonates under simple systems and mild conditions, but also enriches the process of olefin isomerization-addition both in catalytic systems and various reaction types.

A Green Approach to the Synthesis of α-Amino Phosphonate in Water Medium: Carbene Insertion into the N-H Bond by Cu(I) Catalyst.

Synthesis of amino phosphonates is more important owing to their significant applications in the biological systems. There are few methods already known in the literature to make these molecules; however, known methods have their own disadvantages. In this regard, synthesis of different kinds of amino phosphonates have been achieved via phosphonate substituted carbene insertion into the N-H bond of aniline catalyzed by readily available copper salt under mild reaction conditions in water. In order to find an efficient catalyst for carbene insertion reaction in neat water, a large number of transition metal catalysts were screened, and we found that the [Cu(CH3CN)4]ClO4 was the best catalyst under employed reaction conditions. Using this environmentally benign methodology (copper catalyzed reaction in water), a large number of biologically important amino phosphonates have been synthesized, isolated (37 examples), and characterized using standard analytical and spectroscopic techniques.

Zinc Di(l-prolinate)-Mediated Synthesis of α-Aminophosphonates under Mild Conditions

An efficient method has been developed for the preparation of α-aminophosphonates by using zinc di( l -prolinate) as a catalyst under mild reaction conditions. The method has the advantages of high yields, short reaction times, and easy workup conditions.

Synthesis of α-amino phosphonates by diastereoselective addition of diethyl phosphite sodium salt to aldimines derived from Betti base

A diastereoselective (de 80–92%) synthesis of α-amino phosphonates was accomplished by reaction of diethyl phosphite sodium salt with 3-R-1-phenyl-2,3-dihydro-1H-naphth[1,2-e]-[1,3]oxazines being the products of aminoacetalization of aldehydes with 1-(α-aminobenzyl)-2-naphthol (Betti base).

Supported sulfonic acid on magnetic nanoparticles used as a reusable catalyst for rapid synthesis of α-aminophosphonates

ABSTRACT Sulfonic acid was anchored on the surface of silica-coated cobalt ferrite core to obtain a new magnetically separable catalyst. The resultant composite was characterized by various techniques, including FT-IR, X-ray diffraction, FESEM, energy-dispersive X-ray, TEM, TGA, and vibrating sample magnetometer. The immobilized sulfonic acid was shown to be an efficient heterogeneous catalyst for the synthesis of α-aminophosphonates under solvent-free conditions at room temperature. The catalyst is readily recovered by simple magnetic decantation and can be recycled 7 times with no significant loss of catalytic activity.

A heterogeneous catalyst, SiO2-ZnBr2: An efficient neat access for α-aminophosphonates and antimicrobial activity evaluation

An efficient, environmentally benign and green method was developed for the synthesis of α-aminophosphonates by one-pot three-component reaction (Kabachnik-Fields reaction) of amine (4-(4-chlorophenoxy)aniline), aldehydes and diethyl phosphite using catalyst, SiO2-ZnBr 2 under solvent-free conditions. The developed method under conventional conditions was further optimized in microwave and ultrasonication methods. A series of α-aminophosphonates, diethyl (4-(4-chlorophenoxy)phenylamino)(aryl/ heteroaryl)methylphosphonates was synthesized to check the generality. The catalyst, SiO2-ZnBr2 afforded good yields of products in all the methods in the range of 85–97% but variation was observed in reaction time. Microwave irradiation method took very less time (4–8 min) as compared with ultrasonication (35–52 min) and conventional (2–3 h) conditions. The major advantages are simple and mild conditions, short reaction times, high yield of the product with purity, use of cheap catalyst and reusability of the catalyst until to three times without significant loss of activity. Antibacterial and antifungal activities were evaluated for the title compounds (50 and 100 μg/mL) including minimum inhibitory concentrations. A few of the newly synthesized α-aminophosphonates exhibited promising antimicrobial activity at lower MIC values in the range of 15.0–25.0 μg/mL and closer to the standards (5–12 μg/mL). An efficient, neat and green method was developed for α-aminophosphonates by Kabachnik-Fields reaction using catalyst, SiO2-ZnBr2. The developed method under conventional conditions was further optimized in microwave and ultrasonication methods. SiO2-ZnBr2 catalyst afforded good yields of the products (85-97%). Molecules were evaluated for antimicrobial activity including their MIC.

Palladium-Catalyzed Enantioselective Synthesis of α-Amino Phosphonates

Palladium-Catalyzed Enantioselective Synthesis of α-Amino Phosphonates

Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst

A supported acidic catalyst was easily prepared via anchoring imidazolium salt-based ionic liquid onto multiwalled carbon nanotube by covalent bonds. This novel immobilized acidic ionic liquid effectively catalyzed the one-pot synthesis of α-aminophosphonates from the reaction of amines and aldehydes with diethyl phosphite. The catalyst can be easily recovered and reused without appreciable change in its efficiency.

Synthesis of α-Aminophosphonates with l-Cysteine Functionalized MNPs

Synthesis of α-Aminophosphonates with l-Cysteine Functionalized MNPs

Highly efficient synthesis of α-aminophosphonates catalyzed by hafnium(IV) chloride

A highly efficient one-pot method for the synthesis of a variety of α-aminophosphonates via the one-pot three-component reaction of aldehyde, amine, and phosphite has been developed using only 2mol% HfCl4 as the catalyst. The NMR evidence strongly indicated the catalytic roles of Hf(IV) on the activation of aldehyde, phosphite, and imine intermediate.

Enantioselective Synthesis of α-Amino Phosphonates via Pd-Catalyzed Asymmetric Hydrogenation.

A highly enantioselective palladium-catalyzed hydrogenation of a series of linear and cyclic α-iminophosphonates has been achieved, providing efficient access to optically active α-aminophosphonates with up to 99% ee.

Synthesis of α-aminophosphonates using a mesoporous silica catalyst produced from sugarcane bagasse ash

A new green synthesis route is proposed for obtaining a mesoporous material using sugarcane bagasse ash as the silica source.