Three-component Kabachnik Research Articles

Synthesis of novel α-aminophosphonates by methanesulfonic acid catalyzed Kabachnik–Fields reaction

A series of novel α-aminophosphonates of diethyl (2,4-difluorobenzylamino)methylphosphonate derivatives (4a–4g) have been synthesized by applying three-component Kabachnik–Fields reaction, using fluoro derivatives of aldehydes and substituted amines, diethyl phosphonate in the presence of a catalytic amount of methanesulfonic acid (MSA) in good yields with high enantioselectivities (up to 98% ee). The enantioselectivitiy of compounds (4a–4g) was confirmed by chiral HPLC. The direct Kabachnik–Fields reaction with high reactivity under mild reaction conditions and significantly used for synthesis of the α-aminophosphonate. The novel products were characterized by spectral and analytical data.

Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

An efficient one-pot three-component Kabachnik–Fields reaction of aldehydes (acyclic nucleosides), amines (or amino acid), and triethyl phosphite proceeded for the synthesis of aminophosphonates using natural phosphate coated with iodine (I2@NP) as a catalyst. The novel α-aminophosphonate and phosphonic acid acyclic nucleosides were tested for their anti-HCV and anti-HIV activities. The molecular docking showed that the non-activity of these compounds could be due to the absence of hydrophobic pharmacophores.

New Possibilities of the Kabachnik–Fields and Pudovik Reactions in the Phthalocyanine-Catalyzed Syntheses of α-Aminophosphonic and α-Aminophosphinic Acid Derivatives

The results of systematic studies demonstrated wide possibilities of the three-component Kabachnik–Fields and two-component Pudovik reactions catalyzed by metal phthalocyanines in the synthesis of structurally diverse α-aminophosphonates. Extension of this catalytic method to the synthesis α-aminophosphinates gave rise to a series of α-amino- and α-hydrazinophosphinates based on biogenic amino acids. A number of α-hydrazinophosphonates showed a good antioxidant activity.

Nano-Cuo–Au-catalyzed solvent-free synthesis of α-aminophosphonates and evaluation of their antioxidant and α-glucosidase enzyme inhibition activities

ABSTRACTA new green and efficient method has been developed for the synthesis of α-aminophosphonates through one-pot three-component Kabachnik–Fields reaction. It involves the reaction of a 2-aminophenol with different substituted aromatic aldehydes and dimethyl phosphite in the presence of nanocopper oxide–gold (CuO–Au) catalyst under solvent-free conditions at 60 °C. Nano-CuO–Au catalyst was found to have many advantages like high activity, simple workup, and good (87%) to very high yields (96%). The products were characterized by IR, 1H, 13C, and 31P NMR spectra and elemental analysis. All the synthesized compounds were screened for in vitro antioxidant and α-glucosidase inhibition activities. The compound 4b showed higher 2,2-diphenyl-1-picrylhydrazyl and H2O2 radical scavenging activity and compound 4e showed higher NO radical scavenging activity than the standard ascorbic acid. The compound 4j has much higher α-glucosidase enzyme inhibition activity than the standard acarbose.

A new procedure for synthesis of $$\upalpha $$ α -aminophosphonates by aqueous formic acid as an effective and environment-friendly organocatalyst

Aqueous formic acid (37%) as a green organocatalyst was used to synthesis of $$\upalpha $$ -aminophosphonates in one-pot, three-component Kabachnik–Fields reaction. The structures of compounds were determined by FT-IR, $${}^{1}\hbox {H}$$ -NMR and $${}^{13}\hbox {C}$$ -NMR spectroscopy. After optimization of the experimental conditions, the reaction was carried out at $$65\,{^{\circ }}\hbox {C}$$ under solvent- free condition. Use of a nontoxic effective organocatalyst, easy work up process and low-cost cleaning procedure are from the main advantages of this research. Synthesis and characterization of $$\upalpha $$ -aminophosphonates in one-pot, three-component Kabachnik–Fields reaction by formic acid in solvent free condition are reported. Using of a nontoxic effective organocatalyst, easy work up process and low-cost cleaning procedure are from the main advantages of this research.

5-H-1,2-Oxaphosphole 2-oxides, key building blocks for diversity oriented chemical libraries

A simple and effective preparation of 2-hydrogeno-5H-1,2-oxaphosphole 2-oxides 9a–b has been developed involving direct cyclization of H-phosphinic allenes. H-1,2-Oxaphospholenes 9a–b showed to be excellent building blocks for diversity oriented small chemical libraries. Then, reactivity of the cyclic H-phosphinates 9a–b was investigated through Pd(0) catalyzed arylation, Pudovik and three-component Kabachnik–Fields reactions. 5H-1,2-Oxaphospholes are excellent heterocyclic platforms offering different opportunities to modulate the substituent directly bounded to the phosphorus atom.

Camphor-derived thioureas: Synthesis and application in asymmetric Kabachnik-Fields reaction

A series of camphor-derived thiourea organocatalysts 3a–f were designed and synthesized from (1R,3S)-camphoric acid 1 and applied to the one-pot three-component Kabachnik–Fields reaction. Catalyst 3c was found to be an efficient organocatalyst for the reaction of 2-cyclopropylpyrimidin-4-carbaldehyde 4, various amines 5, and diphenylphosphite 6 to yield the corresponding enantioselective α-aminophosphonates 7a–e in 74%–82% yields and 14%–35% ee.

2-[Anilino(diphenylphosphoryl)methyl]phenol from a three-component Kabachnik–Fields reaction

The title compound, C25H22NO2P, was synthesized in high yield by a three-component Kabachnik-Fields reaction of diphenylphosphine oxide, salicylaldehyde and aniline in dry toluene at room temperature. It precipitates as racemic crystals, in which strong hydrogen bonds between the hydroxy group and the P=O group of a neighbouring molecule form one-dimensional heterochiral chains along the crystallographic a axis, with an O···O separation of 2.568 (2) Å. The pseudo-tetrahedral environment of the P atom is distorted, with O-P-C bond angles significantly larger than the C-P-C angles.

Synthesis of α-Aminophosphine Oxides with Chiral Phosphorus and Carbon Atoms

Lipophilic α-aminophosphine oxides are good extractants for liquid and membrane extraction. Optically active α-aminophosphine oxides, containing chiral centers in their structure, can provide selective means for transfer of stereoisomers through supported liquid membranes. We have developed a method for synthesis of such carrier compounds based on a three-component Kabachnik–Fields reaction.

One-pot three-component Kabachnik–Fields synthesis of α-aminophosphonates using H-beta zeolite catalyst

One-pot three-component Kabachnik–Fields synthesis of α-aminophosphonates with high yields from the reaction between carbonyl compound, primary amine, and substituted phosphite can be carried out in a short period, using H-beta zeolite as a reusable catalyst.

Synthesis of a “memory tripeptide” (Arg—Glu—Arg, RER) and the Kabachnik—Fields reaction with di- and tripeptides as a method for the synthesis of phosphorus-containing peptide analogs

Methods for the synthesis of potential “twin-drugs” containing fragments of the glutamate receptor antagonist and cognitive function enhancing oligopeptides were developed. The “memory tripeptide” Arg—Glu—Arg (RER) containing the tripeptide sequence of a protein APP328–330, a gB-amyloid precursor, was synthesized. A method for the synthesis of gA-aminophosphonates with oligopeptides as the amine component of the one-pot three-component Kabachnik—Fields reaction was developed. A method for the synthesis of phosphonopeptides by the introduction of gA-aminophosphonates into the peptide chain was proposed.

Enantioselective Three-Component Kabachnik−Fields Reaction Catalyzed by Chiral Scandium(III)−N,N′-Dioxide Complexes

The N,N'-dioxide-Sc(III) complex has been applied in the three-component Kabachnik-Fields reaction of aldehydes, 2-aminophenol, and diphenyl phosphite, giving the corresponding alpha-amino phosphonates in good yields with high enantioselectivities (up to 87% ee). The direct Kabachnik-Fields reaction proceeded with extremely high reactivity under mild reaction conditions and could be used for large-scale synthesis of the alpha-amino phosphonates.

Microwave‐Assisted Solvent‐Free and Catalyst‐Free Kabachnik—Fields Reactions for α‐Amino Phosphonates.

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Microwave-assisted solvent-free and catalyst-free Kabachnik–Fields reactions for α-amino phosphonates

A highly efficient solvent-free and catalyst-free method for the synthesis of α-amino phosphonates is developed by a microwave-assisted three-component Kabachnik–Fields reaction involving aldehyde, amine, and dimethyl phosphite.