Three-component Synthesis Of Α-aminophosphonates Research Articles

Highly efficient one-pot synthesis of α-aminophosphonates using nanoporous AlSBA-15 catalyst in a three-component system

Nanoporous AlSBA-15 catalysts with different nSi/nAl ratios (41, 129, and 210) were synthesized using a hydrothermal method. These catalysts were characterized by XRD, N2 sorption, TPD-NH3, FT-IR, SEM and TEM. XRD analyses of AlSBA-15 catalysts confirmed the presence of well-ordered crystalline structure with p6mm symmetry. The specific surface area and specific pore volume of the AlSBA-15 catalysts are in the range of 480 to 757 m2/g and 0.65 to 0.95 cm3/g, respectively. The catalytic performance of nanoporous AlSBA-15 catalysts are used as an outstanding catalytic system for one-pot synthesis of α-aminophosphonates via Kabachnik-Fields reaction in a three-component system using amines (primary/secondary), carbonyl compounds (aldehydes/ketones) and diethyl phosphite. The major advantages of the present contributions are excellent yields, short reaction time, simple experimental technique, high chemo-selectivity, catalyst recyclability, easy work-up procedure and green approach. Three-component synthesis of α-aminophosphonates follows first imine formation from amine and aldehyde/ketone followed by phosphate addition. The experimental findings suggest that the nanoporous AlSBA-15 catalysts can be recycled and reused up to six cycles without any loss in the catalytic performance.

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

A green protocol for one-pot three-component synthesis of α-amino phosphonates catalyzed by succinic acid

A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of a-amino phosphonates from a condensation reaction of trialkyl phosphite, aldehydes, and amines in the presence of a catalytic amount of succinic acid (8.5 mol %) (for the first time) under solvent-free conditions. The advantages of this protocol are excellent yields, short reaction time, mild reaction conditions, higher availability, low costs, more environmentally friendly, lack of need for column chromatography and simple work-up procedure.

TfOH/C-catalyzed one-pot three-component synthesis of α-amino phosphonates under solvent-free conditions

The TfOH/C was readily prepared via simple absorption of triflic acid onto activated charcoal. This solid acid was used as an efficient catalyst for the synthesis of α-aminophosphonates through the Kabachnik–Fields reaction of carbonyl compound, amine and diethyl phosphite under solvent-free conditions.

BPy]HSO4 as an Efficient and Recyclable Catalyst for One-Pot Synthesis of α-Aminophosphonates under Solvent-Free Conditions

[BPy]HSO4 was prepared and used as an efficient and recyclable catalyst for the one-pot three-component synthesis of α-aminophosphonates at room temperature under solvent-free conditions with good-to-excellent yields. The workup procedure is very simple, and the catalyst can be reused at least four times without any loss in catalytic activity.

Phenylboronic Acid as Efficient and Eco-Friendly Catalyst for the One-Pot, Three-Component Synthesis of α-Aminophosphonates under Solvent-Free Conditions

A simple, mild, and efficient one-pot, three-component synthetic method has been developed for the preparation of α-aminophosphonates using phenylboronic acid as catalyst under solvent-free conditions at 50 °C. The process involves the reaction of carbonyl compounds (aldehydes or ketones) with benzylamine and dimethyl phosphite. A wide range of carbonyl compounds are compatible with this reaction, producing tertiary and quaternary α-aminophosphonates in moderated to excellent yields in short time.

ChemInform Abstract: Cobalt(II) Chloride Accelerated One‐Pot Three‐Component Synthesis of α‐Aminophosphonates at Room Temperature.

AbstractThe convenient method produces the desired analogues of natural amino acids within a short time with good to excellent yields and many functional groups are tolerated.

Cobalt(II) chloride accelerated one-pot three-component synthesis of α-aminophosphonates at room temperature

Abstract A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of α-aminophosphonates from condensation reaction of trimethyl phosphite, aryl aldehydes and aryl amines in the presence of CoCl 2 ·6H 2 O under solvent-free conditions. Thus α -aminophosphonates were synthesized relatively quickly in good yields at room temperature.

ChemInform Abstract: Solvent‐Free Synthesis of Pyrimidine Nucleoside‐Aminophosphonate Hybrids and Their Biological Activity Evaluation.

AbstractA highly efficient one‐pot three‐component synthesis of α‐aminophosphonates is presented.

One-Pot, Three-Component Synthesis of α-Aminophosphonates Catalyzed by Acyclic Acidic Ionic Liquids

Some acyclic acidic ionic liquids were prepared and used as the catalysts for the one-pot, three-component synthesis of α-aminophosphonates from aldehydes, amines, and trimethylphosphite at room temperature in water. The products could simply be separated from the system of catalyst/water, and the catalysts could be reused at least six times without noticeably decreasing the catalytic activity.

Sodium Dihydrogen Phosphate as an Efficient Catalyst for One-Pot, Three-Component Synthesis of α-Aminophosphonates Under Solvent-Free Conditions at Room Temperature

A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of α-aminophosphonates from a condensation reaction of trimethyl phosphite, aldehydes, and amines in the presence of sodium dihydrogen phosphate under solvent-free conditions. Thus, α-aminophosphonates were synthesized relatively quickly in good yields at room temperature.

Solvent-Free Synthesis of Pyrimidine Nucleoside-Aminophosphonate Hybrids and Their Biological Activity Evaluation

A novel and highly efficient one-pot three-component synthesis of α-aminophosphonates under neat condition was developed. By employing this method, hybrid compounds of aminophosphonate with pyrimidine nucleosides were synthesized in good to excellent yields starting from 5-formyl-2′-deoxyuridine, aniline and dimethyl phosphite. The antiviral and antileishmanial activities of these novel hybrid compounds were also studied but none were found to be active.

A sulfonic acid functionalized ionic liquid as a homogeneous and recyclable catalyst for the one-pot synthesis of α-aminophosphonates

A sulfonic acid functionalized ionic liquid is used as a Brønsted acid catalyst for the one-pot, three-component synthesis of α-aminophosphonates from aldehydes and ketones at room temperature in water. This homogeneous catalytic procedure is simple and efficient and the catalyst can be reused at least six times without any noticeable decrease in catalytic activity.

Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot

A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford α-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and reusable catalyst, mild and solvent-free reaction conditions and tolerance towards various functionalities present in the substrates.

Amino acids in catalytic synthesis of α-aminophosphonates

The reaction of acetophenone with chiral α-amino acids and their esters has been studied in catalytic one-pot three-component synthesis of α-aminophosphonates. α-Aminophosphonates are found to form mixtures of diastereomers in high yields.