Synthesis Of Novel Α-aminophosphonates Research Articles

Facile one pot three component synthesis, characterization, and molecular docking simulations of novel α-aminophosphonate derivatives based pyrazole moiety as potential antimicrobial agent.

An efficient method has been developed for the synthesis of novel α-aminophosphonates (AAP) (3a-m) through a one-pot three-component reaction of 1,3-disubstituted-1H-pyrazol-5-amine, aromatic aldehydes, and phosphite using lithium perchlorate as catalyst. All newly synthesized compounds were characterized via different spectroscopic techniques. The synthesized compounds' mode of action was investigated using molecular docking against the outer membrane protein A (OMPA) and exo-1,3-beta-glucanase, with interpreting their pharmacokinetics aspects. The results of the antimicrobial effectiveness of these compounds revealed a broad spectrum of their biocidal activity and this in-vitro study was in line with the in- silico results. Additionally, it has been demonstrated that these compounds exhibited a minimum inhibitory concentration (MIC) with significant activity at low concentrations (7.5-30.0 mg/mL). Further, the radical scavenging (DPPH*) activity of the synthesized compounds fluctuated, with compounds 3h, 3a, and 3f showing the highest antioxidant activity. Overall, the formulated compounds can be employed as antimicrobial and antioxidant agents in medical applications.

Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction

An effective technique was proposed for the synthesis of novel α-aminophosphonates: a three-component one-pot condensation reaction of aniline, aromatic aldehydes, and triphenyl phosphite in the presence of (MIL-100(Fe)) as a heterogeneous catalyst. Initially, MIL-100(Fe) was synthesized using H3BTC and ferric nitrate at low temperature and atmospheric pressure. Further, MIL-100(Fe) was characterized using various techniques such as XRD, BET surface area, scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR), and thermogravimetric analysis (TGA). Herein, MIL-100(Fe) showed exceptional catalytic performance for the synthesis of α-aminophosphonate and its derivatives compared with conventional solid catalysts, and even homogeneous catalysts. The study demonstrated that MIL-100(Fe) is an ecofriendly and easily recyclable heterogeneous catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yield (98%) and turnover frequency (TOF ~ 3.60 min−1) at room temperature and a short reaction time (30 min).

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.

Synthesis of novel α-aminophosphonates under microwave irradiation, biological evaluation as antiproliferative agents and apoptosis inducers

The synthesis of two series of α-aminophosphonates was achieved by Microwave Irradiation (MW), using the one-pot Kabachnik–Fields reaction. Based on a green chemistry approach, the reactions were carried out using ethanol as the only solvent and without any catalyst, and short reaction times (20–40 min), in variable yields. Both series were tested to determine their cell proliferation inhibition activity in MDA-MB-231, MCF-7 and MCF-10A cell lines. Ethyl 4-(((diphenoxyphosphoryl)(4-(diphenylamino)phenyl)methyl)amino) benzoate 4e and diphenyl (((4-(((S)-2-hydroxy-1-phenylethyl)carbamoyl)phenyl)amino)(4-hydroxyphenyl)methyl)phosphonate 6b, showed cell proliferation inhibition activity only in the cancer cell line MCF-7 and no effect on the normal cell line MFC-10A, both compounds caused cell death by inducing apoptosis.

Design, green synthesis, anti-microbial, and anti-oxidant activities of novel α-aminophosphonates via Kabachnik-Fields reaction

GRAPHICAL ABSTRACT

Protonated trititanate nanotubes: an efficient catalyst for one-pot three-component coupling of benzothiazole amines, heterocyclic aldehydes, and dialkyl/diaryl phosphites with a greener perspective

Nano-size catalysts of TiO2, ZnO, CuO, and protonated trititanate nanotubes (H2Ti3O7) have been investigated for the one-pot three component synthesis of novel α-aminophosphonates from benzothiazole amines, heteroaldehydes, and dialkyl/diaryl phosphites via Kabachnik–Fields reaction. This methodology provides a new and convenient approach to multicomponent reaction and the H2Ti3O7 nanotubes catalyst is recyclable upto seven cycles.

Highly efficient one-pot four-component Kabachnik–Fields synthesis of novel α-amino phosphonates under solvent-free and catalyst-free conditions

A simple and safe one-pot four component synthesis of Kabachnik–Fields synthesis of novel α-amino phosphonates under solvent-free and catalyst-free conditions is reported.

Thiamine hydrochloride (VB1): An efficient catalyst for one-pot synthesis of α-aminophosphonates under ultrasonic irradiation

Abstract An efficient synthesis of novel α-aminophosphonates by the reaction of aldehydes and amines with triethyl phosphite in the presence of the easily available, inexpensive, and nontoxic catalyst thiamine hydrochloride (VB1). This method affords the α-aminophosphonates under the influence of ultrasound irradiation in aqueous medium, in short reaction times (4–6 min), high yields (85–95%), with improved purity. The process is green, mild, inexpensive and excellent yields are the main compensation of this procedure.

Ultrasonic Promoted Synthesis and Antibacterial Screening of Some Novel Piperidine Incorporated α-Aminophosphonates

A simple and high-yielding method was developed for the synthesis of novel α-aminophosphonates from imines, obtained from 4-(piperidine-1-yl)benzaldehyde, by using triethylphosphite in the presence of dilute HCl under ultrasound irradiation. This method, which was developed for the synthesis of α-aminophosphonates, gave excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT

ChemInform Abstract: Microwave Assisted One‐Pot Synthesis of Novel α‐Aminophosphonates and Their Biological Activity.

AbstractVarious new α‐aminophosphonates (IV) are efficiently synthesized by a simple reaction of substituted aromatic/heterocyclic aldehydes (II), benzothiazole (I) and phosphites (III) under microwave irradiation without any catalyst.

Microwave Assisted One-pot Synthesis of Novel α-Aminophosphonates and heir Biological Activity

A variety of synthetic ap-proaches have been reported for them. Of all the methods, the nucleophilic addition of phosphites to imines, catalyzed by Lew-is acid or a base is the most convenient one.Nowadays, microwave irradiation is used to accomplish cer-tain unsuccessful or low-yielding reactions, reducing the re-action time from days to minutes, and improving yields.

An Efficient Synthesis and Antibacterial Screening of Novel Oxazepine α-Aminophosphonates by Ultrasound Approach

An efficient synthesis of novel α-aminophosphonates by the reaction of quino[2,3-b][1,5]benzoxazepines with triethyl phosphite in the presence of the easily available, inexpensive, and nontoxic catalyst p-toluene sulphonic acid (p-TSA). This method affords the α-aminophosphonates under the influence of ultrasound irradiation in solvent-free conditions, in short reaction times (4–6 min), high yields (80–90%), with improved purity. The synthesized α-aminophosphonates show antibacterial activity against Gram-positive and Gram-negative bacteria. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Synthesis of Novel α-Aminophosphonates Containing Adamantyl Fragment

Novel α-aminophosphonates containing an adamantyl fragment were prepared by a microwave-assisted cadmium(II) iodide-catalyzed Kabachnik-Fields reaction.

Simple and High Yielding Synthesis of New α-Aminophosphonates from Imines

A simple and high yielding method was developed for the synthesis of novel α-aminophosphonates from imines, obtained from 2-chloroquinoline-3-carbaldehyde, by using triethylphosphite in the presence of chlorotrimethylsilane (TMSCl). This method developed for the synthesis of α -aminophosphonates gave excellent yields.

Synthesis of Novel α-Aminophosphonates Containing Small Rings

The synthesis of cyclopropyl- and cyclobutyl-substituted α-aminophosphonates by three-component microwave-assisted reaction of cyclopropanecarbaldehydes, benzylamine, and diethyl phosphite in the presence of cadmium iodide as catalyst has been developed.

One-pot synthesis of novel α-amino phosphonates using tetramethylguanidine as a catalyst

α-Aminophosphonates (4a-l) were synthesized in high yields by the Kabachnik-Fields reaction. One-pot simultaneous reaction of indole-3-carboxaldehyde, a dialkyl- or diphenyl phosphite, and different heterocyclic-, cyclic-, or other primary amines in the presence of tetramethylguanidine (10 mole %) as catalyst in toluene at reflux temperature afforded 4a-l. They exhibited moderate to high antimicrobial activity.