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Relevant academic research and scientific papers

Sn(II)-Mediated facile approach for the synthesis of 2-aryl-2: H -indazole-3-phosphonates and their anticancer activities

A convenient three-component method was developed for the synthesis of various 2-aryl-2H-indazole-3-phosphonates using SnCl2·2H2O under conventional heating techniques. The transition metal free reaction, mild reaction conditions, one-pot operation, open flask conditions, wide substrate scope and good yields are a few important features of this methodology. This protocol proceeds with high atom economy via the formation of α-aminophosphonates followed by the generation of an indazole ring through N-N bond formation, eliminating water as a by-product. The cytotoxic properties of the 2-aryl-2H-indazole-3-phosphonate derivatives were investigated against A549 and HepG-2 cells. Interestingly, compounds 4d and 4g showed potent cytotoxic properties against HepG-2 cells and compound 4p showed significant cytotoxic properties against A549 cells. Intracellular visualization was done using a laser scanning confocal microscope. DNA fragmentation, colony formation, and apoptosis studies, flow cytometry and western blot analysis for 4p against A549 cells have also been reported.

Photo-oxidation coupled Kabachnik-Fields and Bigenelli reactions for direct conversion of benzyl alcohols to α-aminophosphonates and dihydropyrimidones

A tandem one-pot solvent free approach for the direct conversion of benzyl alcohols to α-amino phosphonates and dihydropyrimidones is reported. The method relies on a metal free photo-oxidation of benzyl alcohols to benzaldehydes under UV irradiation using ammonium perchlorate followed by Kabachnik-Fields and Biginelli reactions. The reaction conditions are moderate and metal free with good substrate scope. The control experiments were performed to investigate the role of the ammonium perchlorate and molecular oxygen as oxidants. The quenching experiments in the presence of TEMPO and other radical quenchers suggest radical based mechanism.

Magnetic BaFe12O19/Al2O3: An Efficient Heterogeneous Lewis Acid Catalyst for the Synthesis of α-Aminophosphonates (Kabachnik–Fields Reaction)

Abstract: The design and application of environmentally friendly catalysts to reduce the quantity of toxic wastes is critical for improving?the chemical synthesis process. Therefore, BaFe12O19/Al2O3, a magnetic mesoporous nanocomposites, were designed synthesized and characterized using different techniques such as energy dispersive X-ray (EDX) spectroscopy, X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), field emission scanning electron microscopy (FESEM), Brunauer–Emmett–Teller?(BET) adsorption method, and vibrating sample magnetometry (VSM). The prepared BaFe12O19/Al2O3 display a high surface area (1773.22?m2/g) with an average pore diameter of 3.946?nm from nitrogen sorption analysis. In addition, the synthesized nanocomposites prove to be an active heterogeneous Lewis acid catalyst for the solvent free synthesis of α-aminophosphonates at ambient temperature, through three-component reaction of aldehydes/ketones, amines and triethyl phosphite. The use of this catalyst results in an effortless magnetic recoverability and recyclability, high yield and short reaction time under solvent-free conditions. Graphic Abstract: [Figure not available: see fulltext.].

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.

A novel hydrophobic copper complex supported on γ-Fe2O3 as a magnetically heterogeneous catalyst for one-pot three-component synthesis of α-aminophosphonates

A novel hydrophobic copper complex supported on γ-Fe2O3 is synthesized and characterized by different methods such as FT-IR, XRD, TEM, SEM, TGA, VSM, ICP and CHN analysis. It was used as a magnetically recyclable heterogeneous cataly

Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik-Fields reaction under solvent-free condition

Zirconocene bis(perfluorobutanesulfonate) [Cp2Zr(OSO 2C4F9)2·2H2O] was successfully synthesized by treatment of Cp2ZrCl2 with C4F9SO3Ag, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of α-aminophosphonates via Kabachnik-Fields reaction of aldehydes/ketones, amines and diethyl phosphite under mild and solvent-free conditions. Furthermore, it can be reused without loss of activity in a test of five cycles. Compared with our previously reported complex of Cp2Zr(OSO 2C8F17)2·3H 2O·THF, this complex showed better catalytic activity.

Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions

Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.

Highly efficient one-pot synthesis of α-aminophosphonates catalyzed by ytterbium triflate in water

A facile one-pot, three-component synthesis of α-aminophosphonates catalyzed by ytterbium triflate [Yb(OTf)3] in water using polyoxyethanyl α-tocopheryl sebacate (PTS) as amphiphile has been developed. The catalytic system could be readily recycled and reused several times without significant loss in its activity.

Fluorous bis(oxazolines) ligand: Synthesis and application in Kabachnik-Fields reaction

A novel fluorous bis(oxazolines) ligand was synthesized with 70% overall yield in 5 steps starting from 5-aminoisophthalic acid. The ligand was applied in the one-pot synthesis of α-aminophosphonates via copper-catalyzed Kabachnik-Fields reaction, giving the corresponding products in moderate to excellent yields under mild conditions. Furthermore, the fluorous ligand could be easily recovered and reused for four times without significant loss of activity.

Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions

Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines and carbonyl compounds. It also enabled the development of one-pot synthesis of β-phosphonomalonates during the reaction of carbonyl compounds, malononitrile and phosphorus compounds. Excellent results were obtained in each case affording the corresponding organophosphorus adducts in good yields.