CeCl3·7H2O: a highly efficient catalyst for the synthesis of 1-substituted-octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide

Chinthaparthi, Radha Rani; Gangireddy, Chandra Sekhar Reddy; Mudumala, Veeranarayana Reddy; Gundluru, Mohan; Nagaraju, C.; Cirandur, Suresh Reddy

doi:10.1016/j.tetlet.2013.08.115

Cited by 13 publications

(3 citation statements)

References 32 publications

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“…In this present work a cerium (III) complex of new Schiff base (E)-Nbenzylidene-4-methoxyaniline noted (P2-CeCl 3 ) has been synthesized and characterized by elemental analysis, IR, NMR and Mass spectral data [28][29][30][31][32] .…”

Section: Introductionmentioning

confidence: 99%

New Cerium (III) Complex of Schiff Base (E)-N-Benzylidene-4-Methoxyaniline: Synthesis and Density Functional Theoretical Study of Vibrational Spectra

Imanelakehal¹,

Farhihalamia²,

Saoussenlakehal³

et al. 2016

Orient. J. Chem

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Complex of cerium (III) with (E)-N-benzylidene-4-methoxyaniline is synthesized through a one-pot three-component reaction from aromatic aldehyde, aromatic amine and the CeCl 3 · 7 H 2 O, as an efficient catalyst. This cerium (III) complex is characterized by IR, 1H, and 13C NMRspectroscopy and mass-spectral data. Molecular structure, Mullikan charges, thermodynamic parameters; vibrational frequencies and intensities were calculated by Density Functional theory methods (B3LYP, B3PW91, mPW1PW91 and PBEPBE) using the SDD basis set. The comparison between the calculated and experimental data in order to attain the best quality and to predict the structure, the best performance in the vibration spectra perfected of the title compound, we have found that the harmonic vibration computed are in a good agreement with the observed in IR spectrum, for closest match we calculated optimal scaling factors can recommend for the IR spectral future predictions for unknown compounds of this class. In order to better comparison, we also root mean square values of the experimental and calculated IR bands are 16.64, 16.64, 17.45, 17.66 and the mean absolute percentage error values are 1.33, 1.39, 1.40, and 1.5 for B3LYP, B3PW91, mPW1PW91, and PBEPBE methods respectively.

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Section: Introductionmentioning

confidence: 99%

New Cerium (III) Complex of Schiff Base (E)-N-Benzylidene-4-Methoxyaniline: Synthesis and Density Functional Theoretical Study of Vibrational Spectra

Imanelakehal¹,

Farhihalamia²,

Saoussenlakehal³

et al. 2016

Orient. J. Chem

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“…Aryl phosphonates/phosphinates have also been formed at the low temperature of 40 °C using BiCl 3 as the Lewis acid catalyst under nitrogen atmosphere [ 39 ]. Other Lewis catalysts include the Pd 2 (dba) 3 in the presence of PhOTf and in a solvent free environment for triaryl phosphite intramolecular rearrangement [ 40 ], the CeCl 3 .7H 2 O-SiO 2 [ 41 ], the CeCl 3 .7H 2 O [ 42 ], the already-mentioned ZnBr 2 [ 19 , 20 ], the NiCl 2 [ 43 ] that also allows the usage of aryltriflates as reactants [ 44 ], the InBr 3 [ 20 ], the InCl 3 that allows the reaction of N-benzyloxycarbonylaminosulfones with triethyl phosphite to generate α-amino phosphonates [ 45 ], and the NbCl 5 [ 46 ].…”

Section: Improvements In and Variations Of The Ma Reactionmentioning

confidence: 99%

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Kostoudi

Pampalakis

2022

IJMS

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Compounds bearing the phosphorus–carbon (P–C) bond have important pharmacological, biochemical, and toxicological properties. Historically, the most notable reaction for the formation of the P–C bond is the Michaelis–Arbuzov reaction, first described in 1898. The classical Michaelis–Arbuzov reaction entails a reaction between an alkyl halide and a trialkyl phosphite to yield a dialkylalkylphosphonate. Nonetheless, deviations from the classical mechanisms and new modifications have appeared that allowed the expansion of the library of reactants and consequently the chemical space of the yielded products. These involve the use of Lewis acid catalysts, green methods, ultrasound, microwave, photochemically-assisted reactions, aryne-based reactions, etc. Here, a detailed presentation of the Michaelis–Arbuzov reaction and its developments and applications in the synthesis of biomedically important agents is provided. Certain examples of such applications include the development of alkylphosphonofluoridates as serine hydrolase inhibitors and activity-based probes, and the P–C containing antiviral and anticancer agents.

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“…They have been also used as potent enzyme inhibitors, antimicrobial, antitumor, antioxidant, antiviral, antidiabetic, and pesticidal agents. Perhaps the unique structural features of the phosphorus nucleus, particularly when it is linked with heterocycles, show immense potential to serve as pharmaceuticals . Thus, a combination of phosphonyl motifs and heterocyclic ring systems particularly with benzofuran results in a vital class of organophosphorus heterocycles that play a vital role in the fields of synthetic organic and medicinal chemistries …”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of diethyl(substituted 2‐benzylbenzofuran‐3‐yl)phosphonates as antioxidant and antimicrobial agents

Gundluru

Sarva

Murali

et al. 2020

Journal of Heterocyclic Chem

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In continuance of our effort to improve novel and potent synthetic approaches for various bioactive phosphorylated heterocycles via C─P bond formation, a series of diethyl substituted(2‐benzylbenzofuran‐3‐yl)phosphonate derivatives (4a‐j) was synthesized by one‐pot reaction of various diversely substituted salicylaldehydes, phenyl acetylene, and diethyl phosphite using CuO nanoparticles as catalyst in 1:1 ethanol and water under room temperature. The new compounds have been studied for their radical scavenging activity by DPPH, H2O2, and NO approaches and antimicrobial activity assay against bacteria and fungi by disk diffusion method.

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CeCl3·7H2O: a highly efficient catalyst for the synthesis of 1-substituted-octahydro-[1,3,2]diazaphospholo[1,5-a]pyridine-1-oxide

Cited by 13 publications

References 32 publications

New Cerium (III) Complex of Schiff Base (E)-N-Benzylidene-4-Methoxyaniline: Synthesis and Density Functional Theoretical Study of Vibrational Spectra

New Cerium (III) Complex of Schiff Base (E)-N-Benzylidene-4-Methoxyaniline: Synthesis and Density Functional Theoretical Study of Vibrational Spectra

Improvements, Variations and Biomedical Applications of the Michaelis–Arbuzov Reaction

Design and synthesis of diethyl(substituted 2‐benzylbenzofuran‐3‐yl)phosphonates as antioxidant and antimicrobial agents

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