Cu-Modified Magnetic Creatine as an Efficient Catalyst for Regioselective Preparation of 1,2,3-Triazoles Derivatives

Laffafchi, Farin; Tajbakhsh, Mahmood; Sarrafi, Yaghoub; Maleki, Behrooz; Ghani, Milad

doi:10.1080/10406638.2022.2070224

Cited by 32 publications

(22 citation statements)

References 45 publications

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“…), 1599 (C = N); 1 H NMR (400 MHz, DMSO) δ/ppm: 5.22 (s, 2H, NH 2 exchangeable with D 2 O), 5.58 (s, 1H, CH of pyrazole), 7.22-8.36 (m, 9H, Ar-H). 13…”

Section: Synthesis Of 3-(4-nitrophenyl)-1-phenyl-1h-pyrazol-5-amine (1)mentioning

confidence: 99%

“…11. The structure of compound 1 was identified by FT-IR, 1 HNMR, 13 CNMR, and mass spectrometry. The disappearance of the nitrile absorption peak in the FT-IR spectrum and the The starting compound 3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine (1) was condensed with chalcones derivatives 2a-c by one-pot two-component systems in the presence of sulfuric acid to yield the corresponding compounds 3a-c (conventional method) or in the presence of Fe 2 O 3 @SiO 2 /In 2 O 3 nanocatalyst (catalytic method) as shown in Fig.…”

Section: Characterization Of Reaction Products 3a-cmentioning

confidence: 99%

“…Silica nanoparticles were used as nano-adsorbents because it is low-cost and reusable, have tunable pore diameters, excellent chemical, and are thermally stable. It has structural characteristics, a large surface area, high selectivity for organic pollutants, and ease of surface modification [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

et al. 2022

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A novel and reusable nanomagnetic catalyst, Fe2O3@SiO2/In2O3, was synthesized by a facile chemical approach in three successive steps. The nanocatalyst was characterized by FT-IR, XRD, SEM, EDX, TEM, and VSM. The XRD pattern displays the characteristic peaks of Fe2O3 and SiO2, accompanied by new peaks assigned to different planes of In2O3 that confirm the formation of In2O3 on the surface of Fe2O3@SiO2 core/shell spindles. The TEM micrographs show spindle-like particles of Fe2O3 covered with SiO2 shell, and the In2O3 nanoparticles in an average diameter of 20 nm are hung on the surface of the Fe2O3@SiO2. The nanomagnetic catalyst Fe2O3@SiO2/In2O3 was used for the transformation of the (4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine, and chalcones derivatives, into valuable azomethine compounds of 3-(substituted)-1-(pyridine-2-yl)allylidene)-3-(4-nitrophenyl)-1-phenyl-1H-pyrazole-5-amine with high rate and efficient catalyst recovery. The yield obtained through the catalytic route reached 90–95% in shorter reaction times compared with uncatalyzed reaction method. Graphical abstract

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“…), 1599 (C = N); 1 H NMR (400 MHz, DMSO) δ/ppm: 5.22 (s, 2H, NH 2 exchangeable with D 2 O), 5.58 (s, 1H, CH of pyrazole), 7.22-8.36 (m, 9H, Ar-H). 13…”

Section: Synthesis Of 3-(4-nitrophenyl)-1-phenyl-1h-pyrazol-5-amine (1)mentioning

confidence: 99%

Section: Characterization Of Reaction Products 3a-cmentioning

confidence: 99%

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Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

et al. 2022

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“…[ 1–5 ] Up to now, a lot of methods are suggested to prepare important pharmaceuticals and chemicals under catalytic and environmental friendly conditions. [ 6–13 ]…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3][4][5] Up to now, a lot of methods are suggested to prepare important pharmaceuticals and chemicals under catalytic and environmental friendly conditions. [6][7][8][9][10][11][12][13] Benzimidazole scaffolds are significant N-heterocycles with many biological properties such as antiviral, antiinflammatory, anticancer, antihypertensive, and antifungal activities. [14][15][16][17][18][19][20] Although there are many routes for the preparation of 2-substituted benzimidazoles, however, the product may be contaminated by a significant amount of wastes or by-products.…”

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confidence: 99%

Synergistic promotion of the photocatalytic efficacy of CuO nanoparticles by heteropolyacid‐attached melem: Robust photocatalytic efficacy and anticancer performance

Liu

Abbaspour

Rouki

et al. 2022

Applied Organom Chemis

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The in situ photocatalytic oxidation of aromatic alcohols to aldehydes by air under visible-light-driven condition is an attractive and beneficial route regarding environmental crises and worldwide energy economy. Herein, CuOmelem-heteropolyacid nanophotosensitizer is disclosed as an efficient heterostructured nanocomposite involving H 5-n PW 10 V 2 O 40 nÀ … (melem-NH 3 + ) n ionic liquid, successfully prepared via a facile and straightforward procedure.This nanocomposite is characterized employing routine techniques such as Xray diffraction (XRD), Fourier transform infrared (FT-IR), diffuse reflectance spectra (DRS), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), field emission scanning electron microscopy (FE-SEM),and Brunauer-Emmett-Teller (BET). The resultant nanocomposite exhibited superior photocatalytic efficacy than its pristine melem, HPA, and CuO constituents in the in situ photo-oxidation of benzylic alcohols and in the fast condensation with o-phenylenediamine to generate a range of 2-substituted benzimidazoles, as important precursors in the synthesis of important pharmaceuticals under the illumination of a green laser light (λ 535 nm). This study suggests a radical pathway involving reactive species such as •O 2 À and OH• together with h + in a photocatalytic process. Stability and reusability experiments along with hot filtration test ensured sufficient reproducibility of the nanophotocatalyst in the reaction medium. At the final part of this study, the in vitro cellular cytotoxicity of CuO-melem-heteropolyacid nanohybrid material was evaluated on A549 human lung cancer cell line with the MTT assay.The distinct reduction in cell viability affirmed cytotoxicity of the nanomaterial against the performed cell line.

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Use of diformyl‐triazolo Schiff base for Zn²⁺ sensing and intracellular live cell imaging

Maity

Bhunia

Patra

et al. 2023

Applied Organom Chemis

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A diformylphenol Schiff base of triazole‐amine, 4‐methyl‐2, 6‐bis‐[(1H‐[1,2,4] triazol‐3‐ylimino)‐methyl]‐phenol (PTR) has been synthesised and characterised by spectroscopic data (ESI‐MS, UV‐vis, FT‐IR, NMR spectra). The probe, PTR, emits at 610 nm upon excitation at 380 nm and the emission is strongly intensified on interacting with Zn2+ ion in DMSO‐water (99:1, v/v; HEPES buffer, pH, 7.2) solution even in the presence of 15 other cations (Cu2+, Mn2+, Co2+, Ni2+, Pd2+, Cd2+, Pb2+, Hg2+, Fe3+, Cr3+, Al3+, Na+, K+, Ba2+, Ca2+) and the emission band has been shifted to 530 nm. The limit of detection of Zn2+, 0.30 μM is much lower than WHO recommended value (76 μM). The binding constant (Kd) is 4.2585 × 104 M−1. Selective and sensitive chemosensing behaviour of PTR to Zn2+ has been explained by switching off ESIPT quenching of the keto‐enol tautomerisation of the probe along with the chelation enhancement of fluorescence (CHEF) by binding with Zn2+. The Job's plot and NMR titration have been extended to measure the 1:1 M composition [PTR + Zn2+]. The energy calculation by the DFT computation of keto and enol isomers supports easy tautomerisation and helps ESIPT quenching by proton transfer. Intracellular Zn2+ ions in living cells of HEK293 (PBS: phosphate buffer saline; pH, 7.2) have also been identified by the probe, PTR, using fluorescence microscopic imaging technique.

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Cu-Modified Magnetic Creatine as an Efficient Catalyst for Regioselective Preparation of 1,2,3-Triazoles Derivatives

Cited by 32 publications

References 45 publications

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

Synergistic promotion of the photocatalytic efficacy of CuO nanoparticles by heteropolyacid‐attached melem: Robust photocatalytic efficacy and anticancer performance

Use of diformyl‐triazolo Schiff base for Zn²⁺ sensing and intracellular live cell imaging

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Cu-Modified Magnetic Creatine as an Efficient Catalyst for Regioselective Preparation of 1,2,3-Triazoles Derivatives

Cited by 32 publications

References 45 publications

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

Highly efficient and recyclable novel spindles Fe2O3@SiO2/In2O3 nanomagnetic catalyst designed for green synthesis of azomethine compounds

Synergistic promotion of the photocatalytic efficacy of CuO nanoparticles by heteropolyacid‐attached melem: Robust photocatalytic efficacy and anticancer performance

Use of diformyl‐triazolo Schiff base for Zn2+ sensing and intracellular live cell imaging

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Use of diformyl‐triazolo Schiff base for Zn²⁺ sensing and intracellular live cell imaging