12 research outputs found

    Ruthenium Hydride Complex Supported on Gold Nanoparticle Cored Triazine Dendrimers for C–C Coupling Reactions

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    In this work, the unusual ability of a ruthenium hydride catalyst, [RuHCl­(PPh<sub>3</sub>)<sub>3</sub>CO], supported on gold nanoparticle cored triazine dendrimers in the Suzuki–Miyaura cross-coupling reaction and also in the synthesis of diaryl ketones is reported. [Ru-H@AuNPs-TD] was characterized by Fourier transform infrared spectroscopy, CHNS, TEM, SEM, ICP, and TGA analyses. The ruthenium hydride catalyst was used as a heterogeneous catalyst for the C–C coupling reactions of aryl halides with phenylboronic acids, and the biphenyl derivatives were produced in good to excellent yields. On the other hand, this catalytic system was applied for synthesis of diaryl ketones by the reaction of phenylboronic acids with substituted benzaldehydes. Moreover, this catalyst can be well-dispersed in the reaction medium, conveniently separated from the reaction mixture, and reused several times without significant loss of its activity

    Copper Dithiol Complex Supported on Silica Nanoparticles: A Sustainable, Efficient, and Eco-friendly Catalyst for Multicomponent Click Reaction

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    Silica-nanoparticle-supported copper-containing ionic liquid (SNIL-Cu­(II)) provided a highly stable, active, reusable, spherical, and solid-phase catalyst for click chemistry. The SNIL-Cu­(II) catalyst was readily prepared from 1,2-<i>bis</i>(4-pyridylthio)­ethane immobilized on silica nanoparticles modified with 3-chloropropyltrimethoxysilane and Cu­(OTf)<sub>2</sub>, and the morphology, structure, and properties of nanoparticles were investigated through different analytical tools. This catalytic system showed high activity in a one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles by click reactions between a variety of alkynes, organic halides, and sodium azide at room temperature in aqueous polyethylene glycol as a green medium with a high turnover frequency (up to 7920 h<sup>–1</sup>). Moreover, the SNIL-Cu­(II) was also used as an efficient catalyst for the preparation of a series of multifold 1,4-disubstituted 1,2,3-triazoles. Also, this unique catalyst was readily reused without any decrease in its catalytic activity to give the corresponding triazoles quantitatively

    Novel Multicomponent Synthesis of Pyridine–Pyrimidines and Their Bis-Derivatives Catalyzed by Triazine Diphosphonium Hydrogen Sulfate Ionic Liquid Supported on Functionalized Nanosilica

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    In this Research Article, we report an efficient synthesis of 1,3-dimethyl-5-aryl-7-(pyridine-3(2)(4)-yl)­pyrimidine-2,4­(1<i>H</i>,3<i>H</i>)-diones via a three-component reaction of aryl aldehydes, 1,3-dimethyl-6-aminouracil and carbonitriles in the presences of triazine diphosphonium hydrogen sulfate ionic liquid supported on functionalized nanosilica (APTADPHS-<i>n</i>SiO<sub>2</sub>) as a reusable catalyst under microwave irradiation and solvent-free conditions. The bis-derivatives of pyridine–pyrimidines were also efficiently prepared from dialdehydes and dinitriles. In addition, 3-methyl-1<i>H</i>-pyrazole-5-amine was used successfully instead of 1,3-dimethyl-6-aminouracil under the same conditions to afford the corresponding products in high yields. The catalyst can be reused at least five times without any significant loss of its activity. The easy recovery, reusability and excellent activity of the catalyst as well as easy workup are other noteworthy advantages of this method

    A Novel <i>pseudo</i>-Four-Component Domino Reaction for the Synthesis of Naphtho[2,1‑<i>b</i>]furan-2(1<i>H</i>)‑ones Using a Nanocatalyst

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    In this article, an original one-pot method is utilized to synthesize a variety of derivatives of naphtho­[2,1-<i>b</i>]­furan-2­(1<i>H</i>)-one <i>via</i> a <i>pseudo</i>-four-component domino reaction of aryl aldehydes, acetic anhydride, hippuric acids, and 2-naphthols catalyzed by HSW@SPIONs. This reaction illustrates an array of attractive features including, with particular interest in this report, a convenient and unique process of creating and utilizing a powerful recyclable nanocatalyst

    Diphenhydramine Hydrochloride–CuCl as a New Catalyst for the Synthesis of Tetrahydrocinnolin-5(1<i>H</i>)‑ones

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    The current study deals with the synthesis and characterization of a novel catalyst made from diphenhydramine hydrochloride and CuCl ([HDPH]Cl–CuCl). The prepared catalyst was thoroughly characterized using various techniques, such as 1H NMR, Fourier transform-infrared spectroscopy, differential scanning calorimetry, and thermogravimetric analysis and derivative thermogravimetry. More importantly, the observed hydrogen bond between the components was proven experimentally. The activity of this catalyst was checked in the preparation of some new derivatives of tetrahydrocinnolin-5(1H)-ones via a multicomponent reaction between dimedone, aromatic aldehydes, and aryl/alkyl hydrazines in ethanol as a green solvent. Also, for the first time, this new homogeneous catalytic system was effectively used for the preparation of unsymmetric tetrahydrocinnolin-5(1H)-one derivatives as well as mono- and bis-tetrahydrocinnolin-5(1H)-ones from two different aryl aldehydes and dialdehydes, respectively. The effectiveness of this catalyst was further confirmed by the preparation of compounds containing both tetrahydrocinnolin-5(1H)-one and benzimidazole moieties from dialdehydes. The one-pot operation, mild conditions, rapid reaction, and high atom economy, along with the recyclability and reusability of the catalyst, are other notable features of this approach

    Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles

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    Unsymmetrical 1,2,5,6-tetrahydropyridine-3-carboxylates were obtained for the first time from a five-component Fe<sub>3</sub>O<sub>4</sub>@TDSN-Bi­(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and low catalyst loading

    Diastereoselective Synthesis of Symmetrical and Unsymmetrical Tetrahydropyridines Catalyzed by Bi(III) Immobilized on Triazine Dendrimer Stabilized Magnetic Nanoparticles

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    Unsymmetrical 1,2,5,6-tetrahydropyridine-3-carboxylates were obtained for the first time from a five-component Fe<sub>3</sub>O<sub>4</sub>@TDSN-Bi­(III)-catalyzed reaction of aryl aldehydes, aryl amines, and ethyl acetoacetate. This magnetically separable catalyst enabled the selective incorporation of two different aryl amines or two different aryl aldehydes into the product, and provided excellent yields, short reaction times, mild reaction conditions, satisfactory catalyst recyclability, and low catalyst loading

    One-Pot Three-Component Synthesis of Pyrano [3,2‑<i>b</i>]pyrazolo[4,3‑<i>e</i>]pyridin-8(1<i>H</i>)‑ones

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    An efficient one-pot synthesis of novel pyrano­[3,2-<i>b</i>]­pyrazolo­[4,3-<i>e</i>]­pyridin-8­(1<i>H</i>)-ones via three-component condensation of kojic acid, 1-<i>H</i>-pyrazol-5-amines and aldehydes in the presence of a catalytic amount of Zn­(OTf)<sub>2</sub> followed by H<sub>2</sub>O<sub>2</sub>-mediated oxidation is reported. Furthermore, the synthesis of 1′<i>H</i>-spiro­[indoline-3,4′-pyrano­[2,3-<i>b</i>]­pyrazolo­[3,4-<i>e</i>]­pyridine]-2,8′(9′<i>H</i>)-diones were chosen for the library validation

    Copper Immobilized on Nanosilica Triazine Dendrimer (Cu(II)-TD@nSiO<sub>2</sub>)‑Catalyzed Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles and Bis- and Tris-Triazoles via a One-Pot Multicomponent Click Reaction

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    An efficient, atom-economical, and regioselective synthesis of a wide range of 1,4-disubstituted 1,2,3-triazoles in excellent yields has been achieved via a one-pot three-component reaction of alkynes and sodium azide with organic halides or α-bromo ketones catalyzed by Cu­(II)-TD@nSiO<sub>2</sub>/sodium ascorbate at room temperature. This catalytic system also showed excellent activity in the synthesis of bis- and tris-1,4-substituted 1,2,3-triazoles. Moreover, the catalyst could be recycled and reused for seven cycles without any loss in its catalytic activity
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