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NiFe2O4@SiO2–Cu as a novel and efficient magnetically recoverable nanocatalyst for regioselective synthesis of β-thiol-1,2,3-triazoles under benign conditions† † Electronic supplementary information (ESI) available: FT-IR, 1H NMR and 13C NMR spectral information of β-thiol-1,4-disubstituted-1,2,3-triazoles. See DOI: https://doi.org/10.1039/d3ra05433k

ABSTRACT:

SUBMITTER: Eisavi R

PROVIDER: S-EPMC10510628 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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CuFe2O4@SiO2@L-arginine@Cu(I) as a new magnetically retrievable heterogeneous nanocatalyst with high efficiency for 1,4-disubstituted 1,2,3-triazoles synthesis.

Project description:A novel magnetic heterogeneous catalyst was synthesized through the immobilization of copper ions onto the l-arginine functionalized CuFe2O4@SiO2. The prepared catalyst was characterized by Fourier Transform Infrared (FT-IR), X-ray diffraction (XRD), Field emission scanning electron microscopy (FE-SEM), Transmission electron microscopy (TEM), and Energy Dispersive X-Ray spectroscopy (EDX). The resulting catalyst was used in the ultrasonic-assisted synthesis of 1,2,3-triazoles via a one-pot three-component reaction of alkynes, alkyl halides, and sodium azides under green conditions within a short time. The catalyst reusability was investigated after five cycles and no significant loss of activity was observed.

| S-EPMC10227041 | biostudies-literature

Fe3O4@SiO2-PMA-Cu magnetic nanoparticles as a novel catalyst for green synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles.

Project description:The magnetic nanoparticles of Fe3O4 were synthesized through a solid-state reaction of hydrated iron (III) chloride, hydrated iron (II) chloride and NaOH, and then purified by calcination at high temperature. In order to protect ferrite nanoparticles from oxidation and agglomeration, and to manufacture a novel catalytic system of anchored copper on the magnetic substrate, the Fe3O4 was core-shelled by adding tetraethyl orthosilicate. Next, the prepared Fe3O4@SiO2 was supported by phosphomolybdic acid (PMA) as the second layer of nanocomposite at 80 °C in 30 h. Eventually, the new nanocomposite of Fe3O4@SiO2-PMA-Cu was successfully synthesized by adding copper (II) chloride solution and solid potassium borohydride. The structure of magnetic nanocatalyst was acknowledged through different techniques such as EDS, VSM, XRD, TEM, FT-IR, XPS, TGA, BET and FESEM. The synthesis of β-thiolo/benzyl-1,2,3-triazoles from various thiiranes, terminal alkynes and sodium azide was catalyzed by Fe3O4@SiO2-PMA-Cu nanocomposite in aqueous medium. In order to obtain the optimum condition, the effects of reaction time, temperature, catalyst amount and solvent were gauged. The recycled catalyst was used for several consecutive runs without any loss of activity.

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Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism.

Project description:A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.

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Investigation of Fe3O4@boehmite NPs as efficient and magnetically recoverable nanocatalyst in the homoselective synthesis of tetrazoles.

Project description:Magnetic boehmite nanoparticles (Fe3O4@boehmite NPs) were synthesized from a hybrid of boehmite and Fe3O4 nanoparticles. At first, boehmite nanoparticles (aluminum oxide hydroxide) were prepared via a simple procedure in water using commercially available materials such as sodium hydroxide and aluminum nitrate. Then, these nanoparticles were magnetized using Fe3O4 NPs in a basic solution of FeCl2·4H2O and FeCl3·6H2O. Fe3O4@boehmite NPs have advantages of both boehmite nanoparticles and Fe3O4 magnetic materials. Magnetic boehmite nanoparticles have been characterized by various techniques such as TEM, SEM, EDS, WDX, ICP, FT-IR, Raman, XRD and VSM. SEM and TEM images confirmed that particles size are less than 50 nm in diameter with a cubic orthorhombic structure. Then, Fe3O4@boehmite NPs were applied as a homoselective, highly efficient, cheap, biocompatibility, heterogeneous and magnetically recoverable nanocatalyst in the synthesis of 5-substituted 1H-tetrazole derivatives. Fe3O4@boehmite NPs can be recycled for several runs in the synthesis of tetrazoles. Also, all tetrazoles were isolated in high yields, which reveals high activity of Fe3O4@boehmite NPs in the synthesis of tetrazole derivatives. Fe3O4@boehmite NPs shows a good homoselectivity in synthesis of 5-substituted 1H-tetrazole derivatives.

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Ionic liquid immobilized on modified magnetic FSM-16: an efficient and magnetically recoverable nanocatalyst.

Project description:In the present article, a nanocomposite was prepared by immobilizing ionic liquid on the magnetic mesoporous FSM-16 with a core-shell structure (Fe3O4@FSM-16-SO3/IL). Subsequently, the structural properties of the synthesized nanocatalyst were characterized and analyzed by various techniques such as XRD, FT-IR, TEM, FE-SEM, BET, VSM, TGA, and EDS. Fe3O4@FSM-16-SO3/IL was used as a recoverable and efficient nanocatalyst for the synthesis of polyhydroquinoline derivatives. The magnetic nanocatalyst showed remarkable stability and reusability and was reused six consecutive times without considerable loss of its activity.

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Preparation, characterization and application of MgFe2O4/Cu nanocomposite as a new magnetic catalyst for one-pot regioselective synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles.

Project description:Magnesium ferrite magnetic nanoparticles were synthesized by a solid-state reaction of magnesium nitrate, hydrated iron(iii) nitrate, NaOH and NaCl salts and then calcined at high temperatures. In order to prevent oxidation and aggregation of magnesium ferrite particles, and also for preparing a new catalyst of supported copper on the magnetic surface, the MgFe2O4 was covered by copper nanoparticles in alkaline medium. Magnetic nanoparticles of MgFe2O4/Cu were successfully obtained. The structure of the synthesized magnetic nanoparticles was identified using XRD, TEM, EDS, FT-IR, FESEM and VSM techniques. The prepared catalyst was used in the three component one-pot regioselective synthesis of 1,2,3-triazoles in water. The various thiiranes bearing alkyl, allyl and aryl groups with terminal alkynes, and sodium azide in the presence of the MgFe2O4/Cu nanocatalyst were converted to the corresponding β-thiolo/benzyl-1,2,3-triazoles as new triazole derivatives. The effects of different factors such as time, temperature, solvent, and catalyst amount were investigated, and performing the reaction using 0.02 g of catalyst in water at 60 °C was chosen as the optimum conditions. The recovered catalyst was used several times without any significant change in catalytic activity or magnetic property.

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Fe3O4@Sap/Cu(ii): an efficient magnetically recoverable green nanocatalyst for the preparation of acridine and quinazoline derivatives in aqueous media at room temperature.

Project description:Saponin, as a green and available phytochemical, was immobilized on the surface of magnetite nanoparticles then doped with Cu ions (Fe3O4@Sap/Cu(ii)) and used as an efficient nanocatalyst for the synthesis of quinazoline and acridine derivatives, due to their high application and importance in various fields of science. Different spectroscopic and microscopic techniques were used for the catalyst characterization such as FT-IR, XRD, FE-SEM, EDX, TEM, TGA, VSM, BET, DLS, CV, and XPS analyses. All characterization data were correlated with each other so that the structure of the catalyst was accurately characterized. The reactions were performed in the presence of a low amount of Fe3O4@Sap/Cu(ii) (0.42 mol%) as a green catalyst in water over a short period of time. The results show well the effective role of saponin in solving the problem of mass transfer in aqueous medium, which is the challenge of many organic reactions in aqueous medium and in the presence of heterogeneous medium. High catalytic activity was found for the catalyst and high to excellent efficiency was obtained for all quinazoline (68-94% yield) and acridine (66-97% yield) derivatives in short reaction times (less than 1 hour) under mild reaction conditions in the absence of any hazardous or expensive materials. There is not any noticeable by-product found whether for acridine or quinazoline derivatives, which reflects the high selectivity. Two reasonable mechanisms were proposed for the reactions based on observations from control experiments as well as literature reports. The catalyst could be easily recovered magnetically for at least six consecutive runs with insignificant reactivity loss.

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Magnetically recoverable Fe3O4@SiO2@SBA-3@2-ATP-Cu: an improved catalyst for the synthesis of 5-substituted 1H-tetrazoles.

Project description:Functionalization of Fe3O4@SiO2@SBA-3 with double-charged 3-chloropropyltrimethoxysilane (CPTMS) and 2-aminophenol, followed by mechanical mixing of the solid product with copper(i) chloride produces a new, greener and efficient Fe3O4@SiO2@SBA-3@2-ATP-Cu catalyst for the synthesis of 5-substituted 1H-tetrazoles. XRD, SEM, atomic absorption, TGA, N2 adsorption-desorption, and VSM analyses were performed for the characterization of the Fe3O4@SiO2@SBA-3@2-ATP-Cu structure. Nitrogen adsorption-desorption analysis revealed that Fe3O4@SiO2@SBA-3@2-ATP-Cu has a surface area of 242 m2 g-1 and a total pore volume of 55.72 cm3 g-1. In synthesizing 5-substituted 1H-tetrazoles, Fe3O4@SiO2@SBA-3@2-ATP-Cu shows superior yields in short reaction times at 120 °C. This catalyst also showed high thermal stability and recyclability at least for 4 runs without apparent loss of efficiency.

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Regioselective Synthesis of New Family of 2-Substituted 1,2,3-Triazoles and Study of Their Fluorescent Properties.

Project description:Modification of 5-aryl-4-trifluoroacetyltriazoles at the NH-moiety was investigated. Screening of the alkylation conditions revealed that using Na2CO3 as a base and DMF as a solvent of 2-substituted triazoles can be preferentially prepared in up to 86% yield. In the best cases, the amount of minor 1-alkyl isomer was less than 6%. SNAr reaction of the 5-aryl-4-trifluoroacetyltriazoles with aryl halides having electron-withdrawing groups led to regiospecific formation of 2-aryltriazoles isolated in good-to-high yields. Chan-Lam reaction of the 5-aryl-4-trifluoroacetyltriazoles with boronic acids afforded 2-aryltriazoles as single isomers in up to 89% yield. The subsequent reaction of the prepared 2-aryltriazoles with primary and secondary amines gave a set of amides of 4-(2,5-diaryltriazolyl)carboxylic acid. The fluorescent properties of the prepared 2-substituted derivatives of triazoles were investigated to demonstrate their utility as new efficient luminophores having more than 60% quantum yields.

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Cu/SiO2-Pr-NH-Benz as a novel nanocatalyst for the efficient synthesis of 1,4-disubstituted triazoles and propargyl amine derivatives in an aqueous solution.

Project description:In this work, an innovative nanocatalyst (Cu/SiO2-Pr-NH-Benz) was synthesized and applied to coupling and click reaction in an aqueous solution. This work reports an efficient and straightforward approach for synthesizing diverse propargylamine and 1,2,3-triazole derivatives in excellent yield and short-time reaction. Also, a novel method involving the Cu NPs supported on the SiO2 nanocatalyst as a heterogeneous novel catalyst for the "one-pot" three-component A3-coupling of aldehyde, amine, and alkynes and "one-pot" click reaction between alkyne, benzyl halide, and sodium azide in the water at room temperature was developed. Significant advantageous such as enhanced catalytic activity with efficient recycling for the one-pot synthesis of 1,4-disubstituted triazoles and propargyl amine derivatives and in green condition were observed. Also, after five successive reactions, the catalytic activity of recycled Cu/SiO2-Pr-NH-Benz remained high without significant loss in its intrinsic activity.

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