An inorganic–organic hybrid material based on a Keggin‐type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2‐amino‐4<i>H</i>‐chromenes via multicomponent reactions

Hosseinzadeh‐Baghan, Sara; Mirzaei, Masoud; Eshtiagh‐Hosseini, Hossein; Zadsirjan, Vahideh; Heravi, Majid M.; Mague, Joel T.

doi:10.1002/aoc.5793

Cited by 48 publications

(10 citation statements)

References 133 publications

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“…Also, XRD analysis (X’Pert-PRO advanced difractometer operated at 40 kV and 40 mA at r.t.) helped to investigate the crystalline structure of the catalyst. The EDAX spectrum was utilized for the elemental analysis of the Schiff base complex of copper coated on epoxy-modified Fe 3 O 4 @SiO 2 MNPs. − …”

Section: Experimental Sectionmentioning

confidence: 99%

Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core–Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles

et al. 2021

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An ecofriendly inorganic–organic hybrid and novel Schiff base complex of copper coated on epoxy-modified Fe3O4@SiO2 MNPs was successfully designed and prepared from readily available chemicals. In this method, a Schiff base complex as a linker is utilized to protect copper nanoparticles to the core–shell Fe3O4 exterior without agglomeration. The resulted Schiff base complex of copper coated on epoxy-modified Fe3O4@SiO2 MNPs was characterized and confirmed via different analyses such as FT-IR, TGA, XRD, VSM, FE-SEM, TEM, ICP, EDX, and BET. The novel catalyst was examined for the synthesis of various chromene-annulated heterocycles through the one-pot three component reaction of aromatic aldehydes, various phenols (2-hydroxynaphthalene-1,4-dione/resorcinol/β-naphthol), and malononitrile in ethanol at reflux conditions. This method includes important aspects like no usage of column chromatography, very short reaction times, simplicity of product isolation using ethanol, excellent yields, simple procedures, and magnetic recoverability of the catalyst. All in all, our method makes a novel and significant advancement in the synthesis of various chromene-annulated heterocycles.

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Section: Experimental Sectionmentioning

confidence: 99%

Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core–Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles

et al. 2021

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“…Based on the control experiments and known reactions in the literature, [46][47][48][49] a possible mechanism for the synthesis of the pyrano[3, 2-c] coumarin derivatives was proposed (Scheme 4). First, in the presence of the zinc chloride/acetamide DES, a Knoevenagel reaction between benzaldehyde (2a) and ethyl cyanoacetate (3a) produces intermediate product 3a′.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

Xie

Yang

et al. 2021

Synthesis

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4H-Pyrano[3,2-c]coumarin derivatives are an important class of pharmaceutical compounds that are expensive to prepare by previously reported methods. An efficient and green method was developed to obtain these derivatives using the deep eutectic solvent (DES) zinc chloride/acetamide (n:n = 1:4), which acted as both the catalyst and the solvent for the reaction. An aromatic aldehyde, 4-hydroxycoumarin, and cyanoacetate were used as the substrates. The DES, substrate molar ratio, diluent type, temperature, and reaction time were optimized to obtain the 4H-pyrano[3,2-c]coumarin derivatives from a range of aromatic aldehydes in a single step in moderate to high yields and under mild reaction conditions.

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“…In recent decades, polynuclear coordination polymers have garnered significant attention due to their intriguing architectures and fascinating physical and chemical properties. − By integrating polyoxometalates (POMs) into this system, POM-based polynuclear coordination polymers can harness their combined benefits, which not only possess diverse structures but also display exceptional potential for various applications in the fields such as optics, catalysis, medicine, and particularly magnetism and proton conduction. − …”

Section: Introductionmentioning

confidence: 99%

N–N-Bridged Polynuclear POM-Based Coordination Polymers Based on a V-Type Ligand: Proton Conduction and Magnetism

Lun,

Zhang,

Sun

et al. 2023

Inorg. Chem.

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The construction of polyoxometalate (POM)-based coordination polymers, in the presence of a nitrogen heterocyclic ligand, is intriguing due to the potential for obtaining diverse structures. These structures exhibit extensive application possibilities in the fields of proton conductivity and magnetism. Herein, four new POM-based polynuclear coordination polymers with the formulas of {[Fe 2 (btb) 4) have been prepared using the V-type 1,3-bis(4H-1,2,4-triazole-4-yl)benzene (btb) ligand. Compounds 1 and 2 feature similar twodimensional (2D) structures, derived from the binuclear Fe 2 N 6 and Cd 2 N 4 subunits connected by tridentate btb ligands. Meanwhile, in compound 3, hexanuclear Co 6 (OH) 4 units are bound by quadridentate btb ligands forming a 2D layer with the same 4-c sql topology simplification as compounds 1 and 2. In compound 1, Keggin-type polyoxoanions are monodentate-coordinated to metal ions and suspended on the 2D structure, while, in compounds 2 and 3, they act as discrete counterions residing in the interstitial spaces between two adjacent layers, thereby extending the 2D structures into 3D structures through hydrogen bonding interactions. In compound 4, trinuclear Cu 3 (OH) subunits are further constructed into a 3D framework through cooperation with four tridentate and quadridentate btb ligands as well as Strandberg-type anions. Furthermore, the proton conduction of the four compounds has been investigated. They display high proton conductivities at 358 K and 98% RH with powdered samples, which are 1.26 × 10 −3 , 1.24 × 10 −3 , 3.24 × 10 −4 , and 2.57 × 10 −4 S cm −1 , respectively. Interestingly, by mixing with Nafion, the composite membranes of compounds 2 and 4 exhibit enhanced proton conductivities, measuring at 4.87 × 10 −2 and 1.28 × 10 −2 S cm −1 , respectively, at 358 K and 98% RH, which suggests excellent potential for applications. In addition, compounds 1, 3, and 4 display antiferromagnetic behaviors due to similar magnetic interactions. This work can provide research insights into the assembly of 2D POM-based coordination polymers with nitrogen heterocyclic ligands and Keggin-type POMs and further promote their research progress in proton conduction.

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An inorganic–organic hybrid material based on a Keggin‐type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2‐amino‐4H‐chromenes via multicomponent reactions

Abstract: An inorganic-organic hybrid material based on a Keggin-type polyoxometalate@ Dysprosium as an effective and green catalyst in the synthesis of 2-amino-4H-chromenes via multicomponent reactions. Applied Organometallic Chemistry, 34(9), e5793.

Cited by 48 publications

References 133 publications

Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core–Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles

Design of a Schiff Base Complex of Copper Coated on Epoxy-Modified Core–Shell MNPs as an Environmentally Friendly and Novel Catalyst for the One-Pot Synthesis of Various Chromene-Annulated Heterocycles

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

N–N-Bridged Polynuclear POM-Based Coordination Polymers Based on a V-Type Ligand: Proton Conduction and Magnetism

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