Design of novel catalysts for synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones: NH2-MIL-101(Al) as integrated structural scaffold for catalytic materials based on calix[4]arenes

Исаева, В. И.; Timofeeva, Maria N.; Panchenko, Valentina N.; Lukoyanov, Ivan А.; Чернышев, Владимир В.; Капустин, Г. И.; Давшан, Н. А.; Kustov, L. М.

doi:10.1016/j.jcat.2018.10.035

Cited by 30 publications

(3 citation statements)

References 55 publications

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“…768 In 2018, Isaeva, Timofeeva, and co-workers incorporated calix [4]arenes with acidic functionalities into the MOF NH 2 -MIL-101(Al). 769 Calix [4]arenes with differed Lewis acidity would lead to varied conversion and selectivity during the synthesis of 1,5-benzodiazepine, attributed to the hydrogen bonding interactions between the calixarene functional groups and amino groups in the MOF.…”

Section: Homogeneous Supramolecular Catalystsmentioning

confidence: 99%

“…A recent report from the Su group indicates that a cone-calix[4]arene bearing D-π–A units can sensitize a Pt@UiO-66-NH 2 composite, boosting the hydrogen production activity of the catalyst . In 2018, Isaeva, Timofeeva, and co-workers incorporated calix[4]arenes with acidic functionalities into the MOF NH 2 -MIL-101(Al) . Calix[4]arenes with differed Lewis acidity would lead to varied conversion and selectivity during the synthesis of 1,5-benzodiazepine, attributed to the hydrogen bonding interactions between the calixarene functional groups and amino groups in the MOF.…”

Section: Mofs As Enzyme Mimicsmentioning

confidence: 99%

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Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis

et al. 2023

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Enzymatic catalysis has fueled considerable interest from chemists due to its high efficiency and selectivity. However, the structural complexity and vulnerability hamper the application potentials of enzymes. Driven by the practical demand for chemical conversion, there is a long-sought quest for bioinspired catalysts reproducing and even surpassing the functions of natural enzymes. As nanoporous materials with high surface areas and crystallinity, metal−organic frameworks (MOFs) represent an exquisite case of how natural enzymes and their active sites are integrated into porous solids, affording bioinspired heterogeneous catalysts with superior stability and customizable structures. In this review, we comprehensively summarize the advances of bioinspired MOFs for catalysis, discuss the design principle of various MOF-based catalysts, such as MOF−enzyme composites and MOFs embedded with active sites, and explore the utility of these catalysts in different reactions. The advantages of MOFs as enzyme mimetics are also highlighted, including confinement, templating effects, and functionality, in comparison with homogeneous supramolecular catalysts. A perspective is provided to discuss potential solutions addressing current challenges in MOF catalysis.

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Section: Homogeneous Supramolecular Catalystsmentioning

confidence: 99%

Section: Mofs As Enzyme Mimicsmentioning

confidence: 99%

Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis

et al. 2023

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“…MOFs were synthesized according to published procedures. 76–82 The MIL-101(Fe) and NH 2 -MIL-101(Fe) samples were prepared by the MW technique under atmospheric pressure according to a modified previously reported procedure. 78 For the synthesis of MIL-101(Fe), benzene-1,4-dicarboxylic acid (H 2 BDC) (0.230 g, 1.38 mmol) was dissolved in N , N -dimethylformamide (DMF) (60 mL).…”

Section: Experimental Partmentioning

confidence: 99%

Dynamic behavior of metal nanoparticles in MOF materials: analysis with electron microscopy and deep learning

Erokhin

Pentsak

Sorokin

et al. 2023

Phys. Chem. Chem. Phys.

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Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

Chen,

Li,

Wang

et al. 2023

Asian J Org Chem

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Metal coordination polymers are widely applied in the synthesis of heterocyclic compounds due to the advantages of highly dispersed metal active sites, low cost and strong designability. Herein, employing the 9‐benzyl‐3,6‐di(1H‐pyrazol‐1‐yl)‐9H‐carbazole (BPC) as a ligand, the cadmium‐coordinated polymer compound (Cd‐BPC) was facilely prepared by solvothermal method and characterized by energy dispersive spectrometer (EDS), flourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscope (SEM), transmission electron microscopy (TEM) and X‐ray photoelectron spectrometry (XPS). Employing the Cd‐BPC polymer as a catalyst, 1,5‐benzodiazepine derivatives were produced with relatively high yields through the reaction of o‐phenylenediamine with ketones, and o‐phenylenediamine with alcohols. Additionally, Cd‐BPC could be reused for at least 5 times without significant decrease.

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Design of novel catalysts for synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones: NH2-MIL-101(Al) as integrated structural scaffold for catalytic materials based on calix[4]arenes

Cited by 30 publications

References 55 publications

Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis

Bioinspired Framework Catalysts: From Enzyme Immobilization to Biomimetic Catalysis

Dynamic behavior of metal nanoparticles in MOF materials: analysis with electron microscopy and deep learning

Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

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