Synthesis of Benzimidazolo[2,3-<i>b</i>]quinazolinone Derivatives via a One-pot Multicomponent Reaction Promoted by a Chitosan-based Composite Magnetic Nanocatalyst

Maleki, Ali; Aghaei, Morteza; Ghamari, Nakisa

doi:10.1246/cl.141074

Cited by 83 publications

(38 citation statements)

References 38 publications

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“…Chitosan is a multifunctional polymer that has hydroxyl groups of the first and second types, as well as amine groups. Therefore, it can increase the rate of catalytic reactions by hydrogen bond formation and also by using the alkaline property of its surface amino groups …”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Shahbazi

Bahrami

2020

ChemistrySelect

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The palladium metal nanoparticles doped on the modified chitosan nanofibers with 2-aminobenzaldehyde (CSNFs-2-ABÀ Pd (0)) were thoroughly characterized and applied as a novel heterogeneous catalyst in Heck and Suzuki CÀ C coupling reactions. This catalyst is exceptionally simple to handle and ecologically safe and temperate. The catalyst was essentially reused from the reaction mixture and reused sequential five times with low leakage. CSNFs-2-ABÀ Pd (0) was characterized using scanning electron microscopy, transmission electron microscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy and Fourier transform infrared.

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Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Shahbazi

Bahrami

2020

ChemistrySelect

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“…Thus, the incorporation of graphene in the Gr@TiO 2 NCs not only increased the specific area, but also made the active center Ti well dispersed among the catalyst, which made the catalyst structure rather more stable and dramatically improved the catalytic activity compared with pure TiO 2. Functionalized TiO 2 NPs is extensively utilized in catalytic activity, few of them such as ZnO NPs, ZnS NPs, chitosan‐Fe 3 O 4, Fe(OTs) 3 /SiO 2 , Fe 3 O 4 @TiO 2 @O 2 PO 2 (CH 2 )NHSO 3 H, cellulose‐based magnetic NCs, silica‐based magnetic NCs, Fe 3 O 4 /SBA‐15, Fe 3 O 4 @cellulose, chitosan/graphene oxide, cellulose/Ag, CoFe 2 O 4 @B 2 O 3 ‐SiO 2 , SO 3 H‐functionalized magnetic core/shell, cellulose/γ‐Fe 2 O 3 /Ag NCs, graphene oxide‐chitosan and Fe 3 O 4 /SiO 2 are a few magnitude higher than TiO 2 NPs with limited surface area . Hybrid material graphene‐TiO 2 , π‐π noncovalent bonded with graphene, will be able to retain their stability and catalytic activity in the challenging organic reactions like the synthesis of benzodiazepine.…”

Section: Introductionmentioning

confidence: 99%

Graphene‐mesoporous anatase TiO₂ nanocomposite: A highly efficient and recyclable heterogeneous catalyst for one‐pot multicomponent synthesis of benzodiazepine derivatives

Shoeb

Mobin

Ali

et al. 2017

Applied Organom Chemis

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The potential to bias chemical reaction pathways is a significant goal for physicists and material researchers to design revolutionary materials.Recently, two-dimensional materials have appeared as a promising candidate for exploring novel catalyst activity in organic reaction. In this context, herein we report an easy and efficient synthesis of substituted benzodiazepines in high yields through the graphene-based mesoporous TiO 2 nanocomposite (Gr@TiO 2 NCs) catalyst. To validate the merits of the Gr@TiO 2 NCs as a catalyst, we have also designed TiO 2 nanoparticle (NPs) under similar conditions. Successful comprehension realization of Gr@TiO 2 NCs and TiO 2 NPs were concluded from the XRD, SEM, HR-TEM, EDS elemental mapping, FT-IR, Raman, UV-Vis and TGA analysis. Gr@TiO 2 NCs has the propitious catalyst performance (~98%) over the TiO 2 NPs (~77%), which could be scrutinized in terms of graphene support toward the TiO 2 NPs and enable the large contact area between graphene and TiO 2 NPs. Incorporated graphene maintaining TiO 2 as a catalytically active and attracting electron to site isolation, as well as protecting TiO 2 from oxidative degradation during the reaction. Moreover, the role of graphene is suggested to prolonged reaction duration, yield and unaltered throughout the reaction because of the π-π interaction between graphene and TiO 2 NPs. Additionally, the catalyst is recycled by filtration and reprocessed six times without having a significant loss in its catalytic activity.

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“…According to the importance of quinazoline and quinazolinone compounds in medicinal chemistry, Niementowski reaction conditions were developed and modified to gain a diverse library of such compounds . According to our previous research in the field of catalysis, and also due to the importance of nanomagnetic catalysts in organic syntheses, herein, we want to introduce the first application of prepared SrFe 12 O 19 MNPs as catalyst in the modified Niementowski reaction.…”

Section: Introductionmentioning

confidence: 99%

The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

Ziarani

Asl

Gholamzadeh

et al. 2017

Applied Organom Chemis

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Nanomagnetic SrFe 12 O 19 was synthesized through a simple sol-gel auto-combustion and then characterized by FT-IR, XRD, EDXA, VSM, BET and SEM image. Moreover, it was used as catalyst for the first time in the modified Niementowski reaction to investigate its catalytic activity. According to the high yield of quinazolinone products obtained within short reaction times, it was found that SrFe 12 O 19 can be used as an effective and green nanocatalyst in organic reactions.The nanomagnetic catalyst can be easily separated from the reaction mixture using an external magnet.

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Synthesis of Benzimidazolo[2,3-b]quinazolinone Derivatives via a One-pot Multicomponent Reaction Promoted by a Chitosan-based Composite Magnetic Nanocatalyst

Cited by 83 publications

References 38 publications

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Graphene‐mesoporous anatase TiO₂ nanocomposite: A highly efficient and recyclable heterogeneous catalyst for one‐pot multicomponent synthesis of benzodiazepine derivatives

The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

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Synthesis of Benzimidazolo[2,3-b]quinazolinone Derivatives via a One-pot Multicomponent Reaction Promoted by a Chitosan-based Composite Magnetic Nanocatalyst

Cited by 83 publications

References 38 publications

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Palladium Nanoparticles Doped on the Chitosan Nanofibers Modified with 2‐Aminobenzaldehyde as a Nanocatalyst in Cross‐Coupling Reactions

Graphene‐mesoporous anatase TiO2 nanocomposite: A highly efficient and recyclable heterogeneous catalyst for one‐pot multicomponent synthesis of benzodiazepine derivatives

The use of SrFe12O19 magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

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Product

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Graphene‐mesoporous anatase TiO₂ nanocomposite: A highly efficient and recyclable heterogeneous catalyst for one‐pot multicomponent synthesis of benzodiazepine derivatives

The use of SrFe₁₂O₁₉ magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction