Synthesis, characterization and application of a novel nanorod-structured organic–inorganic hybrid material as an efficient catalyst for the preparation of aminouracil derivatives

Zare, Abdolkarim; Atashrooz, Jaleh; Eskandari, Mohammad Mehdi

doi:10.1007/s11164-020-04104-z

Cited by 8 publications

(4 citation statements)

References 75 publications

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“…Therefore, they demonstrated for the efficient synthesis of several the preparation of (6-amino-1,3-dimethyluracil-5-yl)-( 2-hydroxynaphthalene-1,4-dione-3-yl)methanes ( 70) by the one-pot multicomponent reaction of 6-amino-1,3-dimethyluracil, 2-hydroxynaphthalene-1,4-dione (33), and aryl aldehydes (1) in the presence of a catalyst (Scheme 48). 100 Similar to this approach, the authors disclosed the rapid reaction access to a range of novel bis(6-amino-1,3-dimethyluracil-5-yl)methanes (78) under ecofriendly via the pseudo-three-component reaction of 6-amino-1,3-dimethyluracil (2) and aryl aldehydes (1). Scheme 48.…”

Section: Synthesis Of 6-aminouracil Arylmethane Derivativesmentioning

confidence: 99%

“…Synthesis of of bis(6-amino-1,3-dimethyluracil-5-yl)methanes. 100 In this research, Safari et al 101 investigated a cyclization cascade with a catalyst an efficient, robust, recoverable and magnetic nanocomposite, containing 12-phosphotungstic acid-functionalized chitosan@NiCo2O4 NPs (PWA/CS/NiCo2O4) for the construction of for the synthesis of the pyrimido [4,5b]quinoline-tetraone skeleton (70) (Scheme 49). They developed a three-component one-pot cyclo condensation reaction of aromatic aldehydes (1), 6-aminouracil (2), 6-amino-1,3-dimethyluracil with 2hydroxynaphthalene-1,4-dione (33) under reflux conditions in the presence of novel magnetic nanocomposite as a reusable catalyst by using ethanol as a green solvent.…”

Section: Synthesis Of 6-aminouracil Arylmethane Derivativesmentioning

confidence: 99%

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Recent applications of aminouracil in multicomponent reactions

Javahershenas¹

2021

Arkivoc

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6-Aminouracil and its derivatives are versatile heterocyclic compounds and are frequently employed to synthesize a wide array of fused uracils annulated with other heterocyclic rings which can serve to address biological and pharmacological targets. Multicomponent reactions (MCRs) are important in the synthesis of natural products and pharmaceuticals by forming heterocyclic molecular frameworks with generally high atom-economy in a single reaction step. This review embraces various modern synthetic strategies, summarizing recent research developments providing fused 6-aminouracil derivatives and to highlight the progress based on MCRs between 2015 and 2020.

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Section: Synthesis Of 6-aminouracil Arylmethane Derivativesmentioning

confidence: 99%

Section: Synthesis Of 6-aminouracil Arylmethane Derivativesmentioning

confidence: 99%

Recent applications of aminouracil in multicomponent reactions

Javahershenas¹

2021

Arkivoc

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“…[26] Later, many reaction methods of 1,3-dimethyl-6-aminouracil with aldehyde were reported. [27][28][29] However, the literature said the methodology needs to be revised for 6-aminouracil and 1-methyl-6-aminouracil. N-substitution has a significant impact on 6-aminouracil's solubility and reactivity.…”

Section: Introductionmentioning

confidence: 99%

“…first reported the aqueous acidic reaction of uracil and aromatic aldehydes [26] . Later, many reaction methods of 1,3‐dimethyl‐6‐aminouracil with aldehyde were reported [27–29] . However, the literature said the methodology needs to be revised for 6‐aminouracil and 1‐methyl‐6‐aminouracil.…”

Section: Introductionmentioning

confidence: 99%

Surfactant‐Mediated Synthesis of Methylene Bridged 6‐Aminouracils: Development of a Greener Protocol, Water Remediation and Preliminary Biological Screening

Mal,

Das

2023

ChemistrySelect

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Herein, we describe a surfactant‐catalyzed green methodology for electrophilic substitution reaction of 6‐aminouracil derivatives with various aldehydes that were neither reported earlier nor produced using conventional routes. Optimized results show the importance of anionic surfactant (SDS) on the reaction between hydrophilic and hydrophobic compounds in aqueous medium. All synthesized compounds were characterized by various spectroscopic methods like FTIR, NMR, HRMS, and SC‐XRD. Furthermore, the surfactant remediation from the reaction mixture was done using graphene oxide (GO). The results from batch‐adsorption studies indicate prominent sorption of SDS onto the surface of GO with an adsorption efficiency of ~84.9 %. The SDS adsorbed onto GO were analyzed using UV‐vis, FT‐IR, Raman, and HRTEM analysis. Next, the synthesized compounds were screened for their potential anti‐SARS‐CoV2 activity due to their structural resemblance with pyrimidine analogs acting as anti‐viral agents. The in‐silico results indicate that the synthesized compounds exhibit the highest inhibitory activity towards RdRp with binding energy −9.55 kcal/mol. In contrast, Remdesivir showed only −6.45 kcal/mol. In addition, upon preliminary screening of the compounds for possible antimicrobial activity (antifungal and anti‐leishmanial), 4 bf showed moderately high inhibitory activity with IC50 values of 205.48 μM and 124.97 μM for fungal and leishmanial strains, respectively.

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β‐Cyclodextrin‐SO₃H as a Supramolecular Catalyst for Efficient Greener Synthesis of Substituted Bis(6‐aminouracil‐5‐yl)methanes in Water

Gosavi,

Kale,

Dalal

2024

ChemistrySelect

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A simple, straightforward, and highly efficient greener approach for synthesizing bis(6‐aminouracil‐5‐yl)methane derivatives was developed by employing β‐cyclodextrin‐SO3H as supramolecular catalyst in water at 100 °C. A total of 16 bis(6‐aminouracil‐5‐yl)methanes were synthesized via a one‐pot reaction between substituted aromatic aldehydes, 6‐amino‐1,3‐dimethyluracil, and 10% β‐cyclodextrin‐SO3H in water with 84%–92% yield within 20–120 min. The salient features of this protocol included water as green solvent, β‐cyclodextrin‐SO3H as recyclable supramolecular catalyst, mild reaction conditions, easy isolation of pure products, and good to excellent yields.

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Synthesis, characterization and application of a novel nanorod-structured organic–inorganic hybrid material as an efficient catalyst for the preparation of aminouracil derivatives

Cited by 8 publications

References 75 publications

Recent applications of aminouracil in multicomponent reactions

Recent applications of aminouracil in multicomponent reactions

Surfactant‐Mediated Synthesis of Methylene Bridged 6‐Aminouracils: Development of a Greener Protocol, Water Remediation and Preliminary Biological Screening

β‐Cyclodextrin‐SO₃H as a Supramolecular Catalyst for Efficient Greener Synthesis of Substituted Bis(6‐aminouracil‐5‐yl)methanes in Water

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Synthesis, characterization and application of a novel nanorod-structured organic–inorganic hybrid material as an efficient catalyst for the preparation of aminouracil derivatives

Cited by 8 publications

References 75 publications

Recent applications of aminouracil in multicomponent reactions

Recent applications of aminouracil in multicomponent reactions

Surfactant‐Mediated Synthesis of Methylene Bridged 6‐Aminouracils: Development of a Greener Protocol, Water Remediation and Preliminary Biological Screening

β‐Cyclodextrin‐SO3H as a Supramolecular Catalyst for Efficient Greener Synthesis of Substituted Bis(6‐aminouracil‐5‐yl)methanes in Water

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β‐Cyclodextrin‐SO₃H as a Supramolecular Catalyst for Efficient Greener Synthesis of Substituted Bis(6‐aminouracil‐5‐yl)methanes in Water