Visible light-induced green synthesis of 2-amino-4H-chromenes

Chen, Lu; Lin, Chuyuan; Lan, Yongyin; Li, Zhenzhen; Huang, Daixin; Yang, Wei; Li, Yibiao

doi:10.1007/s10311-020-01053-2

Cited by 18 publications

(5 citation statements)

References 34 publications

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Section: Other Techniquesmentioning

confidence: 99%

“…This process offers various benefits, including the use of a green and sustainable solvent, great yields of the desired products, and the use of cheap catalysts with minimal catalyst loadings (Scheme 49). [98] To produce dihydropyrano[3,2-c]chromenes in 2019, Mihiri and colleagues used ammonium acetate (15 mol-%) for multicomponent condensation reaction of aromatic aldehydes ( 14) with 4-hydroxycoumarin (1) and malononitrile (13) in the presence of a flexible solvent Bmim [triflate] to obtain desired products in great yield (70-90 %). The synthetic compounds' cation binding and antibacterial properties were evaluated (Scheme 50).…”

Section: Other Techniquesmentioning

confidence: 99%

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Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review

Joy,

Nizam

et al. 2023

Chemistry & Biodiversity

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Fused coumarins, because of their remarkable biological and therapeutic properties, particularly pyranocoumarins, have caught the interest of synthetic organic chemists, leading to the development of more efficient and environmentally friendly protocols for synthesizing pyranocoumarin derivatives. These compounds are the most promising heterocycles discovered in both natural and synthetic sources, with anti‐inflammatory, anti‐HIV, antitubercular, antihyperglycemic, and antibacterial properties. This review employed the leading scientific databases Scopus, Web of Science, Google Scholar, and PubMed up to the end of 2022, as well as the combining terms pyranocoumarins, synthesis, isolation, structural elucidation, and biological activity. Among the catalysts employed, acidic magnetic nanocatalysts, transition metal catalysts, and carbon‐based catalysts have all demonstrated improved reaction yields and facilitated reactions under milder conditions. Herein, the present review discusses the various multicomponent synthetic strategies for pyranocoumarins catalyzed by transition metal‐based catalysts, transition metal‐based nanocatalysts, transition metal‐free catalysts, carbon‐based nanocatalysts, and their potential pharmacological activities.

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Section: Other Techniquesmentioning

confidence: 99%

Section: Other Techniquesmentioning

confidence: 99%

Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review

Joy,

Nizam

et al. 2023

Chemistry & Biodiversity

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“…Besides that, functionalized 4H-pyrans comprise a building unit of several naturally occurring products and biologically active molecules that enjoy assorted pharmacological activities, namely, antitumor and antibacterial . As a result, several synthetic routes and catalytic systems have been introduced in recent years. , Azimi and coworkers reported a GNP functionalized mesoporous silica-chitosan as an effective heterogeneous nanocatalyst for the facile and expeditious synthesis of 4H-pyran derivatives . In this report, eco-friendly and swift syntheses of pyran scaffolds in appropriate yields were performed via three-component reactions of isatins or benzaldehydes, active methylene compounds, and 1,3-dicarbonyl compounds such as cyclohexane-1,3-dione, dimedone, barbituric and thiobarbituric acid derivatives, and ethyl 3-oxobutanoate in attendance of a catalytic quantity of GNPs/silica-chitosan in H 2 O (Scheme ).…”

Section: Gold Np-catalyzed Mcrsmentioning

confidence: 99%

Gold Nanoparticle-Catalyzed Multicomponent Reactions

Yazdani

Hooshmand

Varma

2021

ACS Sustainable Chem. Eng.

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Nanotechnology and nanoscience hold great promise for many multidisciplinary applications, including catalysis where gold nanoparticles (GNPs) are considered "safer and environmentally benign" on account of the fact that they are relatively nontoxic and efficient for pivotal applications in natural-product synthesis, organic reactions, pharmaceutical industry, and medicinal chemistry. Since the physicochemical characteristics of GNPs pertain to their shape, size, composition, and surface modification, these features contribute to the reactivity and toxicity of nanomaterials in the catalytic systems. Multicomponent reactions (MCRs) lead to expeditious synthesis of biologically active molecules and active pharmaceutical ingredients (APIs) with atom economy and high efficiency, as well as a low E-factor, and they can be performed in one-pot operations deploying three or more reactants. Thus, applications of GNPs as robust catalysts in MCRs comprise an effective synthetic route with an ideal combination for the augmentation of greener and sustainable methods. Accordingly, cutting-edge examples of gold nanoparticle-catalyzed multicomponent reactions leading to a diverse range of valuable organic molecules such as isoxazolines, propargylamines, 3,4dihydropyrimidin-2(1H)-ones, pyrans, chromeno[2,3-d]pyrimidins, pyridines, and benzodiazepines are discussed and highlighted.

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“…Moreover, water extract of pomegranate peel ash (WEPPA), water extract of lemon fruit shell ash (WELFSA), and Water extract of mango peel ash (WEMPA) are some examples of natural aqueous medium catalysts that have participated in producing 4H-chromene derivatives through the multicomponent reactions under exposure to microwave in recent years 53 – 55 . In an engaging report, multi-component reactions in combination with photocatalytic processes for 4H-chromene synthesizing have been investigated 56 . Additionally, green electrocatalytic multicomponent synthesis has been studied as another technique of 4H-chromenes production, exploiting potassium iodide as an electrolyte in undivided cell, which production yields of 86% have been reported 57 .…”

Section: Introductionmentioning

confidence: 99%

CSA@g-C3N4 as a novel, robust and efficient catalyst with excellent performance for the synthesis of 4H-chromenes derivatives

Hosseini,

Azizi

2023

Sci Rep

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A pioneering robust and green heterogeneous acidic catalyst (CSA@g-C3N4) was rationally designed via immobilization of camphorsulfonic acid (CSA) on the g-C3N4 surface under mild conditions. Grafting CSA in the g-C3N4 lattice is distinguished as the root cause of facilitating the structure change of g-C3N4, leading to a unique morphology, accordingly the remarkable catalytic efficiency of CSA@g-C3N4. The morphology of new as-prepared nano-catalyst was specified by means of FT-IR, XRD, SEM, EDS, TEM, TGA, and BET. For the first time, it is exhibited that the efficient catalyst CSA@g-C3N4 can productively accomplish the three-component reactions with high yields and also serve as an inspiration for easily performing various sorts of MCRs based on our finding. The recommended synthesis pathway of chromenes derivatives is facile and cost-effective which applies a condensation reaction of salicylaldehyde, thiophenol, and malononitrile followed by ready purification in a benign manner. Moreover, the CSA@g-C3N4 nanocomposite can be promptly reused, illustrating no sensational decrease in the catalytic activity after ten times.

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Visible light-induced green synthesis of 2-amino-4H-chromenes

Cited by 18 publications

References 34 publications

Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review

Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review

Gold Nanoparticle-Catalyzed Multicomponent Reactions

CSA@g-C3N4 as a novel, robust and efficient catalyst with excellent performance for the synthesis of 4H-chromenes derivatives

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