Sulfonic acid-functionalized poly(4-styrenesulfonic acid) mesoporous graphene oxide hybrid for one-pot preparation of coumarin-based pyrido[2,3-d]pyrimidine-dione derivatives

Sayahi, Mohammad Hosein; Bahadorikhalili, Saeed; Saghanezhad, Seyyed Jafar; Miller, Max A.; Mahdavi, Mohammad

doi:10.1007/s11164-019-03962-6

Cited by 32 publications

(11 citation statements)

References 27 publications

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“…It is found that the occurrence of plant-derived phytochemical constituents on the surface of bio-assisted nanoparticles during the synthesis process, would tune the distinctive parameters of decorated nanomaterials such as morphology and particle-size distribution which in turn improve their catalytic properties rather than plain traditional catalysts 6 . For instance, the utilized biogenic NiO NPs in this study exhibited shorter reaction times and higher yields of products in comparison to poly (4-styrenesulfonic acid) mesoporous graphene oxide hybrid (PSSA-MGO) catalyst in the synthetic reaction of alike pyridopyrimidines 60 . As a result, the designed algal NiO NPs-catalyzed organic synthesis takes major advantages including excellent yields, short time, low cost, simplicity, green chemical reaction condition, and environmental sustainability.…”

Section: Resultsmentioning

confidence: 97%

“… Entrya R Product Time (min) TONc TOFd (min-1) Yieldb (%) MP (ºC) (Ref.) 1 H 5a 45 17,600 391 88 235–237 (236–238) 60 2 2-Cl 5b 47 18,400 391.49 92 215–217 (218–220) 60 3 3-Cl 5c 50 18,000 360 90 220–222 (219–220) 60 4 4-Cl 5d 42 18,800 447.62 …”

Section: Resultsmentioning

confidence: 99%

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Algal magnetic nickel oxide nanocatalyst in accelerated synthesis of pyridopyrimidine derivatives

Moavi

Buazar

Sayahi

2021

Sci Rep

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This research presents a novel biological route for the biosynthesis of nickel oxide nanoparticles (NiO NPs) using marine macroalgae extract as a reducing and coating agent under optimized synthesis conditions. XRD and TEM analyses revealed that phytosynthesized NiO NPs are crystalline in nature with a spherical shape having a mean particle size of 32.64 nm. TGA results indicated the presence of marine-derived organic constituents on the surface of NiO NPs. It is found that biogenic NiO NPs with BET surface area of 45.59 m2g−1 is a highly efficient catalyst for benign one-pot preparation of pyridopyrimidine derivatives using aqueous reaction conditions. This environmentally friendly procedure takes considerable advantages of shorter reaction times, excellent product yields (up to 96%), magnetically viable nanocatalyst (7 runs), low catalyst loadings, and free toxic chemical reagents.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Algal magnetic nickel oxide nanocatalyst in accelerated synthesis of pyridopyrimidine derivatives

Moavi

Buazar

Sayahi

2021

Sci Rep

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“…[1,2] Several materials have been used as support for immobilization of catalysts. Silica, [3,4] mesoporous silica nanoparticles, [5][6][7][8][9] superparamagnetic iron oxide nanoparticles, [10][11][12][13] and various polymeric materials [14][15][16] have been used as support for catalysts. Among all the solid supports, polymers have been of high interest, regarding their beneficial properties, including more simplicity and possibility in the design and synthesis.…”

Section: Introductionmentioning

confidence: 99%

Sulfonic Acid Functionalized Magnetic Starch as an Efficient Catalyst for the Synthesis of Chromeno[4,3‐b]quinoline‐6,8(9H)‐dione Derivatives

et al. 2021

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In this paper, sulfonic acid functionalize magnetic starch (denoted Starch/SPION@SO3H) is fabricated by the polymerization of 4‐styrenesulfonic acid on the surface of magnetic starch. Magnetic starch (Starch/SPION) is synthesized by covalent modification of starch by silica capsulate superparamagnetic iron oxide nanoparticles (SPION). For this purpose, Starch/SPION is modified by allyltrimethoxysilane, follows by the polymerization of 4‐styrenesulfonic acid onto this material. The catalyst is characterized by various characterization techniques, including transmission electron microscopy (TEM), high resolution transmission electron microscopy (HRTEM), thermogravimetric analysis (TGA), vibrating‐sample magnetometer (VSM), X‐ray photoelectron spectroscopy (XPS), and acid/base titration. The characterizations prove the structure of Starch/SPION@SO3H catalyst. The catalytic activity of Starch/SPION@SO3H is evaluated in the multicomponent reaction of 4‐hydroxycoumarin, benzaldehydes, dimedone, and ammonium acetate for the synthesis of chromeno[4,3‐b]quinoline‐6,8(9H)‐dione derivatives. The catalyst shows very good activity in the synthesis of chromeno[4,3‐b]quinoline‐6,8(9H)‐dione derivatives. Several benzaldehydes with electron donating or electron withdrawing functionalities are used as starting material and all the substrates give the desired products in high isolated yields. In addition, the catalyst is extremely reusable during 10 sequential runs. Characterization of Starch/SPION@SO3H catalyst by TEM, VSM, and acid/base titration after recovery from the reaction proves the stability of the catalyst in the reaction conditions.

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“…[30][31][32][33] In addition, is has been observed that immobilization of the catalysts onto nanoparticles could facilitate the reusability of the catalysts and at the same time increase the activity and the efficiency of the catalysts. [34][35][36][37][38][39]52] Among various nanoparticles, which are used as support for the immobilization of the catalysts, magnetic nanoparticles are of high interest, due to their unique properties. [40][41][42][43][44][45] Superparamagnetic iron oxide nanoparticles (SPION) are significant support, due to their chemical and thermal stability and ease of functionalization.…”

Section: Introductionmentioning

confidence: 99%

Copper Supported onto Magnetic Nanoparticles as an Efficient Catalyst for the Synthesis of Triazolobenzodiazepino[7,1‐b]quinazolin‐11(9H)‐ones via Click N‐Arylation Reactions

et al. 2021

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A novel catalyst is designed and synthesized based on immobilization of copper onto modified magnetic nanoparticles. The catalyst was characterized by several characterization techniques. The catalyst was applied for the synthesis of a novel series of heterocyclic scaffold containing a 1,4‐benzodiazepine fused with a 1,2,3‐triazole ring and a quinazolin‐11(9H)‐one skeleton. The method is based on the direct synthesis of quinazolin‐11(9H)‐one ring by the reaction of isatoic anhydride (or anthranilic acid) and propargylamine, and an aldehyde, containing a leaving group on its aromatic ring. The reaction contains an in situ sequential click reaction of azide group with terminal alkyne and subsequent N‐arylation reaction to afford the final products. The method benefits various advantages, such as regioselectivity and high yield of the products. The reusability of the catalyst was evaluated and the results showed that the catalyst is highly reusable in 10 sequential reactions.

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Sulfonic acid-functionalized poly(4-styrenesulfonic acid) mesoporous graphene oxide hybrid for one-pot preparation of coumarin-based pyrido[2,3-d]pyrimidine-dione derivatives

Cited by 32 publications

References 27 publications

Algal magnetic nickel oxide nanocatalyst in accelerated synthesis of pyridopyrimidine derivatives

Algal magnetic nickel oxide nanocatalyst in accelerated synthesis of pyridopyrimidine derivatives

Sulfonic Acid Functionalized Magnetic Starch as an Efficient Catalyst for the Synthesis of Chromeno[4,3‐b]quinoline‐6,8(9H)‐dione Derivatives

Copper Supported onto Magnetic Nanoparticles as an Efficient Catalyst for the Synthesis of Triazolobenzodiazepino[7,1‐b]quinazolin‐11(9H)‐ones via Click N‐Arylation Reactions

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