Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions

Heravi, Majid M.; Malakooti, Reihaneh; Kafshdarzadeh, Kosar; Amiri, Zahra; Zadsirjan, Vahideh; Atashin, Hassan

doi:10.1007/s11164-021-04619-z

Cited by 13 publications

(5 citation statements)

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“…N 2 adsorption‐desorption isotherms for SBA‐15 and MgO/SBA‐15 (Figure S2A), typical irreversible type IV adsorption isotherms defined by IUPAC [17] were observed which indicates the presence of uniform mesopores. The clear hysteresis loops of type H1 situated in the range 0.45 < P / P 0 < 0.85 suggest that materials have regular mesoporous channels with narrow Gaussian pore size distribution centered at 7.2 and 7.6 nm for siliceous SBA‐15 and MgO/‐SBA‐15, respectively (Figure S2B).…”

Section: Resultsmentioning

confidence: 99%

“…Preparations of materials based on MgO or SBA‐15 have been made, Pd–Pb supported on MgO‐SBA‐15 catalysts used in the oxidative esterification reaction [14], Pt/MgO/SBA‐15 an efficient catalyst for selective oxidation [15], and the SBA‐15 mesoporous silica modified which has been used as cadmium adsorbent [16]. In addition, another recyclable PdO/Al‐SBA‐15 catalyst was used for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via one‐pot and multicomponent reaction [17].…”

Section: Introductionmentioning

confidence: 99%

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One‐pot green synthesis, study of fluorescence properties, and biological activity of pyrano[3,2‐c]chromenes derivatives via mesoporous materialsMgO/SBA‐15

Chelihi,

Hassaine,

Nachat

et al. 2023

Journal of Heterocyclic Chem

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This current work describes the preparation of MgO‐SBA‐15 catalysts by ultrasonic method, and it is characterized by the different analysis techniques of XRD, BET, SEM, and IRTF. In order to find out an application for this mesoporous material, MgO/SBA‐15 was used as a heterogeneous catalyst in the one‐pot synthesis of pyrano[3,2‐c]chromenes derivatives isolated at room temperature reaction according to green chemistry criteria. To enhance these derivatives, a spectroscopic study of molecular fluorescence properties was carried out as well as an identification analysis by nuclear magnetic resonance and FTIR was used. Furthermore, biological activity experiment is also carried out, from where the obtained test results were satisfactory for AC09, AC05, and AC10 compounds and they are checked after computation by molecular modeling.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

One‐pot green synthesis, study of fluorescence properties, and biological activity of pyrano[3,2‐c]chromenes derivatives via mesoporous materialsMgO/SBA‐15

Chelihi,

Hassaine,

Nachat

et al. 2023

Journal of Heterocyclic Chem

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“…Sajjadi et al (2023), for instance, reported on the synthesis of dihydropyrano[2,3c]pyrazoles via Knoevenagel-Michael multiple reactions by using green catalyst Fe 3 O 4 @gC 3 N 4 for the reaction of aldehydes, phenylhydrazine, ethyl acetoacetate and malononitrile under 1 h reflux to achieve 97 % yield of product (Route 1). [51] This reaction has also been reported by using numerous catalysts such as 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate ([DBU][Ac], [59] HMS/PrÀ Rh-Zr, [60] H 3 PO 4 /Al 2 O 3 , P 2 O 5 /SiO 2 , starch sulfuric acid, cellulose sulfuric acid, [61] thiourea dioxide (TUD), [62] PVCÀ EDAÀ CeIII, [63] citrus limon (lemon juice), [64] agave leaf ash extract, [65] piperidine, [66] sodium lactate, [67] NiWO 4 , [68] PBCMOamine, [69] CaO nanoparticles, [70] Fe 3 O 4 @chitosan-tannic acid bionanocomposite, [71] FSiPSS nano-catalyst, [72] nano ZrO 2 , [73] lactic acid : urea : NH 4 Cl, [74] H 4 [SiW 12 O 40 ], [75] NiFe 2 O 4 @SiO 2 À H 3 PW 12 O 40 (NFSÀ PWA), [76] Fe 3 O 4 @SiO 2 @CoSB, [77] PAN@melamine/Fe 3 O 4 nanocomposite, [78] isonicotinic acid, [79] nano-[Fe-PSMP]Cl 2 , [80] Fe 3 O 4 /MIP-202-H 4 WO 5 , [81] Zn(L-proline) 2 , [82] baker's yeast, [83] solar radiation, [84] Cu-DABP@Fe 3 O 4 /MCM-41, [85] Fe 3 O 4 @NFC@Co(II), [86] PdO/Al-SBA-15, [87] (MnCoFe 2 O 4 @Niacin-SO 3 H) + Cl À , [88] Zn-CA-MOFs [89] and Na 2 CaP 2 O 7 . [90] In 2022, Nguyen and coworkers reported different routes to the synthesis of pyrano[2,3-c]pyrazole derivatives, which involved a four-component reaction of benzyl alcohols, phenylhydrazine, ethyl acetoacetate and malononitrile with the aid of sulfonated amorphous carbon and eosin Y as c...…”

Section: Synthesis Of Pyranopyrazole and Its Derivativesmentioning

confidence: 99%

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Farooq,

Ngaini

2024

ChemistrySelect

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Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives. Pyranopyrazole is an important structural unit in heterocyclic chemistry and is useful in pharmaceutical and agrochemical industries. The pyranopyrazole‐based compounds are known in the agricultural industry as herbicides, fungicides, and insecticide agents and in medicinal fields as antimicrobial, anticancer, and antiHIV agents. Despite its wide range of applications, the synthesis of pyranopyrazole has several limitations such as the cost of reagents, potential environmental risks, harsh reaction conditions, longer reaction times, laborious workup procedures, and unsatisfactory yields. However, many studies have been recently reported on the synthesis of pyranopyrazoles using mild, green, and environmentally friendly methods that also give higher yields. Different catalysts and conditions have been reported for the synthesis of pyranopyrazole using four, three, and two components. Among these, four‐component synthesis is commonly reported by using benzaldehyde, hydrazine derivatives, ethyl acetoacetate and malononitrile due to the commercial availability and stability of the reagents. This review summarized the recent synthesis of pyranopyrazole i. e., mono‐ and bis‐pyranopyrazole derivatives via four‐, three‐ and two‐component‐based reactions. Mono‐ and bis‐pyranopyrazole derivatives varied due to the number of pyranopyrazole units that contributed to play an important role in increasing the binding interaction and biological activities beneficial for pharmaceutical industries.

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“…They also used the Au@CeO 2 for the visible‐light induced synthesis of triazine using MCR approach as shown in Figure 19 [230] . Recently, Atashin and co‐workers prepared a reusable PdO NPs loaded on a commercially available aluminum‐substituted mesoporous SBA‐15 (Al‐SBA‐15) support to form PdO/Al‐SBA‐15 catalyst and used it to catalyze a multicomponent reaction leading to the formation of pyranopyrazole and benzylpyrazolyl coumarin derivatives using 1 : 1 mixture of H 2 O/EtOH as the solvents under reflux conditions as shown in Figure 20 [231] …”

Section: Multicomponent Reactionsmentioning

confidence: 99%

Solid‐Supported Catalysts for Organic Functional Group Transformations

et al. 2023

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Design of solid‐supported metal catalysts (SSMCs) has made an increasingly important contribution to heterogeneous catalysis in terms of fundamental understanding and technological applications. For instance, industrial use of supported catalysts for oxidation, reduction, and C−C bond formation reactions is highly prevalent. The reason behind this is that such catalysts are economical, have high thermal stability, dispersion, high exposed surface area, and above all, high reusability (up to multiple subsequent cycles). Such characteristics make supported catalysts ideal for green synthesis. However, unlike homogeneous catalysis, heterogeneous catalysis is widely applied in crude oil refining, the pharmaceutical industry, water purification, natural product synthesis, and environmental catalysis. Carbon‐carbon bond formation reactions are frequently used in the organic synthesis using SSMCs. SSMCs are attractive to synthetic chemists due to their easy recovery and excellent stability compared to unsupported metal catalysts. However, the major drawback of SSMCs is related to metal sintering at elevated temperatures caused by weak interactions between the metal and solid support in SSMCs. This review highlights major advancements in SSMCs. Three commonly reported solid supports for metal catalysts, such metal oxides, carbonaceous materials, and polymeric compounds, are discussed. Moreover, a series of thermo‐ and photocatalyzed reactions, such as hydrogenation, carbon‐carbon bond formation, oxidation reactions and multicomponent reactions and the effect of variable supports towards activity and selectivity are demonstrated.

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Supported palladium oxide nanoparticles in Al-SBA-15 as an efficient and reusable catalyst for the synthesis of pyranopyrazole and benzylpyrazolyl coumarin derivatives via multicomponent reactions

Cited by 13 publications

References 129 publications

One‐pot green synthesis, study of fluorescence properties, and biological activity of pyrano[3,2‐c]chromenes derivatives via mesoporous materialsMgO/SBA‐15

One‐pot green synthesis, study of fluorescence properties, and biological activity of pyrano[3,2‐c]chromenes derivatives via mesoporous materialsMgO/SBA‐15

Recent Synthesis of Mono‐ & Bis‐Pyranopyrazole Derivatives

Solid‐Supported Catalysts for Organic Functional Group Transformations

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