Web of Science, ISC, CAS, Google Scholar

Document Type : Original Article


1 Department of Chemistry, Ayatollah Amoli Branch, Islamic Azad University, Amol, Iran

2 Polymer Research Laboratory, Department of Polymer Science and Engineering, University of Bonab, P.O. Box 5551395133, Bonab, Iran


A simple approach for component reaction between aldehydes, anilines or ammonium acetate, and dimedone in ethanol as a solvent is studied using Ag-SiO2 nanoparticles. This approach results for the synthesis of various decahydroacridines in appropriate yields (80-94%). The use of Ag-SiO2 nanoparticles as a heterogeneous catalyst lets a clean procedure.

Graphical Abstract

Ag-SiO2 Nanoparticles: Benign, Expedient, and Facile Nano Catalyst in Synthesis of Decahydroacridines


Main Subjects


Multi-component reactions (MCRs) are the effective pathway in present chemistry because of their substantial features for example conventional reaction planning and atom economy. MCRs ease the synthesis of target products of pharmacological and biological significance by presenting numerous steps in one-pot reaction [1-7].

In cyclic di-carbonyl compounds the situation of C=O groups concludes completely the effortlessness of their cyclization and produces them as suitable found at ion for the preparation of sulfur-, oxygen-, and nitrogen-including heterocycles [8,9].

One of the most investigated types of heterocyclic compounds is decahydroacridine diones. The existence of numerous reaction moieties in decahydroacridinediones increases wide synthetic potentials [10]. Decahydroacridinediones include a 1,4-dihydropyridine ring as basic part and are accessible by several types of Hantzsch synthesis [1114], which is a basic fragment of progressively significant NADH, NADPH, and N–alkylnicotinamides [15]. Decahydroacridinediones display a wide range of pharmacological and biological [16,17] activity, containing antimicrobial properties [18,19] such as antimicrobial [20,21], anticancer [22], cytotoxic [23], antitumor [24], anti-multidrug-resistant [25], fungicidal [26], and broadly approved as calcium blockers [27,28]. Several approaches have been considered for the produce of these target products by using numerous catalysts like Cu(II) [29], [MIMPS]3PW12O40 and [TEAPS]3PW12O40 Schiff base [30], Ag nanoparticle [31], Glutathione-Coated Magnetic Nanoparticles [32], Fe3O4 nanoparticles [33], and  cobalt-alanine metal complex [34].

The nanoparticles are highly applicable in various industries such as electronics, mechanics, and chemistry. They further have potentially been applied in different technologies that deal with catalysts, engineering materials, superconductors, and magnetic materials [35-41]. The nanoparticles of metal oxides have attracted an extraordinary attention. In multiple chemistry fields, they can provide conventional materials with feasible but unusual modifications.  In different organic syntheses, these nanoparticles have been mainly employed as nano-catalysts, thanks to their suitable surface area versus their corresponding compounds in bulk form [42-47].

Silica-coated particles are a category of materials broadly studied in numerous fields of materials and colloid science [48-52]. Mesoporous silica, owing to its proper hydrothermal stability, large surface functionality, and area has been revealed widely for biomedical uses, specifically intracellular drug delivery [5355]. Ag nanoparticles engrossed significant consideration owing to their conducting, catalytic, and optical properties [56,57]. Silica-supported silver nanoparticles (Ag@SiO2 core–shell) were studied as an appropriate catalyst in the field of chemistry [5860].

In viewpoint of the above-mentioned reports and our studies for the produce of heterocyclic products and application of metal oxide nanoparticles catalysts [61-66], herein, we report novel catalytic applications of Ag-SiO2 nanoparticles for the preparation of decahydroacridine 5 via the one-pot three-component reaction of aldehydes 1 with dimedone 2 and anilines 3 or ammonium acetate 4 in ethanol solvent at room temperature (Scheme 1).


Reagent and analysis

The reagents were prepared from Merck and Aldrich. Melting points were measured on a Thermo Scientific apparatus and are uncorrected. FT-IR spectra were attained by a FT-IR Bruker (WQF-510) spectrometer. 1H-NMR spectra were achieved by Bruker DRX‐400 MHz spectrometer. The spectra were measured in CDCl3 relative to TMS (0.00 ppm). Chemical shifts are measured in ppm. Reactions were observed by TLC on aluminum sheets silica gel F254. The products are characterized by linking their melting points, FT-IR, and 1H-NMR and with those studied in published papers.

Scheme 1: synthesis of decahydroacridineby usingcore–shell Ag-SiO2 nanoparticles


General procedure for the preparation of Ag-SiO2 nanoparticles

Silica particles were prepared using sol-gel method. Therefore, a solution of ethanol (100 mL), hydrochloric acid 1% (5 mL) and water (1.98 g; 110 mmol) was prepared. The resulting solution was stirred for 5 min, and then TEOS (10.41 g; 50 mmol) was added dropwise and stirred for 2 h. The resulting SiO2 nanoparticles were stabilized. The silver nitrate was dissolved in minimal water. Next, the prepared silver solution was added to the silica nanoparticles solution and stirred for 10 h to prepare a colorless catalyst solution [67].  

General procedure for the produce of decahydroacridinesby using Ag-SiO2 nanoparticles

A mixture of aldehydes (1 mmol), anilines (1 mmol), or ammonium acetate (0.077 g; 1 mmol), dimedone (0.280 g; 2 mmol), and Ag-SiO2 nanoparticles (2 mol%) at room temperature in ethanol as a solvent (2 mL) was stirred for proper time (Table 2). TLC was used to monitor the reaction progress (ethyl acetate: n-hexane; 2:5). After end of the reaction, the products were isolated by filtration and extracted with CH2Cl2. Thereafter, the organic layer was separated, the solvent was vaporized, and the basic solid purified by recrystallization from ethanol.

Selected spectral data analysis for products  

9,10-Bis(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (Table 2, entry 5):White solid; M.P.: 287-290 oC, Yield: 90%; FT-IR (KBr) (νmax, cm-1): 3043, 2955, 1663, 1341, 1220; 1H-NMR (400 MHz, CDCl3): δ = 0.96 (s, 6H), 1.08 (s, 6H), 1.76–2.18 (m, 8H), 5.20 (s, 1H), 7.13-7.53 (m, 8H).

10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (Table 2, entry 6): White solid; M.P.: 258–260 oC; Yield: 94%; FT-IR (KBr) (νmax, cm–1): 2954, 1675, 1510, 1340, 850; 1H-NMR (400 MHz, CDCl3): δ = 1.14 (s, 6H), 1.26 (s, 6H), 2.38-2.50 (m, 8H), 5.57 (s, 1H), 7.27 (d ,4H, J= 6.6), 8.16 (d, 4H, J= 6.7).

Results and Discussion

Synthesis of decahydroacridine by using Ag-SiO2 nanoparticles as a catalyst

In this study, an expedient and benign process was investigated for the preparation of decahydroacridine using Ag-SiO2 nanoparticles as catalyst.

To assess the effectiveness of Ag-SiO2 nanoparticles, the condensation reaction of 4-nitrobenzaldehyde with dimedone and aniline for the produce of corresponding decahydroacridine was studied as a typical reaction.

The model reaction was studied by using several molar ratios of Ag-SiO2 nanoparticles in ethanol at room temperature (Table 1, entries 1-4). Applying 2 mol% of catalyst resulted in higher yield, while the reaction time became shorter (Table 1). In these conditions, the chosen product was achieved in 89% yield within 5 minutes (Table 1, entry 3). Likewise, when the chosen reaction was approved by 3 mol% of the nano catalyst the yield decreased to 83% (Table 1, entry 4). Optimization was lastly attained at 2 mol% when not much difference in the yield was detected after increasing the amount of Ag-SiO2 nanoparticles up to 3 mol%. However, reducing the catalyst level from 2 mol% to 0.5 mol% (as presented in Table 1, entry 1) led to a reduction in desired product yield, and an increase in reaction time. Correspondingly, when the reaction was performed without the catalyst, the intermediates remain unreacted was formed. SiO2 was further used to evaluate the optimized reaction, where in a reduction in yield (47%), and an increase in reaction time (60 minutes) was observed.

We investigated the effect of several solvents on the selected reaction by using 2 mol% of Ag-SiO2 nanoparticles at room temperature. This reaction was achieved in several solvents for example water, chloroform, acetonitrile, and ethyl acetate (Table 1, entries 5-8). The best results were obtained regarding reaction time and yield attained in ethanol (Table 1). It was observing that polarity of solvent plays a significant role for the reaction achievement. In organic solvents and water, the yield of target product was lower and longer reaction time were necessary, while the reaction by using ethanol led to in suitable yield. Based on the results, among all solvents, the best results obtained from application of ethanol, regarding the target product yield and reaction time.

In further effort, after approving the reaction in reflux condition, no changes observed in the terms of desired product yield and reaction time. Therefore, it was establishing that there was not a correlation between reaction rate and temperature. The quantities of reactants, required to synthesize the desired product, were investigated. Applying 1:2:1 molar ratio of aldehydes, dimedone, and anilines, or ammonium acetate, respectively, obtained the maximal yield.


Table 1: Optimization studies for the preparation of desired decahydroacridine

Later on, the reaction of several aldehydes with dimedone and anilines or ammonium acetate verified the overview and scope of the present process. In all cases, the appropriate yields were achieved as revealed in Table 2. The nature and electronic properties of derivatives on the ring were found effective in respect with yield and time of reaction. As exposed in Table 2, electron-withdrawing substituents in aldehydes enhanced the reaction rate while electron-releasing substituents shrank the reaction rate. In addition, the amines reactivity displays the order: 4-chloroaniline > aniline > ammonium acetate.


Table 2: Synthesis of 1,8-dioxo-decahydroacridines using Ag-SiO2 nanoparticles

a Reaction condition: aldehyde (1 mmol), anilines (1 mmol), or ammonium acetate (1 mmol; 0.077 g), dimedone (2 mmol; 0.280 g),Ag@SiO2 core–shell nanoparticles (2 mol%), C2H5OH as a solvent (2 mL), and room temperature

b Isolated yield    


Scheme 2 depicts the potential mechanism by which the synthesis of 1,8-dioxodecahydroacridines has been occurred using Ag-SiO2 nanoparticlesis [68]. Initially, the Ag-SiO2 nanoparticles activate the carbonyl group of aromatic aldehyde 1. Indeed, one molecule of dimedone 2 entered in a reaction with an aldehyde 1, which resulted in generating an intermediate 6 by removing one molecule of water. Next, another molecule of dimedone 2 stepped in a reaction with 6 via Michael addition to generate intermediate 7. The intermediate 8 was achieved by nucleophilic attack of anilines or ammonia (in situ produced by ammonium acetate) to activated carbonyl group of 7 by removal of second molecule of water which tautomerized to intermediate 9. Finally, the nucleophilic attack of –NH group on C=O group cyclized the intermediate 9 and generate1,8-dioxodecahydroacridines 5 by eliminating the third molecule of water.

The advantage of current method over reported methods was investigated by comparing the attained results with those reported previously (Table 3). The reaction conditions for the synthesis of target molecule (Table 2, entry 3), were compared considering mol% of the catalyst, reaction time, temperature, and yields.


Scheme 2: Suggested mechanism in the preparation of decahydroacridines using Ag-SiO2 nanoparticles


Table 3: Comparison of this approach with further processes for the preparation of target molecule (Table 2, Entry 3)a


In conclusion, a gentle and convenient procedure was developed to generate decahydroacridines from numerous aldehydes, anilines or ammonium acetate, and dimedone using Ag-SiO2 nanoparticles at room temperature in ethanol as a solvent. This procedure includes simple filtration, mild reaction condition, operational ease, good yield of products, and use of Ag-SiO2 as an effective catalyst.

Supporting Information

The supporting data include products' spectral images of FT-IR and 1H-NMR of products.


The authors are grateful for the facilities provided to conduct the present study in the chemistry research laboratory at Ayatollah Amoli Branch, Islamic Azad University.

Disclosure Statement

No potential conflict of interest was reported by the authors.


This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

Authors' Contributions

All authors contributed to data analysis, drafting, and revising of the paper and agreed to be responsible for all the aspects of this work.


Mehdi Hatami



Morteza Farajpour, Seyed Mohammad Vahdat, Seyed Meysam Baghbanian, Mehdi Hatami. Ag-SiO2 Nanoparticles: Benign, Expedient, and Facile Nano Catalyst in Synthesis of Decahydroacridines. Chem. Methodol., 2023, 7(7) 540-551

DOI: https://doi.org/10.22034/CHEMM.2023.386678.1653 

URL: http://www.chemmethod.com/article_171652.html

[1]. Moosavi-Zare A.R., Goudarziafshar H., Jalilian Z., Hosseinabadi F., Efficient Pseudo-Six-Component Synthesis of Tetrahydro-Pyrazolopyridines Using [Zn-2BSMP] Cl2, Chemical Methodologies, 2022, 6:571 [Crossref], [Google scholar], [Publisher]
[2]. Taghavi R., Rostamnia S., Four-Component Synthesis of Polyhydroquinolines via Unsymmetrical Hantzsch Reaction Employing Cu-IRMOF-3 as a Robust Heterogeneous Catalyst, Chemical Methodologies, 2022, 6:639 [Crossref], [Google scholar], [Publisher]
[3]. Baghbanian S.M., Farhang M., Vahdat S.M., Tajbakhsh M., Hydrogenation of arenes, nitroarenes, and alkenes catalyzed by rhodium nanoparticles supported on natural nanozeolite clinoptilolite, Journal of Molecular Catalysis A: Chemical, 2015, 407:128 [Crossref], [Google scholar], [Publisher]
[4]. Vahdat S.M., Chekin F., Hatami M., Khavarpour M. Baghery S., Roshan-kouhi Z., Synthesis of polyhydroquinoline derivatives via a four-component Hantzsch condensation catalyzed by tin dioxide nanoparticles, Chinese Journal of Catalysis, 2013, 34:758 [Crossref], [Google scholar], [Publisher]
[5]. Vahdat S.M., Zolfigol M.A., Baghery S., Straightforward Hantzsch four‐and three‐component condensation in the presence of triphenyl (propyl‐3‐sulfonyl) phosphoniumtrifluoromethanesulfonate {[TPPSP] OTf} as a reusable and green mild ionic liquid catalyst, Applied Organometallic Chemistry, 2016, 30:311 [Crossref], [Google scholar], [Publisher]
[6]. Maleki B., Sedigh Ashrafi S., Tayebee R., Lewis acid free synthesis of 3, 4-dihydro-1 H-indazolo [1, 2-b] phthalazine-1, 6, 11 (2 H, 13 H)-triones promoted by 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol, RSC Advances, 2014, 4:41521 [Crossref], [Google scholar], [Publisher]
[7]. Maleki B., Esmailian Kahoo G.,Tayebee R., One-pot synthesis of polysubstituted imidazoles catalyzed by an ionic liquid, Organic Preparations and Procedures International, 2015, 47:461 [Crossref], [Google scholar], [Publisher]
[8]. Vahdat S.M., Akbari M., An Efficient One-Pot Synthesis of 1, 8-dioxo-Decahydroacridines by Ionic Liquid with Multi-SO3H Groups Under Ambient Temperature in Water, Oriental Journal of Chemistry, 2011, 27:1573 [Google scholar], [Publisher]
[9]. Kim J., Park C., Ok T., So W., Jo M., Seo M., Kim Y., Sohn J.H., Park Y., Ju M.K., Kim J., Discovery of 3, 4-dihydropyrimidin-2 (1H)-ones with inhibitory activity against HIV-1 replication, Bioorganic & medicinal chemistry letters, 2012, 22:2119 [Crossref], [Google scholar], [Publisher]
[10]. Nikolaeva T.G.: Shchekotikhin Y.M., Stereodirected catalytic synthesis of perhydroacridines and their isologs from decahydroacridine-1, 8-diones, Chemistry of Heterocyclic Compounds, 2004, 40:582 [Crossref], [Google scholar], [Publisher]
[11]. Shchekotikhin Y.M., Nikolaeva T.G., Transformations of sym-octahydroxanthene-1, 8-diones and 1, 8-dioxo-sym-octahydroxanthylium salts in recyclization under the influence of amines, Chemistry of Heterocyclic Compounds, 2006, 42:28 [Crossref], [Google scholar], [Publisher]
[12]. Nikolaeva T.G., Shchekotikhin Y.M., Ponomarev A.S., Krivenko A.P., Peculiarities of formation of decahydroacridine-1, 8-diones on the basis of 1, 3-dioxocyclohexane compounds in various media, Chemistry of Heterocyclic Compounds, 2000, 36:403 [Crossref], [Google scholar], [Publisher]
[13]. Shchekotikhin Y.M., Getmanenko Y.A., Nikolaeva T.G., Krivenko A.P., Synthesis of 9-R1-10-R-1, 8-Dioxodecahydroacridines and Dioximes Based on Them, Chemistry of Heterocyclic Compounds, 2001, 37:1228 [Crossref], [Google scholar], [Publisher]
[14]. Chebanov V.A., Saraev V.E., Kobzar K.M., Desenko S.M., Orlov V.D., Gura E.A., Synthesis and Rotamerism of 9, 10-Diarylsubstituted 1, 2, 3, 4, 5, 6, 7, 8, 9, 10-Decahydroacridine-1, 8-Diones, Chemistry of Heterocyclic Compounds, 2004, 40:475 [Crossref], [Google scholar], [Publisher]
[15]. Eisner U., Kuthan J., Chemistry of dihydropyridines, Chemical Reviews, 1972, 72:1 [Crossref], [Google scholar], [Publisher]
[16]. Loev B., Goodman M.M., Snader K.M., Tedechi R., Macko E., Hantzsch-type dihydropyridine hypotensive agents, Journal of medicinal chemistry, 1974, 17:956 [Crossref], [Google scholar], [Publisher]
[17]. Srividya N., Ramamurthy P., Shanmugasundaram P., Ramakrishnan V.T., Synthesis, characterization, and electrochemistry of some acridine-1, 8-dione dyes, The Journal of Organic Chemistry, 1996, 61:5083 [Crossref], [Google scholar], [Publisher]
[18]. Martin N., Quinteiro M., Seoane C., Soto J.L., Mora A., Suarez M., Ochoa E., Morales A., del Bosq R.S., Synthesis and conformational study of acridine derivatives related to 1, 4‐dihydropyridines, Journal of Heterocyclic Chemistry, 1995, 32:235 [Crossref], [Google scholar], [Publisher]
[19]. Edafiogho I.O., Hinko C.N., Chang N., Moore J.A., Mulzac D., Nicholson J.M., Scott K.R., Synthesis and anticonvulsant activity of enaminones, Journal of medicinal chemistry, 1992, 32:2798 [Crossref], [Google scholar], [Publisher]
[20]. Ngadi L., Galy A.M., Galy J.P., Barbe J., Cremieux A., Chevalier J., Sharples D., Some new 1-nitro acridine derivatives as antimicrobial agents, European journal of medicinal chemistry, 1990, 25:67 [Crossref], [Google scholar], [Publisher]
[21]. Wainwright M., Acridine—a neglected antibacterial chromophore, Journal of Antimicrobial Chemotherapy, 2001, 47:1 [Crossref], [Google scholar], [Publisher]
[22]. Gamega.SA., Spicer J.A., Atwell G.J., Finlay G.J., Baguley B.C., Deny W.A., Structure− activity relationships for substituted bis (acridine-4-carboxamides): a new class of anticancer agents, Journal of Medicinal Chemistry, 1999, 42:2383 [Crossref], [Google scholar], [Publisher]
[23]. Antonini I., Polucci P., Kelland L.R., Menta E., Pescalli N., Martelli S., 2, 3-Dihydro-1 H, 7 H-Pyrimido [5, 6, 1-de] Acridine-1, 3, 7-Trione Derivatives, A Class of Cytotoxic Agents Active on Multidrug-Resistant Cell Lines: Synthesis, Biological Evaluation, and Structure− Activity Relationships, Journal of medicinal chemistry, 1999, 42:2535 [Crossref], [Google scholar], [Publisher]
[24]. Mikata Y., Yokoyama M., Mogami K., Kato M., Okura I., Chikira M., Yano S., Intercalator-linked cisplatin: synthesis and antitumor activity of cis-dichloroplatinum (II) complexes connected to acridine and phenylquinolines by one methylene chain, Inorganica chimica acta, 1998, 279:51 [Crossref], [Google scholar], [Publisher]
[25]. Gallo S., Atifi S., Mohamoud A., Santelli-Rouvier C., Wolfart K., Molnar J., Barbe J., Synthesis of aza mono, bi and tricyclic compounds. Evaluation of their anti MDR activity, European journal of medicinal chemistry, 2003, 38:19 [Crossref], [Google scholar], [Publisher]
[26]. Srivastava A., Nizamuddin A., Indian. J. Heterocyclic. Chem., 2004, 13:261 [Google scholar], [Publisher]
[27]. Bossert F., Vater W., 1, 4‐Dihydropyridines—a basis for developing new drugs, Medicinal research reviews, 1989, 9:291 [Crossref], [Google scholar], [Publisher]
[28]. Berkan O., Sarac B., Simsek R., Yildirim S., Sariogli Y., Safak C., Vasorelaxing properties of some phenylacridine type potassium channel openers in isolated rabbit thoracic arteries, European journal of medicinal chemistry, 2002, 37:519 [Crossref], [Google scholar], [Publisher]
[29]. Vahdat S.M., Khaksar S., Akbari M., Baghery S., Sulfonated organic heteropolyacid salts as a highly efficient and green solid catalysts for the synthesis of 1, 8-dioxo-decahydroacridine derivatives in water, Arabian Journal of Chemistry, 2019, 12:1515 [Crossref], [Google scholar], [Publisher]
[30]. Vahdat S.M., Mardani H.R., Golchoubian H., Khavarpour M., Baghery S., Roshankouhi Z., Cu (II) Schiff base as catalyst in the synthesis of 1, 8-dioxodecahydroacridine, Combinatorial chemistry & high throughput screening, 2013, 16:2 [Crossref], [Google scholar], [Publisher]
[31]. Shirazi A., Vahdat S.M., Baghbanian S.M., Ag nanoparticle promoted synthesis of 1, 8-dioxo-decahydroacridines at room temperature, Indian Journal of Chemistry (IJC), 2022, 61:1303 [Crossref], [Google scholar], [Publisher]
[32]. Maleki B., Atharifar H., Reiser O., Sabbaghzadeh R., Glutathione-coated magnetic nanoparticles for one-pot synthesis of 1, 4-dihydropyridine derivatives, Polycyclic Aromatic Compounds, 2021, 41:721 [Crossref], [Google scholar], [Publisher]
[33]. Ghasemzadeh M.A., Safaei-Ghomi J., Molaei H., Fe3O4 nanoparticles: as an efficient, green and magnetically reusable catalyst for the one-pot synthesis of 1, 8-dioxo-decahydroacridine derivatives under solvent-free conditions, Comptes Rendus Chimie, 2012, 15:969 [Crossref], [Google scholar], [Publisher]
[34]. Mujahid Alam M., Mubarak A.T., Assiri M.A., Merajuddin Ahmed S., Fouda A.M., A facile and efficient synthesis of 1, 8-dioxodecahydroacridines derivatives catalyzed by cobalt–alanine metal complex under aqueous ethanol media, BMC chemistry, 2019, 13:40 [Crossref], [Google scholar], [Publisher]
[35]. Farahmandjou M.,Golabiyan N., Synthesis and characterization of Alumina, Int. J. Bio Inorg. Hybr. Nanomater, 2016, 5:73 [Google scholar], [Publisher]
[36]. Sapkal S.,Shelke K.,Shingate B.,Shingare M., An efficient one-pot strategies for the synthesis of [1, 3] oxazine derivatives, Journal of the Korean Chemical Society, 2010, 31:351 [Crossref], [Google scholar], [Publisher]
[37]. Al-Zahra A.A., Al-Sammarraie A.K.M.A., Synthesis and Characterization of Zinc Sulfide Nanostructure by Sol Gel Method, Chemical Methodologies, 2022, 6:67 [Crossref], [Google scholar], [Publisher]
[38]. Hassani M., Zeeb M., Monzavi A.H., Khodadadi Z., Kalaee M.R., Response Surface Modeling and Optimization of Microbial Fuel Cells with Surface-Modified Graphite Anode Electrode by ZSM-5 Nanocatalyst Functionalized, Chemical Methodologies, 2022, 6:253 [Crossref], [Google scholar], [Publisher]
[39]. Zare Kazemabadi F., Heydarinasab A., Akbarzadeh khiyavi A., Ardjmand M., Development, Optimization and In vitro Evaluation of Etoposide loaded Lipid Polymer Hybrid Nanoparticles for controlled Drug Delivery on Lung Cancer', Chemical Methodologies, 2021, 5:135 [Crossref], [Google scholar], [Publisher]
[40]. Sahebnasagh S., Fadaee kakhki J., Ebrahimi M., Bozorgmehr M.R., Abedi M.R., Pre-concentration and Determination of Fluoxetine in Hospital Wastewater and Human Hair Samples using Solid-phase µ-Extraction by Silver Nanoparticles Followed by Spectro-fluorimetric, Chemical Methodologies, 2021, 5:211 [Crossref], [Google scholar], [Publisher]
[41]. Mohammadi S.S., Ghasemi N., Ramezani M., Khaghani S., Biosynthesis of silver nanoparticles using the Falcaria Vulgaris (Alisma Plantago-Aquatica L.) extract and optimum synthesis', Chemical Methodologies, 2021, 5:296 [Crossref], [Publisher]
[42]. Das, V.K., Thakur A.J., Highly active nano-MgO catalyzed, mild, and efficient synthesis of amidines via electrophilic activation of amides, Tetrahedron Letters, 2013, 54:4164 [Crossref], [Google scholar], [Publisher]
[43]. Graf C., Vossen D.L.J., Imhof A., van Blaaderen V., A general method to coat colloidal particles with silica, Langmuir, 2003, 19:6693 [Crossref], [Google scholar], [Publisher]
[44]. Samiei paghaleh E., Vahdat S.M., Hatami M., Facile and benign synthesis of mono-and di-substituted benzimidazoles by using SnO2 nanoparticles catalyst, Journal of Nanostructures, 2021, 11:286 [Crossref], [Google scholar], [Publisher]
[45]. Obaid A.A., Al-ghabban S.S, Al-Hussain R., Appraising Antioxidant and Antibacterial Activities of Zinc Oxide Nanoparticles Synthesized Biologically by Iraqi Propolis, Chemical Methodologies, 2022, 6:366 [Crossref], [Google scholar], [Publisher]
[46]. Abass A.K., Al-Sammarraie A.K.M.A., Synthesis of New PbO-Fe2O3-Polypyrrole Hybrid Nanocomposite to Improve the Structural, Magnetic and Electrical Characteristics of Lead Oxide', Chemical Methodologies, 2022, 6:301 [Crossref], [Google scholar], [Publisher]
[47]. Ebrahimi M., Beitollahi H., Rapid and sensitive quantification of isoproterenol in the presence of theophylline by CuO nanoflowers modified electrochemical sensor, Chemical Methodologies, 2021, 5:397 [Crossref], [Google scholar], [Publisher]
[48]. Aslan K., Wu M., Lakowicz J.R., Geddes C.D., Fluorescent core− shell Ag@ SiO2 nanocomposites for metal-enhanced fluorescence and single nanoparticle sensing platforms, Journal of the American Chemical Society, 2007, 129:1524 [Crossref], [Google scholar], [Publisher]
[49]. Laffafchi F., Tajbakhsh M., Sarrafi Y., Ghani M., Maleki B., Creatine@ SiO2@ Fe3O4 nanocomposite as an efficient sorbent for magnetic solid‐phase extraction of escitalopram and chlordiazepoxide from urine samples through quantitation via HPLC–UV, Journal of Separation Science, 2022, 45:3005 [Crossref], [Google scholar], [Publisher]
[50]. Hajizadeh F., Amiri A., Maleki B., Mohammadi Zonoz F., Fe3O4@ SiO2@ PAMAM-G2 nanocomposite as sorbent for the extraction and preconcentration of estradiol valerate drug from human plasma samples, Microchemical Journal, 2022, 175:107176 [Crossref], [Google scholar], [Publisher]
[51]. Karbasaki S.S., Bagherzade G., Maleki B., Ghani M., Magnetic Fe3O4@ SiO2 Core–Shell Nanoparticles Functionalized with Sulfamic Acid Polyamidoamine (PAMAM) Dendrimer for the Multicomponent Synthesis of Polyhydroquinolines and Dihydro-1H-Indeno [1, 2-b] Pyridines, Organic Preparations and Procedures International, 2021, 53:498 [Crossref], [Google scholar], [Publisher]
[52]. Tang L., Cheng J., Nonporous silica nanoparticles for nanomedicine application, Nano today, 2013, 8:290 [Crossref], [Google scholar], [Publisher]
[53]. Cao L., Zhang H., Cao C., Zhang J., Li F., Huang Q., Quaternized chitosan-capped mesoporous silica nanoparticles as nanocarriers for controlled pesticide release, Nanomaterials, 2016, 6:126 [Crossref], [Google scholar], [Publisher]
[54]. Bharti C., Nagaich U., Kumar Pal A., Gulati N., Mesoporous silica nanoparticles in target drug delivery system: A review. International journal of pharmaceutical investigation, 2015 5:124 [Crossref], [Google scholar], [Publisher]
[55]. Joshi S.S., Patil S.F., Lyer V., Mahumuni S., Radiation induced synthesis and characterization of copper nanoparticles, Nanostructured materials, 1998, 10:1135 [Crossref], [Google scholar], [Publisher]
[56]. Lee J.J., Lee S.J., Kim K., Surface-enhanced Raman scattering of self-assembled monolayers mediated by physisorbed Ag nanoparticles, Molecular Crystals and Liquid Crystals, 2004, 424:1 [Crossref], [Google scholar], [Publisher]
[57]. Khrizanforova M.N., Fedorenkoa S.V., Mustafina A.R., KholinK.V., Nizameeva I.R., StrekalovaS.O., Grinenkoa V.V., Gryaznova T.V., Zairova R.R., Mazzarob R., Morandiс V., Vomierob A., Budnikova Y.H., Silica-supported silver nanoparticles as an efficient catalyst for aromatic C–H alkylation and fluoroalkylation, Dalton Transactions, 2018, 47:9608 [Crossref], [Google scholar], [Publisher]
[58]. Martynova D.O., Kibis L.S., Stonkus O.A., Vodyankina O.V., Izaak T.I., Slavinskaya E.M., Boronin A.I., Synthesis and catalytic activity of porous blocked Ag/SiO 2 composites in low-temperature carbon monoxide oxidation, Kinetics and Catalysis, 2013, 54:492 [Crossref], [Google scholar], [Publisher]
[59]. Wang H., Quan L., Hu B., Wei G., Jiang X., Aerosol method assisted fabrication Ag@ SiO2 and efficient catalytic activity for reduction of 4‐nitrophenol, Micro & Nano Letters, 2017, 12:684 [Crossref], [Google scholar], [Publisher]
[60]. Zhao B., Dong Z., Wang Q., Xu Y., Zhang N., Liu W., Lou F., Wang Y., Highly efficient mesoporous core-shell structured ag@ sio2 nanosphere as an environmentally friendly catalyst for hydrogenation of nitrobenzene, Nanomaterials, 2020, 10:883 [Crossref], [Google scholar], [Publisher]
[61]. Vahdat S.M., Ghafouri Raz S., Baghery S., Application of nano SnO 2 as a green and recyclable catalyst for the synthesis of 2-aryl or alkylbenzoxazole derivatives under ambient temperature, Journal of Chemical Sciences, 2014, 126:579 [Crossref], [Google scholar], [Publisher]
[62]. Vahdat S.M., Chekin F., Hatami M., Khavarpour M., Baghery S., Roshan-Kouhi Z., Synthesis of polyhydroquinoline derivatives via a four-component Hantzsch condensation catalyzed by tin dioxide nanoparticles, Chinese Journal of Catalysis, 2013, 34:758 [Crossref], [Google scholar], [Publisher]
[63]. Maleki B., Baghayeri M., Vahdat S.M., Mohammadzadeh A., Akhoondi S., Ag@ TiO 2 nanocomposite; synthesis, characterization and its application as a novel and recyclable catalyst for the one-pot synthesis of benzoxazole derivatives in aqueous media, RSC Advances, 2015, 5:46545 [Crossref], [Google scholar], [Publisher]
[64]. Chekin F., Vahdat S.M., Asadi M.J., Green synthesis and characterization of cobalt oxide nanoparticles and its electrocatalytic behavior, Russian Journal of Applied Chemistry, 2016, 89:816 [Crossref], [Google scholar], [Publisher]
[65]. Yazdani S., Hatami M., Vahdat S.M., The chemistry concerned with the sonochemical-assisted synthesis of CeO_2/poly (amic acid) nanocomposites, Turkish Journal of Chemistry, 2014, 38:388 [Crossref], [Google scholar], [Publisher]
[66]. Vahdat S.M., Khavarpour M., Mohanazadeh F., A facile and highly efficient three component synthesis of pyran and chromene derivatives in the presence of nano SnO2 as a catalyst, J. Appl. Chem, 2015, 9:41 [Crossref], [Google scholar], [Publisher]
[67]. Qandaleea M., Hatami M., 2nd International Conference on Nanotechnology (ICN 2014), 9-11 July 2014, Istanbul, Turkey [Google scholar], [Publisher]
[68]. Masoudi A.A., Vahdat S.M., Khaksar S., One-Pot Synthesis of 1, 8-Dioxodecahydroacridines using Ag-TiO2 Nanocomposite as a Mild and Heterogeneous Catalytic System, Letters in Organic Chemistry, 2022, 19:999 [Crossref], [Google scholar], [Publisher]