- Synthesis, experimental and DFT studies on the crystal structure, FTIR, 1H NMR and 13C NMR spectra of drivatives of dihydropyridines
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Several derivatives of dihydropyridines are prepared through the condensation of aldehydes, dimedone and NH4OAc in H2O, in the presence of a catalytic amount of nano-Fe3O4. The crystalline products were characte
- Fekri, Leila Zare,Nikpassand, Mohammad
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- Acridinedione as selective flouride ion chemosensor: A detailed spectroscopic and quantum mechanical investigation
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The use of small molecules as chemosensors for ion detection is rapidly gaining popularity by virtue of the advantages it offers over traditional ion sensing methods. Herein we have synthesized a series of acridine(1,8)diones (7a-7l) and explored them for
- Iqbal, Nafees,Ali, Syed Abid,Munir, Iqra,Khan, Saima,Ayub, Khurshid,Al-Rashida, Mariya,Islam, Muhammad,Shafiq, Zahid,Ludwig, Ralf,Hameed, Abdul
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- Fe3O4@SiO2-MoO3H nanoparticles: A magnetically recyclable nanocatalyst system for the synthesis of 1,8-dioxo-decahydroacridine derivatives
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Molybdic acid-functionalized silica-coated nano-Fe3O4 particles (Fe3O4@SiO2-MoO3H) have been prepared as a novel heterogeneous acid catalyst using a facile process. The material was subsequ
- Kiani, Mahtab,Mohammadipour, Mohammad
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- Extraordinary catalytic activity of a Keplerate-type giant nanoporous isopolyoxomolybdate in the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxodecahydroacridines
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(NH4)42[Mo 72 VI Mo 60 V O372(CH3COO)30(H2O)72], a Keplerate-type giant nanoporous isopolyoxomolybdate, denoted as ({Mo132}
- Nakhaei, Ahmad,Davoodnia, Abolghasem,Morsali, Ali
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- An efficient one-pot three-component synthesis of fused 1,4-dihydropyridines using HY-zeolite
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A facile and convenient protocol was developed for the fast (2.5-3.5 h) and high yielding (70-90 %) synthesis of fused 1,4-dihydropyridines from dimedone in the presence of HY-zeolite as an efficient recyclable heterogeneous catalyst.
- Nikpassand, Mohammad,Mamaghani, Manouchehr,Tabatabaeian, Khalil
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- Eco-friendly and facile one-pot multicomponent synthesis of acridinediones in water under microwave
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A rapid, improved, and environmentally benign synthesis of 4-arylacridinediones is reported via one-pot multicomponent reaction of aromatic aldehydes, dimedone, and ammonium acetate in water without any catalyst under microwave irradiation. Excellent yiel
- Singh, Satish Kumar,Singh, Krishna Nand
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- Incorporation of Keggin-based H3PW7Mo5O40into bentonite: synthesis, characterization and catalytic applications
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The Keggin-based molybdo-substituted tungstophosphoric acid, H3[PW7Mo5O40]·12H2O, were synthesized and incorporated with a bentonite clay by using a wetness impregnation method. The catalysts were cha
- Aher, Dipak S.,Khillare, Kiran R.,Shankarwar, Sunil G.
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- An efficient one-pot synthesis of 1, 8-dioxodecahydroacridines using silica-supported polyphosphoric acid (PPA-SiO2) under solvent-free conditions
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Silica gel-supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the synthesis of 1, 8-dioxodecahydroacridines via one-pot three-component condensation of aryl aldehydes, dimedone, and ammonium acetate or 4-methyl a
- Moeinpour, Farid,Khojastehnezhad, Amir
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- Magnetically separable recyclable nano-ferrite catalyst for the synthesis of acridinediones and their derivatives under solvent-free conditions
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Catalytic activity of nano-ferrite is explored in the synthesis of acridinedione and their derivatives under benign conditions; a greener protocol is reported in terms of excellent yield and recyclability under solvent-free reactions without using any add
- Mahesh, Palla,Guruswamy, Kolakaluri,Diwakar, Bhagavathula Subrahmanya,Devi, Bhoomireddy Rama,Murthy, Yellajyosula Lakshmi Narasimha,Kollu, Pratap,Pammi, Sri Venkata Narayan
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- One pot synthesis of acridine analogues from 1,2-diols as key reagents
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Lead tetraacetate have been demonstrated to be efficient, low cost and mild reagents for the one pot synthesis of acridine derivatives from a variety of 1,2-diols. 1,2-Diols are oxidised in situ to aldehydes, which in turn undergo reaction with dimedone and ammonium acetate to yield acridine derivatives. The attractive features of this process are mild reaction conditions, short reaction times, broad functional group tolerance, easy isolation of products and excellent yields. Thus, the current method utilises 1,2-diols instead of benzaldehydes to synthesise acridines derivatives.
- Jagadishbabu, Narasashetty,Shivashankar, Kalegowda
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- Evaluation of sodium acetate trihydrate-urea des as a benign reaction media for the Biginelli reaction. Unexpected synthesis of methylenebis(3-hydroxy-5,5-dimethylcyclohex-2-enones), hexahydroxanthene-1,8-diones and hexahydroacridine-1,8-diones
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In this work, the low melting mixture sodium acetate trihydrate-urea was synthesized and the eutectic composition was determined and characterized using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The physical properties
- Navarro, Camilo A.,Sierra, Cesar A.,Ochoa-Puentes, Cristian
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- An Efficient One-Pot Four-Component Synthesis of 9-Aryl-Hexahydroacridine-1,8-Dione Derivatives in the Presence of a Molecular Sieves Supported Iron Catalyst
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Abstract: A series of 9-aryl-hexahydroacridine-1,8-diones are synthetized with good to excellent yields (50–99%) via a one-pot four-component reaction of dimedone, aromatic aldehydes and ammonium acetate in the presence of 4?? molecular sieves modified wi
- Magyar, ágnes,Hell, Zoltán
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- A Novel Reaction of Aldeoxime with Dimedone under Microwave Irradiation
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The reaction of aldeoxime with dimedone and ammonium acetate in glycol under microwave irradiation has been carried out, elimination and cyclization happened and acridine derivatives were obtained. The structure of the product has been thoroughly studied by x-ray crystallographic analysis.
- Tu, Shujang,Gao, Yuan,Miao, Chunbao,Li, Tuanjie,Zhang, Xiaojing,Zhu, Songlei,Fang, Fang,Shi, Daqing
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- Gd0.7Sr0.3MnO3 perovskite as a novel and efficient catalyst for synthesis of dioxodecahydroacridine derivatives
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In this work, perovskite-type material Gd0.7Sr0.3MnO3 was fabricated by sol-gel method. To prepare this nanopowder, metal salts, citric acid as the complexing agent, and water as solvent were used. A series of common analy
- Tavakkoli, Haman,Sanaeishoar, Tayebeh,Moeinirad, Maryam
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- Ferric hydrogen sulfate supported on silica-coated nickel ferrite nanoparticles as new and green magnetically separable catalyst for 1,8 dioxodecahydroacridine synthesis
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A new magnetically separable catalyst consisting of ferric hydrogen sulfate supported on silica-coated nickel ferrite nanoparticles was prepared. The synthesized catalyst was characterized using vibrating sample magnetometry, X-ray diffraction, transmissi
- Khojastehnezhad, Amir,Rahimizadeh, Mohammad,Eshghi, Hossein,Moeinpour, Farid,Bakavoli, Mehdi
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- Carbon-based solid acid as an efficient and reusable catalyst for the synthesis of 1,8-dioxodecahydroacridines under solvent-free conditions
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Carbon-based solid acid catalyst was found to be highly efficient, eco-friendly and recyclable heterogeneous catalyst for the multicomponent reaction of dimedone, aromatic aldehydes, and a nitrogen source (ammonium acetate or aromatic amines) under solven
- Davoodnia, Abolghasem,Khojastehnezhad, Amir,Tavakoli-Hoseini, Niloofar
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- An efficient 'on-water' synthesis of 1,4-dihydropyridines using Fe3O4@SiO2nanoparticles as a reusable catalyst
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An 'on-water', efficient, high yielding, expeditious method has been developed for the synthesis of 1,4-dihydropyridine (1,4-DHP) derivatives via an one-pot multi-component condensation of dimedone or 4-hydroxycoumarine, aldehydes, and ammonium acetate using Fe3O4@SiO2nanoparticles as a recyclable heterogeneous catalyst. This method takes advantage of the fact that water, a green solvent is used in combination with Fe3O4@SiO2nanoparticles as catalyst which can be easily recovered magnetically and reused for further runs.
- Dam, Binoyargha,Nandi, Sibaji,Pal, Amarta Kumar
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- Nanocrystalline TiO2, via green combustion synthesis, as an efficient and reusable catalyst for the preparation of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines
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Nanocrystalline TiO2 is synthesized using a green combustion method and used as a recyclable catalyst for the one-pot multicomponent synthesis of 1,8-dioxodecahydroacridines and 1,8-dioxooctahydroxanthenes, under solvent-free conditions. This m
- Eidi, Esmaiel,Kassaee, Mohammad Zaman,Nasresfahani, Zahra
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- Synthesis of dibenzoxanthene and acridine derivatives catalyzed by 1,3-disulfonic acid imidazolium carboxylate ionic liquids
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New members of 1,3-disulfonic acid imidazolium carboxylate ionic liquids [DSIM][X] (where X = [CH3COO]-, [CCl3COO]-, [CF3COO]-) were prepared and characterized by 1H NMR,13
- Dutta, Arup Kumar,Gogoi, Pinky,Borah, Ruli
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- Synthesis of 9-Arylhexahydroacridine-1,8-diones Using Phosphate Fertilizers as Heterogeneous Catalysts
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A new strategy has been proposed for the synthesis of 9-arylhexahydroacridine-1,8-diones by three-component condensation of aromatic aldehydes with 5,5-dimethylcyclohexane-1,3-dione and ammonium acetate in ethanol, using nontoxic, available, and inexpensi
- Chehab,Merroun,Ghailane,Ghailane,Boukhris,Akhazzane,Kerbal,Souizi
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- Silica-supported preyssler nanoparticles catalyzed simple and efficient one-pot synthesis of 1,8-dioxodecahydroacridines in aqueous media
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Silica-supported Preyssler nanoparticles (SPNP) was found to be an inexpensive and effective catalyst for the rapid, one-pot three-component synthesis of N-substituted 1,8-dioxodecahydroacridines in high yields, with easy workup procedure. The nanocatalys
- Javid, Ali,Khojastehnezhad, Amir,Heravi, Majid,Bamoharram, Fatemeh F.
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- Mesoporous silica nanoparticles in an efficient, solvent-free, green synthesis of acridinediones
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Mesoporous silica nanoparticles (MSNs) are employed in an efficient, biocompatible and neutral catalytic green synthesis of acridinediones, through one-pot three-component reaction of dimedone with aromatic aldehydes, in the presence of a nitrogen source
- Nasresfahani, Zahra,Kassaee
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- Multicomponent synthesis of dihydropyridines catalyzed by l-proline
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Multicomponent synthesis of mono and bis 4-substituted-1,4-dihydropyridines from aldehydes, dimedone and ammonium acetate in the presence of an efficient recyclable catalyst, l-proline, in high yield and short reaction time is reported.
- Zare, Leila,Nikpassand, Mohammad
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- ZnII doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-SMTU-ZnII): A novel, green and magnetically recyclable bifunctional nanocatalyst for the one-pot multi-component synthesis of acridinediones under solvent-free conditions
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ZnII doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-SMTU-ZnII) was prepared for the first time as a stable, long-lived, highly efficient and exceptional reusable magnetic nanocatalyst for the one-pot multi-component synthesis of acridinediones as an important class of heterocyclic compounds. The synthesized catalyst was characterized by various spectroscopic and microscopic techniques such as Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, Brunauer, Emmett and Teller (BET) surface area analysis, temperature programmed desorption (TPD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), vibrating sample magnetometry (VSM), inductively coupled plasma atomic emission spectroscopy (ICP-OES) and CHNS analysis. The results of characterizations showed the superparamagnetic nature of the catalyst with an average particle size of 20-60 nm which is plate-like in shape. Also, the results of the TPD analysis showed that the nanocatalyst has both acidic sites (site density: 22.66 mmol g-1) and basic sites (site density: 8.49 mmol g-1), and can act as a bifunctional nanocatalyst. The loading amount of ZnII (doped and immobilized) on functionalized magnetic hydrotalcite was indicated to be 4 mmol g-1, obtained from the ICP-OES analysis. The catalytic activity of this new magnetic nanocatalyst (Fe3O4/HT-SMTU-ZnII) was examined in the multi-component reaction of aromatic aldehydes, dimedone, and various primary amines or NH4+ under solvent-free conditions towards the preparation of acridinedione derivatives in a short period of time. In all the cases, the catalyst could be easily recovered magnetically for at least six runs and the obtained product was isolated using a simple work-up procedure. In our protocol, the solvent-free conditions avoid the problems such as cost, handling, safety and pollution which are related to solvent use. The characteristics of the present methodology make the reaction suitable for scale-up and commercialization.
- Zarei,Akhlaghinia
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- Benzyl alcohol-based synthesis of mono- and bis-dihydropyridines in the presence of Al(HSO4)3, sodium nitrite, and sodium bromide under solvent-free conditions
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Dihydropyridines were synthesized in good to excellent yields in the presence of NaNO2, Al(HSO4)3, and a catalytic amount of NaBr at room temperature. Low cost, the use of available reagents, simple methodology, and easy work-up procedure make this method attractive for organic synthesis.
- Fekri,Nikpassand
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- FSG-Hf(NPf2)4 catalyzed, environmentally benign synthesis of 1,8-dioxo-decahydroaridines in water-ethanol
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An efficient, eco-friendly and simple work-up procedure for the synthesis of 1,8-dioxo-decahydroacridines has been developed through one-pot condensation reaction of aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedion and different aromatic amine or ammon
- Hong, Mei,Xiao, Guomin
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- Facile route to synthesize Fe3O4?acacia-SO3H nanocomposite as a heterogeneous magnetic system for catalytic applications
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In this work, a novel catalytic system for facilitating the organic multicomponent synthesis of 9-phenyl hexahydroacridine pharmaceutical derivatives is reported. Concisely, this catalyst was constructed from acacia gum (gum arabic) as a natural polymeric
- Eivazzadeh-Keihan, Reza,Esmaeili, Mir Saeed,Maleki, Ali,Shalan, Ahmed Esmail,Taheri-Ledari, Reza,Varzi, Zahra
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- DABCO–PEG ionic liquid-based synthesis of acridine analogous and its inhibitory activity on alkaline phosphatase
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In world, many people struggle with viral, parasitic, bacterial, cancer, and other diseases. Therefore, numerous chemists seek to develop less toxic, more selective, and effective medicines. Most therapeutic medicines are based on inhibition of specific e
- Faisal, Muhammad,Shahid, Shereena,Ghumro, Sarfaraz Ali,Saeed, Aamer,Larik, Fayaz Ali,Shaheen, Zeenat,Channar, Pervaiz Ali,Fattah, Tanzeela Abdul,Rasheed, Samina,Mahesar, Parvez Ali
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- Catalytic synthesis of fused 1,4-dihydropyridines and 1,4-dihydropyridine derivatives using preyssler heteropolyacids catalyst
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An efficient and convenient method for the synthesis of 1,4-dihydropyridines from β-dicarbonyl compounds, aldehydes, and ammonium acetate and the synthesis of fused 1,4-dihydropyridines from dimedone in the presence of Preyssler heteropolyacid catalyst ar
- Gharib, Ali,Jahangir, Manouchehr,Roshani, Mina,Scheeren
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- An efficient and green preparation of 9-arylacridine-1,8-dione derivatives
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9-Arylacridine-1,8-dione derivatives were prepared in an ionic liquid medium in the presence of CeCl3 · 7H2O through an one-pot procedure. The method presented here has the advantages of environmental benignancy, good-to-excellent yi
- Fan, Xuesen,Li, Yanzhen,Zhang, Xinying,Qu, Guirong,Wang, Jianji
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- Green and cost effective protocol for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines by using sawdust sulphonic acid
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Abstract: A heterogeneous solid acid catalyst has been prepared by covalent grafting of chlorosulphonic acid on the surface of sawdust (SD-OSO3H). The structure of the prepared catalyst was assessed by FT-IR, solid state CP/MAS 13C-N
- Karhale, Shrikrishna,Patil, Monika,Rashinkar, Gajanan,Helavi, Vasant
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- Microwave induced new route to acridine and quinazoline derivatives using TLC plates
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Microwave (MW) assisted synthesis of acridine and quinazoline derivatives was performed on thin layer chromatography (TLC) plates. This versatile, simple and economical green methodology is readily amenable to parallel synthesis of acridine and quinazoline compound libraries.
- Kidwai,Saxena,Mohan
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- A convenient synthesis of 9-aryl-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-diones under microwave irradiation without solvent
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A convenient synthetic method for the title compounds are described. Heating 1, 2 and 3 under microwave irradiation for 3-5 min to afford 4. The structure of the compound 4c has been thoroughly studied by X-ray crystallographic analysis.
- Tu, Shu-Jiang,Lu, Zaisheng,Shi, Daqing,Yao, Changsheng,Gao, Yuan,Guo, Cheng
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- Efficient synthesis of acridinediones in aqueous media
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An efficient synthesis of acridinediones in two steps have been achieved using water as a reaction media without chromatographic purification. First step involves the reaction of dimedone with ammonium acetate to yield enaminone in water which on further
- Tiwari, Keshri Nath,Uttam, Mane Rajendra,Kumari, Puja,Vatsa, Piyush,Prabhakaran
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- Synthesis of 1,8-Dioxo-decahydroacridine Derivatives via Ru-Catalyzed Acceptorless Dehydrogenative Multicomponent Reaction
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A Ru-catalyzed acceptorless dehydrogenative multicomponent reaction has been developed. This reaction offers a cost-effective and simple operational strategy to synthesize biologically active 1,8-dioxodecahydroacridine derivatives. The protocol provides a wide range of substrate scope and various functional groups are also well tolerated under the reaction condition. To shed light on the mechanistic and kinetic study, some controlled experiments and deuterium labeling experiments were executed. A time-dependent product distribution experiment is also presented and the reaction scale-up is performed to highlight the practical utility of this strategy.
- Biswas, Nandita,Srimani, Dipankar
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p. 9733 - 9743
(2021/07/20)
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- Ag/CuO/MCM-48 As a potential catalyst for the synthesis of symmetrical and unsymmetrical polyhydroquinolines
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Ag/CuO/MCM-48 as a heterogeneous catalyst was efficiently employed in the synthesis of diversely substituted symmetrical and unsymmetrical polyhydroquinoline by a multi-component reaction of arylaldehyde, dimedone, ethyl cyanoacetate and ammonium acetate. This novel method is simple, environmentally friendly, rapid, uses a recyclable catalyst and produces the products in high to excellent yields (83-97%) and lower reaction times (17-35 min). The catalyst can be reused at least 10 times without any appreciable decrease in its catalytic activities.
- Bazdid-Vahdaty, Narges,Khalili, Behzad,Mamaghani, Manouchehr,Tavakoli, Fateme
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p. 5136 - 5141
(2021/07/13)
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- Preparation, Antibacterial Activity, and Catalytic Application of Magnetic Graphene Oxide-Fucoidan in the Synthesis of 1,4-Dihydropyridines and Polyhydroquinolines
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Polymer-coated magnetic nanoparticles are emerging as a useful tool for a variety of applications, including catalysis. In the present study, fucoidan-coated magnetic graphene oxide was synthesized using a natural sulfated polysaccharide. The prepared BaF
- Amirnejat, Sara,Javanshir, Shahrzad,Nosrati, Aliakbar
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p. 1186 - 1196
(2021/12/31)
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- Eco-friendly, ultrasound-assisted, and facile synthesis of one-pot multicomponent reaction of acridine-1,8(2H,5H)-diones in an aqueous solvent
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A one-pot, multistep synthesis of acridine-1,8(2H,5H)-diones (4a–m) was achieved by three-component reaction of dimedone (1) with an aromatic aldehyde (2a–m) and an ammonium acetate (3) using water as a green solvent without any catalyst and a simple, eas
- Chavan, Pravin N.,Pansare, Dattatraya N.,Shelke, Rohini N.
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p. 822 - 828
(2019/05/15)
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- Carbon-based nanocatalyst:?An efficient and recyclable heterogeneous catalyst for one-pot synthesis of gem-bisamides, hexahydroacridine-1,8-diones and 1,8-dioxo-octahydroxanthenes
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Abstract: In this abstract, we discuss the progress related to sulfonated carbon-based materials in various acid-catalyzed organic transformations which are then further utilized in medicinal field, laboratories and industries. A simple and novel methodol
- Kour, Jaspreet,Gupta, Monika,Chowhan, Bushra,Gupta, Vivek K.
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p. 2587 - 2612
(2019/07/23)
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- Synergistic catalytic effect between ultrasound waves and pyrimidine-2,4-diamine-functionalized magnetic nanoparticles: Applied for synthesis of 1,4-dihydropyridine pharmaceutical derivatives
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A convenient strategy for synthesis of the various derivatives of 1,4-dihydropyridine (1,4-DHP), as one of the most important pharmaceutical compounds, is presented in this study. For this purpose, firstly, magnetic iron oxide nanoparticles (Fe3O4 NPs) were fabricated and suitably coated by silica network (SiO2) and trimethoxy vinylsilane (TMVS). Then, their surfaces were well functionalized with pyrimidine-2,4-diamine (PDA) as the main active sites for catalyzing the synthesis reactions. In this regard, the performance of three different methods including reflux, microwave (MW) and ultrasound wave (USW) irradiations have been comparatively monitored via studying various analyses on the fabricated nanocatalyst (Fe3O4/SiO2-PDA). Concisely, high efficiency of the USW irradiation (in an ultrasound cleaning bath with a frequency of 50 kHz and power of 250 W/L) has been well proven through the investigation of the main factors such as excellent surface-functionalization, core/shell structure conservation, particle uniformity, close size distribution of the particles, and great inhibition of the particle aggregation. Then, the effectiveness of the USW irradiation as a promising co-catalyst agent has been clearly demonstrated in the 1,4-DHP synthesis reactions. It has been concluded that the USW could provide more appropriate conditions for activation of the catalytic sites of Fe3O4/SiO2-PDA NPs. However, high reaction yields (89%) have been obtained in the short reaction times (10 min) due to the substantial synergistic effect between the presented nanocatalyst and USW.
- Taheri-Ledari, Reza,Rahimi, Jamal,Maleki, Ali
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- The First Recyclable, Nanocrystalline CdS Thin Film Mediated Eco-benign Synthesis Of Hantzsch 1, 4 Dihyropyridines, 1, 8-Dioxodecahydroacridine and Polyhydroquinolines derivatives
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In the present study, we report a recyclable, nanocrystalline CdS thin film mediated efficient one-pot, three component synthesis of Hantzsch 1, 4 Dihydropyridine in good yields. The catalyst is also effective for the efficient synthesis of Polyhydroquinoline and 1, 8-dioxodecahydroacridine derivatives in good to excellent yields. The CdS thin film catalyst was prepared by chemical bath deposition (CBD) technique. The cadmium sulphide thin film was characterized by powder XRD and FT-IR studies. The average crystallite size (D) was calculated from powder XRD by using Scherrer formula and SEM analysis. The elemental composition of the CdS thin film was established by EDS analysis. The effect of temperature, substituent's, catalyst loading and mole ratio on the reaction was also studied. All the products were thoroughly characterized by 1H-NMR, 13C-NMR, FT-IR, Mass spectral and CHN analysis. A plausible mechanism for the CdS thin film catalyzed synthesis of 1, 4 DHP's is proposed. The heterogeneous catalyst could be easily recovered from the reaction mixture and successively reused at least five times without loss of activity.
- Lavanya,Venkatapathy,Magesh,Perumal,Sathishkumar,Amudha
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- Acridine-based (thio)semicarbazones and hydrazones: Synthesis, in vitro urease inhibition, molecular docking and in-silico ADME evaluation
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Urease is a bacterial enzyme that is responsible for virulence of various pathogenic bacteria such as Staphylococcus aureus, Proteus mirabilis, Klebsiella pneumoniae, Ureaplasma urealyticum, Helicobacter pylori and Mycobacterium tuberculosis. Increased urease activity aids in survival and colonization of pathogenic bacteria causing several disorders especially gastric ulceration. Hence, urease inhibitors are used for treatment of such diseases. In search of new molecules with better urease inhibitory activity, herein we report a series of acridine derived (thio)semicarbazones (4a-4e, 6a-6l) that were found to be active against urease enzyme. Molecular docking studies were carried out to better comprehend the preferential mode of binding of these compounds against urease enzyme. Docking against urease from pathogenic bacterium S. pasteurii was also carried out with favorable results. In silico ADME evaluation was done to determine drug likeness of synthesized compounds.
- Isaac, Ibanga Okon,al-Rashida, Mariya,Rahman, Shafiq Ur,Alharthy, Rima D.,Asari, Asnuzilawati,Hameed, Abdul,Khan, Khalid Mohammed,Iqbal, Jamshed
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- Catalytic performance of Preyssler heteropolyacids and synthesis, experimental, theoretical characterizations, fluorescence properties of 1,8-dioxodecahydroacridine derivative
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Two Preyssler heteropolyacids, H14[NaP5W29MoO110] (HPA1) and H14[NaP5W30O110] (HPA2) have been studied for catalytic performance in the synthesis of 1,8-dioxodecahydro
- Baradaran-Sirjani, Zahra,Roshani, Mina,Khashi, Maryam,Ali Beyramabadi
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p. 715 - 721
(2019/05/22)
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- Catalytic application of sulfonic acid-functionalized titana-coated magnetic nanoparticles for the preparation of 1,8-dioxodecahydroacridines and 2,4,6-triarylpyridines via anomeric-based oxidation
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We have developed green, efficient and powerful protocols for the preparation of 2,4,6-triarylpyridines and 1,8-dioxodecahydroacridines in the presence of Fe3O4@TiO2@O2PO2(CH2)2NHSO3H as a sulfonic acid-functionalized titana-coated magnetic nanoparticle catalyst under mild and solvent-free reaction conditions. These protocols furnished the desired products in short reaction times with good to high yields (20–40?min and 80–86% in the case of 2,4,6-triarylpyridines; 15–90?min and 80–93% in the case of 1,8-dioxodecahydroacridines). The final step of the mechanistic route in the synthesis of 2,4,6-triarylpyridines proceeds via an anomeric-based oxidation. Also, the nanomagnetic core–shell catalyst can be recycled and reused in both cases of the scrutinized one-pot multicomponent reactions with high turnover number and turnover frequency.
- Zolfigol, Mohammad Ali,Karimi, Fatemeh,Yarie, Meysam,Torabi, Morteza
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- N-butylpyridinium heptachlorodialuminate: A convenient catalyst for the synthesis of acridine 1,8-diones derivatives by microwave assisted hantzsch reaction
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Acridine-l,8-dione derivatives have been synthesized conveniently by the multicomponent condensation of dimedone, aldehydes, and ammonium acetate in the presence of a catalytic amount of N-butylpyridinium heptachlorodialuminate. This fascinating microwave
- Shirole,Bhalekar,Shelke
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p. 1430 - 1435
(2019/05/22)
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- N-Propyl benzoguanamine sulfonic acid supported on magnetic Fe3O4 nanoparticles: A novel and efficient magnetically heterogeneous catalyst for the synthesis of 1,8-dioxo-decahydroacridine derivatives
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In this study, N-propyl-benzoguanamine-SO3H-stabilized magnetic nanoparticles were prepared as a new heterogeneous acid catalyst in accordance with the principles of green chemistry. The new catalyst is used for the synthesis of derivatives of
- Gholami Dehbalaei, Masoumeh,Foroughifar, Naser,Pasdar, Hoda,Khajeh-Amiri, Alireza
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supporting information
p. 327 - 335
(2017/12/28)
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- Choline chloride catalyzed eco-friend and effective one-pot synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline via Hantzsch type reaction
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Choline chloride was utilized to efficiently catalyzed Hantzsch type reaction for the synthesis of 9-arylacridine-1,8-dione and hexahydroquinoline derivatives. The optimized catalytic system benefits from facile operation and separation procedures, in goo
- Mao, Shengxue,Li, Fei,Lv, Yue,Lv, Chengwei,Yu, Shijun
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p. 1895 - 1902
(2017/10/24)
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- Hollow Fe3O4@DA-SO3H: an efficient and reusable heterogeneous nano-magnetic acid catalyst for synthesis of dihydropyridine and dioxodecahydroacridine derivatives
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Abstract: In this work, for the first time, a highly stable and efficient super-paramagnetic catalyst, H-Fe3O4@DA-SO3H, involving hollow morphology of Fe3O4 as core and dopamine as shell was prepared
- Mirhosseyni, Marzie sadat,Nemati, Firouzeh,Elhampour, Ali
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p. 791 - 801
(2017/02/26)
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- Computational investigations on structural and electronic properties of CuI nanoparticles immobilized on modified poly(styrene-co-maleic anhydride), leading to an unexpected but efficient catalyzed synthesis of 1,4-dihydropyridine via Hantzsch pyridine synthesis
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A, quantitative description for the interaction of Cu(I) with poly(styrene-co-maleic anhydride) modified with 4-aminopyridine (denoted as CuI/SMI complex) is presented using density functional theory (DFT) and quantum theory of atoms in molecules (QTAIM) approaches. Topological analysis of electron density revealed the existence of effective interactions between Cu(I) ions and the nitrogen in the pyridine ring. Interestingly, the results also showed that there is considerable interaction between Cu(I) and the oxygen of the carbonyl motif in the SMI ligand. Thus, CuI/SMI was examined as a heterogeneous and recyclable catalyst in Hantzsch pyridine synthesis under solvent-free conditions, affording diverse 1,4-dihydropyridines (1,4-DHPs) in excellent yields with relatively short reaction times.
- Heravi, Majid M.,Hosseinnejad, Tayebeh,Nazari, Niousha
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p. 530 - 536
(2017/05/31)
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- Green and efficient synthesis of acridine-1,8-diones and hexahydroquinolines via a KH2PO4 catalyzed Hantzsch-type reaction in aqueous ethanol
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Abstract: A simple, clean, and economical methodology for the synthesis of acridine-1,8-dione and hexahydroquinoline derivatives via Hantzsch-type condensation has been described. This study highlights the development of a new green pathway for the prepar
- Yü, Shi-Jun,Wu, Si,Zhao, Xin-Min,Lü, Cheng-Wei
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p. 3121 - 3130
(2017/04/19)
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- Covalently anchored sulfamic acid on cellulose as heterogeneous solid acid catalyst for the synthesis of structurally symmetrical and unsymmetrical 1,4-dihydropyridine derivatives
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A novel heterogeneous solid acid catalyst has been prepared by covalent grafting of chlorosulphonic acid on amino-functionalized cellulose (Cell-Pr-NHSO3H). The structure of the catalyst was assessed by FT-IR, solid-state CP/MAS 13C-
- Karhale, Shrikrishna,Bhenki, Chandrakant,Rashinkar, Gajanan,Helavi, Vasant
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supporting information
p. 5133 - 5141
(2017/07/12)
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- One-pot synthesis of 1,8-dioxo-decahydroacridine derivatives by using nano-Fe2O3 as a highly efficient and reusable heterogeneous catalyst under solvent-free conditions
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A simple and convenient one-step method for synthesis of 1,8-dioxo-decahydroacridines via a multi-component reaction of dimedone, aromatic aldehydes and ammonium acetate catalyzed by nano-Fe2O3 as a catalyst was investigated. The str
- Hatamjafari, Farhad,Hosseinnezhad Lazarjani, Omid
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p. 255 - 260
(2017/07/22)
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- Solvent-free synthesis of polyhydroquinoline and 1,8-dioxodecahydroacridine derivatives through the Hantzsch reaction catalyzed by a natural organic acid: A green method
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Solvent-free and high yielding one-pot synthesis of 1,8-dioxodecahydroacridine and polyhydroquinoline derivatives have been described through Hantzsch condensation of various aldehydes, ammonium acetate with cyclic 1,3-dicarbonyl compounds and ethyl aceto
- Sehout, Imène,Boulcina, Raouf,Boumoud, Boudjemaa,Boumoud, Taous,Debache, Abdelmadjid
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supporting information
p. 1185 - 1191
(2017/06/09)
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- Betainium-based ionic liquids catalyzed multicomponent Hantzsch reactions for the efficient synthesis of acridinediones
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In this study, a series of betainium-based ionic liquids with various anions have been synthesized and their catalytic performances for the Hantzsch reactions have been investigated. It is shown that these ionic liquids have high selectivity for the one-p
- Zhu, Anlian,Liu, Ruixia,Du, Chunyan,Li, Lingjun
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p. 6679 - 6684
(2017/02/05)
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- Synthesis of 9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8(2Н,5Н)-diones
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The reaction in a mixture of 1,3-cyclohexanedione (dimedone), arylaldehyde, and ammonium acetate at 160°C during 10–15 min in the absence of solvent leads to the formation of 9-aryl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-diones. The structure of the pr
- Nasakin,Kazantseva,Gein
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p. 154 - 155
(2017/07/07)
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- Nano-zirconia as an excellent nano support for immobilization of sulfonic acid: A new, efficient and highly recyclable heterogeneous solid acid nanocatalyst for multicomponent reactions
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Nano-zirconia-supported sulfonic acid [nano-ZrO2-SO3H (n-ZrSA)] is synthesized by immobilizing sulfonic acid groups on the surface of nano zirconium dioxide to produce a novel heterogeneous reusable solid acid nanocatalyst. This new nanocatalyst is characterized by FT-IR spectroscopy, thermogravimetric analysis (TGA), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), the Hammett acidity function and pH analysis. The introduced nano-zirconia-supported sulfonic acid is used as an efficient and recyclable catalyst for different heterocyclic multicomponent reactions such as the synthesis of hexahydroquinoline, 1,8-dioxo-decahydroacridine, polyhydroquinoline and 1,8-dioxo-octahydroxanthene derivatives. Optimization of the reaction conditions was studied using a central composite design (CCD) which is one of the most widely used response surface methodologies. The newly prepared heterogeneous solid acid nanocatalyst is easily separated and reusable for five cycles without any apparent loss of its catalytic activity, which confirmed the stability of the covalent bonding of the sulfonic acid groups. n-ZrSA has advantages such as its low cost, low toxicity, ease of preparation, good stability, high reusability and operational simplicity.
- Amoozadeh, Ali,Rahmani, Salman,Bitaraf, Mehrnoosh,Abadi, Fatemeh Bolghan,Tabrizian, Elham
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p. 770 - 780
(2016/01/12)
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- Synthesis of 1,4-dihydropyridine esters using low-melting sugar mixtures as green solvents
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Several low-melting sugar mixtures (LMMs) were synthesized and used for preparation of 1,4-dihydropyridines with aldehydes, 1,3-dicarbonyl compounds, and a nitrogen source as starting materials. Good yields, low reaction times, recyclability of LMMs, and catalyst-free methodology are some of the highlights of this new protocol.
- Kumar, J. Ashwin,Shridhar, Gomathi,Ladage, Savita,Ravishankar, Lakshmy
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supporting information
p. 1989 - 1998
(2016/12/09)
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- SnCl4-functionalized nano-Fe3O4 encapsulated-silica particles as a novel heterogeneous solid acid for the synthesis of 1,4-dihydropyridine derivatives
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A novel type of green heterogeneous solid acid was prepared by the immobilization of SnCl4 on the surface of Fe3O4@SiO2 (Fe3O4@SiO2-SnCl4) and characterized by Fourier
- Bamoniri, Abdolhamid,Fouladgar, Sara
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p. 78483 - 78490
(2015/10/05)
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- Salicyldimine-based Schiff's complex of copper(II) as an efficient catalyst for the synthesis of nitrogen and oxygen heterocycles
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In the present paper, we have reported the synthesis of an imine-based silica-functionalized copper(II) catalyst using salicyldehyde as a ligand. Furthermore, the catalyst is characterized through various spectroscopic techniques, namely FTIR, XRD, TGA, E
- Gupta, Manjulla,Gupta, Monika,Rajnikant,Gupta, Vivek K.
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p. 3578 - 3587
(2015/05/20)
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- TiO2-coated magnetite nanoparticle-supported sulfonic acid as a new, efficient, magnetically separable and reusable heterogeneous solid acid catalyst for multicomponent reactions
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TiO2-coated magnetite nanoparticle-supported sulfonic acid (nano-Fe3O4-TiO2-SO3H (n-FTSA)) is synthesized by immobilizing -SO3H groups on the surface of nano-Fe3O4-TiO2. This catalyst can be isolated readily after completion of the reaction by an external magnetite field. The obtained results demonstrate the use of coated magnetite nanoparticles as an excellent new support for the facile recovery of sulfonic acid catalysts. The newly synthesized heterogeneous solid acid is characterized by X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FE-SEM), a vibrating sample magnetometer (VSM), FT-IR spectroscopy, thermal gravimetric analysis (TGA), Hammett acidity function and pH analysis. Significantly, the as-prepared n-FTSA exhibits a high catalytic activity for the synthesis of heterocyclic compounds such as 1,8-dioxo-decahydroacridine, 1,8-dioxo-octahydroxantene, hexahydroquinoline and polyhydroquinoline derivatives in multicomponent reactions. The magnetically separated n-FTSA can be magnetically separated and reused for several times without significant loss of activity. This confirms that the sulfonic acid groups have high stability. TiO2-coated magnetite nanoparticle-supported sulfonic acid has advantages such as low cost and toxicity, ease of preparation, magnetic separation, high stability, reusability and operational simplicity. This journal is
- Amoozadeh, Ali,Golian, Sanaz,Rahmani, Salman
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p. 45974 - 45982
(2015/06/08)
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- P-Sulfonic acid calix[4]arene as an efficient and reusable catalyst for the synthesis of acridinediones and xanthenes
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p-Sulfonic acid calix[4]arene has been found to be an efficient catalyst for the synthesis of acridinediones and xanthenes under mild conditions in excellent yields. The present approach offers the advantages of simple methodology, short reaction time, an
- Baghbanian, Seyed Meysam,Khanzad, Gonja,Vahdat, Seyed Mohammad,Tashakkorian, Hamed
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p. 9951 - 9966
(2016/01/15)
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- Ionic liquid immobilized on Fe3O4 nanoparticles: A magnetically recyclable heterogeneous catalyst for one-pot three-component synthesis of 1,8- dioxodecahydroacridines
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A magnetically recoverable nanocatalyst based on 1-methylimidazolium hydrogen sulfate ionic liquid has been synthesized by reaction of 1-methylimidazole with 3-(trimethoxysilyl)propyl chloride group, leading to formation of 1-methyl-3- (triethoxysilyl)propyl imidazolium chloride ([pmim]Cl). The ionic liquid was anchored onto silica-coated magnetic Fe3O4 particles, and Cl- anion exchange by treatment with H2SO4 afforded the corresponding immobilized ionic liquid MNP- [pmim]HSO4. The synthesized catalyst was characterized by various techniques such as Fourier-transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD) analysis, scanning electron microscopy (SEM), transmission electron microscopy (TEM), (differential) thermogravimetry (TG/DTG), CHN analysis, and vibratingsample magnetometry (VSM), revealing the superparamagnetic nature of the particles. From electron microscopy (SEM and TEM) studies it can be inferred that the particles were mostly spherical in shape with average size of 20 nm. The loading amount of ionic liquid supported on the magnetic particles was indicated to be 0.98 mmol/g by the results of elemental and thermogravimetric analyses (CHN and TG). The catalytic activity of the supported ionic liquid was examined in synthesis of 1,8-dioxodecahydroacridines by condensation reaction of cyclic diketones with aromatic aldehydes and ammonium acetate or primary amines under solvent-free conditions. The catalyst could be easily recovered by applying an external magnetic field and reused for at least nine runs without deterioration in catalytic activity.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Ghobadi, Neda
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p. 9979 - 9992
(2016/01/15)
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- Alkaline earth metal catalyzed, one-pot, multi-component approach for the synthesis of dihydropyridine, acridine and xanthene derivatives in water
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Ca(II) catalyzed one-pot multicomponent approach for the biologically important diverse heterocyclic compounds such as hexahydroxanthene diones, dihydropyridines and octahydroacridine diones has been described in water. Use of environmentally benign catal
- Yaragorla, Srinivasarao,Singh, Garima,Pareek, Abhishek
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p. 1321 - 1326
(2015/11/10)
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- Synthesis of thioacridine derivatives using Lawesson's reagent
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The synthesis of thioacridine derivatives (5a-j) have been achieved by the reaction of acridines (4a-j) with Lawesson's reagent in toluene under refluxing conditions to yield products in high yields. The yields of the products are promising and the produc
- Mahesh, Palla,Kumar, B. Dilip,Devi, B. Rama,Murthy
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p. 1683 - 1686
(2016/01/26)
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