- Ultrasound/visible light-mediated synthesis of N-heterocycles using g-C3N4/Cu3TiO4 as sonophotocatalyst
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In this investigation, novel g-C3N4/Cu3TiO4 (CNCT) nanocomposite was synthesized by using a simple thermal condensation method. The synthesized CNCT nanocomposite was characterized by X-ray Diffraction, Transmission electron microscopy, Atomic force microscopy, Energy-dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy, UV–vis diffuse reflectance spectroscopy, Photoluminescence, Brunauer–Emmett–Telle, Zeta Potential, and Thermogravimetric analysis. The study revealed that the catalysts prepared have high crystalline nature, optical light-absorbing property, high surface area, and stability. The CNCT- nanocomposite was found to be an extraordinary visible light absorbing catalyst for the synthesis of quinoxaline and quinazolinone derivatives, which have important benefits in a variety of drug applications. Quinoxaline and quinazolinones were prepared from anthranilamide, diamines, benzil, and corresponding aldehydes under Ultrasonic/visible light-medium with a notable amount of g-C3N4/Cu3TiO4. The results exhibit good and excellent yields of product derivatives at mild conditions under Ultrasonic/visible light-medium. Ultrasounds always clean the active site catalyst, promoting activity and reusability. Most notably, with preserved reactivities, this heterogeneous g-C3N4/Cu3TiO4 composite can be used atleast 5 times. Furthermore, we examined the reusability of the catalyst under Ultrasonication coupled with Visible light and in the absence of an Ultrasonication medium. Finally, advantages of the method are non-conventional approach, green solvent, reduced reaction duration, mild condition, and reusable catalyst.
- Arunachalapandi, Murugan,Roopan, Selvaraj Mohana
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- Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products
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A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.
- Pal, Shantanu,Sahoo, Subrata
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p. 18067 - 18080
(2021/12/06)
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- The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale
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Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.
- Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
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- Probing the catalytic activity of highly efficient sulfonic acid fabricated cobalt ferrite magnetic nanoparticles for the clean and scalable synthesis of dihydro, spiro and bis quinazolinones
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An exceptionally productive, rapid, simple, and eco-friendly approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been developed utilizing acidic magnetically retrievable cobalt ferrite nanoparticles (CFNP@SO3H). Herein, we have demonstrated the synthesis of these profoundly demanding N-heterocyclic molecules within 3-10 min in excellent yields at room temperature using the environmentally benign solvent ethanol. Outstanding catalytic performance, ease of retrievability, high turnover frequency (TOF) values (197.13-403.23 h?1), admirable green chemistry metrices, such as theEfactor (0.10), reaction mass efficiency (RME) value (90.9%), carbon efficiency (100%) and atom economy (AE) value (92.6%), and reusability for up to six runs without a significant loss of activity, make the current methodology advantageous from an environmental, as well as industrial perspective.
- Awasthi, Satish K.,Yadav, Priyanka
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supporting information
p. 15928 - 15941
(2021/09/22)
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- Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions
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Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]
- Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh
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p. 2420 - 2435
(2021/01/04)
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- Confinement-Driven Enantioselectivity in 3D Porous Chiral Covalent Organic Frameworks
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3D covalent organic frameworks (COFs) with well-defined porous channels are shown to be capable of inducing chiral molecular catalysts from non-enantioselective to highly enantioselective in catalyzing organic transformations. By condensations of a tetrahedral tetraamine and two linear dialdehydes derived from enantiopure 1,1′-binaphthol (BINOL), two chiral 3D COFs with a 9-fold or 11-fold interpenetrated diamondoid framework are prepared. Enhanced Br?nsted acidity was observed for the chiral BINOL units that are uniformly distributed within the tubular channels compared to the non-immobilized acids. This facilitates the Br?nsted acid catalysis of cyclocondensation of aldehydes and anthranilamides to produce 2,3-dihydroquinazolinones. DFT calculations show the COF catalyst provides preferential secondary interactions between the substrate and framework to induce enantioselectivities that are not achievable in homogeneous systems.
- Hou, Bang,Yang, Shi,Yang, Kuiwei,Han, Xing,Tang, Xianhui,Liu, Yan,Jiang, Jianwen,Cui, Yong
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supporting information
p. 6086 - 6093
(2021/02/01)
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- Anchoring of Cu–dimethylglyoxime complex in MCM-41 matrix: a new, recyclable, and highly efficient nanocatalyst for the green preparation of 2,3-dihydroquinazolin-4(1H)-ones
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A new heterogeneous nanocatalyst containing Cu–dimethylglyoxime complex grafted to an MCM-41 matrix was synthesized. This recoverable nanocomposite was applied as a highly effective, green, thermally stable catalyst in the one-pot reductive cyclization of aromatic aldehydes with 2-aminobenzamide. 2,3-Dihydroquinazolin-4(1H)-ones were obtained in 80–98% yield. The MCM-41-silylcyclopropyl-dimethylglyoxime-Cu heterogeneous nanocomposite was well identified using X‐ray diffraction, field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy‐dispersive X‐ray spectroscopy, Brunauer–Emmett–Teller technique, and thermogravimetric analysis. The eco-friendly nanocatalyst demonstrated excellent recyclability: it could be reused for at least six successive cycles without any notable decrease in its catalytic function. Graphic abstract: [Figure not available: see fulltext.]
- Hassanloie, Nishtman,Noroozi Pesyan, Nader,Ojaghi Aghbash, Khadijeh,Sheykhaghaei, Golaleh
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p. 833 - 844
(2021/07/31)
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- One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water
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Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.
- Rao, Mugada Sugunakara,Hussain, Sahid
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- Sustainable parts-per-million level catalysis with FeIII: One-pot cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones in water
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A silica-supported iron complex has been identified as a highly active and reusable catalyst for the synthesis of medicinally important 2,3-dihydroquinazolin-4(1H)-ones. The catalyst was fully characterized by various spectroscopic analyses such as Fourie
- Dutta, Apurba,Trivedi, Priyanka,Kulshrestha, Akshay,Kumar, Arvind,Chaturvedi, Vinita,Sarma, Diganta
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- Cu(II) complex-decorated hybrid nanomaterial: a retrievable catalyst for green synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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The significant stability of magnetic core and ? OH functional groups on the surface of silica-coated cobalt ferrite (CoFe2O4@SiO2) nanoparticles make it a good candidate for functionalization and catalytic application. In
- Bodaghifard, Mohammad Ali,Safari, Somayeh
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p. 1613 - 1627
(2021/04/26)
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- β-Cyclodextrin: A supramolecular catalyst for metal-free approach towards the synthesis of 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1 H)-one
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β-Cyclodextrin, a green and widespread supramolecular catalyst, has been explored as a highly proficient promoter for the metal-free one-pot multi-component synthesis of a vast range of highly functionalized bioactive heterocyclic moiety, 2-amino-4,6-diphenylnicotinonitriles and 2,3-dihydroquinazolin-4(1H)-one, from easily available precursor aldehydes. The main endeavor of these protocols is to explore this organic supramolecule in one-pot multi-component synthesis. Absence of metal catalyst or toxic acid and harsh reaction conditions, excellent functional group tolerance, inexpensive, greener and environmentally safe protocol are the key advantages of this work.
- Mitra, Bijeta,Chandra Pariyar, Gyan,Ghosh, Pranab
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p. 1271 - 1281
(2021/01/20)
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- Gemini basic ionic liquid as bi-functional catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones at room temperature
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A cascade synthesis of 2,3-dihydroquinazolin-4(1H)-ones has been developed from 2-aminobenzonitriles and carbonyl analogues using Gemini basic ionic liquid as green catalyst cum solvent at room temperature. Both aldehydes and ketones were condensed with 2-aminobenzonitriles affording good to excellent yields of products. Moreover, the ionic liquids can be reused up to 5th cycle without significant loss of catalytic activity.
- Dutta, Apurba,Damarla, Krishnaiah,Kumar, Arvind,Saikia, Prakash J.,Sarma, Diganta
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- Praseodymium(iii) anchored on CoFe2O4 MNPs: An efficient heterogeneous magnetic nanocatalyst for one-pot, multi-component domino synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1: H)-one derivatives
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In the present study, a facile technique to immobilize praseodymium(iii) complex on the surface of magnetic nanoparticles by using available materials is reported. The prepared samples were characterized by chemical and physical methods such as FTIR, SEM, XRD and EDX and were tested in the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives. It was observed that the yields of the reactions in the presence of the prepared nanocatalyst were good to excellent. More importantly, the use of a recoverable and novel magnetic nanocatalyst in these reactions is the outstanding feature of this protocol.
- Tamoradi, Taiebeh,Mousavi, Seyedeh Masoumeh,Mohammadi, Masoud
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p. 3012 - 3020
(2020/03/03)
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- Fe3O4@MCM-41@Zn-Arg: as a novel, magnetically recoverable and ecofriendly nanocatalyst for the synthesis of disulfides, sulfoxides and 2,3-dihydroquinazolin?4(1H)?ones
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The direct supporting of Zn-arginine complex on magnetic core-shell nanostructures (Fe3O4@MCM-41@Zn-Arg) was reported as a novel, heterogeneous and excellent nanocatalyst, which applied for the oxidation reaction of sulfides to sulfoxides, oxidative coupling of thiols to their corresponding disulfides and the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under mild conditions. The structure of the catalyst was studied by X-Ray diffraction, Fourier transform-infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, atomic absorption spectroscopy, and vibrating sample magnetometry techniques. The simple experimental procedure, very good catalytic activity, low cost, and excellent recycling are the noteworthy features of the currently employed heterogeneous catalytic system.
- Nikoorazm, Mohsen,Erfani, Zahra
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p. 642 - 655
(2020/08/19)
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- Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence of Fe3O4@nano-cellulose–OPO3H as a bio-based magnetic nanocatalyst
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In this research, we have used Fe3O4@nano-cellulose–OPO3H as magnetic bio-based nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones via condensation of 2-aminobenzamide and different aldehydes. The major advantages of the present methodology are good yields, ecofriendly catalyst, and easy workup.
- Mirjalili, Bi Bi Fatemeh,Zaghaghi, Zahra,Monfared, Aazam
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p. 197 - 201
(2019/12/03)
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- Synthesis and characterization of VO–vanillin complex immobilized on MCM-41 and its facile catalytic application in the sulfoxidation reaction, and synthesis of 2,3-dihydroquinazolin-4(1H)-ones and disulfides in green media
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In this work, a vanillin complex is immobilized onto MCM-41 and characterized by FT-IR, X-ray diffraction, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and BET techniques. This supported Schiff base complex was found to be an efficient and recoverable catalyst for the chemoselective oxidation of sulfides into sulfoxides and thiols into their corresponding disulfides (using hydrogen peroxide as a green oxidant) and also a suitable catalyst for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in water at 90°C. Using this protocol, we show that a variety of disulfides, sulfoxides, and 2,3-dihydroquinazolin-4(1H)-one derivatives can be synthesized in green conditions. The catalyst can be recovered and recycled for further reactions without appreciable loss of catalytic performance.
- Nikoorazm, Mohsen,Khanmoradi, Maryam
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p. 1477 - 1489
(2020/03/11)
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- An expeditious synthesis of 2,3-dihydroquinozoline-4(1H)-ones using graphene-supported sulfonic acid
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Graphene-supported sulfonic acid (Gr?SO3H) has been prepared by covalent grafting of (3-mercaptopropyl)trimethoxysilane in the matrix of graphene followed by treatment with sulfuric acid and hydrogen peroxide. Gr?SO3H has been successfully characterized by Fourier transform infrared (FT-IR) spectroscopy, Fourier transform Raman (FT-Raman) spectroscopy, CP-MAS 13C NMR spectroscopy, thermogravimetric analysis (TGA), energy dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), Brunauer-Emmett-Teller (BET) analysis, and X-ray diffractometer (XRD) analysis. Gr?SO3H served as a robust heterogeneous catalyst for the synthesis of bioactive 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and aryl aldehydes in ethanol. Recyclability experiments were executed successfully for six consecutive runs.
- Gajare, Shivanand,Jagadale, Megha,Naikwade, Altafhusen,Bansode, Prakash,Patil, Pradnya,Rashinkar, Gajanan
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- A novel magnetic nanocatalyst Fe3O4@PEG–Ni for the green synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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Ni-PEG (polyethylene glycol) complex supported on magnetic nanoparticle was created by grafting. The catalytic activity of Fe3O4@PEG–Ni was explored through one-pot green synthesis of 2,3-dihydroquinazolin-4(1H)-ones and used as an efficient and recoverable nanocatalyst. FT-IR, XRD, EDS, BET, TGA, VSM and SEM techniques were employed to specify the nanocatalyst. This heterogeneous nanocatalyst demonstrated acceptable recyclability and could be reused several times with no considerable loss of its catalytic activity.
- Noroozi Pesyan, Nader,Danandeh Asl, Aria,Namdar, Shadi
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- MWCNTs-ZrO2 as a reusable heterogeneous catalyst for the synthesis of N-heterocyclic scaffolds under green reaction medium
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A simple, efficient, and facile heterogeneous multi-walled carbon nanotubes-zirconia nanocomposite (MWCNTs-ZrO2) has been synthesized using natural feedstock coconut juice (água-de-coco do Ceará). The synthesized catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, and X-ray photoelectron spectroscopy analysis. The heterogeneous nanocomposite has been used for one-pot synthesis of various N-heterocyclic compounds like pyrazoles, 1,2-disubstituted benzimidazoles, 2-arylbenzazoles, and 2,3-dihydroquinazolin-4(1H)-ones under green reaction medium at room temperature. This novel method has several advantages, such as short reaction time, simple work-up, excellent yield, and green reaction conditions. The catalyst was recycled up to four times without significant loss in catalytic activity.
- Halder, Bipasa,Banerjee, Flora,Nag, Ahindra
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- Larvicidal activities of 2-aryl-2,3-dihydroquinazolin -4-ones against malaria vector anopheles arabiensis, in silico ADMET prediction and molecular target investigation
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Malaria, affecting all continents, remains one of the life-threatening diseases introduced by parasites that are transmitted to humans through the bites of infected Anopheles mosquitoes. Although insecticides are currently used to reduce malaria transmission, their safety concern for living systems, as well as the environment, is a growing problem. Therefore, the discovery of novel, less toxic, and environmentally safe molecules to effectively combat the control of these vectors is in high demand. In order to identify new potential larvicidal agents, a series of 2-aryl-1,2-dihydroquinazolin-4-one derivatives were synthesized and evaluated for their larvicidal activity against Anopheles arabiensis. The in silico absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of the compounds were also investigated and most of the derivatives possessed a favorable ADMET profile. Computational modeling studies of the title compounds demonstrated a favorable binding interaction against the acetylcholinesterase enzyme molecular target. Thus, 2-aryl-1,2-dihydroquinazolin-4-ones were identified as a novel class of Anopheles arabiensis insecticides which can be used as lead molecules for the further development of more potent and safer larvicidal agents for treating malaria.
- Abed, Sara Nidal,Akrawi, Sabah H.,Aldhubiab, Bandar E.,Alwassil, Osama I.,Attimarad, Mahesh,Bataineh, Yazan A.,Bhandary, Subhrajyoti,Chandrashekharappa, Sandeep,Chopra, Deepak,Deb, Pran Kishore,Girish, Meravanige B.,Gleiser, Raquel M.,Haroun, Michelyne,Khalil, Hany Ezzat,Mohanlall, Viresh,Morsy, Mohamed A.,Nair, Anroop B.,Palenge, Ramachandra,Pottathil, Shinu,Ramachandra, Pushpalatha,Sreeharsha, Nagaraja,Tratrat, Christophe,Venugopala, Katharigatta N.,Venugopala, Rashmi
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- A Br?nsted Acid Ionic Liquid Immobilized on Fe3O4?SiO2 Nanoparticles as an Efficient and Reusable Solid Acid Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
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Abstract: In the present study, an efficient and magnetically recoverable Br?nsted acid ionic liquid, 1-methyl-3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe3O4?SiO2 magnetic nanoparticles (Fe3O4?SiO2–ImHSO4) has been used for a high-yield synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the condensation of anthranilamide with aldehydes and ketones in EtOH at room temperature or under reflux. The significant features of the present protocol are short reaction times, high yields of products, ecofriendly reaction conditions, simple work-up, and reusability of the catalyst. The catalyst can be simply magnetically recovered and reused at least five times without considerable loss of its catalytic activity.
- Fallah-Mehrjardi, M.,Kalantari, S.
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p. 298 - 306
(2020/04/17)
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- Citrus Extract Modified Graphene Oxide as a Green and Heterogeneous Organocatalyst for the Synthesis of Imidazole Derivatives
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A naturally benign convention was created with a surface change of graphene oxide by citrus extract as catalyst was prepared by a straight-forward chemical modification method. The prepared catalyst′s catalytic activity was examined by the synthesis of imidazole derivatives at room temperature. It shows a strong acidic catalytic and sustainable organocatalyst. The prepared catalyst was characterized using different analytical procedures like elemental analysis, Fourier transforms infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), energy-dispersive X-ray analysis (EDS), scanning electron microscopy images (SEM) and transmission electron microscopy images (TEM) analysis. The catalytic activity shows high activity and can be reused without significant loss of catalytic activity after five times. A present catalyst works easily under room temperature.
- Arunkumar,Chidambara Vinayagam,Lakshmanan,Arul Antony
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p. 2375 - 2380
(2020/09/16)
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- Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 as a novel and recoverable hybrid catalyst for expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones via one-pot three-component reaction
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Benzene-1,3,5-tricarboxylic acid-functionalized MCM-41 (MCM-41-Pr-BTA), as a novel hybrid organosilica, was prepared and properly characterized by the Fourier-transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, Brunauer–Emmett–Teller, thermal gravimetric analysis and energy-dispersive X-ray spectroscopy to evaluate the functional groups, crystallinity, surface area, morphology, particle size distribution and loading of functional groups. Interestingly, the 1,3-propylene linker used in this study incorporates appropriate catalytic activity into the MCM-41 framework compared to the more known trialkoxypropyl silanes. This new organosilica can be used as a hybrid nanocatalyst for the expeditious and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives, as an important pharmaceutical scaffold, in aqueous media via a three-component one-pot condensation of isatoic anhydride and aromatic aldehydes with primary amines or ammonium salts. This method has several advantages such as low catalyst loading, high to excellent yields, short reaction times, working under green conditions and simple workup.
- Nikooei, Niusha,Dekamin, Mohammad G.,Valiey, Ehsan
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p. 3891 - 3909
(2020/06/01)
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- Organocatalytic combinatorial synthesis of quinazoline, quinoxaline and bis(indolyl)methanes
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Aims and Objective: An efficient and practical procedure for the synthesis of heterocyclic compounds such as quinazolines, quinoxalines and bis(indolyl)methanes was developed using 3,5-bis(trifluoromethyl) phenyl ammonium hexafluorophosphate (BFPHP) as a novel organocatalyst. Materials and Methods: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Result: Various products were obtained in good to excellent yields under reaction conditions Conclusion: The BFPHP organocatalyst demonstrates a novel class of non-asymmetric organocatalysts, which has gained much attention in green chemistry.
- Badri, Rashid,Khaksar, Samad,Malamiri, Fatemeh,Tahanpesar, Elham
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- Preparation method of dihydroquinazolinone derivative
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The invention discloses a preparation method of a dihydroquinazolinone derivative. The preparation method comprises the following steps: (1) respectively adding reaction substrate raw materials including aromatic aldehyde and 2-aminobenzamide and a proper amount of water into a pressure-resistant reaction container, (2) heating to 100-180 DEG C in a closed state, and keeping for a certain time, (3) stopping heating, cooling the reaction kettle to room temperature to 80 DEG C, and adding an organic solvent to flush the material into a collecting tank, (4) carrying out solid-liquid separation, washing and recrystallization to obtain the target product xanthene compound, and (5) collecting the solvent mother liquor and recovering the product, wherein the recovered solvent is reused. Comparedwith the prior art, the preparation method has the advantages of low cost and environmental protection.
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Paragraph 0020-0022
(2020/09/16)
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- Glucose as an Eco-Friendly Reductant in a One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
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Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco-friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one-pot sequences involving glucose as a reductant.
- dos Santos, Thiago,Grundke, Caroline,Lucas, Tobias,Gro?mann, Luca,Clososki, Giuliano Cesar,Opatz, Till
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supporting information
p. 6429 - 6432
(2020/09/02)
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- CoFe2O4@SiO2-CPTES-Guanidine-Cu(II): A novel and reusable nanocatalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines and oxidation of sulfides
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CoFe2O4@SiO2-CPTES-Guanidine-Cu(II) magnetic nanoparticles were synthesized and used as a new, inexpensive and efficient heterogeneous catalyst for the synthesis of polyhydroquinolines and 2,3-dihydroquinazoline-4(1H)-ones and for the oxidation of sulfides. The structure of this nanocatalyst was characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, X-ray diffraction and inductively coupled plasma optical emission spectrometry. Simple preparation, high catalytic activity, simple operation, high yields, use of green solvents, easy magnetic separation and reusability of the catalyst are some of the advantages of this protocol.
- Heidari, Leili,Shiri, Lotfi
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- Green and efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and their anthelmintic studies
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A facile and highly efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones derivatives has been developed by the condensation of anthranilamide with aldehydes using sulfonic acid functionalized l-Proline?Fe3O4 nanoparticles as a catalyst. The advantages of this protocol are easy recovery and reusability of the catalyst besides simple work-up procedure and short reaction time. In addition, the anthelmintic activities of some selective compounds were investigated and it was found that 2-phenyl-2,3-dihydroquinazolin-4(1H)-one exhibited profound anthelmintic activity against two helminth models.
- Kharmawlong, George Kupar,Nongrum, Ridaphun,Chhetri, Bhusan,Rani, Jims World Star,Rahman, Noimur,Yadav, Arun Kumar,Nongkhlaw, Rishanlang
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supporting information
p. 2683 - 2695
(2019/08/07)
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- KOH/DMSO: A basic suspension for transition metal-free Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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A novel protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones from 2-aminobenzamides and aldehyde derivatives catalyzed by KOH/DMSO suspension has been developed. The present transition metal free methodology is operationally simple, scalable and varieties of 2,3-dihydroquinazolin-4(1H)-one derivatives were obtained in good to excellent yields in short reaction times.
- Dutta, Apurba,Damarla, Krishnaiah,Bordoloi, Ankur,Kumar, Arvind,Sarma, Diganta
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supporting information
p. 1614 - 1619
(2019/05/24)
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- Facile and efficient protocols for C–C and C–N bond formation reactions using a superparamagnetic palladium complex as reusable catalyst
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Abstract: Facile and efficient protocols for some multicomponent coupling reactions such as the Suzuki reaction and synthesis of polyhydroquinoline and 2,3-dihydroquinazoline-4-(1H)-one derivatives using a superparamagnetic palladium complex as catalyst have been developed. Graphical abstract: [Figure not available: see fulltext.].
- Karimi Zarchi, Mohammad Ali,Darbandizadeh Mohammad Abadi, Seyed Shahab Addin
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p. 2605 - 2639
(2019/02/13)
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- High acidity cellulose sulfuric acid from sulfur trioxide: A highly efficient catalyst for the one step synthesis of xanthene and dihydroquinazolinone derivatives
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A cellulose sulfonate catalyst (HS-cellulose sulfonate) with high stability, excellent catalytic activity and high acidity value (about 1.55 mmol g-1) was successfully prepared by SO3 gas phase sulfonation. The basic morphology and nanostructure of the catalyst were determined by HRTEM, XRD, IR, TG, etc. In addition, the catalyst was applied to the catalytic reaction of a dihydroquinazolinone derivative and a xanthene compound, and very valuable results were obtained. The development and preparation of cellulose sulfonate catalysts provide a good approach for the development and application of cellulose, and also an important application of green organic catalytic synthesis methodology.
- Yue, Xiaofei,Wu, Zhiqiang,Wang, Gang,Liang, Yanping,Sun, Yanyan,Song, Manrong,Zhan, Haijuan,Bi, Shuxian,Liu, Wanyi
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p. 28718 - 28723
(2019/09/30)
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- Electrostatically Enhanced Sulfuric Acid: A Strong Br?nsted Acidic Catalyst for Multi-Component Reactions
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Abstract: A new electrostatically enhanced sulfuric acid as a strong Br?nsted acidic catalyst has been developed for multi-component reactions. A positively charged center in the catalyst electrostatically activates it for acid-catalyzed multi-component reactions and afforded desired products in short reaction time and near room temperature in EtOH as a green solvent. Graphical Abstract: [Figure not available: see fulltext.].
- Anzabi, Mohadese Yaghoobi,Yazdani, Hossein,Bazgir, Ayoob
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p. 1934 - 1940
(2019/04/25)
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- ompg-C3N4/SO3H: an efficient and recyclable organocatalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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In the present work, sulfonated highly ordered mesoporous graphitic carbon nitride (ompg-C3N4/SO3H) was synthesized successfully and employed as an efficient and reusable heterogeneous solid acid catalyst for the rapid and one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones via the condensation of anthranilamide with aldehydes or ketones in good to excellent yields. The organocatalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectrometer, Brunauer–Emmett–Teller surface area, and thermal gravimetric and differential thermal analysis. The substantial advantages of this procedure involve short reaction times, high catalytic activity, easy workup, high purity of the products, and easy recovery and reusability of the catalyst.
- Ghafuri, Hossein,Goodarzi, Nahal,Rashidizadeh, Afsaneh,Douzandegi Fard, Mohammad Ali
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p. 5027 - 5043
(2019/06/17)
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- Boosting Enantioselectivity of Chiral Organocatalysts with Ultrathin Two-Dimensional Metal-Organic Framework Nanosheets
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The development of methodologies for inducing and tailoring enantioselectivities of catalysts is an important issue in asymmetric catalysis. In this work, we demonstrate for the first time that chiral molecular catalysts can be boosted from completely nonselective to highly enantioselective when installed in nanostructured metal-organic frameworks (MOFs). Exfoliation of layered crystals is one of the most direct synthetic routes to unltrathin nanosheets, but its use in MOFs is limited by the availability of layered MOFs. We illustrate that layered MOFs can be designed using ligand-capped metal clusters and angular organic linkers. This leads to the synthesis of two three-dimensional (3D) layered porous MOFs from Zn4-p-tert-butylsulfonyl calix[4]arene and chiral angular 1,1′-binaphthol/-biphenol dicarboxylic acids, which can be ultrasonic exfoliated into one- and two-layer nanosheets. The obtained MOF materials are efficient catalysts for asymmetric cascade condensation and cyclization of 2-aminobenzamide and aldehydes to produce 2,3-dihyroquinazolinones. While both binaphthol and biphenol display no enantioselectivity, restriction of their freedom in the MOFs leads to 56-90% and 46-72% ee, respectively, which are increased to 72-94% and 64-82% ee after exposure to external surfaces of the flexible nanosheets. Moreover, the MOF crystals and nanosheets exhibit highly sensitive fluorescent enhancement in the presence of chiral amino alcohols with enantioselectivity factors being, respectively, increased up to 1.4 and 2.3 times of the values of the diols, allowing them to be utilized in chiral sensing. Therefore, the observed enantioselectivities increase in the order organocatalyst MOF crystals MOF nanosheets in both catalysis and sensing. This work not only provides a strategy to make 3D layered MOFs and their untrathin nanosheets but also paves the way to utilize nanostructured MOFs to manipulate enantioselectivities of molecular catalysts.
- Tan, Chunxia,Yang, Kuiwei,Dong, Jinqiao,Liu, Yuhao,Liu, Yan,Jiang, Jianwen,Cui, Yong
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supporting information
p. 17685 - 17695
(2019/11/05)
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- Supramolecular Fe3O4@PEG/?diaza crown ether@Ni: a novel magnetically reusable nano catalyst for the clean synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones
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Ni@diaza crown ether complex supported on magnetic nanoparticle was provided by grafting technique. The catalytic activity of Fe3O4@diaza crown ether@Ni was explored through one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and it was used as an efficient and recoverably constant nanocatalyst. FT-IR, SEM, TEM, XRD, BET, ICP, EDS, and TGA techniques were employed to specify the nanocatalyst. This heterogeneous catalyst demonstrated acceptable recyclability and could be used again several times with no considerable loss of its catalytic activity.
- Aalinejad, Michael,Noroozi Pesyan, Nader,Heidari, Nosrat,Batmani, Hana,Danandeh Asl, Aria
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- A three-component process for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts
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NiAl2O4 spinel nanocrystals were synthesized as mesoporous catalysts and were fully characterized using Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy-dispersive X-ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via a one-pot, three-component condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium acetate or primary aromatic amine under microwave irradiation. By far, the most obvious advantages of the offered process are efficiency and recyclability of the catalyst as well as a significantly shorter reaction time.
- Safaei-Ghomi, Javad,Teymuri, Raheleh
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- Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3
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2,3-Dihydroquinazolin-4(1H)-one derivatives have been synthesized via one-pot reaction of isatoic anhydride, aromatic aldehyde, and ammonium acetate catalyzed by FeCl3/neutral Al2O3 in tert-butanol under reflux conditions.
- Wu, Suo Juan,Zhao, Zi Qiang,Gao, Jing Shuo,Chen, Bao Hua,Chen, Guo Feng
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p. 2327 - 2339
(2019/02/01)
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- Synthesis of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones using CoAl2O4 nanoparticles as heterogeneous catalyst
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Abstract: The preparation and characterization of cobalt aluminate (CoAl2O4) magnetic nanoparticles and its application as a catalyst for the synthesis of a novel class of pyrazol-quinazolinones and 2,3-dihydroquinazolin-4(1H)-ones is described. The structure of the catalyst was studied by Fourier transform infrared spectroscopy, transmission electron microscopy, X-ray diffraction, and vibrating sample magnetometer analysis. The resulting cobalt aluminate (CoAl2O4) was an efficient catalyst and affords the desired products in good to excellent yields. Moreover, the catalyst could be easily recovered by magnetic separation and recycled for four times without significant loss of its catalytic activity. Graphic abstract: 2,3-Dihydroquinazolin-4(1H)-ones and a novel class of pyrazol-quinazolinones were synthesized through one-pot condensation reaction of isatoic anhydride, aromatic aldehydes, and amines using CoAl2O4 as nanoparticle heterogeneous catalyst in refluxing ethanol.[Figure not available: see fulltext.].
- Ahmadian, Fatemeh,Barmak, Alireza,Ghaderi, Esmali,Bavadi, Masoumeh,Raanaei, Hossein,Niknam, Khodabakhsh
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p. 2647 - 2658
(2019/07/17)
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- One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
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A metal-free and oxidant-free method for the one-pot preparation of quinazolin-4(3H)-ones enabled by electrochemical oxidation is described. Together with 2-aminobenzamides, a variety of aldehydes were successfully applied to an acid-catalyzed annulation and direct anodic oxidation cascade, affording structurally diverse quinazoline-4(3H)-ones in good to excellent yields. Additionally, certain alcohols can be directly applied instead of the corresponding aldehydes to achieve the same final products with the assistance of an electrolysis mediator (TEMPO). The reaction mechanism was carefully examined and the results strongly suggest that the direct and indirect oxidation go through different pathways. As an efficient and environmentally friendly access to a broad range of quinazolin-4(3H)-ones, the synthetic utility of this method was demonstrated by gram-scale operation, as well as the preparation of bioactive mackinazolinone and truncated erlotinib. (Figure presented.).
- Cao, Liu,Huo, Hengrui,Zeng, Haipeng,Yu, Yu,Lu, Dengfu,Gong, Yuefa
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p. 4764 - 4773
(2018/11/10)
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- “On-water” synthesis of quinazolinones and dihydroquinazolinones starting from O-bromobenzonitrile
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A versatile and practical “on-water” protocol was newly developed to synthesize quinazolinones using o-bromobenzonitrile as a novel starting material. Studies have found that air as well as water plays an important role in synthesis of quinazolinones. Further investigation indicated that dihydroquinazolinones can be prepared with this protocol under the protection of N2. The protocol can be extended to other substrates and various quinazolinones and dihydroquinazolinones were obtained. o-Bromobenzamide, o-aminobenzonitrile, and o-aminobenzamide were also evaluated as starting materials, and the results further proved the versatility of this protocol, especially towards dihydroquinazolinones.
- Liu, Zibin,Zeng, Li-Yan,Li, Chao,Yang, Fubiao,Qiu, Fensheng,Liu, Shuwen,Xi, Baomin
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supporting information
(2018/09/26)
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- Q-Tube assisted MCRs for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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A Q-tube assisted, efficient method for the preparation of 2-phenylquinazolin-4-ones is here presented. The target structures were prepared through the one-pot, multicomponent reaction between isatoic anhydride, an aromatic aldehyde and a primary amine following a catalyst-free approach. The use of the commercially available Q-tube apparatus allowed to perform reactions at external temperature higher to the solvent boiling point generating medium pressure conditions, shortening the reaction times and affording good yields in all the example herein reported. Formula parented.
- Sancineto, Luca,Monti, Bonifacio,Merlino, Orsola,Rosati, Ornelio,Santi, Claudio
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p. 270 - 278
(2018/07/05)
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- Magnetic Fe3O4 nanoparticles supported imine/Thiophene-nickel (II) complex: A new and highly active heterogeneous catalyst for the synthesis of polyhydroquinolines and 2, 3-dihydroquinazoline-4(1H)-ones
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A new magnetically separable nickel catalyst (Ni(NO3)2?Imine/Thiophene-Fe3O4@SiO2) was readily prepared and structurally characterized by Fourier transform infrared spectroscopy (FT-IR), Scanning electron microscopy (SEM), Energy-dispersive X-ray spectroscopy (EDX), Vibrating sample magnetometer (VSM), X-Ray diffraction (XRD) and Atomic absorption spectroscopy (AAS). The Ni(NO3)2?Imine/Thiophene-Fe3O4@SiO2 exhibited efficient catalytic activity in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones and polyhydroquinolines. Catalysis research under water and solvent-free conditions makes also this synthetic protocol ideal and fascinating from the environmental point of view. The catalyst can be magnetically recovered after the reaction and can be reused for many times without appreciable decrease in activity.
- Shiri, Lotfi,Heidari, Leili,Kazemi, Mosstafa
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- Synthesis of benzo[4,5]imidazo[1,2-: A] pyrimidines and 2,3-dihydroquinazolin-4(1 H)-ones under metal-free and solvent-free conditions for minimizing waste generation
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Br?nsted acidic ionic liquid was found to be an efficient and recyclable catalyst for the synthesis of benzo[4,5]imidazo[1,2-a]pyrimidines and 2,3-dihydroquinazolin-4(1H)-ones. The reactions proceeded smoothly with a broad scope of substrates providing the expected products in good to excellent yields under an atom-economical pathway. The low-cost recyclable catalyst, metal- and solvent-free conditions, and the ease of product isolation are the highlighted advantages in solving the issue of trace metal contamination in synthesized pharmaceuticals.
- Tran, Phuong Hoang,Thi Bui, Thanh-Phuong,Bach Lam, Xuan-Quynh,Thi Nguyen, Xuan-Trang
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p. 36392 - 36399
(2018/11/20)
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- BF3-grafted Fe3O4@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)
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Current paper represents immobilization of sucrose on the Fe3O4 core and grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3-Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT-IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one gram of NPs than sulfonated homologue which was reported previously.
- Radfar, Iman,Miraki, Maryam Kazemi,Ghandi, Leila,Esfandiary, Naghmeh,Abbasi, Sepideh,Karimi, Meghdad,Heydari, Akbar
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- Sulfamic acid immobilized on amino-functionalized magnetic nanoparticles: A new and active magnetically recoverable catalyst for the synthesis of N-heterocyclic compounds
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Sulfamic acid immobilized on amino-functionalized magnetic nanoparticles (MNPs/DETA-SA) was successfully fabricated and characterized using various techniques. Diameters of approximately 15?nm for the MNPs/DETA-SA were observed from scanning electron microscopy images. The as-fabricated nanocomposite was applied as an efficient and magnetically reusable catalyst for the synthesis of 2,3-dihydroquinazoline-4(1H)-one and polyhydroquinoline derivatives. All products were obtained in good to excellent yields. Recovery tests confirm that the catalyst can be readily recovered using an external magnet and reused many times without significant loss of its catalytic activity.
- Shiri, Lotfi,Narimani, Hojatollah,Kazemi, Mosstafa
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- Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
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Abstract: A simple, efficient and less expensive protocol for the synthesis of Cu(II) immobilized on MCM-41@Serine has been reported. This nanohybrid material was carefully characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, TEM, thermal gravimetric analysis, and N2 adsorption and desorption. The obtained nanostructured compound were also employed as a green, efficient, heterogeneous and reusable catalytic system for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. High surface area, convenient recovery and reusability for several times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable reagents, good reaction times, simple practical methodology and ease of use all make Cu(II) immobilized on MCM-41@Serine a promising candidate for potential applications in some organic reactions; makes this protocol both attractive and economically viable. Graphical Abstract: MCM-41 nanostructured was prepared via simple and versatile procedure and directly immobilized with a new type of Cu–serine complex. After characterization of this catalyst, the catalytic activity of this nanostructure compound has been investigated for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. [Figure not available: see fulltext.].
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 857 - 872
(2018/03/01)
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- Synthesis of a new Pd(0)-complex supported on magnetic nanoparticles and study of its catalytic activity for Suzuki and Stille reactions and synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
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In the present work, we report synthesis of anchored palladium complex on functionalized Fe3O4 nanoparticles via simple and inexpensive procedure. The final nanohybrid compound was characterized by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), inductively coupled plasma optical emission spectroscopy (ICP-OES), X-ray Diffraction (XRD), thermal gravimetric analysis (TGA) and vibrating sample magnetometer (VSM) measurements. The catalytic activity of Fe3O4-Serine-Pd as an efficient and reusable catalyst was investigated for Suzuki and Stille reactions and synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives. The heterogeneous catalyst could be easily separated by applying a simple magnet and reused several consecutive runs without appreciable change in its catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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p. 120 - 130
(2018/02/27)
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- Sulfuric acid heterogenized on magnetic Fe3O4 nanoparticles: A new and efficient magnetically reusable catalyst for condensation reactions
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Immobilized sulfuric acid on magnetic Fe3O4 nanoparticles (Fe3O4 MNPs-OSO3H) as a new solid acid nanocomposite was successfully synthesized and its catalytic activity in a series of condensation reactions was studied. High catalytic activity, simple separation from reaction mixture by an external magnet and good reusability are several eco-friendly advantages of this catalytic system. It is noteworthy that this catalytic system is applicable to a wide range of spectrum of aromatic aldehydes, and the desired products were obtained in good to excellent yields under mild conditions. The use of ecofriendly solvents makes also this synthetic protocol ideal and fascinating from the environmental point of view.
- Shiri, Lotfi,Zarei, Setare,Kazemi, Mosstafa,Sheikh, Davood
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- Silica sulfuric acid-coated Fe3O4 nanoparticles as a highly efficient and reusable solid acid catalyst for the green synthesis of 2, 3-dihydroquinazolin-4(1H)-ones under solvent-free conditions
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An efficient and eco-friendly procedure for the synthesis of 2, 3-dihydroquinazolin-4(1H)- ones and spiroquinazolinones in the presence of sulfuric acid functionalized silica-coated magnetite nanoparticles under solvent-free conditions has been described. The reactions are completed in short times, and the products are obtained in high isolated yields without any undesirable side reaction. This method has several advantages, including short reaction time, facile operation, easy work-up, ecofriendly reaction conditions, high isolated yields, and reusability of the catalyst. The catalyst could be easily separated and recovered from the reaction mixture by an external magnet and reused in subsequent reactions with no considerable loss in activity.
- Beyki, Monire,Fallah-Mehrjardi, Mehdi
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