- 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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- Synthesis, characterization, and application of Fe3O4-SA-PPCA as a novel nanomagnetic reusable catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines
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Piperidine-4-carboxylic acid (PPCA) functionalized Fe3O4 nanoparticles (Fe3O4-PPCA) were prepared by the one pot co-precipitation of iron oxide in the presence of PPCA. Grafting of chlorosulfonic acid on the synthesized Fe3O4-PPCA nanoparticles afforded sulfamic acid-functionalized magnetic nanoparticles (Fe3O4-SA-PPCA). The catalytic activity of Fe3O4-SA-PPCA as a novel catalyst was probed through one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines derivatives. The heterogeneous catalyst could be recovered easily and reused many times without significant loss of its catalytic activity.
- Ghorbani-Choghamarani, Arash,Azadi, Gouhar
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- The first report on the preparation of boehmite silica sulfuric acid and its applications in some multicomponent organic reactions
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Boehmite silica sulfuric acid (boehmite-SSA) has been prepared for the first time via an efficient sequential synthetic procedure. Initially, boehmite nanoparticles were prepared, coated by silica, and then reacted with chlorosulfonic acid to obtain boehmite-SSA. A simple, inexpensive, environmentally friendly and efficient procedure for the synthesis of polyhydroquinoline and 2,3-dihydroquinazolin-4(1H)-one derivatives using this compound as an efficient and novel nanocatalyst has been described. Boehmite-SSA is a stable, heterogeneous, cost-effective, easy to handle, and recoverable catalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. Its structure was characterized by FT-IR spectroscopy, thermogravimetric analysis (TGA), powder X-ray diffraction (XRD) and scanning electron microscopy (SEM).
- Ghorbani-Choghamarani, Arash,Tahmasbi, Bahman
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- One-pot, three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones by montmorillonite K-10 as an efficient and reusable catalyst
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A wide range of mono- and disubstituted dihydroquinazolinones were synthesised via condensation of isatoic anhydride, primary amines, or ammonium salts with aromatic aldehydes in the presence of montmorillonite K-10. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Copyright Taylor & Francis Group, LLC.
- Salehi, Peyman,Dabiri, Minoo,Baghbanzadeh, Mostafa,Bahramnejad, Mahboobeh
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- A new concise synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
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A new T3P-assisted, convenient and efficient procedure for the synthesis of dihydroquinazolinones is described. The main advantages of this protocol include its practical simplicity, short reaction times and particularly the ease with which products are isolated.
- Desroses, Matthieu,Scobie, Martin,Helleday, Thomas
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- Scalable preparation, characterization, and application of alkali-treated starch as a new organic base catalyst
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Preparation, characterization, and application of alkali starch (AS) given by dry co-grinding of starch and alkali is described in this work. Grinding using a mortar (agate) and pestle or, more conveniently, a ball mill has been found to be satisfactory for the preparation of the AS. The AS products were characterized by scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) and x-ray fluorescence (XRF) analyses. The base capacities of ASs were 4.25–4.45 mmol/g, respectively. AS is a low cost and easy to handle base catalyst that showed promising catalytic performance in the synthesis of a dihydroquinazoline-based antibacterial drug that involves tandem hydration or decarboxylative amidation, imination, and Aza-Michael reactions.
- Tamaddon, Fatemeh,KazemiVarnamkhasti, MohammadTaghi
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- Inclusion complex of Isatoic anhydride with β-cyclodextrin and supramolecular one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous media
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The inclusion complex of isatoic anhydride with β-cyclodextrin was formed as a result of intermolecular interaction between isatoic anhydride with β-CD. The inclusion complex was confirmed by IR spectroscopy, X-ray diffraction and DSC studies. From application of complex, herein we have described a simple and efficient protocol for synthesis of 2, 3-dihydroquinazoline-4(1H)-one derivatives by one pot condensation of isatoic anhydride, ammonium acetate or amine and aldehyde using β-CD as a supramolecular catalyst in aqueous media.
- Patil, Dipak R.,Ingole, Pravin G.,Singh, Kripal,Dalal, Dipak S.
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- DABCO containing acidic poly(ionic liquid): An efficient catalyst for the one-pot preparation of 2,3-dihydroquinazoline-4(1H)-ones
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1,4-Diazabicyclo[2.2.2]octane (DABCO) containing acidic poly(ionic liquid) (DAIL) has been prepared via condensation of 1,4-dichloro butane and DABCO, as an efficient acidic catalyst and has been applied in the one-pot preparation of 2,3-dihydroquinazolin
- Mohammadi, Mohammad Kazem,Saghanezhad, Seyyed Jafar,Razzaghiasl, Nima
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- Sulfated polyborate: mild, efficient and eco-friendly catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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Abstract: An efficient, inexpensive and recyclable sulfated polyborate catalyst was applied in a three-component, one-pot cyclocondensation of isatoic anhydride, aldehydes and ammonium acetate/amines to afford the corresponding 2,3-dihydroquinazolin-4(1H)-ones. The key advantages of the present method are high yields, short reaction time, easy workup, recyclability of catalyst and ability to tolerate a variety of functional groups which gives economical as well as ecological rewards. Graphical Abstract: [Figure not available: see fulltext.].
- Khatri, Chetan K.,Patil, Manisha S.,Chaturbhuj, Ganesh U.
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- One-pot, three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones using p-Toluenesulfonic acid-paraformaldehyde copolymer as an efficient and reusable catalyst
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p-Toluenesulfonic acid-paraformaldehyde copolymer (copolymer-PTSA) catalyzes the three-component, one-pot condensation reaction of isatoic anhydride, ammonium salts or aromaticand aliphatic amines, and aldehydes in refluxing ethanol. The catalyst is reusable and could be recycled for several runs without any decrease in its efficiency. Springer-Verlag 2010.
- Saffar-Teluri, Ali,Bolouk, Shiva
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- A Highly Stereocontrolled, One-Pot Approach toward Pyrrolobenzoxazinones and Pyrroloquinazolinones through a Lewis Acid-Catalyzed [3 + 2]-Cycloannulation Process
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We report herein a stereocontrolled [3 + 2]-cycloheteroannulation of bis-silyl dienediolate 1 with 2-aminobenzoic acid- and 2-aminobenzamide-derived imines to furnish highly substituted pyrrolo[1,2-a]benzoxazinones 3 and pyrrolo[1,2-a]quinazolinones 4, respectively, in good overall yields. This one-pot process rapidly generates molecular complexity and comprises a Lewis acid-catalyzed, vinylogous Mannich reaction of 1 followed by an intramolecular N,O-acetal- and N,N-aminal formation, respectively, which proceeds with good to excellent stereocontrol.
- Boomhoff, Michael,Ukis, Rostyslav,Schneider, Christoph
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- Synthesis of new 2-aryl substituted 2,3-dihydroquinazoline-4(1H)-ones under solvent-free conditions, using molecular iodine as a mild and efficient catalyst
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A simple, inexpensive, and efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-one derivatives under solvent-free conditions using a catalytic amount of iodine with excellent product yields is reported. This methodology provides easy, quantitative
- Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Aryan, Reza,Ghaieni, Hamid Reza,Shadjou, Nasrin
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- Organic-inorganic hybrid polyoxometalate and its graphene oxide-Fe3O4 nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1: H)-ones
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The simple and high yield synthesis of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O (PPD = p-phenylenediamine) as a new organic-inorganic hybrid polyoxometalate is reported. The new compound consists of trimetal-substitution polyoxometalate of A-β-SiW9Cu3O3710-, water molecules and coordinated and noncoordinated PPD molecules. H6Cu2[PPD]6[SiW9Cu3O37]·12H2O was firmly grafted on graphene oxide decorated with Fe3O4 nanoparticles. These nanocomposites were characterized by elemental analyses, thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), X-ray photoelectron spectrum (XPS), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX), and alternating gradient force magnetometer (AGFM). The results indicate that the size range of the nanoparticles are between 20 and 60 nm. The catalytic activity of H6Cu2[PPD]6[SiW9Cu3O37]·12H2O and the magnetically reusable nanocomposite of GO@Fe3O4@H6Cu2[PPD]6[SiW9Cu3O37]·12H2O were investigated in the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
- Khoshnavazi, Roushan,Bahrami, Leila,Havasi, Forugh
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p. 100962 - 100975
(2016)
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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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- 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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- Three-component one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in 2,2,2-trifluoroethanol
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Trifluoroethanol (TFE) is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of isatoic anhydride, aldehyde and ammonium acetate or primary amine to afford the corresponding 2,3-dihydroquinazolin-4(1H)-one derivatives in high yields. The solvent (TFE) can be readily separated from reaction products and recovered in excellent purity for direct reuse.
- Khaksar, Samad,Talesh, Saeed Mohammadzadeh
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- A one-pot synthesis of 2-aryl-2,3-dihydro-4(1H)-quinazolinones by use of samarium iodide
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2-Aryl-2,3-dihydro-4(1H)-quinazolines have been prepared in a one-pot synthesis by samarium idoide (SmI2) promoted reaction of o-nitrobenzamide and aldehydes.
- Cai, Guoping,Xu, Xiaoliang,Li, Zhifang,Weber, William P.,Lu, Ping
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- A novel method for the one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones
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One-pot three-component condensation of isatoic anhydride with primary amines or ammonium carbonate and aromatic aldehydes in refluxing ethanol in the presence of catalytic amounts of silica sulfuric acid afforded the corresponding 2,3-dihydroquinazolin-4(1H)-ones in high yields. The catalyst is reusable and can be applied several times without any decrease in product yield.
- Salehi, Peyman,Dabiri, Minoo,Zolfigol, Mohammad Ali,Baghbanzadeh, Mostafa
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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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- Reductive cyclization of nitro and azide compounds with aldehydes and ketones promoted by metallic samarium and catalytic amount of iodine
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Reductive cyclization of nitro and azide compounds was discussed. The cyclization was done with aldehydes and ketones which is promoted by metallic samarium and catalytic amount of iodine. Results showed that three equivalents of samarium were required when the substrate was a nitro compound and one equivalent of samarium was needed for the azide compounds.
- Su, Weike,Yang, Bibo
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- An efficient one pot-three component cyclocondensation in the synthesis of 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones: Potential antitumor agents
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Montmorillonite K10 efficiently catalyzed a one pot-three component cyclocondensation of isatoic anhydride, NH4OAc and aromatic/heteroaromatic aldehydes under ambient conditions to produce the corresponding 2-substituted-2,3-dihydroquinazolin-4(1H)-ones in good yields. The 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones 3a-d were screened for their antitumor activity against Ehrlich Ascites Carcinoma tumor cells
- Roopan, Selvaraj Mohana,Nawaz Khan,Jin, Jong Sung,Senthil Kumar
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- Preparation of choline sulfate ionic liquid supported on porous graphitic carbon nitride nanosheets by simple surface modification for enhanced catalytic properties
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Supported ionic liquids (SILs) have attracted rising interest and the subject of active research in the last decades due to the diversified range of applications and yet reports on ILs is still rapidly increasing. This work reports a choline sulfate ionic liquid supported on fascinating and highly stable porous graphitic carbon nitride (g-C3N4) nanosheets as an inexpensive and an environmentally friendly reusable ionic catalyst in organic synthesis typically requiring a harmful organic solvent and highly toxic acids. g-C3N4?SO3Ch was prepared by mixing sulfonic acid functionalized graphitic carbon nitride nanosheets (g-C3N4?SO3H) with choline hydroxide or via a novel approach. The introduction of a choline sulfate could significantly enlarge specific surface areas with rich reaction sites and suppressed the recombination of sheets. This work provides a new way to improve the chemical property of g-C3N4 along with the recyclability of the ionic liquid. g-C3N4?SO3Ch (IL/g-C3N4) offers an effective, reusable, inexpensive, environmentally friendly and low-cost catalyst for the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones, 2,3-dihydroquinazolin-4 (1H)-ones and bisindolylmethanes in good to excellent yields. The prepared catalyst synthesized compounds were well characterized by different techniques such as FT-IR, XRD, SEM, EDX and TGA.
- Azizi, Najmedin,Edrisi, Mahtab
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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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- An efficient transition-metal-free route to quinazolin-4(3H)-onesvia2-aminobenzamides and thiols
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An efficient approach to quinazolin-4(3H)-ones was developed by a one-pot intermolecular annulation reaction ofo-amino benzamides and thiols. This method has the features of good functional group tolerance, being transition metal and external oxidant free, and easy operation. Varieties of 2-aryl (heteroaryl) quinazolin-4(3H)-one, 2-phenyl-pyrido[2,3-d]pyrimidin-4(3H)-one and 3-phenyl-2H-1,2,4-benzo thiadiazine-1,1-dioxide derivatives were obtained with a yield of up to 98%. The control experiment revealed that the thiol substrate could promote the dehydroaromatization step.
- Dong, Yibo,Wu, Yangjie,Yan, Congcong,Yang, Jinchen,Zhang, Jinli
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p. 15344 - 15349
(2021/09/07)
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- A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones
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In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.
- Gupta, Radhika,Arora, Gunjan,Yadav, Priya,Dixit, Ranjana,Srivastava, Anju,Sharma, Rakesh Kumar
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p. 890 - 898
(2021/02/03)
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- Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
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A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
- Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
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supporting information
p. 15117 - 15127
(2021/10/25)
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- Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage
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This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.
- Xie, Zongbo,Lan, Jin,Yan, Liyuan,Chen, Xuehua,Li, Qian,Meng, Jia,Le, Zhanggao
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p. 2436 - 2441
(2021/04/02)
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- Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst
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Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.
- Thorve, Pradip Ramdas,Maji, Biplab
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p. 1116 - 1124
(2021/02/26)
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- Linear-Organic-Polymer-Supported Iridium Complex as a Recyclable Auto-Tandem Catalyst for the Synthesis of Quinazolinones via Selective Hydration/Acceptorless Dehydrogenative Coupling from o-Aminobenzonitriles
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A linear-organic-polymer-supported iridium complex Cp*Ir@P4VP, which is designed and synthesized by the coordinative immobilization of [Cp*IrCl2]2 on poly(4-vinylpyridine), was proven to be an efficient heterogeneous autotandem catalyst for synthesizing quinazolinones via selective hydration/acceptorless dehydrogenative coupling from o-aminobenzonitriles. Furthermore, the synthesized catalyst was recycled five times without an obvious decrease in the catalytic activity.
- Hao, Shushu,Yang, Jiazhi,Liu, Peng,Xu, Jing,Yang, Chenchen,Li, Feng
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p. 2553 - 2558
(2021/04/13)
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- Visible light induced tandem reactions: An efficient one pot strategy for constructing quinazolinones using in-situ formed aldehydes under photocatalyst-free and room-temperature conditions
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A facile tandem route has been developed for constructing quinazolinones from various aminobenzamides and in-situ generated aldehydes. Visible light was found to play a dual role: first oxidizes the alcohol to the aldehyde and then facilitates its cyclization with o-substituted aniline. Furthermore, alcohols are perfect alternatives to aldehydes because they are greener, more available, more economical, more stable, and less toxic than aldehydes. The first reaction step continuously provides material for the second step, which effectively reduces loss through volatilization, oxidation, and polymerization of the aldehyde, while avoiding its toxicity. A variety of quinazolinones can be prepared in the presence of visible light without any additional photocatalyst. The developed synthesis protocol proceeds with the merits of mild conditions, broad substrate scope, operational simplicity, and high atom efficiency, with an eco-energy source under metal-free, photocatalyst-free, and ambient conditions.
- Xie, Zongbo,Lan, Jin,Zhu, Haibo,Lei, Gaoyi,Jiang, Guofang,Le, Zhanggao
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p. 1427 - 1431
(2020/11/02)
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- Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
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A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.
- Balaji, Sundarraman,Balamurugan, Gunasekaran,Ramesh, Rengan,Semeril, David
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p. 725 - 734
(2021/04/06)
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- Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones
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In the present work, we have developed a novel and environmentally friendly method for the synthesis of quinazolinones using fluorescein as a photocatalyst via a condensation reaction of o-aminobenzamides and aldehydes under visible light irradiation. In this protocol, neither toxic oxidants nor transition-metal catalysts were needed, and a series of quinazolinones could be obtained in high efficiencies. In addition, this reaction can be extended to gram levels and has a large potential of wide application in future industrialization.
- Wang, Rongzhou,Liu, Shiyuan,Li, Longfei,Song, Ao,Yu, Shengsheng,Zhuo, Shuping,Xing, Ling-Bao
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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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- Mukaiyama's reagent promoted mild protocol for one-pot metal-free synthesis of dihydro quinazolinones
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We have developed a fast and convenient method to prepare dihydroquinazolin-4(1H)-ones from anthranilamide and different aromatic aldehydes by using the Mukaiyama reagent. The reactions proceeded smoothly with a broad scope of substrates providing the expected products in good to excellent yields under with a low environmental factor and high atom economy. The metal-free condition and the ease of product isolation are the highlighted advantages in solving the issue of trace metal contamination in synthesized pharmaceuticals.
- Rajput, Chatrasal S.,Srivastava, Shweta,Kumar, Ashish,Pathak, Arunendra
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supporting information
(2021/01/25)
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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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- 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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- 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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- Copper-Catalyzed One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1 H)-ones from 2-Nitrobenzonitriles and Carbonyl Compounds Mediated by Diboronic Acid in Methanol-Water
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A copper-catalyzed one-pot synthesis of 2,3-dihydroquinazolin-4(1 H)-ones with diboronic acid as a reductant in an aqueous medium is described. Various 2,3-dihydroquinazolin-4(1 H)-ones were prepared with good functional-group tolerance in good yields under mild conditions from readily available 2-nitrobenzonitriles and various carbonyl compounds.
- Chen, Yongsheng,Liu, Qixing,Sui, Yuebo,Zhang, Kaili,Zhang, Yin,Zhou, Haifeng
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supporting information
p. 275 - 279
(2020/02/15)
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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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- Ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H)-ones: A convergent synthetic route to bouchardatine and sildenafil
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A facile access to fused pyrimidin-4(3H)-one derivatives has been established by using the metal-free ortho-naphthoquinone-catalyzed aerobic cross-coupling reactions of amines. The utilization of two readily available amines allowed a direct coupling strategy to quinazolinone natural product, bouchardatine, as well as sildenafil (Viagra) in a highly convergent manner. This journal is
- Kim, Hun Young,Kim, Kyeongha,Oh, Kyungsoo
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p. 31101 - 31105
(2020/09/23)
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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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- Cobalt complexes of redox noninnocent azo-aromatic pincers. Isolation, characterization, and application as catalysts for the synthesis of quinazolin-4(3: H)-ones
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Herein we report the synthesis, characterization and catalytic application of three new cobalt(ii)-complexes of redox noninnocent arylazo ligands, 2-(phenylazo)-1,10-phenanthroline (L1a), 2-(4-chlorophenylazo)-1,10-phenanthroline (L1b) and 2,9-bis(phenyldiazo)-1,10-phenanthroline (L2) respectively. The reaction of L1a with CoIICl2·6H2O produced a μ-dichloro bridged binuclear cobalt(ii)-complex [CoII2(L1a)2Cl2] (1a) while the same reaction when carried out with 2-(4-chlorophenyl)azo-1,10-phenanthroline (L1b) and 2,9-bis(phenyldiazo)-1,10-phenanthroline (L2) ligands produced two new mononuclear five-coordinate cobalt(ii)-complexes 1b and 2 respectively. In complex 1a and 1b, the ligands L1a and L1b are coordinated to the cobalt(ii)-center in a tridentate mode utilizing all of its nitrogen donor sites while in complex 2 one of the azo-donor sites of the ligand L2 remain pendant. All these complexes were characterized using available spectroscopic techniques and DFT studies. We further explored the potential of these complexes as catalysts for the synthesis of pharmaceutically important organic compounds via the functionalization of alcohols. A variety of substituted quinazolin-4(3H)-ones were synthesized under aerobic conditions via the coupling of alcohols and 2-aminobenzamide using 1b as the catalyst. Mechanistic investigations revealed that both cobalt and the arylazo scaffold act synergistically during catalysis. This journal is
- Das, Siuli,Mandal, Sutanuva,Mondal, Rakesh,Paul, Nanda D.,Sinha, Suman
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p. 8448 - 8459
(2020/07/10)
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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 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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- 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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- 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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- 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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- Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions
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A series of 2,3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational simplicity are the main highlights. Furthermore, the catalyst can be recovered and reused without evident loss of reactivity. This method provides a green and much improved protocol over the existing methods.
- Yang, Yang,Fu, Renzhong,Liu, Yang,Cai, Jing,Zeng, Xiaojun
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- Corrigendum to “Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions” [Tetrahedron Lett. 76/27 (2020) 131312] (Tetrahedron (2020) 76(27), (S004040202030466X), (10.1016/j.tet.2020.131312))
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The authors regret the following errors: 1. In page 1, “Additionally, 2,3-dihydroquinazolin-4(1H). -one derivatives can easily…” should be changed to “Additionally, 2,3-dihydroquinazolin-4(1H)-one derivatives can easily…” 2. In page 1, “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21], [?] [29] lewis acids [30–36],…” should be changed to “… numerous protocols have been developed recently for the synthesis using catalysts including acidic reagents [21–29], lewis acids [30–36],…” 3. In page 1, “… alternative methods to perform organic. synthesis under environmentally benign conditions is in…” should be changed to “… alternative methods to perform organic synthesis under environmentally benign conditions is in…” 4. In page 2, “… condensation, which were. readily available based on our previous publicationsn…” should be changed to “… condensation, which were readily available based on our previous publications…” 5. In page 3, “… while bringing down the catalyst loading to 1 mol % led. to a reduction in the yield to…” should be changed to “… while bringing down the catalyst loading to 1 mol % led to a reduction in the yield to…” 6. In page 3, “… transformation to different substituted isatoic. anhydrides was performed.” should be changed to “… transformation to different substituted isatoic anhydrides was performed.” 7. In page 3, “… easily separated from the. reaction mixture via simple centrifugation…” should be changed to “… easily separated from the reaction mixture via simple centrifugation…” 8. The chemical structure 4a-4g should be changed in Table 2 as below: Table 2. HPAIL catalyzed three-component condensation of isatoic anhydrides, amines and aldehydes (or ketones).a [Figure presented] The authors would like to apologise for any inconvenience caused.
- Cai, Jing,Fu, Renzhong,Liu, Yang,Yang, Yang,Zeng, Xiaojun
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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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- One-pot synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones utilizing N-(2-aminobenzoyl)benzotriazoles
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A convenient and efficient method has emerged for the one-pot synthesis of substituted quinazolin-4(3H)ones and nonaromatic alkaloids. 2-Substituted quinazolin-4(3H)-ones, 2,3-disubstituted quinazolin-4(3H)-ones, and 2,3-dihydroquinazolin-4(1H)-ones were obtained at yields of 46% to 95% by a one-pot reaction of N-(2-aminobenzoyl) benzotriazoles with amines and orthoesters or aldehydes under catalyst-free conditions.
- ?enol, ?lbilge Merve,?elik, ?lhami,Avan, ?lker
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p. 1580 - 1596
(2020/01/03)
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- Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles
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A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.
- Wang, Qi,Lv, Miao,Liu, Jianping,Li, Yang,Xu, Qing,Zhang, Xu,Cao, Hongen
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p. 3043 - 3048
(2019/03/17)
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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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- 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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- 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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- 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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- 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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- 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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- 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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- “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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- Bismuth-catalyzed synthesis of 2-substituted quinazolinones
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The bismuth-catalyzed oxidative condensation of aldehydes with 2-aminobenzamide under aerobic conditions is reported using ethanol as the solvent. Good to excellent isolated yields (68–95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The quinazolinones were further functionalized to afford N-allylated quinazolinones, 2-aminopyridine derivatives, and annulated polyheterocyclic compounds via transition-metal catalyzed reactions.
- Vemula, Sandeep R.,Kumar, Dinesh,Cook, Gregory R.
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supporting information
p. 3801 - 3805
(2018/09/18)
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- Dihydroquinoxalinone compound and preparation method thereof
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The invention relates to a dihydroquinoxalinone compound and a preparation method, and the specific structure is shown in III. The method uses cheap and readily available o-nitrobenzonitrile (I) and aldehyde or ketone (II) as raw materials, and alcohol and water as solvent. The target product (III) is obtained by a nitro reduction, a cyano hydrolysis, and a condensation reaction in a one-pot reaction system under the action of tetrahydroxydiboron, glacial acetic acid and catalytic amount of cuprous chloride. The preparation method uses 2-nitrobenzonitrile (I) as a raw material for the first time, which is easy to operate, easy to obtain raw materials, high in yield, and has the advantages of green synthesis such as step economy, atomic economy, mild reaction conditions and the like. The specific formula is shown in the description.
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Paragraph 0022-0075
(2018/10/19)
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