- Basic ionic liquid as catalyst and surfactant: green synthesis of quinazolinone in aqueous media
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Basic imidazolium-based ionic liquids not only possess the extraordinary physicochemical properties of ionic liquids, but also have excellent basicity and surfactivity. 1-Propyl-3-alkylimidazole hydroxide ionic liquids ([PRIm][OH]) were synthesized and their catalytic and surfactant behavior were studied in this work. [PRIm][OH] owned excellent surfactivity, and their alkyl chains and ion pairs benefit hydrophobicity and hydrophilicity respectively. The surfactivity of [PRIm][OH] increased with increasing alkyl chain length. [PRIm][OH] showed better catalytic performance than NaOH in the condensation of 2-aminobenzonitrile with cyclohexanone in aqueous medium, and the catalytic performance was well coincident with their surfactant behavior. [PRIm][OH] could decrease the interfacial tension of solvent effectively and form micelles in water. The formed micelles could solubilise more reactants into water and effectively increase the chance of contact between reactants and catalytic active sites. The catalyst dosage obviously affected catalytic performance. The catalytic system is a promising recyclable system.
- Zhang, Yaping,Zhen, Bin,Li, Hansheng,Feng, Yaqing
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- Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines
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The cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2′-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.
- Gnyawali, Krishna,Kirinde Arachchige, Pandula T.,Yi, Chae S.
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supporting information
(2022/01/15)
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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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- 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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- Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation
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Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.
- Nguyen, Linh Ho Thuy,Nguyen, Trang Thi Thu,Dang, Minh-Huy Dinh,Tran, Phuong Hoang,Doan, Tan Le Hoang
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- Effect of Fe(iii)-based MOFs on the catalytic efficiency of the tandem cyclooxidative reaction between 2-aminobenzamide and alcohols
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The catalytic properties of metal-organic frameworks (MOFs) containing triangular Fe(iii) clusters in the promotion of organic syntheses and photocatalysis applications have been receiving substantial attention for decades. These clusters are appealing due to the strong Lewis acidity afforded by coordinatively unsaturated sites upon the removal of solvent from the framework. In this paper, triangular Fe(iii) cluster-based MOFs were shown to be highly efficient heterogeneous catalysts for the solvent-free one-pot condensation of 2-aminobenzamide and alcohols to form quinazolin-4-ones under microwave irradiation. The Fe-MOF catalysts ranging from microporous to mesoporous structures with a variety of geometrical pore structures were investigated. Because of the open accessible spaces for reactants and high density of active sites, MOF-907, built from trimer Fe clusters and a mixture of two linkers, was more effective than other Fe(iii)-MOFs. The catalyst can be used for a broad substrate scope and recycled several times without a significant drop-off in its activity.
- Dang, Minh-Huy Dinh,Nguyen, Trang Thi Minh,Nguyen, Linh Ho Thuy,Nguyen, Trang Thi Thu,Phan, Thang Bach,Tran, Phuong Hoang,Doan, Tan Le Hoang
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supporting information
p. 14529 - 14535
(2020/10/02)
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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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- 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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- 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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- 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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- 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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- 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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- 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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- Copper-Catalyzed Intramolecular α-C-H Amination via Ring-Opening Cyclization Strategy to Quinazolin-4-ones: Development and Application in Rutaecarpine Synthesis
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A copper-catalyzed intramolecular α-C-H amination has been developed for the synthesis of quinazolin-4(3 H)-one derivatives from commercially available isatoic anhydride and primary and secondary benzylamines via ring-opening cyclization (ROC). This method shows good functional group tolerance and allows access to a range of 2-aryl, 2-alkyl, and spiroquinazolinone derivatives. However, 2-methylquinazolin-4(3 H)-one was synthesized from 2-amino- N -isopropylbenzamide by C-C bond cleavage, and N -benzyl-2-(methylamino)benzamide afforded 1-methyl-2-phenylquinazolin-4(1 H)-one along with 2-phenylquinazolin-4(3 H)-one by N-C bond cleavage for aromatization. It is the first general method to construct the potentially useful 2-methylquinazolin-4(3 H)-one by copper-catalyzed intramolecular C-H amination. Also this ROC strategy has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.
- Biswal, Sonali,Chada, Harika,Patel, Srilaxmi M.,Sharada, Duddu S.,Sharma, Sonika
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p. 3160 - 3170
(2019/08/07)
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- Synthesis of 2,3-dihydroquinazolin-4(1H)-ones from anthranilamide and ketones over Hβ zeolite in aqueous media*
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The synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation of anthranilamide with ketones in aqueous media using Hβ zeolite is reported. The scope of the reaction was explored by various ketones such as aromatic, aliphatic and cyclic ketones. Based on the preliminary mechanistic results, a tentative mechanism for the formation of 2,3-dihydroquinazolin-4(1H)-ones using zeolite catalyst (Hβ) is predicted. The reusability study, large-scale experiment and water as solvent showed significant benefits of this catalytic protocol in comparing to earlier methods.
- Gajula, Krishna Sai,Mameda, Naresh,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Kutepov, Boris Ivanovich,Nama, Narender
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supporting information
p. 2866 - 2876
(2018/12/04)
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- Microwave-assisted synthesis of quinazolin-4(3H)-ones catalyzed by SbCl
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Antimony(III) trichloride (SbCl3) is an effective catalyst (1 mol%) for the condensation of anthranilic amide with various aldehydes or ketones to quinazolin-4(3H)-one derivatives in good to excellent yields under microwave irradiation. The process is carried out within several minutes under solvent-free conditions. This general methodology has the advantages of simplicity, mild reaction conditions and high yields of products.
- Kang, Huaiyuan,Wang, Weili,Sun, Qinqiang,Yang, Shuya,Jin, Juan,Zhang, Xuewen,Ren, Xiaoliang,Zhang, Jiming,Zhou, Jianhua
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p. 293 - 296
(2018/11/27)
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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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- 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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- Amino acid catalyzed synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
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A simple, convenient and facile approach for the synthesis of a series of 2,3-dihydroquinazolin-4(1H)-ones in an environmentally benign method has been developed. This method involves a direct cyclocondensation of 2-aminobenzamide with aromatic aldehydes and ketones using aspartic acid as a catalyst in water.
- Mustaque, K. Mohammed,Subramani,Shabeer,Thajudeen,Ahamed, V. S. Jamal
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p. 246 - 250
(2018/04/20)
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- SbCl3 as effective catalyst for the preparation of 2,3-Dihydroquinazolin-4(1H)-ones, spectroscopic investigation and DFT study
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A simple and efficient method has been developed for the synthesis of Quinazolines using SbCl3 as a heterogeneous catalysis at room temperature. This method provides a good pathway for the synthesis of 2,3-Dihydroquinazolin-4(1H)-ones derivatives in the terms of excellent yields and short reaction times. Also we studied theoretically and experimentally on 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (PDQ). Using density functional theory (DFT), the tautomerism of PDQ was also studied. Thermal stability of PDQ was studied by thermo gravimetric analysis (TGA). The spectroscopic results and theoretical calculations indicate that the strength of intramolecular hydrogen bonding (IHB) of PDQ is stronger than that in 2-methyl-4-quinolinol (2MQ). The absorption spectra of the PDQ in solvents with different polarity were obtained and the results show that PDQ exists in both keto-amine and enol-imine forms in THF, while it has keto-amine form in other solvents. Theoretical results show that the conductance of the two tautomers (keto-amine and enol-imine) varies greatly, which offers that the potential usage of this molecule is as a molecular device.
- Pourmousavi, Seied Ali,Kanaani, Ayoob,Fatahi, Hamid Reza,Ghorbani, Fatemeh,Ajloo, Davood
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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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p. 1683 - 1689
(2017/06/27)
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- A kind of ethanol to promote [...] catalytic efficient preparation of the quinazolinone derivatives
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The invention discloses a method for efficiently preparing quinazolinone derivants under promotion of ethyl alcohol and catalysis of titanocene dichloride. According to the method, aminobenzamide and aldehyde or ketone are used as raw materials, ethyl alcohol is used as a solvent and a promoter, titanocene dichloride is used as a catalyst, and the quinazolinone derivants are efficiently prepared in high yield under the synergetic promotion action of titanocene dichloride and ethyl alcohol. The catalyst is less in dosage, cheap, nontoxic, and stable to air; the reaction conditions are mild, and the reaction time is short; the operation is simple; the atom economy is high; after the reaction is finished, the product only needs to be subjected to simple separation and recrystallization to obtain the quinazolinone derivants; a new, low-cost, environment-friendly and efficient path is opened up for preparation of the quinazolinone derivants, and wide application prospects are achieved.
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Paragraph 0047-0050
(2017/11/08)
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- Facile method for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by SiO2–H3PW12O40 in water
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The 12-tungstophosphoric acid supported on silica gel (PW/SiO2) exhibits excellent activity in the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation reaction of 2-aminobenzamide with carbonyl compounds in water under reflux conditions. The desired products have been obtained in short reaction times in high yields. Our method has been successfully applied for both aldehydes and ketones (aromatic and aliphatic). Easy recovery and reusable catalyst, easy work-up and avoidance of using harmful organic solvents are the major advantages of our method in comparison to existing methods.
- Alinezhad, Heshmatollah,Soleymani, Elham,Zare, Mahboobeh
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p. 457 - 466
(2017/01/14)
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- Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
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Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.
- Majumdar, Biju,Mandani, Sonam,Bhattacharya, Tamalika,Sarma, Daisy,Sarma, Tridib K.
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p. 2097 - 2106
(2017/02/26)
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- The Remarkable Cooperative Effect of a Br?nsted-Acidic Ionic Liquid in the Cyclization of 2-Aminobenzamides with Ketones
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An unprecedented role of an imidazolium Br?nsted acidic ionic liquid was found in the formation of 2,2-disubstituted quinazolin-4(1H)-one derivatives; both the C2-H of the imidazolium moiety and an acidic proton were necessary and simultaneously took part in the catalysis. A library of quinazolin-4(1H)-ones was prepared from readily available ketones and 2-aminobenzamides; excellent yields were obtained through simple crystallization under solvent-free conditions with lower E factors. The catalyst could be reused over five consecutive runs without any significant loss in catalytic activity. This method produces only water as a byproduct and represents a green synthetic protocol. A clean reaction, no chromatographic purification, easily accessible reactants, a metal-free and solvent-free process, and environmentally friendly reaction conditions are the notable advantages of this procedure. The possible role of the C2-H of the imidazolium moiety in catalysis was studied by mass spectrometry.
- Das, Sudarshan,Santra, Sougata,Jana, Sourav,Zyryanov, Grigory V.,Majee, Adinath,Hajra, Alakananda
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p. 4955 - 4962
(2017/09/13)
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- Glycerol assisted eco-friendly strategy for the facile synthesis of 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ols) and 2-aryl-2,3-dihydroquinazolin-4(1H)-ones under catalyst-free conditions
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Abstract: This article describes glycerol mediated eco-friendly approaches for the convenient access of structurally diverse 4,4′-(arylmethylene)bis(3-methyl-1H-pyrazol-5-ol) and 2-aryl-2,3-dihydroquinazolin-4(1H)-one motifs under catalyst-free conditions. Prominent advantages include clean processes, atom-efficiency, simplicity of the work-up, neutral conditions, low-cost reaction medium, excellent product yield and solvent reusability, in addition to relatively shorter reaction times. Graphical Abstract: [Figure not available: see fulltext.]
- Ramesh, Rathinam,Nagasundaram, Nagarajan,Meignanasundar, Durairaj,Vadivel, Pullar,Lalitha, Appaswami
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p. 1767 - 1782
(2017/02/15)
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- Cu(II) immobilized on Fe3O4–diethylenetriamine: A new magnetically recoverable catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and oxidative coupling of thiols
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Cu(II) immobilized on Fe3O4–diethylenetriamine was designed as a new, inexpensive and efficient heterogeneous catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones and the oxidative coupling of thiols. The structure of the nanomagnetic catalyst was comprehensively characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, X-ray diffraction and atomic absorption spectroscopy. Simple preparation of the catalyst from commercially available materials, high catalytic activity, simple operation, high yields, use of green solvents, easy magnetic separation and reusability of the catalyst with unaltered activity make our protocol a green and feasible synthetic strategy.
- Shiri, Lotfi,Ghorbani-Choghamarani, Arash,Kazemi, Mosstafa
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- Synthesis and characterization of bromine source supported on magnetic Fe3O4 nanoparticles: A new, versatile and efficient magnetically separable catalyst for organic synthesis
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Tribenzylammonium tribromide supported onto magnetic nanoparticles (Br3-TBA-Fe3O4) as a bromine source was successfully synthesized and characterized using Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy and vibrating sample magnetometry. The synthesized catalyst is shown to be a versatile and highly efficient heterogeneous catalyst for the Knoevenagel condensation and synthesis of 2,3-dihydroquinazolin-4(1H)-one and polyhydroquinoline derivatives. To the best of the authors' knowledge, this is the first report of the use of a bromine source immobilized on Fe3O4 nanoparticles as a magnetically separable catalyst for these reactions. The nanosolid catalyst can be magnetically recovered and reused readily several times without significant loss in catalytic efficiency.
- Shiri, Lotfi,Ghorbani-Choghamarani, Arash,Kazemi, Mosstafa
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- Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones
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A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract: [Figure not available: see fulltext.].
- Ameen, Mohamed A.,Ahmed, Essam Kh.,Ramadan, Mohamed,Abd El-Naby, Hisham A.,Abdel-Haseeb, Asmaa A.
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p. 1513 - 1523
(2017/07/18)
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- Magnetic Fe3O4 nanoparticles supported amine: a new, sustainable and environmentally benign catalyst for condensation reactions
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Abstract: Diethylenetriamine immobilized on magnetic Fe3O4 nanoparticles (DETA-Fe3O4) was successfully prepared as a new and well dispersed magnetically separable amine catalyst. The structure of the resulting catalyst was well characterized by a series of analysis techniques such as FT-IR, SEM, EDX, VSM, TGA and XRD. The catalytic activity of DETA-Fe3O4 was evaluated with Knoevenagel condensation of active methylene compounds with aromatic aldehydes. Interestingly, the cyclocondensation of anthranilamide and aldehydes were effectively catalyzed by DETA-Fe3O4 in water, and the desired products (2,3-dihydroquinazoline-4(1H)-ones) were afforded in admirable yields. Catalysis research under aqueous medium (water) also makes this synthetic protocol ideal and fascinating from the environmental point of view. The amine catalyst can be magnetically recovered after the reaction and can be reused many times without appreciable decrease in activity.
- Shiri, Lotfi,Kazemi, Mosstafa
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p. 4813 - 4832
(2017/07/22)
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- Cholinesulfuric acid ionic liquid catalyzed an eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-one in aqueous media
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An efficient and straightforward approach to the synthesis of 2,3-dihydroquinazolin-4(1H)-one from 2-aminobenzamide and carbonyl compounds (aldehydes and ketones) using biocompatible choline sulfate-based acidic ionic liquid as a cheap and readily available catalyst in water has been developed. Various 2,3-dihydroquinazolin-4(1H)-one have been prepared using low-cost and environmental friendly solvent and catalyst in good to excellent yields in a shorter reaction time. The choline sulfate catalyst was prepared using a simple method from readily available starting material and was confirmed by 1H NMR, FTIR, and TGA. The ease of the product separation without organic solvent and column chromatography and the reusability of the acidic ionic liquid catalyst makes this method economically affordable for large-scale synthesis.
- Azizi, Najmedin,Shirdel, Fatemeh
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p. 3873 - 3882
(2017/06/20)
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- Self-Assembled Nanoliposomes of Phosphatidylcholine: Bridging the Gap between Organic and Aqueous Media for a Green Synthesis of Hydroquinazolinones
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Self-assembly of phosphatidylcholine in water creates liposomal nanoreactors for environmentally friendly synthesis of hydroquinazolinones by two- or three-component reactions, without the use of an extra catalyst or solvent. Recycling of the reaction medium and the absence of a need for other organic reagents are further advantages of this protocol.
- Tamaddon, Fatemeh,KazemiVarnamkhasti, MohammadTaghi
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p. 2510 - 2514
(2016/10/20)
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- Substituted fused pyrimidinone and dihydro-pyrimidone
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The use of substituted fused pyrimidinones and dihydropyrimidinones of the formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description, for enhancing stress tolerance in plants to abiotic stress, and for invigorating plant growth and/or for increasing plant yield.
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Paragraph 0198-0200; 0252-0254
(2016/10/08)
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- Ethanol promoted titanocene Lewis acid catalyzed synthesis of quinazoline derivatives
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An efficient catalytic system involving in situ activation of kinetically inert titanocene dichloride with alcoholic solvent for the synthesis of quinazoline derivatives was developed. 1 mol% Cp2TiCl2 at 30 °C afforded 17 examples of quinazoline derivatives with yields of 95-98% in 7-12 minutes. Mechanistic experiments using in situ NMR and HRMS established that the coordination of ethanol to the titanocene moiety released the catalytic species [Cp2Ti(OCH2CH3)2].
- Luo, Yanlong,Wu, Ya,Wang, Yunyun,Sun, Huaming,Xie, Zunyuan,Zhang, Weiqiang,Gao, Ziwei
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p. 66074 - 66077
(2016/07/26)
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- Synthesis of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones catalyzed by graphene oxide nanosheets in an aqueous medium: "on-water" synthesis accompanied by carbocatalysis and selective C-C bond cleavage
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Graphene oxide (GO) nanosheet catalyzed new and straightforward strategies for the construction of 2,3-dihydroquinazolinones and quinazolin-4(3H)-ones starting from anthranilamide (2-aminobenzamide) and an aldehyde/ketone in aqueous medium at room temperature have been realized. This catalyst is also found to be efficient for the expedient construction of quinazolin-4(3H)-ones starting from anthranilamide and a β-ketoester/1,3-diketone following selective C-C bond cleavage of the β-ketoester/1,3-diketone at an elevated temperature under metal and oxidant free conditions.
- Kausar, Nazia,Roy, Indranil,Chattopadhyay, Dipankar,Das, Asish R.
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p. 22320 - 22330
(2016/03/15)
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- Sulfamic acid as energy efficient catalyst for synthesis of flurophores, 1-H-spiro [isoindoline-1,2′-quinazoline]-3,4′(3′H)-diones
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An energy efficient synthesis of 1-H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′ H)-diones has been expediently accomplished by a reaction of isatin(s) / cyclic ketone and anthranilamide in ethanol at ambient temprature. Excellent yields of the products in short time duration, operational simplicity, and simple work-up procedure are the attractive features of the present protocol. Synthesized 1-H-spiro[isoindoline-1,2′-quinazoline]-3,4′(3′ H)-diones were found to be fluorescent with absorption in UV region (302, 362 nm) and emission in visible region (413-436 nm) with Stokes shift of 44-72 nm.
- Mane, Mansing M.,Pore, Dattaprasad M.
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p. 657 - 662
(2016/04/20)
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- Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs
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A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.
- Ghosh, Suman Kr,Nagarajan, Rajagopal
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p. 27378 - 27387
(2016/04/04)
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- PEG-SO3H as eco-friendly polymeric catalyst for the synthesis of 2,3-dihydroquinazolinones in water
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A facile, efficient, green, and environmentally benign method is described for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones by direct cyclocondensation of 2-aminobenzamide with aldehydes or ketones in water using PEG-SO3H as an acidic catalyst under room temperature. This new method totally avoids the use of organic acids, toxic or expensive solvents and affording the corresponding product in good to excellent yields in this reaction.
- Huang, Guoli,Liu, Bo,Teng, Mingyu,Chen, Yegao
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p. 453 - 458
(2016/10/18)
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- An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions
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An efficient protocol has been developed for the synthesis of 2,3-dihydroquinazolinone compounds from anthranilamide and aldehydes or ketones via ionic liquid catalyzed cyclization reaction. The reaction features high efficiency, shorter reaction duration, mild reaction conditions and inexpensive reagents. The catalyst was recovered and reused. The recyclability of ionic liquid resulted in excellent yields of products without loss of any catalytic activity.
- Nagarajan,Shaikh, Tanveer Mahamadali,Kandasamy, Elango
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supporting information
p. 9693 - 9699
(2015/12/05)
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- Sulfonic acid functionalized Wang resin (Wang-OSO3H) as polymeric acidic catalyst for the eco-friendly synthesis of 2,3-dihydroquinazolin-4(1H)-ones In memory of Dr. K. Anji Reddy, the founder of Dr. Reddy's Laboratories Ltd DRL Communication no.: IPDO IPM-00443
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Abstract An efficient and green approach has been developed for the synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones directly from corresponding substituted aromatic and aliphatic aldehyde and anthranilamide using recyclable polymer supported sulfonic acid catalyst under aqueous conditions. Environmental acceptability, operational simplicity, low cost, excellent functional group compatibility, and high yields are the important features of this protocol.
- Dhanunjaya Rao,Vykunteswararao,Bhaskarkumar,Jogdand, Nivrutti R.,Kalita, Dipak,Lilakar, Jaydeep Kumar D.,Siddaiah, Vidavalur,Douglas Sanasi, Paul,Raghunadh, Akula
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p. 4714 - 4717
(2015/08/06)
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- 2,3-Dihydroquinazolin-4(1H)-one derivatives as potential non-peptidyl inhibitors of cathepsins B and H
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A direct correlation between cathepsin expression-cancer progression and elevated levels of cathepsins due to an imbalance in cellular inhibitors-cathepsins ratio in inflammatory diseases necessitates the work on the identification of potential inhibitors to cathepsins. In the present work we report the synthesis of some 2,3-dihydroquinazolin-4(1H)-ones followed by their evaluation as cysteine protease inhibitors in general and cathepsin B and cathepsin H inhibitors in particular. 2,3-Dihydroquinazolin-4(1H)-ones, synthesized by the condensation of anthranilamide and carbonyl compound in presence of PPA-SiO2 catalyst, were characterized by spectral analysis. The designed compounds were screened as inhibitors to proteolysis on endogenous protein substrates. Further, a distinct differential pattern of inhibition was obtained for cathepsins B and H. The inhibition was more to cathepsin B with Ki values in nanomolar range. However, cathepsin H was inhibited at micromolar concentration. Maximum inhibition was shown by compounds, 1e and 1f for cathepsin B and compounds 1c and 1f for cathepsin H. The synthesized compounds were established as reversible inhibitors of cathepsins B and H. The results were also compared with the energy of interaction between enzyme active site and compounds using iGemdock software.
- Singh, Mamta,Raghav, Neera
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- Copper-Catalyzed Intramolecular C-C Bond Cleavage to Construct 2-Substituted Quinazolinones
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An efficient method for a copper-catalyzed intramolecular C-C bond cleavage to construct 2-substituted quinazolinones has been developed. The C-C bond at the 2-position of 2,2-disubstituted-1,2,3,4-tetrahydroquinazolinone was selectively cleaved by a Cu/air catalytic system. The trend for the cleavage was dependent on the leaving group in the order of: alkyl > methyl > phenyl > substituted aryl. The process described herein provides an explanation for the mechanism of the reaction between substituted 2-halobenzamides and α-substituted arylmethanamines to construct 2-substituted quinazolinones, which were previously reported and limited to the construction of 2-arylquinazolinones. The C-C bond at the 2-position of 2,2-disubstituted-1,2,3,4-tetrahydroquinazolinones was selectively cleaved by a Cu/air catalytic system to construct 2-substituted quinazolinones. The trend for the cleavage of the C-C bond was dependent on the leaving group in the order of: alkyl > methyl > phenyl > substituted aryl.
- Hu, Ben-Quan,Wang, Li-Xia,Yang, Luo,Xiang, Jun-Feng,Tang, Ya-Lin
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supporting information
p. 4504 - 4509
(2015/07/27)
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- Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO3H as a recyclable catalyst
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A new β-cyclodextrin-SO3H-assisted, convenient and efficient strategy for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media is described. The catalyst can be readily recovered and reused for the next reaction for at least three runs without any significant impact on the yields of the products. The main advantages of this protocol include short reaction times, practical simplicity, high yields, recyclable catalysts, safety, and cheapness of benign solvents. This journal is the Partner Organisations 2014.
- Wu, Jian,Du, Xianli,Ma, Juan,Zhang, Yuping,Shi, Qingcai,Luo, Lijun,Song, Baoan,Yang, Song,Hu, Deyu
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supporting information
p. 3210 - 3217
(2014/06/10)
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- CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
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A CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement yielding quinazolin-4(3H)-ones. The catalyst is recyclable four times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance (46 quinazolinones are synthesized and 9 of them are reported firstly), and providing moderate to excellent yield of the products under mild conditions.
- Zhang, Jin,Ren, Decheng,Ma, Yangmin,Wang, Weitao,Wu, Hao
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p. 5274 - 5282
(2014/07/08)
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- CuO nanoparticles catalyzed simple and efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
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A CuO nanoparticle-catalyzed one-pot process has engineered for the preparation of diverse quinazolinones from the readily available isatoic anhydride, aldehydes and amine or ammonium. For amine substrates the reactions afford 2,3-dihydroquinazolin-4(1H)-ones in aqueous ethanol promoted by ultrasound irradiation. However, the ammonium substrates undergo intramolecular electron transfer and rearrangement yielding quinazolin-4(3H)-ones. The catalyst is recyclable four times without loss of substantial activity. Other remarkable features include the wide range of functional group tolerance (46 quinazolinones are synthesized and 9 of them are reported firstly), and providing moderate to excellent yield of the products under mild conditions.
- Zhang, Jin,Ren, Decheng,Ma, Yangmin,Wang, Weitao,Wu, Hao
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p. 5274 - 5282
(2014/12/10)
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- Amberlyst A26 OH as a recyclable catalyst for hydration of nitriles and water-based synthesis of 4(1 H)-quinazolinones from 2-aminobenzonitrile and carbonyl compounds
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Selective hydration of nitriles to primary amides as well the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H2O-EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives. Georg Thieme Verlag Stuttgart New York.
- Tamaddon, Fatemeh,Pouramini, Farzaneh
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p. 1127 - 1131
(2014/05/20)
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- Metal modified SSA as a heterogeneous catalyst to promote the cyclocondesation of o-aminobenzonitriles with cycloketones in water
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A novel solid catalyst based on silica sulfuric acid (SSA) was prepared. When SSA was treated with Lewis acids, metal ions can be easily immobilized on silica surface, which results in strengthening Lewis acidity. The novel solid catalyst was demonstrated to be efficient in promoting the cyclocondesation of o-aminobenzonitriles with cycloketones in water, and hence promising in the application of pharmaceutical study and production.
- Zhang, Li Jun,Yu, Jian Ling,Wang, Wei Li,Li, Heng,Xu, Dan Dan,Bi, Ya Dong,Liu, Fu De
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p. 710 - 712
(2014/01/23)
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- From waste biomass to solid support: Lignosulfonate as a cost- Effective and renewable supporting material for catalysis
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Lignosulfonate (LS) is an organic waste generated as a byproduct of the cooking process in sulfite pulping in the manufacture of paper. In this paper, LS was used as an anionic supporting material for immobilizing cationic species, which can then be used as heterogeneous catalysts in some organic transformations. With this strategy, three lignin-supported catalysts were prepared including 1) lignin- SO3Sc(OTf)2, 2) lignin-SO3Cu(OTf), and 3) lignin-IL@NH2 (IL= ionic liquid). These solid materials were then examined in many organic transformations. It was finally found that, compared with its homogeneous counterpart as well as some other solid catalysts that are prepared by using different supports with the same metal or catalytically active species, the lignin-supported catalysts showed better performance in these reactions not only in terms of activity but also with regard to recyclability.
- Sun, Shaohuan,Bai, Rongxian,Gu, Yanlong
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supporting information
p. 549 - 558
(2014/04/03)
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- Eco-friendly syntheses of 2,2-disubstituted- and 2-spiroquinazolinones
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Environmentally friendly methods were applied to prepare quinazolin-4(1H)-one derivatives in either aqueous or solventless medium from anthranilamide and a number of ketones. With dialkyl-substituted ketones, acetophenone and cycloalkanones, the ring closure proceeded smoothly under either aqueous or solventless conditions. With poorly water-soluble cycloalkanones, the ring closure was carried out under mechanochemical ball-milling conditions, in the presence of molecular iodine as catalyst. The environmentally friendly protocols applied resulted in the corresponding quinazolinones in quantitative yields.
- Mikls, Ferenc,Hum, Veronika,Fül?p, Ferenc
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