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1

Asif, Mohammad. "Chemical Characteristics, Synthetic Methods, and Biological Potential of Quinazoline and Quinazolinone Derivatives." International Journal of Medicinal Chemistry 2014 (November 13, 2014): 1–27. http://dx.doi.org/10.1155/2014/395637.

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The heterocyclic fused rings quinazoline and quinazolinone have drawn a huge consideration owing to their expanded applications in the field of pharmaceutical chemistry. Quinazoline and quinazolinone are reported for their diversified biological activities and compounds with different substitutions bring together to knowledge of a target with understanding of the molecule types that might interact with the target receptors. Quinazolines and quinazolinones are considered as an important chemical for the synthesis of various physiological significance and pharmacological utilized molecules. Quinazolines and quinazolinone are a large class of biologically active compounds that exhibited broad spectrum of biological activities such as anti-HIV, anticancer, antifungal, antibacterial, antimutagenic, anticoccidial, anticonvulsant, anti-inflammatory, antidepressant, antimalarial, antioxidant, antileukemic, and antileishmanial activities and other activities. Being considered as advantaged scaffold, the alteration is made with different substituent.
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2

Abu-Hashem, Ameen. "Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity." Molecules 23, no. 11 (October 27, 2018): 2793. http://dx.doi.org/10.3390/molecules23112793.

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Substituted-6-methyl-1-thioxo-1,2-dihydro-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (5a,b) were synthesized from condensation of visnagenone (2a) or khellinone (2b) with 6-amino-thiouracil (3) in dimethylformamide or refluxing of (4a) or (4b) in dimethylformamide. Hence, compounds (5a,b) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (6a,b), furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazolinone (7a,b), substituted-benzylidene-furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (8a–f), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (9a,b), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (10a,b), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (11a–d), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (12a,b), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (13a,b) and 6-methyl-1-((piperazine) or morpholino)-3H-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (14a–d). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, 1H-NMR, 13C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines 8a–f and 11a–d displayed results excellent for growth inhibition of bacteria and fungi.
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3

Komar, Mario, Maja Molnar, and Anastazija Konjarević. "Screening of Natural Deep Eutectic Solvents for Green Synthesis of 2-methyl-3-substituted Quinazolinones and Microwave-Assisted Synthesis of 3-aryl Quinazolinones in Ethanol." Croatica chemica acta 92, no. 4 (2020): 511–17. http://dx.doi.org/10.5562/cca3597.

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In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1 : 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.
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4

Mishra, AD. "A New Route for the Synthesis of Quinazolinones." Nepal Journal of Science and Technology 12 (July 22, 2012): 133–38. http://dx.doi.org/10.3126/njst.v12i0.6491.

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Quinazolinone derivatives are highly bioactive heterocyclic compounds with wider range of microbial activities such as anti-malarial, anti-cancer, anti-inflammatory, anti-hypertensive, anti-convulsant, anti-HIV, etc. Solid supported microwave synthesis of some 3-substituted-4-(2H)-quinazolinones has been carried out by the reaction of anthranilic acid, formaldehyde and primary aromatic amines. The usage of hazardous reagents and organic solvents has been avoided. The reactions were conducted in presence of acidic alumina where formaldehyde entered into cycloaddition to yield the quinazolinone derivatives. The reactions completed within 2-4 minutes with 82-94% of yields in microwave reactions while it took 5-7 hours for completion affording only 56-68% of the yields in conventional reactions. The synthesized quinazolinone derivatives showed moderate to promising antibacterial and antifungal activities.DOI: http://dx.doi.org/10.3126/njst.v12i0.6491 Nepal Journal of Science and Technology 12 (2011) 133-138
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5

Mahmoud, Mahmoud Refaee, Manal Mohamed El-Shahawi, and Fatma Saber Mohamed Abu El-Azm. "Synthesis of novel quinazolinone and fused quinazolinones." European Journal of Chemistry 2, no. 3 (September 30, 2011): 404–9. http://dx.doi.org/10.5155/eurjchem.2.3.404-409.267.

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6

Abdel-Megeed, Mohamed Farghali, and Abderrahman Teniou. "Synthesis of some 3-substituted 4(3H)-quinazolinone and 4(3H)-quinazolinethione derivatives and related fused biheterocyclic ring systems." Collection of Czechoslovak Chemical Communications 53, no. 2 (1988): 329–35. http://dx.doi.org/10.1135/cccc19880329.

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The reactions of 2-phenyl-4(3H)-quinazoline, 2-phenyl-3-amino-4(3H)-quinazolinone, and corresponding thiones with phenyl isocyanate or phenyl isothiocyanate were investigated. The resulting urea and thiourea quinazolinone or quinazolinethione derivatives reacted with hydrazine hydrate, phenylhydrazine, and urea or thiourea to form fused biheterocyclic ring systems with potential biological activities. The products were identified by IR, 1H NMR, and mass spectroscopy.
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7

Peter Osarodion Osarumwense, Mary Olire Edema, and Cyril Odianosen Usifoh. "Synthesis and antibacterial activities of quinazolin-4(3h)-one, 2-methyl-4(3h)-quinazolinone and 2–phenyl-4(3h)-quinazolinone." International Journal of Biological and Pharmaceutical Sciences Archive 1, no. 2 (April 30, 2021): 077–84. http://dx.doi.org/10.30574/ijbpsa.2021.1.2.0027.

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Background: Quinazoline and quinazolinone scaffolds represent an important class of biologically active nitrogen heterocyclic compounds. Many marketed drugs are based on these moieties. A diverse range of molecules with quinazoline/quinazolinone moieties have been reported to exhibit broad spectrum of biological activities Objective: This study is aimed at the synthesis of these quinazolinone derivatives, quinazolin-4(3H)-One, 2-Methyl-4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one and evaluate them for their antibacterial activities. Method: The consolidation of 2-amino-methyl-4-methoxybenzoate with acetic anhydride produced the cyclic compound 2-methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which also produce a novel 2,3-disubstituted quinazolin-4 ones via the reaction with hydrazine hydrate. The quinazolinone derivatives quinazolin-4(3H)-One, 2-Methyl-4(3H)-quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one were evaluated pharmacologically for their in vivo analgesic activities by acetic acid induced writhing in mice. The compounds synthesized were assuredly validated by means of Infrared, Nuclear Magnetic Resonance (1H and 13C), Gas Chromatography Mass Spectrophotometer and Elemental analysis. The synthesized compounds were tested for their antibacterial activity.Compounds 1,2 and 3 showed significant antibacterial activities. Discussion: Compound 1 was identified by the absence of methyl group and the presence of methyl group for compound 2. The test analysed compounds exhibited significant antibacterial activities. The compounds synthesized exhibited promising antibacterial activities against the tested organisms. Conclusion: The compounds have high antibacterial activities. Compound 2 has a higher activity compared to Compound 1 and 3. Compound 2 has a higher antibacterial against Escherichia coli, Klebsiella pneumonia and Pseudomonas aeuriginosa
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8

D, Priya, Srimathi R, and Anjana Gv. "SYNTHESIS AND EVALUATION OF SOME MANNICH BASES OF QUINAZOLINONE NUCLEUS." Asian Journal of Pharmaceutical and Clinical Research 11, no. 2 (February 1, 2018): 407. http://dx.doi.org/10.22159/ajpcr.2018.v11i2.22644.

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Objective: In the present work, a series of five Mannich bases of quinazolinone nucleus synthesized by treating quinazolinones with various aromatic amines.Methods: A series of Mannich bases of quinazolinone synthesized by refluxing quinazolinone with anthranilic acid, amine, and formaldehyde in ethanol. The chemical structures of synthesized compounds were confirmed by thin-layer chromatography using the suitable solvent system and characterized by melting point and IR. The compounds screened for their antibacterial activity and antioxidant activity.Results: Antioxidant activity of the synthesized compounds was done using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals scavenging method. Compounds II and III showed values at 53% and 36%, respectively, when compared to that of standard ascorbic acid 24% at 10 μg/ml. Compounds II and IV showed excellent activity against Gram-negative organism Escherichia coli using ciprofloxacin as standard.Conclusion: All the synthesized compounds were screened for antimicrobial activity by cup plate by measuring inhibition zone using E. coli at a concentration range of 200–600 mcg/ml, and antioxidant activity was determined by DPPH method.
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9

Abdou, Ibrahim M., and Shaikha S. Al-Neyadi. "Synthesis of quinazolines and quinazolinones via palladium-mediated approach." Heterocyclic Communications 21, no. 3 (June 1, 2015): 115–32. http://dx.doi.org/10.1515/hc-2014-0181.

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AbstractQuinazoline derivatives have drawn attention in the field of heterocyclic chemistry because of their unique skeleton and interesting biological applications. This review summarizes the recent palladium-catalyzed reactions used to construct quinazoline and its related 4(3H)-quinazolinone analogues. The mechanisms of some Pd-catalyzed reactions are also discussed.
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10

Koketsu, Mamoru, Amol Sonawane, Yunnus Shaikh, and Dinesh Garud. "Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes." Synthesis 51, no. 02 (September 21, 2018): 500–507. http://dx.doi.org/10.1055/s-0037-1610910.

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A new route for the expedient synthesis of a specific regioisomer of isoquinoline-fused quinazolinones is reported. Silver(I)-catalyzed cascade cyclization of 2-aminobenzamides and 2-alkynylbenzaldehydes followed by in situ oxidation gives 12-butyl- or 12-aryl-6H-isoquinolino[2,1-a]quinazolin-6-ones in 69–91% yields. The structure of the isoquinoline-fused quinazolinone was confirmed by X-ray crystallography analysis.
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11

Amrutkar, Rakesh D., Sunil V. Amrutkar, and Mahendrasing S. Ranawat. "Quinazolin-4-One: A Varsatile Molecule." Current Bioactive Compounds 16, no. 4 (June 19, 2020): 370–82. http://dx.doi.org/10.2174/1573407215666181120115313.

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Background:Quinazolines and quinazolinones constitute a major class of biologically active molecules both from natural and synthetic sources. We will limit this review to compounds possessing the 4(3H)-quinazolinone skeleton, which is found in compounds displaying significant biological and pharmacological properties. The molecular design of potential lead compound is still a key line of approach for the discovery and development of new chemical entities. A combination of two or more chemical moieties into one is a common approach of operation and this can most likely result in the improvement of pharmacological activity and removal of unwanted side effects.Methods:We undertake search for peer-reviewed and research literature on quinazolinone moiety using different tools of literature survey. The quality of superior papers was assess using standard tools. The distinctiveness of screened papers was shorted and high-quality content was reorganiz and written in own language.Results:The review will be expressed in two main sections, the first section will be related to synthetic procedures and the second section includes the biological importance of Quinazoline derivatives. Total hundred (100) to one hundred and ten (110) research papers ware searched. Out of these, seventy-eight papers were included in the review, the majority of research papers were from international journals. Fifty fours papers defined the different synthetic schemes considering the general strategies using orthosubstituted anilines such as 2-aminobenzoic acid (anthranilic acid) and its analogues, or isatoic anhydride as starting materials, which are condensed with acid chlorides, imidates or aldehydes. Microwave irradiation was also proven to be very useful to improve the yields, and in particular, it has been successfully applied to the Niementowski procedure involving the fusion of anthranilic acid with formamide. The remaining part of the review focuses on biological importance of the 4(3H)-quinazolinone scaffold as therapeutic agents and a broad range of activities like antibacterial, antifungal, antiviral, anticonvulsant, antitumor, antihypertensive, analgesic and anti-inflammatory agents has been highlighted.Conclusion:The present review focuses on simplified, efficient and widespread literature of the methods of synthesis and diverse pharmacological activities of quinazoline and its derivatives have been highlighted.
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12

Yadav, Meena K., Laxmi Tripathi, and Diptendu Goswami. "SYNTHESIS AND ANTICONVULSANT ACTIVITY (CHEMO SHOCK) OF N-1(SUBSTITUTED-N-4[(4-OXO-3-PHENYL-3, 4-DIHYDRO-QUINAZOLINE-2-YLMETHYL) SEMICARBAZONES." Asian Journal of Pharmaceutical and Clinical Research 10, no. 4 (April 1, 2017): 359. http://dx.doi.org/10.22159/ajpcr.2017.v10i4.16876.

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Objective: This work is designed at finding new structure leads with potential anticonvulsant activities of 4(3H)-quinazolinone pharmacophore scaffold.Methods: A new series of 4(3H)-quinazolinone pharmacophore was designed with substituted moieties possesses different electronic environment in the hope of developing potent and safe new effective compounds. In such fashion, in this paper, we report the synthesis and anticonvulsant activity (Chemo shock) of N-1(substituted-N-4[(4-oxo-3-phenyl-3, 4-dihydro-quinazoline-2-ylmethyl) semicarbazones 3A-d (1-7), 3B-d (1-7), 3C-d (1-7), their chemical structure were characterized using IR, H-H NMR, and elemental analysis techniques. Their anticonvulsant activity was evaluated using chemicals strychnine, thiosemicarbazide and 4-aminopyridine induced seizure models at a dose of 30, 100, 300 mg/kg unto 2 hrs tests in mice. The rotarod assay was performed in mice to evaluate the neurotoxicity of the compounds. 1Results: Compounds 3C (d-4), 3B (d-4), and 3A (d-4) were observed to be most feasible to act against glutamate receptor for anticonvulsant activity.Conclusions: The results obtained revealed that numbers of novel quinazolinone semicarbazone derivatives are effective in chemical to induce (chemo shock) model and showing good anticonvulsant activity.Keywords: Quinazolinone, Semicarbazones, Strychnine, Thiosemicarbazide, 4-aminopyridine, Anticonvulsant activity, Chemo shock.
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13

Bollini, Mariela, Ana M. Bruno, María E. Niño, Juan J. Casal, Leandro D. Sasiambarrena, Damián A. G. Valdez, Leandro Battini, Vanesa R. Puente, and María E. Lombardo. "Synthesis, 2D-QSAR Studies and Biological Evaluation of Quinazoline Derivatives as Potent Anti-Trypanosoma cruzi Agents." Medicinal Chemistry 15, no. 3 (April 12, 2019): 265–76. http://dx.doi.org/10.2174/1573406414666181005145042.

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Background: Chagas disease affects about 7 million people worldwide. Only two drugs are currently available for the treatment for this parasite disease, namely, benznidazol (Bzn) and nifurtimox (Nfx). Both drugs have limited curative power in the chronic phase of the disease. Therefore, continuous research is an urgent need so as to discover novel therapeutic alternatives. Objective: The development of safer and more efficient therapeutic anti-T. cruzi drugs continues to be a major goal in trypanocidal chemotherapy. Method: Synthesis, 2D-QSAR and drug-like physicochemical properties of a set of quinazolinone and quinazoline derivatives were studied as trypanocidal agents. All compounds were screened in vitro against Trypanosoma cruzi (Tulahuen strain, Tul 2 stock) epimastigotes and bloodstream trypomastigotes. Results: Out of 34 compounds synthesized and tested, six compounds (5a, 5b, 9b, 9h, 13f and 13p) displayed significant activity against both epimastigotes and tripomastigotes, without exerting toxicity on Vero cells. Conclusion: The antiprotozoal activity of these quinazolinone and quinazoline derivatives represents an interesting starting point for a medicinal chemistry program aiming at the development of novel chemotherapies for Chagas disease.
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Deshmukh, M. B., and Savita Dhongade (Desai). "Synthesis and QSAR Study of Some HDL Cholesterol Increasing Quinazolinone Derivatives." E-Journal of Chemistry 1, no. 1 (2004): 17–31. http://dx.doi.org/10.1155/2004/671567.

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We describe here an easy and efficient method to obtainS-alkylated derivatives of thio-quinazolinone using different alkylating agents via a solvent-free microwave-assisted method. The alkylated thio quinazolinones were further sequentially condensed with hydrazine hydrate and different aromatic aldehydes to get the hydrazones, which were studied for QSAR. The synthesized compounds were subjected to a prediction of biological activities. A software application (PASS) was used for this purpose. The relationship between structure and different biological activities was studied and the different derivatives were recommended for the screening of some specific activities like anti-tuberculosic, anti-mycobacterial and HDL cholesterol increasing activities.
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Bairy, Gurupada, Arijit Nandi, Kartic Manna, and Ranjan Jana. "Ruthenium(II)-Catalyzed Migratory C–H Allylation/Hydroamination Cascade for the Synthesis of Rutaecarpine Analogues." Synthesis 51, no. 12 (April 26, 2019): 2523–31. http://dx.doi.org/10.1055/s-0037-1611525.

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An unprecedented allyl migration from a remote position of a quinazoline moiety through a ruthenium(II) shuttle is reported. This present cascade reaction is initiated through the formation of an η3-ruthenium–allyl complex followed by C–H allylation at the ortho position of the 2-aryl moiety. Finally, hydroamination with the quinazolinone -NH group, which is formed through tautomerization of the quinazoline, furnishes the annulation product. This exceedingly fast cascade reaction is complete within 10 minutes to provide rutaecarpine analogues in a single operation.
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16

Nerkar, A. G., A. K. Saxena, S. A. Ghone, and A. K. Thaker. "In SilicoScreening, Synthesis andIn VitroEvaluation of Some Quinazolinone and Pyridine Derivatives as Dihydrofolate Reductase Inhibitors for Anticancer Activity." E-Journal of Chemistry 6, s1 (2009): S97—S102. http://dx.doi.org/10.1155/2009/506576.

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Dihydrofolate reductase (DHFR) is the important target for anticancer drugs belonging to the class of antimetabolites as the enzyme plays important role in the de novo purine synthesis. We here report thein silicoscreening to obtain best fit molecules as DHFR inhibitors, synthesis of some ʻbest fitʼ quinazolinone from 2-phenyl-3-(substituted-benzilidine-amino) quinazolinones (Quinazolinone Shiff's bases) QSB1-5and pyridine-4-carbohydrazide Shiff's bases (ISB1-5) derivatives and theirin vitroanticancer assay. Synthesis of the molecules was performed using microwave assisted synthesis. The structures of these molecules were elucidated by IR and1H-NMR. These compounds were then subjected forin vitroanticancer evaluation against five human cancer cell-lines for anticancer cyto-toxicity assay. Methotrexate (MTX) was used as standard for this evaluation to give a comparable inhibition of the cell proliferation by DHFR inhibition. Placlitaxel, adriamycin and 5-fluoro-uracil were also used as standard to give a comparable activity of these compounds with other mechanism of anticancer activity. ISB3(4-(N, N-dimethyl-amino)-phenyl) Schiff''s base derivative of pyridine carbohydrazide showed equipotent activity with the standards used inin vitroanticancer assay as per the NCI (National Cancer Institute) guidelines.
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Smith, Keith, Gamal A. El-Hiti, Mohamed F. Abdel-Megeed, and Mohamed A. Abdo. "Convenient Synthesis of More Complex 2-Substituted 4(3H)-Quinazolinones via Lithiation of 2-Alkyl-4(3H)-quinazolinones." Collection of Czechoslovak Chemical Communications 64, no. 3 (1999): 515–26. http://dx.doi.org/10.1135/cccc19990515.

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2-Methylquinazolin-4(3H)-one has been doubly lithiated, at nitrogen and in the 2-methyl group, with n-butylithium. The lithium reagent thus obtained reacts with a variety of electrophiles (iodomethane, D2O, phenyl isocyanate, benzaldehyde, benzophenone, cyclopentanone, 2-butanone, carvone) to give the corresponding 2-substituted derivatives in very good yields. Reaction of the dilithio reagent with acetonitrile gives an α,β-unsaturated imine by tautomerization of the initial addition product. Double lithiation of 2-ethyl- and 2-propyl-4(3H)-quinazolinones can be achieved using lithium diisopropylamide and the lithiated reagents thus obtained react with similar electrophiles to give the corresponding products in very good yields. In the reaction of the dianion of the 2-ethyl-4(3H)-quinazolinone with iodine, an oxidatively dimerised product was obtained. Lithiation of 2-unsubstituted 4(3H)-quinazolinone does not take place on C-2 under similar conditions.
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Fekri, Leila Z. "NiFe2O4@SiO2 @amino Glucose Magnetic Nanoparticle under Solvent-free Condition: A New, mild, Simple and Effective Avenue for the Synthesis of Quinazolinone, Imidazo[1,2-a]Pyrimidinone and Novel Derivatives of Amides." Current Organic Synthesis 17, no. 4 (July 27, 2020): 304–12. http://dx.doi.org/10.2174/1570179417666200409151330.

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Background: Imidazo[1,2-a]pyrimidinone, quinazolinone and amide derivatives have attracted a lot of interest because of their broad scope of biological and pharmacological activities. There are a lot of methods reported in the literature for their synthesis. Therefore, we became interested in developing a convenient synthetic method for the preparation of imidazoquinazolinone and amide derivatives. Objective: NiFe2O4@SiO2 @glucose amine were synthesized, characterized and have been used for the green, effective and mild multicomponent synthesis of quinazolinones, benzoimidazo[1,2-a]pyrimidinones and amides under solvent-free conditions in short reaction times and excellent yields. To expand of the scope of this avenue, multicomponent synthesis of mono and bis novel amides was tested for the first time. All of the products were characterized by mp, FT-IR, NMR and elemental analysis. Methods: Aldehyde (1mmol), 2-amino benzimidazole (1 mmol), dimedone (1mmol) or indane-1,3-dione (1 mmol) for the synthesis of quinazoline or imidazopyrimidinones and arene (1mmol), anhydride (1mmol), 2- aminobenzimidazole (1mmol) for the synthesis of amides in the nanocatalyst NiFe2O4@SiO2@glucose amine (0.15mol%: 0.05g) were stirred by a magnet for the required reaction time. After completion of the reaction, as indicated by TLC, the products were collected and recrystallized from ethanol if necessary. Results: We present a novel avenue for the synthesis of benzimidazo[1,2-a] pyrimidinones, quinazolinones and amides in the presence of NiFe2O4@SiO2@glucose amine under solvent-free conditions. Conclusion: In conclusion, we developed NiFe2O4@SiO2 @glucose amine-catalysed multicomponent synthesis of quinazolinones and imidazo[1,2-a]pyrimidinones using the reaction of benzaldehyde, dimedone or indane-dione and 2-aminobenzimidazole and multicomponent synthesis of amides using arenes, cyclic anhydrides and 2-aminobenzimidazole by a solvent-free technique. This method proves to be a robust and innovative approach for the synthesis of a biologically important structure. The operational simplicity, the excellent yields of products, ease of separation and recyclability of the magnetic catalyst, waste reduction and high selectivity are the main advantages of this method. Furthermore, this new avenue is cheap and environmentally benign.
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Zhang, Jinjin, Baohua Huang, Yujing Lu, Wenbin Li, Zichong Zhuang, Donghua Ke, Jingpeng Zhong, Jinlin Zhou, and Qian Chen. "Synthesis and Biological Evaluation of Isofebrifugine Analogues." Letters in Organic Chemistry 16, no. 12 (October 9, 2019): 1004–10. http://dx.doi.org/10.2174/1570178616666190417115639.

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: Isofebrifugine, as a kind of natural quinazolinone alkaloid with important physiological activities and good pharmacological effects, was isolated from a Chinese medicinal plant, Chang Shan (Dichroa febrifuga). In this paper, the synthesis of a series of novel isofebrifugine analogues was accomplished by employing the N-alkylation of 4(3H)-quinazolinones with benzyl (3aR,7aR)-rel-2- (bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)carboxylates and the subsequent N-deprotection. These analogues were characterized by 1H NMR, 13C NMR and HRMS spectra. The MTT assay was used to examine the inhibitory effects of these analogues on the growth of human hepatoma cells (HepG2). The results indicated that some halogenated or hemiketal analogues showed interesting inhibition activity.
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Fišnerová, Ludmila, Bohumila Brunová, Zuzana Kocfeldová, Jana Tíkalová, Eva Maturová, and Jaroslava Grimová. "Synthesis and analgetic efficiency of some oxy and oxo derivatives of 4(3H)-quinazolinone." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2373–81. http://dx.doi.org/10.1135/cccc19912373.

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A series of 3-substituted 4(3H)-quinazolinone derivatives have been prepared by alkylation of 4(3H)-quinazolinone with halogenoethers, halogenoketones, and Mannich bases, and the products have been tested for analgetic effects.The most interesting representatives of the oxy and oxo derivatives are 3-[2-(2’,4’-difluoro-4-biphenylyloxy)ethyl]-4(3H)-quinazolinone (Ib) and 3-[2-oxo-2-(4-biphenylyl)ethyl]-4(3H)-quinazolinone (IIi), respectively. Among the group of oxy derivatives also the 2-methylderivative Ig has been prepared, viz. by alkylation of 2’,4’-difluoro-4-hydroxybiphenyl with 2-methyl-3-(2-chloroethyl)-4(3H)-quinazolinone; the activity of Ig is lower than that of Ib.
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Shafii, Behnaz, Mina Saeedi, Mohammad Mahdavi, Alireza Foroumadi, and Abbas Shafiee. "Novel Four-Step Synthesis of Thioxo-quinazolino[3,4-a]quinazolinone Derivatives." Synthetic Communications 44, no. 2 (October 29, 2013): 215–21. http://dx.doi.org/10.1080/00397911.2013.800211.

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Huang, Cheng, Yuan Fu, Hua Fu, Yuyang Jiang, and Yufen Zhao. "Highly efficient copper-catalyzed cascade synthesis of quinazoline and quinazolinone derivatives." Chemical Communications, no. 47 (2008): 6333. http://dx.doi.org/10.1039/b814011a.

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23

Vijayakumar, K., A. Jafar Ahamed, and G. Thiruneelakandan. "Synthesis, Antimicrobial, and Anti-HIV1 Activity of Quinazoline-4(3H)-one Derivatives." Journal of Applied Chemistry 2013 (September 12, 2013): 1–5. http://dx.doi.org/10.1155/2013/387191.

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The present investigation aims to synthesize 11 compounds of quinazoline-1 derivatives and to test their antimicrobial and anti-HIV1 activities. A quick-witted method was developed for the synthesis of novel substituted quinazolinone derivatives by summarizing diverse diamines with benzoxazine reactions, and it demonstrated the benefits of typical reactions, handy operation, and outstanding product yields. These compounds were confirmed by elemental analysis, I R, 1H NMR, 13C NMR, and mass spectra. Then antimicrobial and anti-HIV1 activities of the compounds were tested in-vitro. It was found that compounds 7–11 possessed a wide range of anti microbial and anti-HIV1 activity.
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Patel, Sachin, Manish Patel, and Ranjan Patel. "Synthesis and characterization of heterocyclic substituted fluoran compounds." Journal of the Serbian Chemical Society 72, no. 11 (2007): 1039–44. http://dx.doi.org/10.2298/jsc0711039p.

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New quinazolinone-substituted fluoran compounds were synthesized by reaction of keto acid, 2?-carboxy-2-hydroxy-4-N-pyrrolidinylbenzophenone with different quinazolinone derivatives in the presence of conc. sulphuric acid. All the synthesized fluoran compounds were characterized by spectroscopic methods (IR, 1H-NMR and UV-visible spectroscopy) and elemental analysis. The fluoran compounds are colorless or nearly colorless and develop color on contact with electron-accepting compounds.
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25

Gong, Tang, Liu, and Liu. "Synthesis and Evaluation of Novel 2H-Benzo[e]-[1,2,4]thiadiazine 1,1-Dioxide Derivatives as PI3Kδ Inhibitors." Molecules 24, no. 23 (November 25, 2019): 4299. http://dx.doi.org/10.3390/molecules24234299.

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In previous work, we applied the rotation-limiting strategy and introduced a substituent at the 3-position of the pyrazolo [3,4-d]pyrimidin-4-amine as the affinity element to interact with the deeper hydrophobic pocket, discovered a series of novel quinazolinones as potent PI3Kδ inhibitors. Among them, the indole derivative 3 is one of the most selective PI3Kδ inhibitors and the 3,4-dimethoxyphenyl derivative 4 is a potent and selective dual PI3Kδ/γ inhibitor. In this study, we replaced the carbonyl group in the quinazolinone core with a sulfonyl group, designed a series of novel 2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide derivatives as PI3Kδ inhibitors. After the reduction of nitro group in N-(2,6-dimethylphenyl)-2-nitrobenzenesulfonamide 5 and N-(2,6-dimethylphenyl)-2-nitro-5-fluorobenzenesulfonamide 6, the resulting 2-aminobenzenesulfonamides were reacted with trimethyl orthoacetate to give the 3-methyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide derivatives. After bromination of the 3-methyl group, the nucleophilic substitution with the 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine provided the respective iodide derivatives, which were further reacted with a series of arylboronic acids via Suzuki coupling to furnish the 2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide derivatives 15a–J and 16a–d. In agreement with the quinazolinone derivatives, the introduction of a 5-indolyl or 3,4-dimethoxyphenyl at the affinity pocket generated the most potent analogues 15a and 15b with the IC50 values of 217 to 266 nM, respectively. In comparison with the quinazolinone lead compounds 3 and 4, these 2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide derivatives exhibited much decreased PI3Kδ inhibitory potency, but maintained the high selectivity over other PI3K isoforms. Unlike the quinazolinone lead compound 4 that was a dual PI3Kδ/γ inhibitor, the benzthiadiazine 1,1-dioxide 15b with the same 3,4-dimethoxyphenyl moiety was more than 21-fold selective over PI3Kγ. Moreover, the introducing of a fluorine atom at the 7-position of the 2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide core, in general, was not favored for the PI3Kδ inhibitory activity. In agreement with their high PI3Kδ selectivity, 15a and 15b significantly inhibited the SU-DHL-6 cell proliferation.
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26

Sharma, Saurabh, Dhananjay Bhattacherjee, and Pralay Das. "Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis." Organic & Biomolecular Chemistry 16, no. 8 (2018): 1337–42. http://dx.doi.org/10.1039/c7ob03064a.

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27

Kavitha, K., Nehla Yahoob, B. Vijayakumar, and K. Reshma Fathima. "Synthesis and Evaluation of Quinazolinone Derivatives." Asian Journal of Research in Chemistry 10, no. 4 (2017): 577. http://dx.doi.org/10.5958/0974-4150.2017.00096.7.

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28

Mahdavi, Mohammad, Vahid Lotfi, Mina Saeedi, Ebrahim Kianmehr, and Abbas Shafiee. "Synthesis of novel fused quinazolinone derivatives." Molecular Diversity 20, no. 3 (May 21, 2016): 677–85. http://dx.doi.org/10.1007/s11030-016-9675-x.

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29

Palaniraja, Jeyakannu, and Selvaraj Mohana Roopan. "Iodine-mediated synthesis of indazolo-quinazolinones via a multi-component reaction." RSC Advances 5, no. 12 (2015): 8640–46. http://dx.doi.org/10.1039/c4ra13779e.

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30

El-Sayed, Amira A., Mahmoud F. Ismail, Abd El-Galil E. Amr, and Ahmed M. Naglah. "Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one(thione) Derivatives with DFT Study." Molecules 24, no. 20 (October 21, 2019): 3787. http://dx.doi.org/10.3390/molecules24203787.

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The current study was chiefly designed to examine the antiproliferative and antioxidant activities of some novel quinazolinone(thione) derivatives 6–14. The present work focused on two main points; firstly, comparing between quinazolinone and quinazolinthione derivatives. Whereas, antiproliferative (against two cell lines namely, HepG2 and MCF-7) and antioxidant (by two methods; ABTS and DPPH) activities of the investigated compounds, the best quinazolinthione derivatives were 6 and 14, which exhibited excellent potencies comparable to quinazolinone derivatives 5 and 9, respectively. Secondly, we compared the activity of four series of Schiff bases which included the quinazolinone moiety (11a–d). In addition, the antiproliferative and antioxidant activities of the compounds with various aryl aldehyde hydrazone derivatives (11a–d) analogs were studied. The compounds exhibited potency that increased with increasing electron donating group in p-position (OH > OMe > Cl) due to extended conjugated systems. Noteworthy, most of antiproliferative and antioxidant activities results for the tested compounds are consistent with the DFT calculations.
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31

B. Deshmukh, M., and Savita Dhongade (Desai). "Synthesis and QSAR Study of (4-Oxo-3-aryl-3,4-dihydro-quinazolin-2-ylsulfanyl)-propionic Acid arylidene/aryl-ethylidene-hydrazides via Microwave Assisted Solvent Free Reations." E-Journal of Chemistry 1, no. 2 (2004): 115–26. http://dx.doi.org/10.1155/2004/142148.

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In the present work,s-alkylated derivatives of thio-quinazolinone were obtained using Methyl 2-chloro propionate via a solvent-free microwave-assisted method. The alkylated thio quinazolinones were further sequentially condensed with hydrazine hydrate and different aromatic aldehydes to get the hydrazides, which were studied for QSAR. The synthesized compounds were subjected to a prediction of biological activities. A software application (PASS) was used for this purpose. . The relationship between structure and different biological activities was studied and the different derivatives were recommended for the screening of some specific activities like anti-tuberculosic, anti-mycobacterial & HDL cholesterol increasing activities.
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32

Zhang, Yaping, Bin Zhen, Hansheng Li, and Yaqing Feng. "Basic ionic liquid as catalyst and surfactant: green synthesis of quinazolinone in aqueous media." RSC Advances 8, no. 64 (2018): 36769–74. http://dx.doi.org/10.1039/c8ra06378h.

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33

Shafii, Behnaz, Mina Saeedi, Mohammad Mahdavi, Alireza Foroumadi, and Abbas Shafiee. "ChemInform Abstract: Novel Four-Step Synthesis of Thioxo-quinazolino[3,4-a]quinazolinone Derivatives." ChemInform 45, no. 24 (June 2, 2014): no. http://dx.doi.org/10.1002/chin.201424178.

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34

Yang, Fan, Wei-Ping He, Jia-Qi Yao, Dong Zou, Pu Chen, and Jie Li. "Synthesis and Neuroprotective Biological Evaluation of Quinazolinone Derivatives via Scaffold Hopping." Current Organic Synthesis 16, no. 5 (October 17, 2019): 772–75. http://dx.doi.org/10.2174/1570179416666190328233501.

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Objective: To develop efficient method for the synthesis of quinazolinone derivatives bearing different functional groups on ring A and ring B and evaluation as neuroprotective agents. Methods: Synthetic route to quinazolinone derivatives was furnished by condensation/cyclocondensation/ reduction sequence of the activated N-acylbenzotriazoles. The structures of the targets compounds have been deduced upon their spectral data (1HNMR, 13CNMR and Mass spectroscopy). The neuroprotective activities of the synthesized compounds are also evaluated. Results: Preliminary screening on a MPP+ induced SH-SY5Y cell injury model of the synthesized compounds resulted in four compounds (6q, 6r, 6u, and 8e) showed promising neural cell protection activities. The action mechanisms of these compounds on neuroprotection were then analyzed by docking and reverse docking modeling. Conclusion: A series of quinazolinone derivatives, including different substitution types on rings A and B were designed and synthesized via scaffold hopping. With the help of neuroprotective biological evaluation, several efficient therapeutic neuroprotective agents were found for further evaluation as drug candidate against neurodegenerative disorder.
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35

Ramadan, Sayed K., Eman Z. Elrazaz, Khaled A. M. Abouzid, and Abeer M. El-Naggar. "Design, synthesis and in silico studies of new quinazolinone derivatives as antitumor PARP-1 inhibitors." RSC Advances 10, no. 49 (2020): 29475–92. http://dx.doi.org/10.1039/d0ra05943a.

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36

Solomos, Marina A., Jeffery A. Bertke, and Jennifer A. Swift. "One step synthesis of a fused four-ring heterocycle." New Journal of Chemistry 42, no. 9 (2018): 7125–29. http://dx.doi.org/10.1039/c8nj00629f.

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37

Leggott, Abbie, Justin E. Clarke, Shiao Chow, Stuart L. Warriner, Alex J. O’Neill, and Adam Nelson. "Activity-directed expansion of a series of antibacterial agents." Chemical Communications 56, no. 58 (2020): 8047–50. http://dx.doi.org/10.1039/d0cc02361b.

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38

Masood, Mir Mohammad, Mohammad Irfan, Parvez Khan, Mohamed F. Alajmi, Afzal Hussain, Jered Garrison, Md Tabish Rehman, and Mohammad Abid. "1,2,3-Triazole–quinazolin-4(3H)-one conjugates: evolution of ergosterol inhibitor as anticandidal agent." RSC Advances 8, no. 69 (2018): 39611–25. http://dx.doi.org/10.1039/c8ra08426b.

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39

Abdel Hamid, S., H. El-Obeid, K. Al-Rashood, A. Khalil, and H. El-Subbagh. "Substituted Quinazolines, 1. Synthesis and Antitumor Activity of Certain Substituted 2-Mercapto-4(3H)-quinazolinone Analogs." Scientia Pharmaceutica 69, no. 4 (December 28, 2001): 351–66. http://dx.doi.org/10.3797/scipharm.aut-01-205.

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A new series of 4(3H)-quinazolinone analogs bearing 6-iodo and 2-thioether functions were synthesized and screened for their in vitro antitumor activity. Eight compounds were identified as active anticancer agents. 2-Mercapto-3-benzyl-4-thioxo-6-iodo-3H-quinazolin (2) and 2-(2,4-dinitrophenyl)-3-benzyl-6-iodo-4-(3H)-quinazolinone(9) proved to be the most active compounds in this study. They showed MG-MID GI50, TGI, LC50 values of 3.9, 25.2, 82.3 and 2.7, 12.3, 38.7 μM, respectively. The detailed synthesis and biological screening data are reported.
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40

Shelat, C. D., and R. T. Vashi. "Synthesis, Characterization, Chelating Properties and Anti-Fungal Activity of 2-(4-Phenylpiperazinyl) Methyl-3-(8-Quinolinol-5-YL)- 4(3H)-Quinazolinone." E-Journal of Chemistry 2, no. 1 (2005): 86–90. http://dx.doi.org/10.1155/2005/973414.

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A new quinazolinone derivative namely 2-(4-phenylpiperazinyl)methyl-3-(8-quinolinol-5-yl)- 4(3h)-quinazolinone(HL) was prepared and characterized. Various transition metal (Cu2+, Co2+, Ni2+, Zn2+, Mn2+) chelates of HL were prepared and characterized by metal ligand (M:L) ratio, IR and reflectance spectral studies, magnetic moment, and antimicrobial activity.
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41

Huang, Hui, Jian-Fang Gao, Ling-Hua Cao, Duo-Zhi Wang, Jian-Bin Zhang, Shu-Bao Zhou, and Yu-Qiang Zhou. "Synthesis of Novel Thioglycoside Derivatives Containing Quinazolinone." Journal of the Chinese Chemical Society 56, no. 2 (April 2009): 419–24. http://dx.doi.org/10.1002/jccs.200900062.

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42

Habib, Osman M. O., Hussein M. Hassan, and Ahmed El-Mekabaty. "Novel quinazolinone derivatives: synthesis and antimicrobial activity." Medicinal Chemistry Research 22, no. 2 (May 4, 2012): 507–19. http://dx.doi.org/10.1007/s00044-012-0079-x.

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43

Bergman, Jan, and Ivan Romero. "Synthesis of 2-ethynyl-4(3H)quinazolinone and 2-(1,3-butadienyl)-4(3H)quinazolinone." Arkivoc 2009, no. 6 (March 22, 2009): 191–95. http://dx.doi.org/10.3998/ark.5550190.0010.620.

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44

Kumar, Atul, and Ajay Kumar Bishnoi. "Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides." RSC Adv. 4, no. 78 (2014): 41631–35. http://dx.doi.org/10.1039/c4ra06804a.

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We have demonstrated the first ligand free CuI-nanoparticle catalyzed N-arylation of amides/cyclic amides in an ethylene glycol/2-propanol solvent system under mild conditions. This is further extended for one pot synthesis of benzimidazole, and quinazolinone via intermolecular amidation followed by cyclization.
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45

He, Lin, Haoquan Li, Jianbin Chen, and Xiao-Feng Wu. "Recent advances in 4(3H)-quinazolinone syntheses." RSC Adv. 4, no. 24 (2014): 12065–77. http://dx.doi.org/10.1039/c4ra00351a.

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46

Malasala, Satyaveni, Jitendra Gour, Md Naiyaz Ahmad, Srikanth Gatadi, Manjulika Shukla, Grace Kaul, Arunava Dasgupta, Y. V. Madhavi, Sidharth Chopra, and Srinivas Nanduri. "Copper mediated one-pot synthesis of quinazolinones and exploration of piperazine linked quinazoline derivatives as anti-mycobacterial agents." RSC Advances 10, no. 71 (2020): 43533–38. http://dx.doi.org/10.1039/d0ra08644d.

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A facile method was developed for the synthesis of quinazolinone derivatives in a one-pot condensation reaction via in situ amine generation using ammonia as the amine source and with the formation of four new C–N bonds in good to excellent yields.
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47

Break, Laila Mohammed, and Wafa Saad Al-harthi. "Synthesis New of Nucleoside of 1,3-bis-(2,3,5-tri-O-Benzoyl-β-D-Ribofuranosyl)-8-(Trifluoromethyl)-2-Methyl-4-Quinazolinone." Proceedings 9, no. 1 (November 14, 2018): 57. http://dx.doi.org/10.3390/ecsoc-22-05694.

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Fluorinated nucleosides are very important for increased biological and chemical stability of organ fluorine compounds. Synthesis of (1H)-8-trifluloromethyl-2-methyl-4-quinazolinone 3 from 2-amino-3-(trifluoromethyl) benzoic acid 1 was performed. Ribosylation of compound 4 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose 5 using the silylation method created the benzoylated nucleoside derivative 6. Debenzoylation of the protected nucleoside 6 via reaction with sodium metal in dry methanol to create the corresponding free nucleoside 1,3-bis-(2,3,5-tri-O-benzoyl-β-d-ribofuranosyl)-8-(trifluoromethyl)-2-methyl-4-quinazolinone 7. The structures of the newly synthesis compounds have been confirmed on the basis of IR, 1HNMR, 13CNMR, and mass spectral data.
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48

Kakati, Praachi, Preeti Singh, Priyanka Yadav, and Satish Kumar Awasthi. "Aiding the versatility of simple ammonium ionic liquids by the synthesis of bioactive 1,2,3,4-tetrahydropyrimidine, 2-aminothiazole and quinazolinone derivatives." New Journal of Chemistry 45, no. 15 (2021): 6724–38. http://dx.doi.org/10.1039/d1nj00280e.

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49

Allen, Eric E., Stephen E. de Laszlo, Song X. Huang, Carol S. Quagliato, William J. Greenlee, Raymond S. L. Chang, Tsing-Bau Chen, Kristie A. Faust, and Victor J. Lotti. "Quinazolinones 1: design and synthesis of potent quinazolinone- containing AT1-selective angiotensin-II receptor antagonists." Bioorganic & Medicinal Chemistry Letters 3, no. 6 (June 1993): 1293–98. http://dx.doi.org/10.1016/s0960-894x(00)80334-0.

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50

Ozaki, Ken-ichi, Yoshihisa Yamada, Toyonari Oine, Tōru Ishizuka, and Yoshio Iwasawa. "Studies on 4(1H)-Quinazolinones. 5. Synthesis and Antiinflammatory Activity of 4(1H)-Quinazolinone Derivatives." Journal of Medicinal Chemistry 28, no. 5 (May 1985): 568–76. http://dx.doi.org/10.1021/jm50001a006.

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