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Journal articles on the topic 'Quinazolin-4(3H) one'

Author: Grafiati

Published: 2 June 2025

Last updated: 31 July 2025

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1

Alla, Manjula, Gal Potuganti, and Divakar Indukuri. "An Efficient One-Pot Multicomponent Synthesis of Tetracyclic Quinazolino[4,3-b]quinazolines by Sequential C–N Bond Formation and Copper-Mediated Aerobic Oxidative Cyclization." Synlett 29, no. 13 (2018): 1717–22. http://dx.doi.org/10.1055/s-0036-1591578.

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An efficient one-pot synthesis of quinazolino[4,3-b]quinazoline derivatives has been accomplished, starting from 2-(2-bromophenyl)quinazolin-4(3H)-one, aldehydes, and various nitrogen sources under aerobic conditions. The multicomponent protocol is mediated by copper(I) salts and involves amination of 2-(2-bromophenyl)quinazolin-4(3H)-one, followed by condensation with the aldehyde and an oxidative cyclization to give the target compounds in moderate to good yields.

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2

Pan, Wan-Chen, Mei-Mei Zhang, Jian-Quan Liu, and Xiang-Shan Wang. "Silver Triflate Catalyzed Synthesis of Isoquinolino[2,1-a]quinazolino[3,2-c]quinazoline Derivatives via Alkyne Hydroamination." Synthesis 51, no. 16 (2019): 3101–8. http://dx.doi.org/10.1055/s-0037-1611808.

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Using 2-(2-aminophenyl)quinazolin-4(3H)-one and 2-(2-phenylethynyl)benzaldehyde as the reactants, silver triflate (AgOTf) was proved to be an efficient catalyst to promote not only quinazoline cyclization, but also the intramolecular hydroamination of alkyne for the synthesis of 6-aryl-17H,18aH-isoquinolino[2,1-a]quinazolino[3,2-c]quinazolin-17-one derivatives in high yields.

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3

Patel, Harun, Rahul Pawara, and Sanjay Surana. "Resolving the Mystery of Ring Opening in the Synthesis of Benzo[d][1, 3]oxazin-4-one and Quinazolin-4(3H)-one." Letters in Organic Chemistry 16, no. 11 (2019): 898–905. http://dx.doi.org/10.2174/1570178616666181217114030.

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Quinazoline is the six-membered heterocyclic ring system reported for its versatile biological activities. This characteristic feature of quinazoline makes it a good template for a lead generation library. Ring opening is one of the major concerns in the synthesis of quinazolin-4(3H)-one that results in diamide formation. Here, alternative fusion strategy is reported, which is a time-saving and costeffective method to overcome the ring opening problem associated with the synthesis of benzo[ d][1,3]oxazin-4-one and quinazolin-4(3H)-one.

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4

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 (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-

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5

Appani, Ramgopal, Baburao Bhukya, and Kiran Gangarapu. "Synthesis and Antibacterial Activity of 3-(Substituted)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one." Scientifica 2016 (2016): 1–5. http://dx.doi.org/10.1155/2016/1249201.

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A series of novel 3-(substituted)-2-(substituted quinazolinylamino)quinazolin-4(3H)-ones were synthesized by the reaction of 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting materials 3-(substituted)-2-hydrazino-quinazolin-4(3H)-ones were synthesized from various primary amines by a multistep synthesis. All the title compounds were tested for their antibacterial activity using ciprofloxacin as reference standard. Compounds 3-(4-fluorophenyl)-2-(4-oxo-2-phenylquinazolin-3(4H)-ylamino)quinazolin-4(3H)-one (9a) and 3-(4-chlorophenyl)-2-(4-oxo-2-p

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6

Osarumwense, P. O., M. O. Edema, and C. O. Usifoh. "Synthesis And Anagesic activities of Quinazolin-4(3H)-One, 2-Methyl-4(3H)-Quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one." Journal of Drug Delivery and Therapeutics 10, no. 4-s (2020): 87–91. http://dx.doi.org/10.22270/jddt.v10i4-s.4209.

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Background: Objective: The current 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 analgesic activity. Method: The condensation of 2-amino-methyl-4-methoxybenzoate with acetic anhydride yielded the cyclic compound 2-methyl-4, 5-disubstituted-1, 3-benzo-oxazine-4-one which further 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–Ph

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7

Kulya, D., D. Kut, M. Kut, and M. Onysko. "SYNTHESIS OF 2,3-DIALKENYL DERIVATIVES OF QUINAZOLIN-4-ONE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 53, no. 1 (2025): 40–44. https://doi.org/10.24144/2414-0260.2025.1.40-44.

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In the course of this study, alkylation of two starting thiols — 3-allyl-2-mercaptoquinazolin-4-one and 3-methallyl-2-mercaptoquinazolin-4-one — was carried out using allyl bromide and metallyl chloride in an alcoholic-alkaline medium. As a result of these reactions, new 2,3-dialkenyl derivatives of quinazolin-4-one were obtained, which have not been previously reported in the literature. The structures of the newly synthesized compounds were confirmed by NMR spectroscopy (¹H and ¹³C), as well as elemental analysis. The absence of thioamide proton signals in the ¹H NMR spectra indicates that a

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8

Widiyana, Anita Puspa. "COMPUTATION DESIGN OF QUINAZOLINE-4(3H)-ON DERIVATIVES AS CYCLOOXYGENASE-2 (COX-2) INHIBITOR." Jurnal Farmasi Sains dan Praktis 7, no. 2 (2021): 163–70. http://dx.doi.org/10.31603/pharmacy.v7i2.4827.

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    The 3-(benzylideneamino)-2-(2,4-dichlorophenyl)-quinazoline-4(3H)-ones (BDCQ) are compounds developed as anticancer drugs and quinazolines. The activity and bioavailability of BDCQ derivatives as anticancer compounds that inhibit COX-2 can be predicted by computer programs and online servers. Substituents are added at positions 2 and 3 to the quinazoline-4(3H)-on ring, such as -H, -NO2, -OCH3, -N(CH3)2, -SO2NH2, -OH, and –OCH3. QSAR as COX-2 inhibitor analysis was performed by SPSS Ver. 21 software. Lipinski’s rule of five for determining bioavailability is performe

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9

Srinivasan, T., S. Suhitha, M. Gnana Ruba Priya, K. Girija, N. Ravi Chandran, and D. Velmurugan. "3-(4-Bromophenyl)quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 67, no. 11 (2011): o2928. http://dx.doi.org/10.1107/s1600536811040736.

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10

Priya, M. Gnana Ruba, T. Srinivasan, K. Girija, N. Ravi Chandran, and D. Velmurugan. "3-(4-Chlorophenyl)quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2310. http://dx.doi.org/10.1107/s1600536811030935.

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11

Sulthana, M. T., K. Chitra, and V. Alagarsamy. "Anti-HIV, Antitubercular and Antibacterial Activities of Novel 3-(Substituted Quinazolinylamino)-2-phenyl quinazolin-4(3H)ones." Asian Journal of Chemistry 32, no. 2 (2019): 281–86. http://dx.doi.org/10.14233/ajchem.2020.22280.

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In the present study, we have synthesized a series of novel 2-phenyl-3-(substituted quinazolinylamino)quinazolin-4(3H)-ones by the reaction of 3-(substituted)-2-hydrazinoquinazoline-4(3H)-ones with 2-phenyl-3,1-benzoxazin-4-one. The starting material 3-(substituted)-2-hydrazinoquinazolin-4(3H)-ones were synthesized from various primary amines. All the synthesized compounds were screened for their antitubercular, anti-HIV and antibacterial activity against different Grampositive and Gram-negative strains by agar dilution method. Among the test compounds, 3-(4-nitrophenyl)-2-(4-oxo-2-phenylquina

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12

Jianghong, Man, Qi Jianbin, Jiang Jie, and Li Sha. "Microwave Reaction Improved Heterocyclization of Quinazolinone Ring in Synthesis of Erlotinib Analogues." Journal of Pharmaceutical and Biomedical Sciences 10, no. 05 (2020): 99–105. https://doi.org/10.1234/zenodo.3876.

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Background Tinibs were a kind of important epidermal growth factor receptor (EGFR) inhibitors used as potential therapeutic agents in treating non-small cell lung cancer (NSCLC) in clinic. The drug resistance of clinical used tinibs made the development of more active tinib analogues an attractive field in research. Quinazoline ring was regarded as the key fragment in tinibs and quinazolinone was indispensible intermediate in the synthesis of quinazoline. Thus, synthesis of quinazolinone intermediates was a key step which would further limit the overall yield of final product of tinib analogue

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13

Wang, Ke, Hao Chen, Xinyan Dai, Xupeng Huang, and Zhiqiang Feng. "Palladium-catalyzed one-pot synthesis of 2-substituted quinazolin-4(3H)-ones from o-nitrobenzamide and alcohols." RSC Advances 11, no. 22 (2021): 13119–23. http://dx.doi.org/10.1039/d1ra01755a.

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Palladium-catalyzed 2-substituted quinazolin-4(3H)-one formation from readily available o-nitrobenzamides and alcohols using hydrogen transfer is described. Various quinazolin-4(3H)-ones were obtained in good to high yields.

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14

Chatterjee, Tapasi, Subhagata Chattopadhyay, Ranjan Mukhopadhyay, Basudeb Achari, Santu Chakraborty, and Alok K. Mukherjee. "Reaction of 2-[(E)-styryl]Quinazolin-4(3H)-one with Acetylenic Esters: Formation of Unexpected N-3 Alkenylation Products." Journal of Chemical Research 2005, no. 7 (2005): 429–31. http://dx.doi.org/10.3184/030823405774309212.

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Attempted hetero Diels–Alder reaction with 2-[(E)-styryl]quinazolin-4(3H)-one (1) and dimethyl acetylenedicarboxylate (2) resulted in unexpected N-3 alkenylation products, 2-[(E)-styryl]-3-[(Z)-1,2-bis(methoxycarbonyl)vinyl]quinazolin-4(3H)-one (4a) and 3-[(E)-1,2-bis(methoxycarbonyl) vinyl] 2-[(E)-styryl]-quinazolin-4(3H)-one (4b) in low yield. Treating 1 and 2-methylquinazolin-4(3H)-one (9) with methyl propiolate (7) also furnished N-3 alkenylation products in low yield. The structure of 4b has been established by X-ray analysis. The molecules of 4b are linked by intermolecular C-H. … N hydr

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15

Danylchenko, Svitlana Yuriyivna, Oleksandr Grygorovych Drushlyak, Svitlana Sergiyivna Kovalenko, and Sergiy Mykolayovych Kovalenko. "Formation of 1-methyl[1,2,4]triazolo[4,3-a] quinazolin-5(4H)-ones by reaction of 2-hydrazinoquinazolin-4(3H)-ones with acetylacetone." Heterocyclic Communications 21, no. 4 (2015): 195–97. http://dx.doi.org/10.1515/hc-2015-0104.

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AbstractReaction of 2-hydrazinoquinazolin-4(3H)-ones with acetylacetone results in the formation of 1-methyl[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-ones instead of 2-(3,5-dimethyl-1H-pyrazol-1-yl)quinazolin-4(3H)-ones. Under similar conditions, the 7-hydrazinocarbonyl group in quinazolin-4(3H)-one moiety is transformed into a pyrazole derivative, which can be replaced by amine with the amide formation.

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16

Thapa, Susila, and Jeanne L. Bolliger. "6-Amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one." Molbank 2024, no. 4 (2024): M1942. https://doi.org/10.3390/m1942.

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The titular compound, 6-amino-7-((4-methoxybenzyl)thio)quinazolin-4(3H)-one, was prepared from 7-fluoro-6-nitroquinazolin-4(3H)-one via a nucleophilic aromatic substitution reaction followed by a reduction of the nitro group. Characterization of the target compound via 1H NMR, 13C NMR, and HRMS confirmed its structure.

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17

Kumar, Dinesh, Pradeep S. Jadhavar, Manesh Nautiyal, et al. "Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs." RSC Advances 5, no. 39 (2015): 30819–25. http://dx.doi.org/10.1039/c5ra03888j.

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Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions.

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18

Muchlashi, Luthfi Ahmad. "Synthesis of 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one by Conventional heating and Microwave Irradiation." Journal of Islamic Pharmacy 6, no. 2 (2022): 84–87. http://dx.doi.org/10.18860/jip.v6i2.14134.

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This study aims to compare conventional heating with microwave irradiation in order to obtain the optimal method for 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one synthesis. For the compound to be completely synthesised, one needs to carry out much heating for a long period of time. 10 hours are required for the reaction using conventional heating; yet it takes only 5 minutes using microwave with 800 watts of power. It was found in this study that there was an improvement in percent yields of 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one, 87 % using microwave irradiation compared to 79 % usi

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19

Rahman, Mujeeb Ur, Ankita Rathore, Anees A. Siddiqui, Gazala Parveen, and M. Shahar Yar. "Synthesis and Antihypertensive Screening of New Derivatives of Quinazolines Linked with Isoxazole." BioMed Research International 2014 (2014): 1–13. http://dx.doi.org/10.1155/2014/739056.

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A series of 7-substituted-3-(4-(3-(4-substitutedphenyl)-4,5-dihydroisoxazol-5-yl)phenyl)-2-substituted quinazolin-4(3H)-one(1–30)have been synthesized by the cyclization of (E)-3-(4-(3-substitutedphenyl)acrylolyl)phenyl)-2-(substitutedphenyl)-7-substituted quinazolin-4-(3H)-one with hydroxylamine hydrochloride. The synthesized compounds were examined for theirin vivoantihypertensive activity using albino rats. All the titled compounds exhibited good to moderate antihypertensive activity. Compounds 7-Chloro-3-(4-(3-(4-chlorophenyl)-4,5- dihydroisoxazol-5-yl)phenyl)-2-p-tolylquinazolin-4(3H)-one

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20

He, Yueling, Zhongtao Yang, Danyang Luo, Xiai Luo, Xiaodong Chen, and Weiguang Yang. "An Oxidant-Free and Mild Strategy for Quinazolin-4(3H)-One Synthesis via CuAAC/Ring Cleavage Reaction." Molecules 28, no. 15 (2023): 5734. http://dx.doi.org/10.3390/molecules28155734.

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An oxidant-free and highly efficient synthesis of phenolic quinazolin-4(3H)-ones was achieved by simply stirring a mixture of 2-aminobenzamides, sulfonyl azides, and terminal alkynes. The intermediate N-sulfonylketenimine underwent two nucleophilic additions and the sulfonyl group eliminated through the power of aromatization. The natural product 2-(4-hydroxybenzyl)quinazolin-4(3H)-one can be synthesized on a large scale under mild conditions with this method.

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21

Eweas, Ahmad Farouk, Qasem Mahmoud Aref Abdallah, and Mohamed Fouad Elbadawy. "Synthesis and biological evaluation of some new 2-pyridylquinazoline derivatives." Current Chemistry Letters 10, no. 4 (2021): 459–70. http://dx.doi.org/10.5267/j.ccl.2021.4.005.

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2-pyridyl [3H]-quinazolin-4-one derivatives fused or substituted with different oxygen or nitrogen heterocycle moieties as potential anti-tumor and anti-microbial agents were prepared, characterized and biologically screened. The synthesis process started from 5-bromo-2-[pyridin-4-ylcarbonyl]amino]benzoic acid which was converted to the crucial building block 6-Bromo-2-(pyridin-4-yl)quinazolin-4(3H)-one via two alternative routes. Compound 3 underwent halogenation reaction POCl3 and PCl5 to afford compound 6-Bromo-4-chloro-2-(pyridin-4-yl)quinazoline 4. The novel cyclized products 5a,b-10 were

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22

H., D. Navadiya, K. Undavia N., and S. Patwa B. "Studies on synthesis of 2-methyl-3,1-benzoxazine-4(4H)-one dyes and their application on nylon and polyester fibres." Journal of Indian Chemical Society Vol. 86, Oct 2009 (2009): 1118–20. https://doi.org/10.5281/zenodo.5820642.

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Department of Chemistry, Department of Industrial Chemistry, Sir P. P. Institute of Science, Bhavnagar University, Bhavnagar-364 002, Gujarat, India <em>E-mail </em>: dr.navadiya@yahoo.com <em>Manuscript received 15 December 2008, accepted 3 July 2009</em> A series of 3-{4-[4-(4-arylazo)-benzenesulfonyl]phenyl}-2-methyl-3H-quinazolin-4-one derivatives (3) have been obtained by a reaction of a various coupling agent (a-g) with diazonium salt containing 4-oxo-quinazolin moiety (2). The diazonium salt 2 is obtained by the reaction of 4-(2-methyl-4-oxo-3-quinazolinyl)-4<em>'</em>-aminodiphenyl

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23

Mishra, Shweta, Debashree Das, Adarsh Sahu, Shailendra Patil, Ram Kishor Agarwal, and Asmita Gajbhiye. "Transition Metal-free Approach for the Synthesis of 2-substituted Quinazolin-4(3H)-one via Anhydrous Magnesium Perchlorate." Current Organocatalysis 7, no. 2 (2020): 118–23. http://dx.doi.org/10.2174/2213337207666200220101535.

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Background: A convenient and efficient methodology for the synthesis of quinazolin- 4(3H)-ones from simple and readily available 2-amino benzamides and aromatic aldehydes in ethanol using Magnesium perchlorate are being reported in the present study. Good to excellent isolated yields (68-95%) of the corresponding 2-substituted quinazolinones were obtained under mild reaction conditions with excellent functional group tolerance. The affordability of the catalyst, the wide availability of the starting materials, transition metal free synthesis and the simplicity of the procedure renders the pres

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24

Debnath, Subal, and S. Y. Manjunath. "Conventional and Microwave Assisted Synthesis of 3-(Substituted)-2-phenyl quinazolin-4(3H)-one and their Antibacterial and Anthelmintic Activity." International Journal of Pharmaceutical Sciences and Nanotechnology 4, no. 2 (2011): 1408–11. http://dx.doi.org/10.37285/ijpsn.2011.4.2.6.

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The present research work was aimed to synthesize a series of various substituted quinazolinone containing 3-(substituted)-2-phenylquinazolin-4(3H)-one. The compound 3-[(2-oxo-4-phenylazetidin-1-yl)-carbonyl]-2-phenylquinazolin-4(3H)-one, II was prepared by treating 4-oxo-2-phenyl-N-[(E)-phenylmethylidene]quinazoline-3(4H)-carboxamide, I with acetyl chloride and triethylamine (TEA) in benzene by conventional and microwave irradiation method. Synthesis of 3-[{2-oxo-3-(2,4-dichlorophenoxy)-4-phenylazetidin-carbonyl]-2-phenylquinazolin-4(3H)-one, III was carried out by reacting, I with 2,4-dichlo

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25

Moshkina, Tatyana N., Emiliya V. Nosova, Julia V. Permyakova, et al. "Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines." Molecules 27, no. 21 (2022): 7156. http://dx.doi.org/10.3390/molecules27217156.

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Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3H)-ones and 4-cyano-2-arylquinazolines with Et2N-, Ph2N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3H)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3H)-one. Moreover, triphenylamino derivati

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Prasad, Malavattu G., C. Vijaya Lakshmi, Naresh K. Katari, Sreekantha B. Jonnalagadda, and Manojit Pal. "Lemon Juice Mediated Synthesis of 3-Substituted Quinazolin-4(3H)-Ones and their Pharmacological Evaluation." Anti-Cancer Agents in Medicinal Chemistry 19, no. 16 (2020): 2001–9. http://dx.doi.org/10.2174/1871520619666190723151909.

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Background: Compounds containing the quinazoline-4(3H)-one framework constitute an important class of fused N-heterocycles that are found in more than 200 naturally occurring alkaloids. These compounds also show a diverse range of pharmacological activities including antitumor properties. This prompted us to explore a series of quinazolin-4-(3H)-one derivatives having no substituent at C-2 as potential cytotoxic agents. Objective: The objective of this study was to synthesize and evaluate 3-substituted quinazolin-4(3H)-one derivatives for their potential cytotoxic properties. Methods: A conven

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27

Kut, D. Zh, M. M. Kut, M. Yг Onysko, and V. G. Lendel. "Electrophilic cyclization of propargyl thioethers of 3-methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones by tellurium tetrahalides." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 6 (December 2021): 40–44. http://dx.doi.org/10.32434/0321-4095-2021-139-6-40-44.

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The paper presents the results of the study of the process of electrophilic intramolecular cyclization of 3-methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones by tellurium tetrahalides. 3-Methyl(phenyl)-2-(prop-2-yn-1-ylthio)-7-(trifluoromethyl)quinazolin-4(3H)-ones were prepared by the alkylation of the corresponding thions with propargyl bromide in an alkaline alcohol medium. It is found that the interaction of propargyl thioethers of 3-substituted 2-thioxo-7-(trifluoromethyl)-2,3-dihydroquinazolin-4(1H)-ones with tellurium tetrahalides, which were obtained in sit

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28

M., B. Deshmukh, and Patil Suresh. "Synthesis of new N3-substituted quinazolin-4(3H)one derivatives." Journal of Indian Chemical Society Vol. 83, Apr 2006 (2006): 393–96. https://doi.org/10.5281/zenodo.5836850.

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Department of Chemistry, Shivaji University, Kolhapur-4Jf, U04, Maharashtra. India Padmabuhshan Dr. Vasantraodada Patil Mahavidyalaya, Tasgaon, Sangli-416 311, Maharashtra, India E-mail: m_deshmukhl@rediffmail.com <em>Manuscript received 20 June 2005, revised 16 December 2005, accepted 22 December 2005</em> Quinazolin-4-one (1) was synthesized by reacting anthranilic acid with excess of formamide, which was N-alkylated with chloroncetone to form quinazolin-4-one-3-yl propan-2-one (2). The interaction of 2 with phenylhydrazine, 2,4-dinitropheny lhydrazine and semicarbazide gave the correspondin

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29

Rajan, K. Subramanian, A. Raghu Ram Rao, K. Mogilaiah, and M. Raghu Prasad. "[1,2,4]triazolo[1,5-c]quinazolin-2(3H)-ones and their thio analogues: a one pot synthesis†1." Journal of Chemical Research 2002, no. 10 (2002): 490–92. http://dx.doi.org/10.3184/030823402103170682.

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A facile synthetic route for 5-aryl[1,2,4]triazolo[1,5-c]quinazolin-2(3H)-ones and 2(3H)-thiones (3, 4) via 3,1-benzoxazin-4(3H)-ones in good yields under anhydrous conditions has been devised in an effort to develop new bronchodilators for the treatment of asthma.

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30

Amrutkar, Rakesh D., Sunil V. Amrutkar, and Mahendrasing S. Ranawat. "Quinazolin-4-One: A Varsatile Molecule." Current Bioactive Compounds 16, no. 4 (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

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31

Suresh, Patil, D. Jadhav S., M. Patil B., and B. Deshmukh M. "Synthesis and antimicrobial screening of some new N3-substituted derivatives of quinazolin-4(3H)-one." Journal of Indian Chemical Society Vol. 91, Jan 2014 (2014): 113–16. https://doi.org/10.5281/zenodo.5623967.

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Padmabhushan Dr. Vasantraodada Patil Mahavidyalaya, Tasgaon-416 312, Dist. Sangli, Maharashtra, India <em>E-mail</em> : sanyujapatil@yahoo.com Department of Chemistry, Shivaji University, Kolhapur-416 004, Maharashtra, India <em>Manuscript received online 31 December 2012, revised 15 February 2013, accepted 05 March 2013</em> 3-(2-Oxopropyl)quinazolin-4(3<em>H</em>)-one (1) when reacts with phenyl hydrazine, 2,4-dinitro phenyl hydrazine gave the corresponding hydrazones (<strong>2a,b</strong>). Also 1 on treatment with malononitrile forms intermediate dicyano compound 3 which again on reaction

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Nerdinger, Sven, Marijan Stefinovic, Frank Richter, et al. "Crystal structure of idelalisib tert-butanol monosolvate dihydrate." Acta Crystallographica Section E Crystallographic Communications 75, no. 3 (2019): 414–17. http://dx.doi.org/10.1107/s2056989019002743.

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In the title structure, 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one (= idelalisib) tert-butanol monosolvate dihydrate, C22H18FN7O·C4H10O·2H2O, the idelalisib molecule displays planar quinazoline and purine systems which are nearly perpendicular to one another. Seven distinct hydrogen-bonding interactions link the idelalisib, t-BuOH and water molecules into a complex chain structure with the topology of a 2,3,4,5-connected 4-nodal net having the point symbol (3.4.52.62)(3.4.52.64.72)(3.5.6)(5).

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Zhang, Qian, Yuan-Hong Jiao, Bin Liu, Xue-Mei Chen, Min Ruan, and Ling-Hua Xu. "2-(4-Fluoroanilino)-3-(2-hydroxyethyl)quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (2009): o638. http://dx.doi.org/10.1107/s1600536809006254.

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Yang, Xu-Hong, and Ming-Hu Wu. "3-(2-Aminoethyl)-2-(4-fluoroanilino)quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 64, no. 11 (2008): o2240. http://dx.doi.org/10.1107/s1600536808035058.

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35

Wang, Hong-Ling, Xu-Hong Yang, and Ming-Hu Wu. "2-(4-Chloroanilino)-3-(2-hydroxyethyl)quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 64, no. 12 (2008): o2325. http://dx.doi.org/10.1107/s1600536808036623.

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36

Bireddy, Srinivasa Reddy, Mohammad Rafeeq, and Venkata Ramana Reddy Chittireddy. "Synthesis of 2‐(3‐methyl‐5‐oxo‐4,5‐dihydro‐1H‐pyrazol‐1‐yl) quinazolin‐4(3H)‐one derivatives." Vietnam Journal of Chemistry 59, no. 1 (2021): 73–78. http://dx.doi.org/10.1002/vjch.202000122.

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AbstractA simple, synthesis of 2‐(3‐methyl‐5‐oxo‐4, 5‐dihydro‐1h‐pyrazol‐1‐yl) quinazolin‐4(3H)‐one 6(a‐d) derivatives, an easy, clean, and economical methodology has been defined. The development of a new pathway for the preparation of substituted derivatives of Quinazoline Pyrazole is highlighted in this report. The mild, inexpensive polyphosphoric acid has proven to be an effective catalyst for excellent yields in the above multi‐component reaction. Widely available and mostly benign catalyst and easy purification are among the several attractive features.

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37

Gaman, Barat*. "NOVEL 6-IODO-3H-QUINAZOLIN-4-ONE DERIVATIVES: CLASS OF PHARMACEUTICAL ACTIVE SCAFFOLD." INTERNATIONAL JOURNAL OF ENGINEERING SCIENCES & RESEARCH TECHNOLOGY 6, no. 2 (2017): 371–78. https://doi.org/10.5281/zenodo.291844.

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Quinazolinone, a hetetocyclic compound, has been extensively studied and used in certain specific biological activities. 3H-quinazolin-4 one and its derivative constitute an important class of fused heterocycles that are found in more than 200 naturally occurring alkaloids. With passage of time newer and more complex variants of quinazolinone structure are being discovered. Novel scaffold of 3H-quinazolin-4 one was synthesized by the base catalysed cyclisation of cromenamodo with 3:5-dinitrophenyl hydrazine hydrate. The overall reaction was conventional multistep process. The structure of synt

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38

Peng, Fei, Hua Tian, Pengxiang Zhang, Haijun Yang, and Hua Fu. "Iridium-catalyzed intramolecular enantioselective allylation of quinazolin-4(3H)-one derivatives." Organic & Biomolecular Chemistry 17, no. 26 (2019): 6461–64. http://dx.doi.org/10.1039/c9ob01057b.

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An efficient chiral cyclic phosphoramidite ligand-enabled iridium-catalyzed intramolecular allylation of quinazolin-4(3H)-one derivatives has been developed with high reactivity and high to excellent enantioselectivity.

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39

Xiong, Hao, Shengbo Xu, Song Sun, and Jiang Cheng. "Cp*Rh(iii)-catalyzed annulation of N-methoxybenzamide with 1,4,2-bisoxazol-5-one toward 2-aryl quinazolin-4(3H)-one derivatives." Organic Chemistry Frontiers 5, no. 19 (2018): 2880–84. http://dx.doi.org/10.1039/c8qo00800k.

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40

Alagarsamy, Veerachamy, Viswas Solomon, G. Krishnamoorthy, M. T. Sulthana, and B. Narendar. "Synthesis and antimicrobial activities of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl)-4-(substituted)thiosemicarbazide derivatives." Journal of the Serbian Chemical Society 80, no. 12 (2015): 1471–79. http://dx.doi.org/10.2298/jsc150103053a.

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A series of 1-(3-benzyl-4-oxo-3H-quinazolin-2-yl)-4-(substituted) thiosemicarbazides (AS1-AS10) were obtained by the reaction of 2-hydrazino- 3-benzyl quinazolin-4(3H)-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate 3-benzyl-2-thioxo-2,3-dihydro-1Hquinazolin-4-one (4) was obtained by reacting benzyl amine (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulfate to yield the dithiocarbamic acid methyl ester (2) and condensed with methyl anthranilate (3) in ethanol y

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41

Saleh, Mohamed A., Yehia A. Hafez, Foad E. Abdel-Hay, and Wagdy I. Gad. "SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME NEW 3H-QUINAZOLIN-4-ONE DERIVATIVES DERIVED FROM 3-PHENYLAMINO- 2-THIOXO-3H-QUINAZOLIN-4-ONE." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 2 (2004): 411–26. http://dx.doi.org/10.1080/10426500490262559.

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42

Kumar, Krishnan Suresh, Swastika Ganguly, VijaiPandi P., Ravichandran Veerasamy, and John Balzarini. "Synthesis, Antiviral and Cytotoxic Investigations of 2-(4-chlorophenyl)-3- substituted quinazolin-4(3H) ones." International Journal of Drug Design and Discovery 3, no. 1 (2025): 702–12. https://doi.org/10.37285/ijddd.3.1.5.

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Derivatives of 2-(4-chlorophenyl)-3-substituted quinazolin-4(3H) one were designed, synthesized and characterized by spectral studies. The compounds were also investigated for their antiviral and cytotoxicity against a panel of human pathogenic viruses in four cell cultures including Hel, HeLa, Vero and MDCK cell cultures. The results indicated that new 3-(2-hydroxybenzylideneamino)-2-(4-chlorophenyl)-quinazoline-4(3H)-one (C25) was found to inhibit the replication of herpes simplex virus-1 (KOS), herpes simplex virus-2 (G), vaccinia virus and herpes simplex virus-1 TK- KOS ACVr with a selecti

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Cai, Zhao-Hui, Xiao-Bao Chen, Xu-Hong Yang, and Xiang Wang. "3-(2-Aminoethyl)-2-[4-(trifluoromethoxy)anilino]quinazolin-4(3H)-one." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (2010): o1854—o1855. http://dx.doi.org/10.1107/s1600536810024645.

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Jianghong, Man, Qi Jianbin, Jiang Jie, and Li Sha. "Microwave Reaction Improved Heterocyclization of Quinazolinone Ring in the Synthesis of Erlotinib Analogues." Journal of Pharmaceutical and Biomedical Sciences 10, no. 05 (2020): 99–105. https://doi.org/10.5281/zenodo.3903346.

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Core tip: Drug resistance caused by point mutations in epidermal growth factor receptor (EGFR) weakened therapeutic efficacy of EGFR inhibitors of tinibs. Thus, the discovery of new tinib analogues of greater efficacy was an attractive focus. As an important intermediate of nitrogen-containing heterocyclic compounds with diverse chemical reactivity and a wide range of biological activity, quinazoline was regarded as an important fragment of tinib analogues. Thus, the synthesis of quinazolinone intermediates was a key step which would limit the overall yield of tinib analogues. Based on this si

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45

Szczepankiewicz, W., and J. Suwinski. "One-pot synthesis of 3-(2-cyanophenyl)quinazolin-4(3H)-one." Chemistry of Heterocyclic Compounds 36, no. 7 (2000): 809–10. http://dx.doi.org/10.1007/bf02256914.

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46

Bera, Shyamal Kanti, Rosalin Bhanja, and Prasenjit Mal. "DDQ in mechanochemical C–N coupling reactions." Beilstein Journal of Organic Chemistry 18 (June 1, 2022): 639–46. http://dx.doi.org/10.3762/bjoc.18.64.

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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is a commonly known oxidant. Herein, we report that DDQ can be used to synthesize 1,2-disubstituted benzimidazoles and quinazolin-4(3H)-ones via the intra- and intermolecular C–N coupling reaction under solvent-free mechanochemical (ball milling) conditions. In the presence of DDQ, the intramolecular C(sp2)–H amidation of N-(2-(arylideneamino)phenyl)-p-toluenesulfonamides leads to 1,2-disubstituted benzimidazoles and the one-pot coupling of 2-aminobenzamides with aryl/alkyl aldehydes resulted in substituted quinazolin-4(3H)-one derivatives in hig

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47

El-Sharief, A. M. Sh, Y. A. Ammar, M. A. Zahran, and A. H. Ali. "Oxidation of 3-Aminoquinazolinones with Lead Tetraacetate. A Novel Synthesis of Naphtho-Fused Azirino-Pyrazolo- and 1,4,5-Oxadiazepino-Quinazolinones." Journal of Chemical Research 2002, no. 5 (2002): 205–8. http://dx.doi.org/10.3184/030823402103171870.

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Oxidation of 3-aminoquinazolin-4(3H)-one derivative 3c using lead tetraacetate in methylene chloride at −20°C gave aziridine 4, while reaction of 7b and 7c under similar conditions gave the oxadiazepine derivatives 7H-naphtho[2′,1′:6,7][1,4,5]oxadiazepino[3,4-b]quinazolin-9(15H)-one (9) and 16H-naphtho[1′,2′:6,7][1,4,5]oxadiazepino[3,4-b]quinazolin-14(8H)-one (11), respectively.

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Kulkarni, RS, NK Sathish, AA Kempwade, and SA Kavatagimath. "Synthesis and Evaluation of Novel Quinazolin-4-(3h)-one Analogues for their Anti-Inflammatory Activity." INTERNATIONAL JOURNAL OF PHARMACEUTICAL QUALITY ASSURANCE 14, no. 04 (2023): 933–41. http://dx.doi.org/10.25258/ijpqa.14.4.20.

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New 2, 3-disubstituted quinazolin-4-(3H)ones was conceived and synthesized through the substitution of various primary amines at the 3-position and a range of aldehydes at the 2-position. These compounds were characterized using elemental analysis, IR spectroscopy, 1H NMR spectroscopy and MS. Subsequently, the anti-inflammatory activity of these newly developed quinazoline derivatives was investigated by in-vitro protein denaturation method. In-vitro studies revealed that compounds QB1, QB2, QB4, QB8, QB9, QF1, QF3, QF4, QF8 and QF10 have significant anti-inflammatory potential. In-vivo anti-i

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Molnar, Maja, Mario Komar, and Igor Jerković. "Methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate." Molbank 2022, no. 3 (2022): M1434. http://dx.doi.org/10.3390/m1434.

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A green synthetic procedure was developed for the two-step synthesis of methyl 2-((3-(3-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)thio)acetate from anthranilic acid, using two green chemistry approaches: utilization of the DES and microwave-induced synthesis. The first step includes a synthesis of 2-mercapto-3-(3-methoxyphenyl)quinazolin-4(3H)-one which was performed in choline chloride:urea DES. In the second step S-alkylation of 2-mercapto-3-(3-methoxyphenyl)quinazolin-4(3H)-one was performed in a microwave-induced reaction. The desired compound was successfully obtained in a yield of

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A. El-Hiti, Gamal, and Mohamed F. Abdel-Megeed. "Synthesis of Glycosides Containing Quinazolin-4(3H)-one Ring System." HETEROCYCLES 65, no. 12 (2005): 3007. http://dx.doi.org/10.3987/rev-05-602.

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