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Journal articles on the topic '3-dihydroquinazolin-4(1H)-ones'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Tashrifi, Zahra, Mohammad Mohammadi-Khanaposhtani, Mahmood Biglar, Bagher Larijani, and Mohammad Mahdavi. "Isatoic Anhydride: A Fascinating and Basic Molecule for the Synthesis of Substituted Quinazolinones and Benzo di/triazepines." Current Organic Chemistry 23, no. 10 (2019): 1090–130. http://dx.doi.org/10.2174/1385272823666190701142930.

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This review article is focused on the synthesis of compounds with quinazolinones and benzo di/triazepine scaffolds. These invaluable derivatives are of great interest in medicinal and pharmaceutical studies because of their important biological properties. Quinazolinones have diverse applications due to their antibacterial, analgesic, antiinflammatory, antifungal, antimalarial, antihypertensive, CNS depressant, anticonvulsant, antihistaminic, antiparkinsonism, antiviraland and anticancer activities. On the other hand, pharmacological properties of benzodiazepines include antianxiety, anticance

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2

Shaabani, Ahmad, Abbas Rahmati, and Jafar Moghimi Rad. "Ionic liquid promoted synthesis of 3-(2′-benzothiazolo)-2,3-dihydroquinazolin-4(1H)-ones." Comptes Rendus Chimie 11, no. 6-7 (2008): 759–64. http://dx.doi.org/10.1016/j.crci.2007.11.007.

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3

Lin, Zhenwei, Jing Qian, Ping Lu, and Yanguang Wang. "Syntheses of 2-Iminoindolin-3-ones and 2-Alknyl-2,3-dihydroquinazolin-4(1H)-ones from 3-Diazoindolin-2-imines." Journal of Organic Chemistry 85, no. 18 (2020): 11766–77. http://dx.doi.org/10.1021/acs.joc.0c01548.

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4

Mandal, Arkalekha, and Bhisma K. Patel. "A Three Component Synthesis of 2-Aryl-3-imidamide Substituted 1,2-Dihydroquinazolin-4(1H )-ones." ChemistrySelect 2, no. 4 (2017): 1717–22. http://dx.doi.org/10.1002/slct.201601728.

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5

Wu, Liqiang. "Zr(HSO4)4: An Efficient Catalyst for the Synthesis of 3-(2'- Benzothiazolyl)-2,3-dihydroquinazolin- 4(1H)-ones." E-Journal of Chemistry 9, no. 2 (2012): 739–43. http://dx.doi.org/10.1155/2012/515029.

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A simple and efficient synthesis of 3-(2'-benzothiazolyl)-2,3-dihydro quinazolin-4(1H)- ones has been accomplished by the one-pot condensation of isatoic anhydride, aldehyde and 2-aminobenzothiazole under solvent-free conditions in the presence of Zr(HSO4)4.

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6

Farat, O. K., E. V. Zaliznaya, S. A. Varenichenko, and V. I. Markov. "Rearrangement of substituted pyrimidin-4-ones under the Vilsmeier-Haack reaction." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 1 (January 2021): 101–9. http://dx.doi.org/10.32434/0321-4095-2021-134-1-101-109.

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The article describes the result of our study on rearrangements of four heterocyclic systems with variation of oxygen and nitrogen atoms, in particular, the results of formylation of 2,2-disubstituted hydroquinazolones under the conditions of the Vilsmeier-Haack reaction. A new rearrangement of spiro derivatives of quinazolin-4(3H)-ones was discovered under the action of a formylating reagent with the formation of predicted 1-cyclohex(pent)-1-en-1-ylchinazolin-4-(1H)-ones. The absence of this rearrangement for 2,2-dimethyl-2,3-dihydroquinazolin-4(1H)-one is explained. 6',7',7'-Trimethyl-1',5',

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7

Shinde, Achut R., Yogesh D. Mane, and Dnyanoba B. Muley. "One-pot B(C6F5)3 catalyzed cascade synthesis of 2-substituted-2,3-dihydroquinazolin-4(1H)-ones." Synthetic Communications 50, no. 1 (2019): 33–40. http://dx.doi.org/10.1080/00397911.2019.1679539.

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8

Wang, Min, Ting Ting Zhang, Yan Liang, and Jing Jing Gao. "Strontium chloride-catalyzed one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in protic media." Chinese Chemical Letters 22, no. 12 (2011): 1423–26. http://dx.doi.org/10.1016/j.cclet.2011.06.002.

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9

Khurana, Jitender M., and Sanjay Kumar. "An efficient, catalyst free synthesis of 3-(2′'-benzothiazolyl)-2,3-dihydroquinazolin-4(1H)-ones in aqueous medium." Green Chemistry Letters and Reviews 4, no. 4 (2011): 321–25. http://dx.doi.org/10.1080/17518253.2011.571718.

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10

Sahoo, Biswa Mohan, S. C. Dinda, Ravi Kumar B V V, and J. R. Panda. "Green Synthesis and Evaluation of 3-(Aryl)-2-Thioxo-2,3-Dihydroquinazolin- 4(1H)-ones as Novel Anticonvulsant Drugs." International Journal of Pharmaceutical Sciences and Nanotechnology 6, no. 2 (2013): 2046–52. http://dx.doi.org/10.37285/ijpsn.2013.6.2.6.

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Epilepsy is a chronic neurological disorder characterized by recurrent seizure attacks which are caused by an abnormal electrical discharge in the brain. Currently, there is a need for improved medicinal agents to treat epilepsy, since the currently available drugs are effective only in 60-80% of epileptic patients. So the indirect type of molecular modeling study was carried out to find out the 3D structural similarity between some reported anticonvulsant drugs and the newly designed quinazolinone derivatives. Thus, a new series of 3-(aryl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones were synth

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11

Kumar, Prashant, Akanksha Matta, Snigdha Singh, et al. "Facile, catalyst-free, microwave-assisted access toward the synthesis of 2-aryl/alkyl-3-(1H-benzo[d]imidazol-2-yl)-2, 3-dihydroquinazolin-4(1H)-ones." Synthetic Communications 47, no. 8 (2017): 756–63. http://dx.doi.org/10.1080/00397911.2016.1277761.

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12

Rupnar, Balaji D., Tejswini R. Kachave, Pramod D. Jawale, Suresh U. Shisodia, and Rajendra P. Pawar. "Green and efficient synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous medium using ZnFe2O4 catalyst under microwave irradiation." Journal of the Iranian Chemical Society 14, no. 9 (2017): 1853–58. http://dx.doi.org/10.1007/s13738-017-1124-y.

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13

Šačkus, Algirdas, Vilija Kriščiūnienė, Gita Matulevičiūtė, and Osvaldas Paliulis. "Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions." HETEROCYCLES 93, no. 1 (2016): 150. http://dx.doi.org/10.3987/com-15-s(t)12.

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14

Sina, Kiana F., Asieh Yahyazadeh, Nosrat O. Mahmoodi, Kurosh R. Moghadam, Mohammad Nikpassand та Mahdi Rasa. "Ultrasonic Assisted Synthesis of 2, 3-Dihydroquinazolin-4(1H)-ones Involving Three-Component Reaction of Isatoic Anhydride, Amines and Pyrazole Carbaldehydes Catalyzed by [γ-Fe2O3@HAp-SO3H]". Letters in Organic Chemistry 17, № 1 (2019): 24–30. http://dx.doi.org/10.2174/1570178616666190401183953.

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The combination of [&#947;-Fe2O3@HAp-SO3H] as a catalyst and ultrasonic effect catalyzed the synthesis of diverse derivatives of 2, 3-dihydroquinazolin-4(1H)-ones which is reported in this study. The products were synthesized via the one-pot three-component reaction of isatoic anhydride, amines and pyrazole carbaldehydes in water: EtOH catalyzed by recoverable [&#947;-Fe2O3@HAp-SO3H]. This paper conducted an investigation of the effect of various solvents, temperatures and catalysts on the reactions. Short reaction times, mild reaction conditions, simple work-up, the desired yields and

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15

Shaabani, Ahmad, Abbas Rahmati, and Jafar Moghimirad. "Synthesis of a novel class of 3-(2′-benzothiazolyl)-2,3-dihydroquinazolin-4(1H)-ones under solvent-free and catalyst-free conditions." Journal of Heterocyclic Chemistry 45, no. 6 (2008): 1629–32. http://dx.doi.org/10.1002/jhet.5570450612.

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16

Molnar, Maja, Jelena Klenkar, and Tena Tarnai. "Eco-friendly rapid synthesis of 3-substituted-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones in choline chloride based deep eutectic solvent." Synthetic Communications 47, no. 11 (2017): 1040–45. http://dx.doi.org/10.1080/00397911.2017.1291815.

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17

Khandelwal, Sarita, Anshu Rajawat, Yogesh Tailor, and Mahendra Kumar. "Efficient and Environmentally Benign Diversity Oriented Synthesis of 2, 3- dihydroquinazolin-4(1H)-ones Using GAAS As a Bio-based Green Solvent." Current Green Chemistry 2, no. 2 (2015): 156–62. http://dx.doi.org/10.2174/2213346102666150121224434.

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18

Nagaladinne, Nizamuddin, Abdul Ahad Hindustan, and Devanna Nayakanti. "Design, Synthesis and Molecular Modelling Studies of 1-Methyl-3-(4-Substituted phenyl-1,3- thiazol-2-yl)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones as Potent Anticancer Agents." Asian Journal of Chemistry 32, no. 12 (2020): 3067–74. http://dx.doi.org/10.14233/ajchem.2020.22930.

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The present study involves the design, synthesis, characterization and molecular docking studies of biologically active quinazolin-4-ones, which were synthesized by condensing 2-amino-4-substituted phenylthiazole with N-methylbenzoxazin-4-one. The N-methylbenzoxazin-4-one and 2-amino-4- substituted phenylthiazole were synthesized from N-methylanthranilic acid and substituted ketones, respectively. The ADME properties determined the synthetic accessibility of quinazolin-4-ones by in silico Swiss ADME. The colorectal anticancer screening was done by using cell HT-29 human colorectal adenocarcino

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19

Patil, Dipak R., Pravin G. Ingole, Kripal Singh та Dipak S. Dalal. "Inclusion complex of Isatoic anhydride with β-cyclodextrin and supramolecular one-pot synthesis of 2, 3-dihydroquinazolin-4(1H)-ones in aqueous media". Journal of Inclusion Phenomena and Macrocyclic Chemistry 76, № 3-4 (2012): 327–32. http://dx.doi.org/10.1007/s10847-012-0203-z.

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20

Roopan, Selvaraj Mohana, F. Nawaz Khan, Jong Sung Jin, and R. Senthil Kumar. "An efficient one pot–three component cyclocondensation in the synthesis of 2-(2-chloroquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones: potential antitumor agents." Research on Chemical Intermediates 37, no. 8 (2011): 919–27. http://dx.doi.org/10.1007/s11164-011-0301-3.

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21

Szczepankiewicz, W., N. Kuźnik, S. Boncel, and A. Siewniak. "Unexpected Formation of 2-Acetyl-3-Aryl-2-Methyl-2,3-Dihydroquinazolin-4(1H)-Ones in the Reaction of 2-Amino-N'-Arylbenzamidines with Butanedione." Chemistry of Heterocyclic Compounds 50, no. 9 (2014): 1291–97. http://dx.doi.org/10.1007/s10593-014-1591-3.

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22

Ramesh, Rathinam, Nagarajan Nagasundaram, Durairaj Meignanasundar, Pullar Vadivel, and Appaswami Lalitha. "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." Research on Chemical Intermediates 43, no. 3 (2016): 1767–82. http://dx.doi.org/10.1007/s11164-016-2728-z.

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23

Szczepankiewicz, W., N. Kuznik, S. Boncel, and A. Siewniak. "ChemInform Abstract: Unexpected Formation of 2-Acetyl-3-aryl-2-methyl-2,3-dihydroquinazolin-4(1H)-ones in the Reaction of 2-Amino-N′-arylbenzamidines with Butanedione." ChemInform 46, no. 26 (2015): no. http://dx.doi.org/10.1002/chin.201526223.

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24

Mohammadpoor-Baltork, Iraj, Ahmad R. Khosropour, Majid Moghadam, et al. "Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3·5H2O: Investigating the role of the catalyst." Comptes Rendus Chimie 14, no. 10 (2011): 944–52. http://dx.doi.org/10.1016/j.crci.2011.05.003.

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25

Guda, Ramu, Kumara Swamy Battula, Srujana Muthadi, et al. "Synthesis, characterization and antimicrobial investigation of Rh(III), Ru(III) and Ag(I) complexes with some derivatives of 3-amino-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones." European Journal of Chemistry 7, no. 3 (2016): 334–40. http://dx.doi.org/10.5155/eurjchem.7.3.334-340.1446.

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26

Olyaei, Abolfazl, Fatemeh Rahbarian, and Mahdieh Sadeghpour. "Green and Catalyst-free One-pot Synthesis Of 2,3-dihydroquinazolin-4(1h)-ones in Water." Chemistry of Heterocyclic Compounds 51, no. 10 (2015): 899–902. http://dx.doi.org/10.1007/s10593-015-1793-3.

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27

El-Azab, Adel S., Nasr Y. Khalil, and Alaa A. M. Abdel-Aziz. "Remarkable Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones into the Corresponding Quinazoline-2,4(1H,3H)-diones: Spectroscopic Analysis and X-Ray Crystallography." Journal of Chemistry 2021 (April 2, 2021): 1–8. http://dx.doi.org/10.1155/2021/6612177.

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A simple and efficient new synthetic method to obtain 3-substituted quinazolin-2,4-diones 9–16 by the reaction of 3-substituted 2-thioxo-quinazolin-4-ones 1–8 with sodamide under mild conditions was presented. The structure of the newly synthesized compounds was determined by infrared spectroscopy, UV-visible spectroscopy, nuclear magnetic resonance, and single-crystal X-ray crystallographic analysis. The crystal structure of 6-methyl-3-phenylquinazoline-2,4(1H,3H)-dione (11) [C15H12N2O2: MF = 252.27, triclinic, P-1, a = 7.8495 (13) Å, b = 12.456 (2) Å, c = 13.350 (2) Å, α = 103.322 (3)°, β =

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28

Saffar-Teluri, Ali, and Shiva Bolouk. "One-pot, three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones using p-toluenesulfonic acid–paraformaldehyde copolymer as an efficient and reusable catalyst." Monatshefte für Chemie - Chemical Monthly 141, no. 10 (2010): 1113–15. http://dx.doi.org/10.1007/s00706-010-0376-3.

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29

Davoodnia, Abolghasem, Maryam Khashi, and Niloofar Tavakoli-Hoseini. "Cerium (IV) sulfate: A highly efficient reusable heterogeneous catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones under solvent-free conditions." Chinese Journal of Catalysis 35, no. 7 (2014): 1054–58. http://dx.doi.org/10.1016/s1872-2067(14)60041-3.

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30

Ghorbani-Choghamarani, Arash, and Gouhar Azadi. "Synthesis, characterization, and application of Fe3O4-SA-PPCA as a novel nanomagnetic reusable catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and polyhydroquinolines." RSC Advances 5, no. 13 (2015): 9752–58. http://dx.doi.org/10.1039/c4ra15315d.

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31

Khoshnavazi, Roushan, Leila Bahrami, and Forugh Havasi. "Organic–inorganic hybrid polyoxometalate and its graphene oxide–Fe3O4nanocomposite, synthesis, characterization and their applications as nanocatalysts for the Knoevenagel condensation and the synthesis of 2,3-dihydroquinazolin-4(1H)-ones." RSC Advances 6, no. 103 (2016): 100962–75. http://dx.doi.org/10.1039/c6ra15339a.

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Organic–inorganic hybrid of H<sub>6</sub>Cu<sub>2</sub>[PDA]<sub>6</sub>[SiW<sub>9</sub>Cu<sub>3</sub>O<sub>37</sub>]·12H<sub>2</sub>O (HybPOM), was synthesized and grafted on graphene oxide decorated with Fe<sub>3</sub>O<sub>4</sub>. The structures of HybPOM and GO@Fe<sub>3</sub>O<sub>4</sub>@HybPOM nanocomposites were characterized and their catalytic activities investigated.

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32

Kut, D., М. М. Kut, M. Onysko, I. Balog, and V. Lendel. "CHALCOGENATION OF N-ALKENYL DERIVATIVES OF 2-THIOXO-2,3-DIHYDRO QUINAZOLINE-4(1H)-ONE." Scientific Bulletin of the Uzhhorod University. Series «Chemistry» 45, no. 1 (2021). http://dx.doi.org/10.24144/2414-0260.2021.1.90-94.

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Oxo- and thio-substituted quinazolines are promising biologically active objects. A special place in a number of quinazolines is occupied by its condensed analogues, namely thiazoloquinazolines, which exhibit antioxidant, antimicrobial and antitumor activity. An effective method for the synthesis of condensed quinazoline derivatives is electrophilic intramolecular cyclization of its unsaturated derivatives. The usage of pharmacoformic chalcogen-containing electrophiles in these reactions has been insufficiently studied. Organochalcogen-containing heterocyclic compounds are the promising biolog

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33

Sina, Kiana Faraji, Asieh Yahyazadeh, and Nosrat Ollah Mahmoodi. "Synthesis, Characterization and Antibacterial Evaluation of 2, 3Dihydroquinazolin-4 (1H)-Ones and Some New Bis 2, 3-Dihydroquinazolin-4 (1H)-Ones Using Pre-made Pyrazole Carbaldehyde Derivatives." Letters in Organic Chemistry 17 (July 6, 2020). http://dx.doi.org/10.2174/1570178617999200706010203.

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: 2, 3-Dihydroquinazolinones are of popular compounds with the diversification of biological and pharmacological activities. Among many discovered methods, there are efficient and convenient methods used for the synthesis of 2, 3- dihydroquinazoline-4 (1H)-one and some new bis 2, 3-dihydroquinazoline-4 (1H)-one derivatives which are reported in this study. The mentioned methods include the two-component condensation of one molecule of anthranilamide and one molecule of DOI: pyrazole carbaldehyde using montmorillonite-K10 as a catalyst for the preparation of 2, 3 dihydroquinazoline4 (1H)-ones.

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34

"One Pot Green Synthesis of Pyrazolo[4, 3-d]pyrimidin-7(4H)-ones and Dihydroquinazolin-4(1H)-ones Derivatives Catalyzed by Efficient Recyclable Amberlite IR-120H Resin." Chemical Science Transactions, October 30, 2016. http://dx.doi.org/10.7598/cst2016.1262.

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35

Shaabani, Ahmad, Abbas Rahmati, and Jafar Moghimirad. "ChemInform Abstract: Synthesis of a Novel Class of 3-(2′-Benzothiazolyl)-2,3-dihydroquinazolin-4(1H)-ones under Solvent-Free and Catalyst-Free Conditions." ChemInform 40, no. 15 (2009). http://dx.doi.org/10.1002/chin.200915164.

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36

Memarian, Hamid Reza, and Reza Aghalar. "Photooxidation of 2,3-dihydroquinazolin-4(1H)-ones: retention or elimination of 2-substitution." Molecular Diversity, January 15, 2021. http://dx.doi.org/10.1007/s11030-020-10174-3.

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