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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
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Original Articles

Synthesis of 2-Arylquinazolin-4(3H)-one Derivatives Catalyzed by Iodine in [bmim+][]

Xiang-Shan Wang School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, China; Key Laboratory of Biotechnology on Medical Plants, Xuzhou, Jiangsu, ChinaCorrespondence[email protected]
,
Ke Yang School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, China
,
Mei-Mei Zhang Key Laboratory of Biotechnology on Medical Plants, Xuzhou, Jiangsu, China
&
Chang-Sheng Yao School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu, China
Pages 2633-2646 | Received 29 Apr 2009, Published online: 05 Aug 2010

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Sara Moghadam Farid, Ali Moazzam, Keyvan Pedrood, Yahya Dashti, Samanesadat Hosseini, Bagher Larijani & Mohammad Mahdavi. (2023) A Facile, One-pot, and Green Method for Synthesis of 2-Aryl-3-(Phenylamino)Dihydroquinazolin-4(1H)-One Derivatives Using Sodium Lauryl Sulfate (SLS) in Aqueous Media at the Room Temperature. Polycyclic Aromatic Compounds 0:0, pages 1-13.
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Jutika Devi, Subarna Jyoti Kalita & Dibakar Chandra Deka. (2017) Expeditious synthesis of 2,3-dihydroquinazolin-4(1H)-ones in aqueous medium using thiamine hydrochloride (VB1) as a mild, efficient, and reusable organocatalyst. Synthetic Communications 47:17, pages 1601-1609.
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Rajesh H. Vekariya & Hitesh D. Patel. (2015) Sulfonic Acid–Functionalized Silica (SiO2-Pr-SO3H) as a Solid and a Heterogeneous Catalyst in Green Organic Synthesis: Recent Advances. Synthetic Communications 45:9, pages 1031-1054.
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P. Paradesi Naidu, Akula Raghunadh, K. Raghavendra Rao, Ramamohan Mekala, J. Moses Babu, B.R. Rao, V. Siddaiah & Manojit Pal. (2014) Urea/Thiourea as Ammonia Surrogate: A Catalyst-Free Synthesis of 2-Substituted 2,3-Dihydroquinazolin-4(1H)-ones/Quinazoline-4(3H)-ones. Synthetic Communications 44:10, pages 1475-1482.
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Xun Zhu, Wenlei Ge & Yunyang Wei. (2013) Cerium(III)-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Aminobenzamide and Aldehydes in Dimethyl Carbonate. Polycyclic Aromatic Compounds 33:5, pages 467-472.
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Dan Zhan, Tianbin Li, Xiaoping Zhang, Chuan Dai, Haidong Wei, Yuyu Zhang & Qingle Zeng. (2013) Vanadium-Catalyzed Synthesis of 4(3H)-Quinazolinones from Anthranilamides and Aryl Aldehydes. Synthetic Communications 43:18, pages 2493-2500.
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Articles from other publishers (33)

Emiliya V. Nosova, Ilya I. Butorin, Margarita D. Likhacheva & Svetlana K. Kotovskaya. (2023) Synthesis and cytotoxic activity of (2-arylquinazolin-4-yl)hydrazones of 2-hydroxybenzaldehydes. Chimica Techno Acta 10:2.
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Alageswaran Jayaram, Karthick Govindan, Vijaya Raghavan Kannan, Vijay Thavasianandam Seenivasan, Nian-Qi Chen & Wei-Yu Lin. (2023) Iodine-Promoted Oxidative Cyclization of Acylated and Alkylated Derivatives from Epoxides toward the Synthesis of Aza Heterocycles. The Journal of Organic Chemistry 88:3, pages 1749-1761.
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Vanessza Judit Kolcsár & György Szőllősi. (2022) Synthesis of a Pyrrolo[1,2-a]quinazoline-1,5-dione Derivative by Mechanochemical Double Cyclocondensation Cascade. Molecules 27:17, pages 5671.
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Mugada Sugunakara Rao & Sahid Hussain. (2021) One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water. Tetrahedron Letters 74, pages 153159.
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Kyeongha Kim, Hun Young Kim & Kyungsoo Oh. (2020) ortho -Naphthoquinone-catalyzed aerobic oxidation of amines to fused pyrimidin-4(3 H )-ones: a convergent synthetic route to bouchardatine and sildenafil . RSC Advances 10:52, pages 31101-31105.
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Shankar Ram, Shaifali, Arvind Singh Chauhan, Sheetal, Ajay Kumar Sharma & Pralay Das. (2019) Polystyrene‐Supported Palladium (Pd@PS)‐Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2‐Aryl Quinazolinones. Chemistry – A European Journal 25:64, pages 14506-14511.
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Suman Das, Jayeeta Bhattacharjee & Tarun K. Panda. (2019) Guanylation/cyclisation of amino acid esters using an imidazolin-2-iminato titanium initiator. Dalton Transactions 48:21, pages 7227-7235.
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Huaiyuan Kang, Weili Wang, Qinqiang Sun, Shuya Yang, Juan Jin, Xuewen Zhang, Xiaoliang Ren, Jiming Zhang & Jianhua Zhou. (2018) Microwave-assisted synthesis of quinazolin-4(3 H )-ones catalyzed by SbCl 3 . Heterocyclic Communications 24:6, pages 293-296.
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Mariateresa Badolato, Francesca Aiello & Nouri Neamati. (2018) 2,3-Dihydroquinazolin-4(1 H )-one as a privileged scaffold in drug design . RSC Advances 8:37, pages 20894-20921.
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K. Kumar G. Ramakrishna, Ravi Kumar Thakur, Venkata Reddy Pasam, Jyotsana Pandey, Rohit Mahar, Sanjeev K. Shukla, Akhilesh K. Tamrakar & Rama Pati Tripathi. (2017) Synthesis of novel glycosyl-1,2,3-1H-triazolyl methyl quinazolin-4(3H)-ones and their effect on GLUT4 translocation. Tetrahedron 73:2, pages 187-203.
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Rohit Sharma, Ram A. Vishwakarma & Sandip B. Bharate. (2016) Bimetallic Cu-Mn-Catalyzed Synthesis of 2-Arylquinazolin-4(3 H )-ones: Aqueous Ammonia as Source of a Ring Nitrogen Atom . European Journal of Organic Chemistry 2016:31, pages 5227-5233.
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Rupesh U. Shelke, Mariam S. Degani, Archana Raju, Mukti Kanta Ray & Mysore G. R. Rajan. (2016) Fragment Discovery for the Design of Nitrogen Heterocycles as Mycobacterium tuberculosis Dihydrofolate Reductase Inhibitors . Archiv der Pharmazie 349:8, pages 602-613.
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Yongke Hu, Lei Chen & Bindong Li. (2016) Iron nitrate/TEMPO-catalyzed aerobic oxidative synthesis of quinazolinones from alcohols and 2-aminobenzamides with air as the oxidant. RSC Advances 6:69, pages 65196-65204.
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Ágnes Magyar & Zoltán Hell. (2016) One-Pot Three-Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst. Catalysis Letters 146:6, pages 1153-1162.
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Dezhi Qiu, Yanyan Wang, Dongming Lu, Lihong Zhou & Qingle Zeng. (2015) Potassium hydroxide-promoted transition-metal-free synthesis of 4(3H)-quinazolinones. Monatshefte für Chemie - Chemical Monthly 146:8, pages 1343-1347.
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Y. Nagasawa, Y. Matsusaki, T. Nobuta, N. Tada, T. Miura & A. Itoh. (2015) Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine. RSC Advances 5:78, pages 63952-63954.
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S. Nagarajan, Tanveer Mahamadali Shaikh & Elango Kandasamy. (2015) An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions. New Journal of Chemistry 39:12, pages 9693-9699.
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Javad Safari & Soheila Gandomi-Ravandi. (2014) Efficient synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in the presence of nanocomposites under microwave irradiation. Journal of Molecular Catalysis A: Chemical 390, pages 1-6.
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Javad Safari & Soheila Gandomi-Ravandi. (2014) Silver decorated multi-walled carbon nanotubes as a heterogeneous catalyst in the sonication of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones. RSC Adv. 4:23, pages 11654-11660.
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Muhammad Sharif, Julita Opalach, Peter Langer, Matthias Beller & Xiao-Feng Wu. (2014) Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes. RSC Adv. 4:1, pages 8-17.
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Jian Wu, Xianli Du, Juan Ma, Yuping Zhang, Qingcai Shi, Lijun Luo, Baoan Song, Song Yang & Deyu Hu. (2014) Preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives in aqueous media with β-cyclodextrin-SO 3 H as a recyclable catalyst . Green Chem. 16:6, pages 3210-3217.
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Haoquan Li, Lin He, Helfried Neumann, Matthias Beller & Xiao-Feng Wu. (2014) Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction. Green Chem. 16:3, pages 1336-1343.
Crossref
Moni Sharma, Rohit Mahar, Sanjeev K. Shukla, Ruchir Kant & Prem M.S. Chauhan. (2013) Potassium carbonate mediated unusual transformation of 2,3-dihydroquinazolinone via cascade reaction. Tetrahedron Letters 54:46, pages 6171-6177.
Crossref
Huamin Wang, Xiangxiang Cao, Fuhong Xiao, Saiwen Liu & Guo-Jun Deng. (2013) Iron-Catalyzed One-Pot 2,3-Diarylquinazolinone Formation from 2-Nitrobenzamides and Alcohols. Organic Letters 15:18, pages 4900-4903.
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Xiao‐Feng Wu, Lin He, Helfried Neumann & Matthias Beller. (2013) Palladium‐Catalyzed Carbonylative Synthesis of Quinazolinones from 2‐Aminobenzamide and Aryl Bromides. Chemistry – A European Journal 19:38, pages 12635-12638.
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Javad Safari & Soheila Gandomi-Ravandi. (2013) WITHDRAWN: Ultrasound-based approach to 2-aryl-2,3-dihydroquinazolin-4(1H)-ones in presence of silver supported multi-walled carbon nanotubes. Catalysis Communications.
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Dan Zhan, Tianbin Li, Haidong Wei, Wen Weng, Khashayar Ghandi & Qingle Zeng. (2013) A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones. RSC Advances 3:24, pages 9325.
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Wenlei Ge, Xun Zhu & Yunyang Wei. (2013) Iodine-catalyzed oxidative system for cyclization of primary alcohols with o-aminobenzamides to quinazolinones using DMSO as the oxidant in dimethyl carbonate. RSC Advances 3:27, pages 10817.
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Hidemasa Hikawa, Yukari Ino, Hideharu Suzuki & Yuusaku Yokoyama. (2012) Pd-Catalyzed Benzylic C–H Amidation with Benzyl Alcohols in Water: A Strategy To Construct Quinazolinones. The Journal of Organic Chemistry 77:16, pages 7046-7051.
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Quan-Sheng Ding, Ji-Lei Zhang, Jiu-Xi Chen, Miao-Chang Liu, Jin-Chang Ding & Hua-Yue Wu. (2012) Tandem synthesis of 2,3-dihydroquinazolin-4(1H)-ones on grinding under solvent-free conditions. Journal of Heterocyclic Chemistry 49:2, pages 375-380.
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Moni Sharma, Shashi Pandey, Kuldeep Chauhan, Deepty Sharma, Brijesh Kumar & Prem M. S. Chauhan. (2012) Cyanuric Chloride Catalyzed Mild Protocol for Synthesis of Biologically Active Dihydro/Spiro Quinazolinones and Quinazolinone-glycoconjugates. The Journal of Organic Chemistry 77:2, pages 929-937.
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Marjan Jereb, Dejan Vražič & Marko Zupan. (2011) Iodine-catalyzed transformation of molecules containing oxygen functional groups. Tetrahedron 67:7, pages 1355-1387.
Crossref
Xiang‐Shan Wang, Ke Yang, Mei‐Mei Zhang & Chang‐Sheng Yao. (2010) ChemInform Abstract: Synthesis of 2‐Arylquinazolin‐4(3H)‐one Derivatives Catalyzed by Iodine in [bmim + ][BF ‐ 4 ]. . ChemInform 42:4.
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