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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 17
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Original Articles

Microwave‐Assisted Synthesis of Quinoline Derivatives from Isatin

El Sayed H. El Ashry Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, EgyptCorrespondence[email protected] [email protected]
,
El Sayed Ramadan Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt
,
Hamida Abdel Hamid Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt
&
Mohamed Hagar Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt
Pages 2243-2250 | Received 12 Nov 2004, Published online: 18 Aug 2006

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Read on this site (13)

Farrhat F. Mohammed, Mohamad Hagar, Shazia Parveen, Rua B. Alnoman, Hoda A. Ahmed, El Sayed H. El Ashry & Hanaa A. Rasheed. (2022) 2-(Alkylthio)-3-(Naphthalen-1-yl)Quinazolin-4(3H)-Ones: Ultrasonic Synthesis, DFT and Molecular Docking Aspects. Polycyclic Aromatic Compounds 42:7, pages 4034-4048.
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Negar Omidkhah & Razieh Ghodsi. (2021) Synthesis of novel 2-methyl-4-carboxyquinolines, the new by-products of the Doebner reaction. Synthetic Communications 51:13, pages 1947-1955.
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MohamedR. Aouad, Nadjet Rezki, Mouslim Messali & El Sayed H. El Ashry. (2013) Synthesis of Bis-Acyclonucleoside Analogues Bearing Benzothienyl-1,2,4-Triazol-3-Yl-Disulfide under Conventional and Microwave Methods. Nucleosides, Nucleotides & Nucleic Acids 32:1, pages 28-41.
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N. Rezki, N. Rashed, L.F. Awad, E. Ramadan, S.M. Abdel-Maggeed & E.S. H. El Ashry. (2009) Regio- and Stereoselective Synthesis of Thioglycosides from 4,5-Diphenyl- and 3,4,5-Triphenylimidazole-2-thione. Phosphorus, Sulfur, and Silicon and the Related Elements 184:7, pages 1759-1767.
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H.A. El-Sayed, A.H. Moustafa, A.Z. Haikal & E.S. H. El-Ashry. (2009) Synthesis and Antibacterial Activity of Some Glucosyl- and Ribosyl-Pyridazin-3-ones. Nucleosides, Nucleotides & Nucleic Acids 28:3, pages 184-192.
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E. S. H. El Ashry, K. F. Atta, S. Aboul‐Ela & R. Beldi. (2007) MAOS of Sugar Phenylosazones and their Derived Pyrazoles and Triazoles. Journal of Carbohydrate Chemistry 26:8-9, pages 429-437.
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E.S. H. El Ashry, L. F. Awad, H. Abdel Hamid & A. I. Atta. (2007) MAOS of D‐Gluconic Acid, D‐Glucono‐1,4‐ and 1,5‐Lactones, Esters, Hydrazides, and Benzimidazoles Thereof . Journal of Carbohydrate Chemistry 26:5-6, pages 329-338.
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E.S. H. El Ashry, A.A. Kassem, H. Abdel-Hamid, F.F. Louis, Sh.A. N. Khattab & M.R. Aouad. (2007) Novel Regioselective Formation of S- and N-Hydroxyl-Alkyls of 5-(3-Chlorobenzo[b]Thien-2-yl)-3-Mercapto-4H-1,2,4-Triazole and A Facile Synthesis of Triazolo-Thiazoles and Thiazolo-Triazoles. Role of Catalyst and Microwave. Nucleosides, Nucleotides & Nucleic Acids 26:5, pages 437-451.
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E.S. H. El Ashry, N. Rashed, L.F. Awad, E. Ramadan, S.M. Abdel-Maggeed & N. Rezki. (2007) Novel Regioselective Hydroxyl-Alkylation of 4,5-Diphenylimidazole-2-Thione and A Competitive Intramolecular Ring Closure of the S-Hydroxyalkyl-Imidazoles to Imidazo[2,1-b]Thiazines and Thiazoles. Role of Catalyst, Microwave Irradiation, and Solid Support. Nucleosides, Nucleotides & Nucleic Acids 26:5, pages 423-435.
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El Sayed H. El Ashry, Kamal F. Atta, Salah Aboul‐Ela & Razika Beldi. (2007) MAOS of Quinoxalines, Conjugated Pyrazolylquinoxalines and Fused Pyrazoloquinoxalines from l‐Ascorbic and d‐Isoascorbic Acid . Journal of Carbohydrate Chemistry 26:1, pages 1-16.
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E. S. H. El Ashry, N. Rashed, A. Abdel-Rahman, L.F. Awad & H.A. Rasheed. (2006) Synthesis of 2-Bromomethyl-3-Hydroxy-2-Hydroxymethyl-Propyl Pyrimidine and Theophylline Nucleosides Under Microwave Irradiation. Evaluation of Their Activity Against Hepatitis B Virus. Nucleosides, Nucleotides & Nucleic Acids 25:8, pages 925-939.
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E.S. H. El Ashry, L.F. Awad, H.M. Abdel Hamid & A.I. Atta. (2006) Microwave-Assisted Organic Synthesis of 3-(D-gluco- Pentitol-1-Yl)-1H-1,2,4-Triazole. Nucleosides, Nucleotides & Nucleic Acids 25:3, pages 325-335.
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El Sayed H. El Ashry, Laila F. Awad, H. M. Abdel Hamid & Atta I. Atta. (2005) Synthesis of Interglycosidically S‐Linked 1‐Thio‐Oligosaccharides Under Microwave Irradiation* . Journal of Carbohydrate Chemistry 24:7, pages 745-753.
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Articles from other publishers (27)

Manesh S. Tople, Navin B. Patel & Parth P. Patel. (2022) Microwave irradiation for the synthesis of quinoline scaffolds: a review. Journal of the Iranian Chemical Society 20:1, pages 1-28.
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Muhammad Zaheer, Muhammad Zia-ur-Rehman, Rubina Munir, Nadia Jamil, Saiqa Ishtiaq, Rahman Shah Zaib Saleem & Mark R. J. Elsegood. (2021) (Benzylideneamino)triazole–Thione Derivatives of Flurbiprofen: An Efficient Microwave-Assisted Synthesis and In Vivo Analgesic Potential . ACS Omega 6:46, pages 31348-31357.
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Badvel Pallavi, Rajnish Prakash Singh, Prabhat Nath Jha, Subhash Chander, Sankaranarayanan Murugesan, Prachi Sharma & Paritosh Shukla. (2019) Green Synthesis, in-vitro Antimicrobial Evaluation, Docking, and SAR Studies of Potent Quinoline-4-Carboxylic Acids. Letters in Organic Chemistry 16:11, pages 874-883.
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Suraj S. Kapale, Suraj N. Mali & Hemchandra K. Chaudhari. (2019) Molecular modelling studies for 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as anticancer agents. Medicine in Drug Discovery 2, pages 100008.
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Beatriz BaragañaNeil R. NorcrossCaroline WilsonAchim PorzelleIrene HallyburtonRaffaella GrimaldiMaria Osuna-CabelloSuzanne NorvalJennifer RileyLaste StojanovskiFrederick R. C. SimeonsPaul G. WyattMichael J. DelvesStephan Meister, Sandra Duffy, Vicky M. Avery, Elizabeth A. Winzeler, Robert E. SindenSergio Wittlin, Julie A. FrearsonDavid W. GrayAlan H. FairlambDavid Waterson, Simon F. Campbell, Paul Willis, Kevin D. ReadIan H. Gilbert. (2016) Discovery of a Quinoline-4-carboxamide Derivative with a Novel Mechanism of Action, Multistage Antimalarial Activity, and Potent in Vivo Efficacy. Journal of Medicinal Chemistry 59:21, pages 9672-9685.
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Nataraj Poomathi, Sivakalai Mayakrishnan, Doraiswamy Muralidharan, Rajagopal Srinivasan & Paramasivan T. Perumal. (2015) Reaction of isatins with 6-amino uracils and isoxazoles: isatin ring-opening vs. annulations and regioselective synthesis of isoxazole fused quinoline scaffolds in water. Green Chemistry 17:6, pages 3362-3372.
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Sai Li, Rui Jiang, Mingze Qin, Haicheng Liu, Guangyan Zhang & Ping Gong. (2013) Synthesis and Antitumor Activity of Novel 4‐(2‐ F luorophenoxy)quinoline Derivatives Bearing the 4‐ O xo‐1,4‐dihydroquinoline‐3‐carboxamide Moiety . Archiv der Pharmazie 346:7, pages 521-533.
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Sai Li, Qiang Huang, Yajing Liu, Xiaolong Zhang, Shuang Liu, Chao He & Ping Gong. (2013) Design, synthesis and antitumour activity of bisquinoline derivatives connected by 4-oxy-3-fluoroaniline moiety. European Journal of Medicinal Chemistry 64, pages 62-73.
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Qinghua Lv, Lizhen Fang, Pengfei Wang, Chenjuan Lu & Fulin Yan. (2012) A simple one-pot synthesis of quinoline-4-carboxylic acid derivatives by Pfitzinger reaction of isatin with ketones in water. Monatshefte für Chemie - Chemical Monthly 144:3, pages 391-394.
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Balakrishna Dulla, Baojie Wan, Scott G. Franzblau, Ravikumar Kapavarapu, Oliver Reiser, Javed Iqbal & Manojit Pal. (2012) Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents. Bioorganic & Medicinal Chemistry Letters 22:14, pages 4629-4635.
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Lizhen Fang, Qinghua Lv, Chenjuan Lu & Pengfei Wang. (2012) Improved Synthesis of 1-Oxo-1,2,3,4-tetrahydroacridine-9-carboxylic Acids from Isatins and 1,3-Cyclohexanedione. HETEROCYCLES 85:6, pages 1457.
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A. I. Moskalenko, A. V. Boeva & V. I. Boev. (2011) Heterocyclic ketones in the pfitzinger reaction. Russian Journal of General Chemistry 81:2, pages 397-404.
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Anil Argade, Rajesh Bahekar, Jigar Desai, Pravin Thombare, Kiran Shah, Sanjay Gite, Rajesh Sunder, Ramchandra Ranvir, Debdutta Bandyopadhyay, Ganes Chakrabarti, Amit Joharapurkar, Jogeswar Mahapatra, Abhijit Chatterjee, Harilal Patel, Mubeen Shaikh, Kalapatapu V. V. M. Sairam, Mukul Jain & Pankaj Patel. (2011) Design, synthesis and biological evaluation of γ-lactam hydroxamate based TACE inhibitors. MedChemComm 2:10, pages 966.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 2188 2192 .
Wentao Gao, Xiaofei Zhang, Yang Li & Kimiaki Imafuku. (2010) First Synthesis of 2-Tropolonylquinoline-4-carboxylic Acid Derivatives via Pfitzinger Reaction in Water. HETEROCYCLES 81:7, pages 1689.
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Hui Zhu, Ri Fang Yang, Liu Hong Yun & Jin Li. (2010) Facile and efficient synthesis of quinoline-4-carboxylic acids under microwave irradiation. Chinese Chemical Letters 21:1, pages 35-38.
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Shirshendu DasGupta, Prashant R. Murumkar, Rajani Giridhar & Mange Ram Yadav. (2009) Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: Design, synthesis, molecular modeling, and preliminary biological evaluation. Bioorganic & Medicinal Chemistry 17:10, pages 3604-3617.
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El Sayed H. El Ashry, Ahmed A. Kassem, Hamida M. Abdel-Hamid, Farida Louis, Sherine A.N. Khattab & Mohamed R. Aouad. (2009) Regioselectivity in the glycosylation of 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thiol. Carbohydrate Research 344:6, pages 725-733.
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Mohamed. R. Aouad, Nadje T. Rezki & El Sayed H. El Ahsry. (2009) Regioselectivity of the reactions of 4,5‐diphenylimidazole‐2‐thione with 1‐chloro‐2,3‐epoxy‐propane and 1‐bromo‐propene, efficient precursors for imidazo[2,1‐ b ]thiazine and thiazole. Effect of microwave and solid support . Journal of Heterocyclic Chemistry 45:5, pages 1321-1327.
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Erika Morizzo, Francesca Capelli, Ombretta Lenzi, Daniela Catarzi, Flavia Varano, Guido Filacchioni, Fabrizio Vincenzi, Katia Varani, Pier Andrea Borea, Vittoria Colotta & Stefano Moro. (2007) Scouting Human A 3 Adenosine Receptor Antagonist Binding Mode Using a Molecular Simplification Approach: From Triazoloquinoxaline to a Pyrimidine Skeleton as a Key Study . Journal of Medicinal Chemistry 50:26, pages 6596-6606.
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Hideyuki Ito, Takahiro Okuda, Toshiyuki Fukuda, Tsutomu Hatano & Takashi Yoshida. (2007) Two Novel Dicarboxylic Acid Derivatives and a New Dimeric Hydrolyzable Tannin from Walnuts. Journal of Agricultural and Food Chemistry 55:3, pages 672-679.
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E. S. H. El Ashry, A. A. Kassem, H. Abdel‐Hamid, F. F. Louis, S. H. A. N. Khattab & M. R. Aouad. (2009) Synthesis and alkylation of 5‐(3‐chlorobenzo[ b ]thien‐2‐yl)‐4 H ‐1,2,4‐triazole‐3‐thiol under classical and microwave conditions. AM1 semiemperical calculations for investigating the regioselectivity of alkylation . Journal of Heterocyclic Chemistry 43:6, pages 1421-1429.
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E. Sayed H. El Ashry, El Sayed Ramadan, Hamida Abdel Hamid & Mohamed Hagar. (2005) Microwave‐Assisted Synthesis of Quinoline Derivatives from Isatin.. ChemInform 37:3.
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E.S.H. El Ashry, A.A. Kassem & E. Ramadan. 2006. Advances in Heterocyclic Chemistry Volume 90. Advances in Heterocyclic Chemistry Volume 90 1 123 .

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