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Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines
Khaled Khalil (1)
, Hamad Al-Matar (2,*) , Mohamed Elnagdi (3) (1) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(2) Chemistry Department, Faculty of Science, University of Kuwait, KW-13060, Kuwait
(3) Chemistry Department, Faculty of Science, University of Kuwait, KW-13060, Kuwait
(*) Corresponding Author
Received: 21 Jul 2010 | Revised: 30 Nov 2010 | Accepted: 25 Jul 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
Depending on their nature, nitrile activated methylene compounds add readily to β-enaminones in presence of chitosan to yield dienamides, pyridones or pyridine thiones. The dienamides, formed in this manner, can be readily converted to pyridones by stirring in refluxing acetic acid. Reaction of pyridazinones with a mixture containing benzaldehyde, malononitrile and chitosan affords phthalazines that are also produced by reaction of pyridazinone with benzylidene-malononitrile.
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DOI: 10.5155/eurjchem.1.4.252-258.211
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[1]. Sarah Aldulaijan, Sara Nabil, Salha Alharthi, Bushra AL Abdullatif, Abir S. Abdel-Naby
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DOI: 10.1039/D2NJ05513A
[2]. Metwally Madkour, Khaled D. Khalil, Fakhreia A. Al-Sagheer
Heterogeneous Hybrid Nanocomposite Based on Chitosan/Magnesia Hybrid Films: Ecofriendly and Recyclable Solid Catalysts for Organic Reactions
Polymers 13(20), 3583, 2021
DOI: 10.3390/polym13203583
[3]. Bhausaheb S. Narsale, Anil G. Gadhave, Ketan S. Raut, Dilip R. Thube
One Pot Approach of Novel Xanthan Perchloric Acid Catalyst in Synthesis of Bis(Indolyl)Methane Derivatives via Greener Perspective
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DOI: 10.1080/10406638.2022.2108075
[4]. Abdulaziz Alnajjar, Marzouq Alsaiedi, Morsy Ahmed El-Apasery
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DOI: 10.5155/eurjchem.4.1.53-57.733
[5]. Khaled Khalil, Hoda Ahmed, Ali Bashal, Stefan Bräse, AbdElAziz Nayl, Sobhi Gomha
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DOI: 10.3390/polym14163347
[6]. R. Yuvan raj, P. Tamizhdurai, C. Kavitha, V.L. Mangesh, Nadavala Siva Kumar, Ahmed S. Al-Fatesh, Salwa B. Alreshaidan, Jehad K. Abu-Dahrieh, R. Kumaran
The catalytic activity of copper/nickel supported on mesoporous aluminum catalyst towards cyclohexene epoxidation in continuous reactor
Journal of Saudi Chemical Society 27(5), 101715, 2023
DOI: 10.1016/j.jscs.2023.101715
[7]. Khaled Khalil, Hamad Al-Matar
Chitosan Based Heterogeneous Catalyses: Chitosan-Grafted-Poly(4-Vinylpyridne) as an Efficient Catalyst for Michael Additions and Alkylpyridazinyl Carbonitrile Oxidation
Molecules 18(5), 5288, 2013
DOI: 10.3390/molecules18055288
[8]. Sara Zhaleh, Nourallah Hazeri, Mohammad Reza Faghihi, Malek Taher Maghsoodlou
Chitosan: a sustainable, reusable and biodegradable organocatalyst for green synthesis of 1,4-dihydropyridine derivatives under solvent-free condition
Research on Chemical Intermediates 42(12), 8069, 2016
DOI: 10.1007/s11164-016-2579-7
[9]. Sayed Riyadh, Khaled Khalil, Ateyatallah Aljuhani
Chitosan-MgO Nanocomposite: One Pot Preparation and Its Utility as an Ecofriendly Biocatalyst in the Synthesis of Thiazoles and [1,3,4]thiadiazoles
Nanomaterials 8(11), 928, 2018
DOI: 10.3390/nano8110928
[10]. Latifah A. Alshabanah, Sobhi M. Gomha, Laila A. Al-Mutabagani, Tariq Z. Abolibda, Nahed A. Abd El-Ghany, Waleed A. M. A. El-Enany, Ahmed K. El-Ziaty, Rania S. Ali, Nadia A. Mohamed
Cross-Linked Chitosan/Multi-Walled Carbon Nanotubes Composite as Ecofriendly Biocatalyst for Synthesis of Some Novel Benzil Bis-Thiazoles
Polymers 13(11), 1728, 2021
DOI: 10.3390/polym13111728
[11]. Sayed M. Riyadh, Sobhi M. Gomha, Elmahdi A. Mahmmoud, Mahmoud M. Elaasser
Synthesis and Anticancer Activities of Thiazoles, 1,3-Thiazines, and Thiazolidine Using Chitosan-Grafted-Poly(vinylpyridine) as Basic Catalyst
HETEROCYCLES 91(6), 1227, 2015
DOI: 10.3987/COM-15-13210
[12]. Fabio Moccia, Luca Rigamonti, Alessandro Messori, Valerio Zanotti, Rita Mazzoni
Bringing Homogeneous Iron Catalysts on the Heterogeneous Side: Solutions for Immobilization
Molecules 26(9), 2728, 2021
DOI: 10.3390/molecules26092728
[13]. Pratibha Rai, Madhulika Srivastava, Jaya Singh, Jagdamba Singh
Chitosan/ionic liquid forms a renewable and reusable catalyst system used for the synthesis of highly functionalized spiro derivatives
New Journal of Chemistry 38(7), 3181, 2014
DOI: 10.1039/c3nj01545a
[14]. Zeba N. Siddiqui, Kulsum Khan
Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions
New Journal of Chemistry 37(5), 1595, 2013
DOI: 10.1039/c3nj00069a
[15]. Hamad M. Al-Matar, Khaled D. Khalil, Mona F. Al-Kanderi, Mohamed H. Elnagdi
Studies on 3-Oxoalkanenitriles: Novel Rearrangement Reactions Observed in Studies of the Chemistry of 3-Heteroaroyl-3-Oxoalkanenitriles as Novel Routes to 2-Dialkylaminopyridines
Molecules 17(1), 897, 2012
DOI: 10.3390/molecules17010897
[16]. Premchand B. Shelke, Suraj N. Mali, Hemchandra K. Chaudhari, Amit P. Pratap
Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives
Journal of Heterocyclic Chemistry 56(11), 3048, 2019
DOI: 10.1002/jhet.3700
[17]. Peiyun Jiang, Bingwei Hu, Xu Yuan, Jimei Yang, Xingjiang Yang, Jun Lin, Yi Jin
Synthesis of 2-Aminofurans and 2-Aminothiophenes through Elemental Sulfur-Promoted Switchable Redox Condensation Reaction of Enaminones with Methylene Nitriles
The Journal of Organic Chemistry 87(22), 15312, 2022
DOI: 10.1021/acs.joc.2c01882
[18]. Ahmed El‐Mekabaty, Hanem M. Awad
Convenient synthesis of novel sulfonamide derivatives as promising anticancer agents
Journal of Heterocyclic Chemistry 57(3), 1123, 2020
DOI: 10.1002/jhet.3849
[19]. Maria A. Vodolazhenko, Nikolay Yu. Gorobets, Sergey A. Yermolayev, Vladimir V. Musatov, Valentin A. Chebanov, Sergey M. Desenko
Application of stable fused dienolates for diversity oriented synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamides
RSC Adv. 2(3), 1106, 2012
DOI: 10.1039/C1RA00723H
[20]. Rajender S. Varma
Biomass-Derived Renewable Carbonaceous Materials for Sustainable Chemical and Environmental Applications
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DOI: 10.1021/acssuschemeng.8b06550
[21]. Fatereh Asghari-Haji, Kurosh Rad-Moghadam, Nosrat O. Mahmoodi
An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan
RSC Advances 6(33), 27388, 2016
DOI: 10.1039/C5RA26580K
[22]. Khaled D. Khalil, Enas I. Ibrahim, Fakhreia A. Al-Sagheer
A novel, efficient, and recyclable biocatalyst for Michael addition reactions and its iron(iii) complex as promoter for alkyl oxidation reactions
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DOI: 10.1039/C5CY01034A
[23]. Amit Kumar, Chetananda Patel, Pooja Patil, Shivam Vyas, Abha Sharma
Chemoselective synthesis of bis(indolyl)methanes using sulfonic acid-functionalized chitosan
Chemical Papers 73(12), 3095, 2019
DOI: 10.1007/s11696-019-00846-2
[24]. Hossein Mousavi
A comprehensive survey upon diverse and prolific applications of chitosan-based catalytic systems in one-pot multi-component synthesis of heterocyclic rings
International Journal of Biological Macromolecules 186, 1003, 2021
DOI: 10.1016/j.ijbiomac.2021.06.123
[25]. Sobhi M. Gomha, Sayed M. Riyadh, Elmahdi A. Mahmmoud, Mahmoud M. Elaasser
Synthesis and anticancer activity of arylazothiazoles and 1,3,4-thiadiazoles using chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst
Chemistry of Heterocyclic Compounds 51(11-12), 1030, 2015
DOI: 10.1007/s10593-016-1815-9
[26]. Ebtesam Abdul Aziz Hafez, Saleh Mohammed Al-Mousawi, Moustafa Sherief Moustafa, Kmal Usef Sadek, Mohamed Hilmy Elnagdi
Green methodologies in organic synthesis: recent developments in our laboratories
Green Chemistry Letters and Reviews 6(3), 189, 2013
DOI: 10.1080/17518253.2012.740078
[27]. Olivier Mahé, Jean‐François Brière, Isabelle Dez
Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis
European Journal of Organic Chemistry 2015(12), 2559, 2015
DOI: 10.1002/ejoc.201403396
[28]. Pragya Bradu, Antara Biswas, Chandralekha Nair, Salini Sreevalsakumar, Megha Patil, Sandra Kannampuzha, Anirban Goutam Mukherjee, Uddesh Ramesh Wanjari, Kaviyarasi Renu, Balachandar Vellingiri, Abilash Valsala Gopalakrishnan
Recent advances in green technology and Industrial Revolution 4.0 for a sustainable future
Environmental Science and Pollution Research , , 2022
DOI: 10.1007/s11356-022-20024-4
[29]. Guangho Huang, Amaury Laporte, Lucas Pagès, Cyrille Kouklovsky, Aurélien de la Torre
Total Synthesis of Lucidumone: Attempted Shortcuts, Dead Ends and Lessons Learnt
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DOI: 10.1055/s-0042-1751529
[30]. Pauline Fournier, Caroline R. Szczepanski, René-Paul Godeau, Guilhem Godeau
Chitosan Extraction from Goliathus orientalis Moser, 1909: Characterization and Comparison with Commercially Available Chitosan
Biomimetics 5(2), 15, 2020
DOI: 10.3390/biomimetics5020015
[31]. Safura Zahedi, Javad Safaei Ghomi, Hossein Shahbazi-Alavi
Preparation of chitosan nanoparticles from shrimp shells and investigation of its catalytic effect in diastereoselective synthesis of dihydropyrroles
Ultrasonics Sonochemistry 40, 260, 2018
DOI: 10.1016/j.ultsonch.2017.07.023
[32]. Pramod K. Sahu, Praveen K. Sahu, Sushil K. Gupta, Dau D. Agarwal
Chitosan: An Efficient, Reusable, and Biodegradable Catalyst for Green Synthesis of Heterocycles
Industrial & Engineering Chemistry Research 53(6), 2085, 2014
DOI: 10.1021/ie402037d
[33]. Sraa Abu-Melha, Sobhi Gomha, Amr Abouzied, Mastoura Edrees, Ahmed Abo Dena, Zeinab Muhammad
Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-Pyridazinediones as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria
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DOI: 10.3390/molecules26144260
References
[1]. Niola, F.; Basora, N.; Chornet, E.; Vidal, P. F. Carbohyd. Res.1993, 238, 1-9.
doi:10.1016/0008-6215(93)87001-9
[2]. Bader, H. J.; Birkholz, E. Praxis der Naturwissenschaften,Chemie1996, 45(6), 24-30.
[3]. Rege, P. R.; Block, L. H. Carbohyd. Res.1999, 321, 235-245.
doi:10.1016/S0008-6215(99)00172-X
[4]. Gomha, S. M.; Riyadh, S. M. Arkivoc2009, 11, 58-68.
[5]. Al-Matar, H. M.; Khalil, K. D.; Meier, H.; Kolshorn, H.; Elnagdi, M. H. Arkivoc 2008, 16, 288-301.
[6]. Alnajjar, A.; Abdelkhalik, M. M.; Al-Enezi, A.; Elnagdi, M. H. Molecules2009, 14(1), 68-77.
doi:10.3390/molecules14010068
PMid:19127238
[7]. Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocyclic Chem.2005, 42(4), 563-566.
doi:10.1002/jhet.5570420414
[8]. Schmidt, U.; Kubitzek, H. Chemische Berichte1960, 93,1559-65.
doi:10.1002/cber.19600930716
[9]. Boatman, S.; Harris, T. M.; Hauser, C. R. J. Org. Chem.1965, 30(11), 3593-7.
doi:10.1021/jo01022a003
[10]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Elnagdi, M. H. Arkivoc2006, 13, 147-157.
[11]. Al-Mousawi, S. M.; Moustafa, M. S.; Abdelkhalik, M. M.; Elnagdi, M. H. Arkivoc2009, 11, 1-10.
[12]. Al-Omran, F.; Al-Awadi, N.; Abdelkhalik, M. M.; Kaul, K.; Elkhair, A. A.; Elnagdi, M. H. J. Chem. Res. (S) 1997, 84, 601-613.
[13]. Abdelrazek, F. M.; Elsayed, A. N. J. Heterocyclic Chem. 2009, 46, 949-953.
doi:10.1002/jhet.181
[14]. Gorobets, N. Y.; Sedash, Y. V.; Shishkina, S. V.; Shishkin, O. V.; Yermolayev, S. A.; Desenko, S. M. Arkivoc2009, 13, 23-30.
[15]. Abdelrazek, F. M.; Michael, F. A. J. Heterocyclic Chem. 2006, 43(1), 7-10.
doi:10.1002/jhet.5570430102
[16]. Al-Mousawi, S.; Moustafa, M. S.; Elnagdi, M. H. Arkivoc2008, 10, 17-25.
[17]. Al-Saleh, B.; Hilmy, Noha M.; El-Apasery, M. A.; Elnagdi, M. H. J. Heterocyclic Chem.2006, 43(6), 1575-1581.
doi:10.1002/jhet.5570430622
[18]. Mogilaiah, K.; Rani, J. Uma. Indian J. Heterocycl. Chem.2003, 13(2), 169-170.
[19]. Xu, Da-Zh.; Liu,Y.; Shi S.; Wang, Y.GreenChem.2010, 12, 514-517.
doi:10.1039/b918595j
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