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In this work, we have synthesised a new disubstituted tetrahydroquinolines by the Povarov [4+2] cycloaddition reaction between imines derivatives and an electron-rich olefin such as vinyl ethers. These reactions were carried out in the presence of different acid catalysts in its two versions, multi-step reaction starting with imine synthesis and multi-component reaction in which the imine is formed in situ. The reactivity of the cycloaddition reaction is directly attributed to the nature of the reagents, the used synthetic strategy, in which the obtained yield is found in the case of multi-step reactions lower than that in the multi-component reaction one. Additionally, the multi-step reactions are faster kinetically in comparison with that of the multi-component one. The nature of the catalyst directly increases the rate and enhances the yield of the reactions.
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Czasopismo
Rocznik
Tom
Strony
295--308
Opis fizyczny
Bibliogr. 20 poz., rys.
Twórcy
autor
- Laboratoire des Sciences Appliquées et Didactiques, Ecole Normale Supérieure de Laghouat, Laghouat, Algeria
autor
- Department of Basic Formation, Faculty of Natural and Life Sciences University of Batna 2, Batna, Algeria
- Laboratory of Physical Chemistry and Biology of Materials, Department of Physics and Chemistry, Higher Normal School of Technological Education of Skikda, Azzaba 21300, Skikda, Algeria
Bibliografia
- [1] Sridharan, V.; Suryavanshi, P.A.; Menéndez, J.C. Advances in the chemistry of tetrahydroquinolines. Chem. Rev. 2011, 111, 7157-7259. DOI:10.1021/cr100307m
- [2] Chung, P.-Y.; Bian, Z.-X.; Pun, H.-Y.; Chan, D.; Chan, A.S.-C.; Chui, C.-H.; Tang, J.C.-O.; Lam, K.-H. Recent Advances in Research of Natural and Synthetic Bioactive Quinolines. Future Med. Chem. 2015, 7, 947-967. DOI:10.4155/fmc.15.34
- [3] Ghashghaei, O.; Masdeu, C.; Alonso, C.; Palacios, F.; Lavilla, R. Recent Advances of the Povarov Reaction in Medicinal Chemistry. Drug Discov. Today Technol. 2018, 29, 71-79. DOI:10.1016/j.ddtec.2018.08.004
- [4] Cai, J.; Li, F.; Deng, G.-J.; Ji, X.; Huang, H. The cyclopropylimine rearrangement/Povarov reaction cascade for the assembly of pyrrolo [3, 2-c] quinoline derivatives. Green Chem. 2016, 18, 3503-3506. DOI:10.1039/C6GC00779A
- [5] Jørgensen, K.A. Catalytic asymmetric Hetero-Diels-Alder reactions of carbonyl compounds and imines. Angew. Chem. In. Ed. Engl. 2000, 39, 3558-3588. DOI:10.1002/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO;2-I
- [6] Ren, X.R.; Bai, B.; Zhang, Q.; Hao, Q.; Guo, Y.; Wan, L.J.; Wang, D. Constructing Stable Chromenoquinoline-Based Covalent Organic Frameworks via Intramolecular Povarov Reaction. J. Am. Chem. Soc. 2022, 144, 2488-2494. DOI:10.1021/jacs.1c13005
- [7] Bello, D.; Ramon, R.; Lavilla, R. Mechanistic variations of the Povarov multicomponent reaction and related processes. Curr. Org. Chem. 2010, 14, 332-356. DOI:10.2174/138527210790231883
- [8] Slobbe, P.; Ruijter, E.; Orru, R.V.A. Recent applications of multicomponent reactions in medicinal chemistry. Med. Chem. Comm. 2012, 3, 1189-1218. DOI:10.1039/C2MD20089A
- [9] Ruijter, E.; Orru, R. Multicomponent reactions-Opportunities for the pharmaceutical industry. Drug Discov. Today Technol. 2013, 10, 15-20. DOI: 10.1016/j.ddtec.2012.10.012
- [10] Forero, J.S.B.; Jones Junior, J.; da Silva, F.M. The Povarov reaction as a versatile strategy for the preparation 1,2,3,4-tetrahydroquinoline derivatives: An overview. Curr. Org. Synth. 2016, 13, 157-175. DOI:10.2174/1570179412666150706183906
- [11] Buonora, P.; Olsen, J.-C.; Oh, T. Recent developments in imino Diels-Alder reactions. Tetrahedron 2001, 57, 6099-6138. DOI:10.1016/S0040-4020(01)00438-0
- [12] Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction. J. Am. Chem. Soc. 2009, 131, 4598-4599. DOI:10.1021/ja900806q
- [13] Doyle, A.G.; Jacobsen, E.N. Small-molecule H-bond donors in asymmetric catalysis. Chem. Rev. 2007, 107, 5713-5743. DOI:10.1021/cr068373r
- [14] Lamri, S.; Heddam, A.; Kara, M.; Yahia, W.; Nacereddine, A.K. The Role of the Catalyst on the Reactivity and Mechanism in the Diels-Alder Cycloaddition Step of the Povarov Reaction for the Synthesis of a Biological Active Quinoline Derivative: Experimental and Theoretical Investigations. Organics 2021, 2, 57-71. DOI:10.3390/org2010006
- [15] Hellel, D.; Chafaa, F.; Nacereddine, A.K.; Djerourou, A.; Vrancken, E. Regio- and stereoselective synthesis of novel isoxazolidine heterocycles by 1,3-dipolar cycloaddition between C-phenyl-N-methylnitrone and substituted alkenes. Experimental and DFT investigation of selectivity and mechanism. RSC Adv. 2017, 7, 30128-30141. DOI:10.1039/C7RA00258K
- [16] Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Schiff bases: A short survey on an evergreen chemistry tool. Molecules 2013, 18, 12264-12289. DOI:10.3390/molecules181012264
- [17] Grieco, P.A.; Bahsas, A. Role reversal in the cyclocondensation of cyclopentadiene with heterodienophiles derived from aryl amines and aldehydes: Synthesis of novel tetrahydroquinolines. Tetrahedron Lett. 1988, 29, 5855-5858. DOI:10.1016/S0040-4039(00)82208-X
- [18] Katritzky, A.; Rachwal, B.; Rachwal, S. Reactions of Alkyl-N-phenyl-1H-benzotriazole-1-methanamines with N-Vinilamides and N-Vinylcarbazole. A Convenient Synthesis of 4-(Dialkylamino)tetrahydroquinolines. J. Org. Chem. 1995, 60, 3993-4001. DOI: 10.1021/jo00118a014
- [19] Hadden, M.; Nieuwenhuyzen, M.; Osborne, D.; Stevenson, P.J.; Thompson, N.; Walker, A.D. Synthesis of the heterocyclic core of martinelline and martinellic acid. Tetrahedron 2006, 62, 3977-3984. DOI:10.1016/j.tet.2006.02.029
- [20] Talukdar, S.; Chen, C.-T.; Fang, J.-M. A Stereoselective Route to Polysubstituted Tetrahydro-quinolines by Benzotriazole-Promoted Condensation of Aliphatic Aldehydes and Aromatic Amines. J. Org. Chem. 2000, 65, 3148-3153. DOI:10.1021/jo000033x
Uwagi
Opracowanie rekordu ze środków MNiSW, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2024).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-04be6cc0-6927-4669-8186-6f291f6f0915