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

References (66)

1. 1 Vo, 2014, Synthesis of Saturated N-Heterocycles [DOI]
2. 2 Paoletti, 2007, NMDA receptor subunits: Function and pharmacology [DOI]
3. 3 Rano, 2009, Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform [DOI]
4. 4 Ramesh, 2010, Synthesis and cha-racterization of iodinated tetrahydroquinolines targeting the G protein-coupled estrogen receptor GPR30 [DOI]
5. 5 Caprio, 2000, A novel inhibitor of human telomerase derived from 10H-indolo [3, 2-b] quinoline [DOI]
6. 6 Senthilkumar, 2009, Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids [DOI]
7. 7 Delgado, J., and Wilson, R.W. (1998). Gisvold’s Textbook of Organic Medicinal and Pharmaceutical Chemistry, Lippinicott Williams and Wilkins.
8. 8 Guo, 2009, Design and synthesis of 5-alkoxy-[1, 2, 4] triazolo [4, 3-a] quinoline derivatives with anticonvulsant activity [DOI]
9. 9 Clemence, 1988, 4-Hydroxy-3-quinolinecarboxamides with antiarthritic and analgesic activities [DOI]
10. 10 Sircar, 1992, Synthesis and biological activity of 4-(diphenylmethyl)-alpha-[(4-quinolinyloxy)methyl]-1-piperazineethanol and related compounds [DOI]
11. 11 Kouznetsov, 2009, Recent synthetic developments in a powerful imino Diels-Alder reaction (Povarov reaction): Application to the synthesis of N-polyheterocycles and related alkaloids [DOI]
12. 12 Katritzky, 1996, Recent progress in the synthesis of 1, 2, 3, 4,-tetrahydroquinolines [DOI]
13. 13 Oikawa, 2004, Enzymatic catalysis of the Diels-Alder reaction in the biosynthesis of natural products [DOI]
14. 14 Lucchini, 1992, Acid-catalysed addition of N-aryl imines to dihydrofuran. Postu-lated dependence of the reaction mechanism on the relative face of approach of reactants [DOI]
15. 15 Makioka, 1995, Ytterbium (III) triflate catalyzed synthesis of quinoline derivatives from N-arylaldimines and vinyl ethers [DOI]
16. 16 Liu, 2012, Simple and practical synthesis of pyrano- and furano[3,2-c]-quinoline derivatives under non-Lewis acid catalysis [DOI]
17. 17 Povarov, 1967, αβ-Unsaturated ethers and their analogues in reactions of diene synthesis [DOI]
18. 18 Grieco, 1988, Role reversal in the cyclocondensation of cyclopentadiene with heterodienophiles derived from aryl amines and aldehydes: Synthesis of novel tetrahydroquinolines [DOI]
19. 19 Kobayashi, 1996, A New Methodology for Combinatorial Synthesis. Preparation of Diverse Quinoline Derivatives Using a Novel Polymer-Supported Scandium Catalyst [DOI]
20. 20 Ma, 1999, Lanthanide Chloride Catalyzed Imino Diels-Alder Reaction. One-Pot Synthesis of Pyrano [3, 2-c]-and Furo [3, 2-c] quinolines [DOI]
21. 21 Lavilla, 2003, Dihydropyridine-based multicomponent reactions. Efficient entry into new tetrahydroquinoline systems through Lewis acid-catalyzed formal [4+ 2] cycloadditions [DOI]
22. 22 Powell, 2003, Lanthanide(III)-catalyzed multi-component aza-Diels-Alder reaction of aliphatic N-arylaldimines with cyclopentadiene [DOI]
23. 23 Batey, 2001, Multi-component coupling reactions: Synthesis of a guanidine containing analog of the hexahydro-pyrrolo [3, 2-c] quinoline alkaloid martinelline [DOI]
24. 24 Yadav, 2001, Lithium perchlorate/diethylether catalyzed aza-Diels-Alder reaction: An expeditious synthesis of pyrano, indeno quinolines and phenanthridines [DOI]
25. 25 Legros, 2006, Facile synthesis of tetrahydroquinolines and julolidines through mul-ticomponent reaction [DOI]
26. 26 Nacereddine, 2015, A DFT study of the role of the Lewis acid catalysts in the [3 + 2] cycloaddition reaction of the electrophilic nitrone isomer of methyl glyoxylate oxime with nucleophilic cyclopentene [DOI]
27. 27 Barama, 2018, A mechanistic MEDT study of the competitive catalysed [4+2] and [2+2] cycloaddition reactions between 1-methyl-1-phenylallene and methyl acrylate: The role of Lewis acid on the mechanism and selectivity [DOI]
28. 28 Bouacha, 2013, A theoretical study of the mechanism, stereoselectivity and Lewis acid catalyst on the Diels-Alder cycloaddition between furan and activated alkenes [DOI]
29. 29 Yahia, 2014, Towards Understanding the Role of Lewis Acid on the Regioselectivity and Mechanism for the Acetylation Reaction of 2-benzoxazolinone with Acetyl Chloride: A DFT Study [DOI]
30. 30 Lachtar, 2020, Understanding the origin of the enantioselectivity and the mechanism of the asymmetric re-duction of ketimine generated from acetophenone with oxazaborolidine catalyst [DOI]
31. 31 Eyring, 1935, The Activated Complex in Chemical Reactions [DOI]
32. 32 Geerlings, 2003, Conceptual Density Functional Theory [DOI]
33. 33 Domingo, L.R., Ríos-Gutiérrez, M., and Pérez, P. (2016). Applications of the conceptual density functional theory indices to organic che-mistry reactivity. Molecules, 21. [DOI]
34. 34 Wascinska, 2008, Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles [DOI]
35. 35 Nic, M., Hovorka, L., Jirat, J., Kosata, B., and Znamenacek, J. (2005). IUPAC Compendium of Chemical Terminology—The Gold Book, International Union of Pure and Applied Chemistry.
36. 36 Schiff, 1864, Eine Reihe
37. 37 Layer, 1963, The Chemistry of Imines [DOI]
38. 38 Posson, 2000, Imino Diels-Alder Reaction: Application to the Synthesis of Diverse Cyclopenta[c]Quinoline Derivatives [DOI]
39. 39 Kiselyov, 1998, Immobilized aldehydes and olefins in the solid support synthesis of tetrahydroquinolines via a three component condensation [DOI]
40. 40 Seeley, H.W., and Van Demark, P.J. (1962). Microbes in Action. A Laboratory Manual of Microbiology, W. H. Freeman & Co.
41. 41 Lemaur, 2013, Free radical scavenging by natural po-lyphenols: Atom versus electron transfer [DOI]
42. 42 Salah, 1995, Polyphenolic Flavanols as Scavengers of Aqueous Phase Radicals and as Chain-Breaking Antioxidants [DOI]
43. 43 Blois, 1958, Antioxidant Determinations by the Use of a Stable Free Radical [DOI]
44. 44 Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2010). Gaussian09, Gaussian Inc.
45. 45 Becke, 1988, Density-functional exchange-energy approximation with correct asymptotic behavior [DOI]
46. 46 Becke, 1988, A new mixing of Hartree-Fock and local density functional in atoms molecules and solids by the spin-density-functional formalism [DOI]
47. 47 Lee, 1988, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density [DOI]
48. 48 Reed, 1988, Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint [DOI]
49. 49 Parr, 1999, Electrophilicity Index [DOI]
50. 50 Parr, 1983, Absolute hardness: Companion parameter to absolute electronegativity [DOI]
51. 51 Domingo, 2008, Understanding the Reactivity of Captodative Ethylenes in Polar Cycloaddition Reactions. A Theoretical Study [DOI]
52. 52 Kohn, 1965, Self-Consistent Equations Including Exchange and Correlation Effects [DOI]
53. 53 Domingo, 2013, Understanding the local reactivity in polar organic reactions through electrophilic and nucleophilic Parr functions [DOI]
54. 54 Domingo, 2014, A new C–C bond formation model based on the quantum chemical topology of electron density [DOI]
55. 55 Chafaa, 2016, A DFT study of [3 + 2] cycloaddition reactions of an azomethine imine with N-vinyl pyrrole and N-vinyl tetrahydroindole [DOI]
56. 56 Nacereddine, 2012, A theoretical study of the mechanism and stereoselectivity of the Diels–Alder cycloaddition between difluoro-2-methylencyclopropane and furan [DOI]
57. 57 Hellel, 2017, 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 [DOI]
58. 58 Bayoud, 2021, Shedding light on the factors controlling the mechanism, selectivity and reactivity of the Diels-Alder reactions between substituted pyridinones and ethylenes: A MEDT study [DOI]
59. 59 Nacereddine, 2020, A MEDT computational study of the mechanism, reactivity and selectivity of non-polar [3+2] cycloaddition between quinazoline-3-oxide and methyl 3-methoxyacrylate [DOI]
60. 60 Chermette, 1999, Chemical reactivity indexes in density functional theory [DOI]
61. 61 Domingo, 2002, Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels-Alder reactions [DOI]
62. 62 Jaramillo, 2008, A further exploration of a nucleophilicity index based on the gas-phase ionization potentials [DOI]
63. 63 Domingo, 2012, Origin of the synchronicity in bond formation in polar Diels-Alder reactions: An ELF analysis of the reaction between cyclopentadiene and tetracyanoethylene [DOI]
64. 64 Domingo, 2014, A DFT analysis of the participation of zwitterionic TACs in polar [3+2] cycloaddition reactions [DOI]
65. 65 2016, First example of stepwise, zwitterionic mechanism for bicyclo [2.2. 1] hept-5-ene (norbornene) formation process catalyzed by the 1-butyl-3-methylimidazolium cations [DOI]
66. 66 Domingo, 2014, The mechanism of ionic Diels-Alder reactions. A DFT study of the oxa-Povarov reaction [DOI]

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