A Domino Heck Coupling–Cyclization–Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

Abstract

An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

Keywords

quinolines - palladium catalysis - Heck coupling - deuterated quinolines - iodoanilines

Publikationsverlauf

Eingereicht: 12. Juli 2021

Angenommen nach Revision: 17. August 2021

Accepted Manuscript online:
17. August 2021

Artikel online veröffentlicht:
13. Oktober 2021

• References

• 1 Michael JP. Nat. Prod. Rep. 2008; 25: 166
• 2 Musiol R, Magdziarz T, Kurczyk A. Quinoline Scaffold as a Privileged Substructure in Antimicrobial Drugs. In Science Against Microbial Pathogens: Communicating Current Research and Technological Advances, Vol. 1. Méndez-Vilas A. Formatex Research Center; Badajoz (Spain): 2011: 72
• 3 Jain S, Chandra V, Kumar Jain P, Pathak K, Pathak D, Vaidya A. Arabian J. Chem. 2019; 12: 4920
• 4 Weyesa A, Mulugeta E. RSC Adv. 2020; 10: 20784
• 5 Musiol R. Expert Opin. Drug Discovery 2017; 12: 583
• 6 Afzal O, Kumar S, Haider MR, Ali MR, Kumar R, Jaggi M, Bawa S. Eur. J. Med. Chem. 2015; 97: 871
• 7 Prajapati SM, Patel KD, Vekariya RH, Panchal SN, Patel HD. RSC Adv. 2014; 4: 24463
• 8 Stålhandske T, Kalland T. Immunopharmacology 1986; 11: 87
• 9 Thatcher TH, Luzina I, Fishelevich R, Tomai MA, Miller RL, Gaspari AA. J. Invest. Dermatol. 2006; 126: 821
• 10 Ridley RG. Nature 2002; 415: 686
• 11 Chen Y.-L, Zhao Y.-L, Lu C.-M, Tzeng C.-C, Wang J.-P. Bioorg. Med. Chem. 2006; 14: 4373
• 12 Benedetti P, Mannhold R, Cruciani G, Ottaviani G. Bioorg. Med. Chem. 2004; 12: 3607
• 13 Narender P, Srinivas U, Ravinder M, Ananda Rao B, Ramesh Ch, Harakishore K, Gangadasu B, Murthy US. N, Jayathirtha Rao V. Bioorg. Med. Chem. 2006; 14: 4600
• 14 Tong H, Wang L, Jing X, Wang F. Macromolecules 2003; 36: 2584
• 15 Foley M, Tilley L. Pharmacol. Ther. 1998; 79: 55
• 16 Bawa S, Kumar S, Drabu S, Kumar R. J. Pharm. Bioallied Sci. 2010; 2: 64
• 17 Deraeve C, Boldron C, Maraval A, Mazarguil H, Gornitzka H, Vendier L, Pitié M, Meunier B. Chem. Eur. J. 2008; 14: 682
• 18 Camps P, Formosa X, Galdeano C, Muñoz-Torrero D, Ramírez L, Gómez E, Isambert N, Lavilla R, Badia A, Clos MV, Bartolini M, Mancini F, Andrisano V, Arce MP, Rodríguez-Franco MI, Huertas Ó, Dafni T, Luque FJ. J. Med. Chem. 2009; 52: 5365
• 19 Abonia R, Insuasty D, Castillo J, Insuasty B, Quiroga J, Nogueras M, Cobo J. Eur. J. Med. Chem. 2012; 57: 29
• 20 Martirosyan AR, Rahim-Bata R, Freeman AB, Clarke CD, Howard RL, Strobl JS. Biochem. Pharmacol. 2004; 68: 1729
• 21 Tsotinis A, Vlachou M, Zouroudis S, Jeney A, Timar F, Thurston DE, Roussakis C. Lett. Drug Des. Discovery 2005; 2: 189
• 22 Vangapandu S, Jain M, Jain R, Kaur S, Pal Singh P. Bioorg. Med. Chem. 2004; 12: 2501
• 23 Keri RS, Patil SA. Biomed. Pharmacother. 2014; 68: 1161
• 24 Muruganantham N, Sivakumar R, Anbalagan N, Gunasekaran V, Leonard JT. Biol. Pharm. Bull. 2004; 27: 1683
• 25 Campbell SF, Hardstone JD, Palmer MJ. J. Med. Chem. 1988; 31: 1031
• 26 Ahmed N, Brahmbhatt KG, Sabde S, Mitra D, Singh IP, Bhutani KK. Bioorg. Med. Chem. 2010; 18: 2872
• 27 Chokkar N, Kalra S, Chauhan M, Kumar R. Mini-Rev. Med. Chem. 2019; 19: 510
• 28 Li J, Zhang J, Yang H, Jiang G. J. Org. Chem. 2017; 82: 3284
• 29 Das S, Maiti D, De Sarkar S. J. Org. Chem. 2018; 83: 2309
• 30 Lee SY, Jeon J, Cheon C.-H. J. Org. Chem. 2018; 83: 5177
• 31 Lee SY, Cheon C.-H. J. Org. Chem. 2018; 83: 13036
• 32 Nan J, Hu Y, Chen P, Ma Y. Org. Lett. 2019; 21: 1984
• 33 Zhao P, Wu X, Zhou Y, Geng X, Wang C, Wu Y, Wu A.-X. Org. Lett. 2019; 21: 2708
• 34 Gharpure SJ, Nanda SK, Adate PA, Shelke YG. J. Org. Chem. 2017; 82: 2067
• 35 Zou L.-H, Zhu H, Zhu S, Shi K, Yan C, Li P.-G. J. Org. Chem. 2019; 84: 12301
• 36 Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
• 37 Reetz MT, Westermann E. Angew. Chem. Int. Ed. 2000; 39: 165
• 38 Yin L, Liebscher J. Chem. Rev. 2007; 107: 133
• 39 Giri R, Thapa S, Kafle A. Adv. Synth. Catal. 2014; 356: 1395
• 40 Balanta A, Godard C, Claver C. Chem. Soc. Rev. 2011; 40: 4973
• 41 Kumar GS, Singh D, Kumar M, Kapur M. J. Org. Chem. 2018; 83: 3941
• 42 Saini G, Kumar P, Kumar GS, Mangadan AR. K, Kapur M. Org. Lett. 2018; 20: 441
• 43 Kumar GS, Kumar P, Kapur M. Org. Lett. 2017; 19: 2494
• 44 Yao Q, Kinney EP, Yang Z. J. Org. Chem. 2003; 68: 7528
• 45 McNulty J, Keskar K. Eur. J. Org. Chem. 2011; 6902
• 46 Tullberg E, Schacher F, Peters D, Frejd T. Synthesis 2006; 1183
• 47 Katayama S, Ae N, Nagata R. J. Org. Chem. 2001; 66: 3474
• 48 Tanaka D, Myers AG. Org. Lett. 2004; 6: 433
• 49 Reddy AG. K, Krishna J, Satyanarayana G. ChemistrySelect 2016; 1: 1151
• 50 Siva Sankara C, Namboothiri IN. N. Org. Lett. 2021; 23: 4618
• 51 Larock RC, Kuo M.-Y. Tetrahedron Lett. 1991; 32: 569
• 52 Stone MT. Org. Lett. 2011; 13: 2326
• 53 Selvakumar K, Lingam KA. P, Varma RV. L, Vijayabaskar V. Synlett 2015; 26: 646
• 54 Jeffery T. Tetrahedron Lett. 1994; 35: 3051
• 55 Jeffery T. Tetrahedron 1996; 52: 10113
• 56 Jose DE, Kanchana US, Mathew TV, Anilkumar G. J. Organomet. Chem. 2020; 927: 121538
• 57 Iosub AV, Stahl SS. ACS Catal. 2016; 6: 8201
• 58 Chen S, Lu G, Cai C. Synthesis 2015; 47: 976
• 59 Nallagangula M, Sujatha C, Bhat VT, Namitharan K. Chem. Commun. 2019; 55: 8490
• 60 Chakraborty G, Sikari R, Das S, Mondal R, Sinha S, Banerjee S, Paul ND. J. Org. Chem. 2019; 84: 2626