Synthesis, Table of Contents Synthesis 2025; 57(01): 147-153DOI: 10.1055/a-2349-6836 paper Special Topic Dedicated to Prof. H. Ila Iron(III)-Catalysed Povarov Cyclisation for the Synthesis of Fused Dibenzo[b,f][1,7]naphthyridine Embedded Arylpyrrolo Scaffolds Raj Kamal Sahoo , Gopal Rana , Abhishek Kar , Sourav Ghosh , Umasish Jana ∗ Recommend Article Abstract Buy Article All articles of this category Abstract An FeCl3-catalyzed Povarov reaction for the efficient synthesis of dibenzo[b,f][1,7]naphthyridines utilizing 1-(2-alkynylaryl)-2-pyrrolecarbaldehydes and arylamines in excellent yields is demonstrated. The essential features of the present strategy are easy preparation of substrates, broad substrate scope, mild reaction conditions, and high atom economy and yields, in the presence of environmentally friendly iron catalysis. Key words Key wordsarylpyrrolecarbaldehydes - phosphorus oxychloride - arylamines - 1,7-naphthyridines - ferric chloride Full Text References References 1 Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 2020; 25: 1909 2a Wang X, Sun G, Routh P, Kim DH, Huang W, Chen P. Chem. Soc. Rev. 2014; 43: 7067 2b Stepien M, Gonka E, Zyla M, Sprutta N. Chem. Rev. 2017; 117: 3479 3a Alonso C, Fuertes M, González M, Rubiales G, Tesauro C, Knudsen BR, Palacios F. Eur. J. Med. Chem. 2016; 115: 179 3b Madaan A, Verma R, Kumar V, Singh AT, Jain SK, Jaggi M. Arch. Pharm. 2015; 348: 837 3c Johns BA, Weatherhead JG, Allen SH, Thompson JB, Garvey EP, Foster SA, Jeffrey JL, Miller WH. Bioorg. Med. Chem. Lett. 2009; 19: 1802 4a Wang KY, Chen C, Liu FJ, Wang Q, Chang J, Zhu HJ, Li C. Org. Biomol. Chem. 2012; 10: 6693 4b Sutradhar T, Misra A. J. Phys. Chem. A 2018; 122: 4111 4c Stuck F, Dietl MC, Meibner M, Sebastian F, Rudolph M, Rominger F, Kramer P, Hashmi AS. K. Angew. Chem. Int. Ed. 2022; 61: e202114277 4d Mato AF, Quintela JM, Peinador C. New J. Chem. 2012; 36: 1634 5a Ho TL, Lin Q. Tetrahedron 2008; 64: 10401 5b England DB, Padwa A. J. Org. Chem. 2008; 73: 2792 5c Deiters A, Pettersson M, Martin SF. J. Org. Chem. 2006; 71: 6547 5d Takasu K, Nishida N, Tomimura A, Ihara M. J. Org. Chem. 2005; 70: 3957 6 Tsopmo A, Kamnaing P, Watchueng J, Gao JM, Konishi Y, Sterner O. Can. J. Chem. 2009; 87: 397 7a Woods JR, Riofski MV, Zheng MM, O’Banion MA, Mo H, Kirshner J, Colby DA. Bioorg. Med. Chem. Lett. 2013; 23: 5865 7b Nidhiry JE, Prasad KR. Tetrahedron 2013; 69: 5525 7c Prasad KR, Nidhiry JE. Synlett 2012; 23: 1477 7d Lancefield CS, Zhou L, Lebl T, Slawin AM. Z, Westwood NJ. Org. Lett. 2012; 14: 6166 8a Natsugari H, Ikeura Y, Kiyota Y, Ishichi Y, Ishimaru T, Saga O, Shirafuji H, Tanaka T, Kamo I, Doi T, Otsuka M. J. Med. Chem. 1995; 38: 3106 8b Ikeura Y, Doi T, Fujishima A, Natsugari H. Chem. Commun. 1998; 2141 9a Yapi AD, Mustofa M, Valentin A, Chavignon O, Teulade JC, Mallie M, Chapat JP, Blache Y. Chem. Pharm. Bull. 2000; 48: 1886 9b Natsugari H, Ikeura Y, Kamo I, Ishimaru T, Ishichi Y, Fujishima A, Tanaka T, Kasahara F, Kawada M, Doi T. J. Med. Chem. 1999; 42: 3982 10 Kaila N, Green N, Li H.-Q, Hu Y, Janz K, Gavrin LK, Thomason J, Tam S, Powell D, Cuozzo J, Hall JP, Telliez J.-B, Hsu S, Nickerson-Nutter C, Wang Q, Lin L.-L. Bioorg. Med. Chem. 2007; 15: 6425 11a Trifilieff A, Wyss D, Walker C, Mazzoni L, Hersperger R. J. Pharmacol. Exp. Ther. 2002; 301: 241 11b Dress K, Johnson T, Plewe M, Tanis S, Zhu H. U.S. Patent 2007099915A1, 2007 12 Arepalli SK, Park B, Lee K, Jo H, Jun K.-Y, Kwon Y, Kang J.-S, Jung J.-K, Lee H. Bioorg. Med. Chem. 2017; 25: 5586 13 Vázquez-Vera Ó, Segura-Olvera D, Rincón-Guevara MA, Gutiérrez-Carrillo A, García-Sánchez MA, Ibarra IA, Lomas-Romero L, Islas-Jácome A, González-Zamora E. Molecules 2018; 23: 2029 14 Jiang B, Fan W, Sun M.-Y, Ye Q, Wang S.-L, Tu S.-J, Li G. J. Org. Chem. 2014; 79: 5258 15 Arepalli SK, Choi Y, Lee K, Kang J.-S, Jung J.-K, Lee H. Tetrahedron 2018; 74: 1646 16 Sultan S, Gupta V, Shah BA. ChemPhotoChem 2017; 1: 120 17 Chahal K, Vani D, Pranay K, Madhu I, Sridhar B, Reddy KR. ChemistrySelect 2023; 8: e202304260 18 Arepalli SK, Lee C, Sim S, Lee K, Jo H, Jun K.-Y, Kwon Y, Kang J.-S, Jung J.-K, Lee H. Bioorg. Med. Chem. 2018; 26: 5181 For recent review articles on iron catalysis, see: 19a Bauer I, Knolker H.-J. Chem. Rev. 2015; 115: 3170 19b Rana S, Biswas JP, Paul S, Paik A, Maiti D. Chem. Soc. Rev. 2021; 50: 243 19c Guðmundsson A, Bäckvall J.-E. Molecules 2020; 25: 1349 19d Fürstner A. ACS Cent. Sci. 2016; 2: 778 20a Paul K, Bera K, Jalal S, Sarkar S, Jana U. Org. Lett. 2014; 16: 2166 20b Jalal S, Paul K, Jana U. Org. Lett. 2016; 18: 6512 20c Paul K, Jalal S, Kundal S, Jana U. J. Org. Chem. 2016; 81: 1164 20d Chakraborty B, Jalal S, Paul K, Kundal S, Jana U. J. Org. Chem. 2018; 83: 8139 20e Chanda R, Ghosh T, Jana U. J. Org. Chem. 2023; 88: 658 20f Chakraborty B, Kar A, Chanda R, Jana U. J. Org. Chem. 2020; 85: 9281 20g Kar A, Rana G, Sahoo R, Ghosh S, Jana U. J. Org. Chem. 2024; 89: 7295 20h Hou J, Yin J, Han H, Yang Q, Li Y, Lou Y, Wu X, You Y. Org. Lett. 2023; 25: 4359 21 Nayak M, Kim I. Org. Biomol. Chem. 2015; 13: 9697 22 CCDC 2334809 (3eb) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures Supplementary Material Supplementary Material Supporting Information
