Synthesis of Fused Pyrrolo-napthridinone via Ligand-free Copper Catalysed Ullmann (C-N coupling) Type Reaction

References

1. Woods K. Mastracchio A. Lai C. Gandhi V.B. Penning T.U.S. Patent WO2013126656A1, 2013
2. Helissey P. Giorgi-Renault S. Renault J. Cros S. Chem. Pharm. Bull. 1989 37 9 2413 2416 10.1248/cpb.37.2413 2557983
   [Google Scholar]
3. Sherlock M.H. Kaminski J.J. Tom W.C. Lee J.F. Wong S.C. Kreutner W. Bryant R.W. McPhail A.T. J. Med. Chem. 1988 31 11 2108 2121 10.1021/jm00119a010 2903244
   [Google Scholar]
4. Manera C. Malfitano A.M. Parkkari T. Lucchesi V. Carpi S. Fogli S. Bertini S. Laezza C. Ligresti A. Saccomanni G. Savinainen J.R. Ciaglia E. Pisanti S. Gazzerro P. Di Marzo V. Nieri P. Macchia M. Bifulco M. Eur. J. Med. Chem. 2015 97 10 18 10.1016/j.ejmech.2015.04.034 25935384
   [Google Scholar]
5. Lucchesi V. Hurst D.P. Shore D.M. Bertini S. Ehrmann B.M. Allarà M. Lawrence L. Ligresti A. Minutolo F. Saccomanni G. Sharir H. Macchia M. Di Marzo V. Abood M.E. Reggio P.H. Manera C. J. Med. Chem. 2014 57 21 8777 8791 10.1021/jm500807e 25272206
   [Google Scholar]
6. Ohashi T. Oguro Y. Tanaka T. Shiokawa Z. Shibata S. Sato Y. Yamakawa H. Hattori H. Yamamoto Y. Kondo S. Miyamoto M. Tojo H. Baba A. Sasaki S. Bioorg. Med. Chem. 2012 20 18 5496 5506 10.1016/j.bmc.2012.07.039 22910224
   [Google Scholar]
7. Brown T.H. Ife R.J. Keeling D.J. Laing S.M. Leach C.A. Parsons M.E. Price C.A. Reavill D.R. Wiggall K.J. J. Med. Chem. 1990 33 2 527 533 10.1021/jm00164a010 2153816
   [Google Scholar]
8. Suzuki F. Kuroda K. Patent 0459505A1, 1991
9. Campiani G. Morelli E. Gemma S. Nacci V. Butini S. Hamon M. Novellino E. Greco G. Cagnotto A. Goegan M. Cervo L. Dalla Valle F. Fracasso C. Caccia S. Mennini T. J. Med. Chem. 1999 42 21 4362 4379 10.1021/jm990151g 10543880
   [Google Scholar]
10. a Akula A. Padma S. J. Yogeeswari P. Sriram D. Bhattacharya A Monatsh. Chem. 2014 145 8 811 819 10.1007/s00706‑013‑1141‑1
    [Google Scholar]
11. b Akula M. Thigulla Y. Davis C. Jha M. Bhattacharya A. Org. Biomol. Chem. 2015 13 12 2600 2605 10.1039/C4OB02224F
    [Google Scholar]
12. c Akula A. Padma S. J. Yogeeswari P. Sriram D. Jha M. Bhattacharya A. RSC Adv. 2016 6 46 46073 46080 10.1039/C6RA03187K
    [Google Scholar]
13. Duelfer T. Blythin D.J.U.S. U.S. patent 4996212, 1991
14. Zhang Z. Qian J. Zhang G. Ma N. Liu Q. Liu T. Sun K. Shi L. Org. Chem. Front. 2016 3 3 344 348 10.1039/C5QO00417A
    [Google Scholar]
15. Frankowski K.J. Hedrick M.P. Gosalia P. Li K. Shi S. Whipple D. Ghosh P. Prisinzano T.E. Choenen F.J. Su Y. Vasile S. Sergienko E. Gray W. Hariharan S. Milan L. Genel S.H. Novo A.A. Vicchiarelli M. Smith L.H. Streicher J.M. Caron M.G. Barak L.S. Bohn L.M. J. ACS Chem. Neurosci. 2012 3 221 236 10.1021/cn200128x 22737280
    [Google Scholar]
16. Abbiati G. Beccalli E.M. Broggini G. Paladino G. Rossi E. Synthesis 2005 17 2881 2886 10.1055/s‑2005‑916033
    [Google Scholar]
17. Tanimori S. Nishimura T. Kirihata M. Bioorg. Med. Chem. Lett. 2009 19 15 4119 4121 10.1016/j.bmcl.2009.06.007 19539470
    [Google Scholar]
18. Tanimori S. Kashiwagi H. Nishimura T. Kirihata M. Adv. Synth. Catal. 2010 352 14-15 2531 2537 10.1002/adsc.201000323
    [Google Scholar]
19. a Truong V.L. Morrow M. Tetrahedron Lett. 2010 51 4 758 760 10.1016/j.tetlet.2009.11.133
    [Google Scholar]
20. b Podrezova E.V. Okhina A.A. Rogachev A.D. Baykov S.V. Kirschning A. Yusubov M.S. Soldatova N.S. Postnikov P.S. Org. Biomol. Chem. 2023 21 9 1952 1957 10.1039/D2OB02122F 36757159
    [Google Scholar]
21. c Teo Yong-Chua Tan Yun-Ru M. Kyra Saanvi Loh Chu-Ken Tan Swee-Ngin Synth. Commun. 2023 53 1143 1152 10.1080/00397911.2023.2212093
    [Google Scholar]
22. Van Leusen A.M. Org. React. 2003 57 419
    [Google Scholar]
23. Rathke M.W. Nowak M. J. Org. Chem. 1985 50 15 2624 2626 10.1021/jo00215a004
    [Google Scholar]
24. a van Leusen A.M. Siderius H. Hoogenboom B.E. van Leusen D. Tetrahedron Lett. 1972 13 52 5337 5340 10.1016/S0040‑4039(01)85244‑8
    [Google Scholar]
25. b Di Santo R. Costi R. Forte M. Galeffi C. ARKIVOC 2004 5 181 195 10.3998/ark.5550190.0005.517
    [Google Scholar]
26. c Hu Z. Li Y. Pan L. Xu X. Adv. Synth. Catal. 2014 356 14-15 2974 2978 10.1002/adsc.201400468
    [Google Scholar]
27. d Lu X.M. Li J. Cai Z.J. Wang R. Wang S.Y. Ji S.J. Org. Biomol. Chem. 2014 12 46 9471 9477 10.1039/C4OB01580K 25329918
    [Google Scholar]
28. e Kumar K. ChemistrySelect 2020 5 33 10298 10328 10.1002/slct.202001344
    [Google Scholar]
29. a Surry D.S. Buchwald S.L. Chem. Sci. 2010 1 1 13 31 10.1039/c0sc00107d 22384310
    [Google Scholar]
30. b Ruiz-Castillo P. Buchwald S.L. Chem. Rev. 2016 116 19 12564 12649 10.1021/acs.chemrev.6b00512 27689804
    [Google Scholar]
31. c Heravi M.M. Kheilkordi Z. Zadsirjan V. Heydari M. Malmir M. J. Organomet. Chem. 2018 861 17 104 10.1016/j.jorganchem.2018.02.023
    [Google Scholar]
32. a Yang Q. Zhao Y. Ma D. Org. Process Res. Dev. 2022 26 1690 1750 10.1021/acs.oprd.2c00050
    [Google Scholar]
33. b Árvai C. Mika L.T. J. Organomet. Chem. 2024 1005 122976 10.1016/j.jorganchem.2023.122976
    [Google Scholar]