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

References

1. WoodsK. MastracchioA. LaiC. GandhiV.B. PenningT.U.S. Patent WO2013126656A12013
2. HelisseyP. Giorgi-RenaultS. RenaultJ. CrosS. Chem. Pharm. Bull.19893792413241610.1248/cpb.37.2413 2557983
   [Google Scholar]
3. SherlockM.H. KaminskiJ.J. TomW.C. LeeJ.F. WongS.C. KreutnerW. BryantR.W. McPhailA.T. J. Med. Chem.198831112108212110.1021/jm00119a010 2903244
   [Google Scholar]
4. ManeraC. MalfitanoA.M. ParkkariT. LucchesiV. CarpiS. FogliS. BertiniS. LaezzaC. LigrestiA. SaccomanniG. SavinainenJ.R. CiagliaE. PisantiS. GazzerroP. Di MarzoV. NieriP. MacchiaM. BifulcoM. Eur. J. Med. Chem.201597101810.1016/j.ejmech.2015.04.034 25935384
   [Google Scholar]
5. LucchesiV. HurstD.P. ShoreD.M. BertiniS. EhrmannB.M. AllaràM. LawrenceL. LigrestiA. MinutoloF. SaccomanniG. SharirH. MacchiaM. Di MarzoV. AboodM.E. ReggioP.H. ManeraC. J. Med. Chem.201457218777879110.1021/jm500807e 25272206
   [Google Scholar]
6. OhashiT. OguroY. TanakaT. ShiokawaZ. ShibataS. SatoY. YamakawaH. HattoriH. YamamotoY. KondoS. MiyamotoM. TojoH. BabaA. SasakiS. Bioorg. Med. Chem.201220185496550610.1016/j.bmc.2012.07.039 22910224
   [Google Scholar]
7. BrownT.H. IfeR.J. KeelingD.J. LaingS.M. LeachC.A. ParsonsM.E. PriceC.A. ReavillD.R. WiggallK.J. J. Med. Chem.199033252753310.1021/jm00164a010 2153816
   [Google Scholar]
8. SuzukiF. KurodaK. Patent 0459505A1,1991
9. CampianiG. MorelliE. GemmaS. NacciV. ButiniS. HamonM. NovellinoE. GrecoG. CagnottoA. GoeganM. CervoL. Dalla ValleF. FracassoC. CacciaS. MenniniT. J. Med. Chem.199942214362437910.1021/jm990151g 10543880
   [Google Scholar]
10. (a AkulaA. PadmaS.J. YogeeswariP. SriramD. BhattacharyaA. Monatsh. Chem.2014145881181910.1007/s00706‑013‑1141‑1
    [Google Scholar]
11. (b AkulaM. ThigullaY. DavisC. JhaM. BhattacharyaA. Org. Biomol. Chem.201513122600260510.1039/C4OB02224F
    [Google Scholar]
12. (c AkulaA. PadmaS.J. YogeeswariP. SriramD. JhaM. BhattacharyaA. RSC Adv.2016646460734608010.1039/C6RA03187K
    [Google Scholar]
13. DuelferT. BlythinD.J.U.S. U.S. patent 4996212,1991
14. ZhangZ. QianJ. ZhangG. MaN. LiuQ. LiuT. SunK. ShiL. Org. Chem. Front.20163334434810.1039/C5QO00417A
    [Google Scholar]
15. FrankowskiK.J. HedrickM.P. GosaliaP. LiK. ShiS. WhippleD. GhoshP. PrisinzanoT.E. ChoenenF.J. SuY. VasileS. SergienkoE. GrayW. HariharanS. MilanL. GenelS.H. NovoA.A. VicchiarelliM. SmithL.H. StreicherJ.M. CaronM.G. BarakL.S. BohnL.M.J. ACS Chem. Neurosci.2012322123610.1021/cn200128x 22737280
    [Google Scholar]
16. AbbiatiG. BeccalliE.M. BrogginiG. PaladinoG. RossiE. Synthesis2005172881288610.1055/s‑2005‑916033
    [Google Scholar]
17. TanimoriS. NishimuraT. KirihataM. Bioorg. Med. Chem. Lett.200919154119412110.1016/j.bmcl.2009.06.007 19539470
    [Google Scholar]
18. TanimoriS. KashiwagiH. NishimuraT. KirihataM. Adv. Synth. Catal.201035214-152531253710.1002/adsc.201000323
    [Google Scholar]
19. (a TruongV.L. MorrowM. Tetrahedron Lett.201051475876010.1016/j.tetlet.2009.11.133
    [Google Scholar]
20. (b PodrezovaE.V. OkhinaA.A. RogachevA.D. BaykovS.V. KirschningA. YusubovM.S. SoldatovaN.S. PostnikovP.S. Org. Biomol. Chem.20232191952195710.1039/D2OB02122F 36757159
    [Google Scholar]
21. (cTeo, Yong-Chua; Tan, Yun-Ru; M., Kyra Saanvi; Loh, Chu-Ken; Tan, Swee-Ngin.Synth. Commun.2023531143115210.1080/00397911.2023.2212093
    [Google Scholar]
22. Van LeusenA.M. Org. React.200357419
    [Google Scholar]
23. RathkeM.W. NowakM. J. Org. Chem.198550152624262610.1021/jo00215a004
    [Google Scholar]
24. (a van LeusenA.M. SideriusH. HoogenboomB.E. van LeusenD. Tetrahedron Lett.197213525337534010.1016/S0040‑4039(01)85244‑8
    [Google Scholar]
25. (b Di SantoR. CostiR. ForteM. GaleffiC. ARKIVOC2004518119510.3998/ark.5550190.0005.517
    [Google Scholar]
26. (c HuZ. LiY. PanL. XuX. Adv. Synth. Catal.201435614-152974297810.1002/adsc.201400468
    [Google Scholar]
27. (d LuX.M. LiJ. CaiZ.J. WangR. WangS.Y. JiS.J. Org. Biomol. Chem.201412469471947710.1039/C4OB01580K 25329918
    [Google Scholar]
28. (e KumarK. ChemistrySelect2020533102981032810.1002/slct.202001344
    [Google Scholar]
29. (a SurryD.S. BuchwaldS.L. Chem. Sci.201011133110.1039/c0sc00107d 22384310
    [Google Scholar]
30. (b Ruiz-CastilloP. BuchwaldS.L. Chem. Rev.201611619125641264910.1021/acs.chemrev.6b00512 27689804
    [Google Scholar]
31. (c HeraviM.M. KheilkordiZ. ZadsirjanV. HeydariM. MalmirM. J. Organomet. Chem.20188611710410.1016/j.jorganchem.2018.02.023
    [Google Scholar]
32. (a YangQ. ZhaoY. MaD. Org. Process Res. Dev.2022261690175010.1021/acs.oprd.2c00050
    [Google Scholar]
33. (b ÁrvaiC. MikaL.T. J. Organomet. Chem.2024100512297610.1016/j.jorganchem.2023.122976
    [Google Scholar]