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Synthesis 2023; 55(03): 451-456
DOI: 10.1055/a-1942-7110
DOI: 10.1055/a-1942-7110
paper
Electrochemical Intramolecular Oxidative C(sp3)–H/C(sp3)–H Coupling for the Synthesis of 4-Quinolones
We gratefully acknowledge the financial support from the Natural Science Foundation of Anhui Province (2008085QB66), the Talent Foundation of Anhui Science and Technology University (HCYJ201903), College Students’ Innovation and Entrepreneurship Training Program (S202110879088, S202210879086).
Abstract
An efficient electrochemical approach for the synthesis of 4-quinolones via intramolecular C(sp3)–H/C(sp3)–H cross-coupling has been developed under metal- and external oxidant-free conditions. This electrochemical approach provides a simple and efficient route to construct useful 4-quinolone derivatives in moderate to good yields.
Key words
electrochemical - C(sp3)–H/C(sp3)–H cross-coupling - 2-aryl-4-quinolones - chemical oxidant-free - undivided cellSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1942-7110.
- Supporting Information
Publication History
Received: 26 July 2022
Accepted after revision: 14 September 2022
Accepted Manuscript online:
14 September 2022
Article published online:
13 October 2022
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References
- 1a Pozharskii AF, Soldatenkov AT, Katritzky AR. Heterocycles and Health . In Heterocycles in Life and Society . Wiley; Chichester: 1997: 135-164
- 1b Sabbasani VR. K, Wang P, Streeter MD, Spiegel DA. Angew. Chem. Int. Ed. 2019; 58: 18913
- 2a Pham TD. M, Ziora ZM. Z, Blaskovich MA. T. MedChemComm 2019; 10: 1719
- 2b Oliphant CM, Green GM. Am. Fam. Physician 2002; 65: 455
- 2c Huse H, Whiteley M. Chem. Rev. 2011; 111: 152
- 2d Mugnaini C, Pasquini S, Corelli F. Curr. Med. Chem. 2009; 16: 1746
- 2e Zhi Y, Gao LX, Jin Y, Tang CL, Li JY, Li J, Long YQ. Bioorg. Med. Chem. 2014; 22: 3670
- 2f Aldred KJ, Kerns RJ, Osheroff N. Biochemistry 2014; 53: 1565
- 2g Ghosh S, Bishayee K, Khuda-Bukhsh AR. Phytother. Res. 2014; 28: 1153
- 2h Zhanel GG, Ennis K, Vercaigne L, Walkty A, Gin AS, Embil J, Smith H, Hoban D. Drugs 2002; 62: 13
- 3a Llinas-Brunet M, Bailey MD, Ghiro E, Gorys V, Halmos T, Poirier M, Rancourt J, Goudreau N. J. Med. Chem. 2004; 47: 6584
- 3b Xia Y, Yang Z.-Y, Xia P, Hackl T, Hamel E, Mauger A, Wu J.-H, Lee K.-H. J. Med. Chem. 2001; 44: 3932
- 3c Nilsen A, Miley GP, Forquer IP, Mather MW, Katneni K, Li YX, Pou S, Pershing AM, Stickles AM, Ryan E, Kelly JX, Doggett JS, White KL, Hinrichs DJ, Winter RW, Charman SA, Zakharov LN, Bathurst I, Burrows JN, Vaidya AB, Riscoe MK. J. Med. Chem. 2014; 57: 3818
- 4a Niementowski S. Ber. Dtsch. Chem. Ges. 1894; 27: 1394
- 4b Fuson RC, Burness DM. J. Am. Chem. Soc. 1946; 68: 1270
- 4c Ogata Y, Kawasaki A, Tsujimura K. Tetrahedron 1971; 27: 2765
- 4d Son JK, Kim SI, Jahng Y. Heterocycles 2001; 55: 1981
- 5a Brouet JC, Gu S, Peet NP, Williams JD. Synth. Commun. 2009; 39: 1563
- 5b Romek A, Opatz T. Eur. J. Org. Chem. 2010; 5841
- 5c Zewge D, Chen C.-Y, Deer C, Dormer PG, Hughes DL. J. Org. Chem. 2007; 72: 4276
- 7a Torii S, Okumoto H, Xu LH. Tetrahedron Lett. 1991; 32: 237
- 7b Haddad N, Tan J, Farina V. J. Org. Chem. 2006; 71: 5031
- 7c Wu J, Zhou Y, Wu T, Zhou Y, Chiang C.-W, Lei A. Org. Lett. 2017; 19: 6432
- 7d Ghosh P, Nandi AK, Das S. Tetrahedron Lett. 2018; 59: 2025
- 7e Genelot M, Dufaud V, Djakovitch L. Tetrahedron 2011; 67: 976
- 7f Åkerbladh L, Nordeman P, Wejdemar M, Odell LR, Larhed M. J. Org. Chem. 2015; 80: 1464
- 8 Wang F, Jin L, Kong L, Li X. Org. Lett. 2017; 19: 1812
- 9 Fürstner A, Hupperts A, Ptock A, Janssen E. J. Org. Chem. 1994; 59: 5215
- 10a Singh S, Nerella S, Pabbaraja S, Mehta G. Org. Lett. 2020; 22: 1575
- 10b Jones CP, Anderson KW, Buchwald SL. J. Org. Chem. 2007; 72: 7968
- 11a Tang E, Chen B, Zhang L, Li W, Lin J. Synlett 2011; 5: 707
- 11b Seppänen O, Muuronen M, Helaja J. Eur. J. Org. Chem. 2014; 4044
- 11c Romek A, Opatz T. Eur. J. Org. Chem. 2010; 5841
- 11d Huang J, Chen Y, King AO, Dilmeghani M, Larsen RD, Faul MM. Org. Lett. 2008; 10: 2609
- 11e Liu R, Zhang Y, Xu K, Tan G. Synth. Commun. 2017; 47: 1
- 11f Seppänen O, Muuronen M, Helaja J. Eur. J. Org. Chem. 2014; 4044
- 11g Marques EF, Bueno MA, Duarte PD, Silva RS. P, Martinelli AM, Santos CY, Severino RP, Brömme DP, Vieira C, Corrêa AG. Eur. J. Med. Chem. 2012; 54: 10
- 12 Hu W, Lin J.-P, Song L.-R, Long Y.-Q. Org. Lett. 2015; 17: 1268
- 13 Ma H, Guo C, Zhan Z, Lu G, Zhang Y, Luo X, Cui X, Huang G. New J. Chem. 2017; 41: 5280
- 14a Yuan Y, Yang J, Lei A. Chem. Soc. Rev. 2021; 50: 10058
- 14b Xiong P, Xu H.-C. Acc. Chem. Res. 2019; 52: 3339
- 14c Jiao K.-J, Xing Y.-K, Yang QL, Qiu H, Mei T.-S. Acc. Chem. Res. 2020; 53: 300
- 14d Shi S.-H, Liang Y, Jiao N. Chem. Rev. 2021; 121: 485
- 14e Yan M, Kawamata Y, Baran PS. Chem. Rev. 2017; 117: 13230
- 14f Moeller KD. Chem. Rev. 2018; 118: 4817
- 14g Minteer SD, Baran PS. Acc. Chem. Res. 2020; 53: 545
- 14h Qian P, Zha Z, Wang Z. ChemElectroChem 2020; 7: 2527
- 15a Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
- 15b Yuan Y, Lei A. Nat. Commun. 2020; 11: 802
- 15c Frontana-Uribe BA, Little RD, Ibanez JG, Palma A, Vasquez-Medrano R. Green Chem. 2010; 12: 2099
- 16a Wu Z.-J, Xu H.-C. Angew. Chem. Int. Ed. 2017; 56: 4734
- 16b Yang Y.-Z, Wu Y.-C, Song R.-J, Li J.-H. Chem. Commun. 2020; 56: 7585
- 16c Liu Y, Shi B, Liu Z, Gao R, Huang C, Alhumade H, Wang S, Qi X, Lei A. J. Am. Chem. Soc. 2021; 143: 20863
- 17a Herold S, Bafaluy D, Muniz K. Green Chem. 2018; 20: 3191
- 17b Hou Z.-W, Liu D.-J, Xiong P, Lai X.-L, Song J, Xu H.-C. Angew. Chem. Int. Ed. 2021; 60: 2943
- 17c Wu J, Zhou Y, Zhou Y, Chiang C.-W, Lei A. ACS Catal. 2017; 7: 8320
- 18a Zhang S, Li L, Wang H, Li Q, Liu W, Xu K, Zeng C. Org. Lett. 2018; 20: 252
- 18b Bu F, Lu L, Hu X, Wang S, Zhang H, Lei A. Chem. Sci. 2020; 11: 10000
- 19 Li K.-J, Jiang Y.-Y, Xu K, Zeng C.-C, Sun B.-G. Green Chem. 2019; 21: 4412
- 20 Wu J, Liao Z, Liu D, Chiang C.-W, Li Z, Zhou Z, Yi H, Zhang X, Deng Z, Lei A. Chem. Eur. J. 2017; 23: 15874