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Synthesis 2025; 57(23): 3611-3616
DOI: 10.1055/a-2705-5409
DOI: 10.1055/a-2705-5409
Paper
Aerobic Oxidation of Imidazolines to 2-Arylimidazoles Using CuSO4∙H2O as a Catalyst
Autoren
Funding Information This work was financially supported by the Russian Science Foundation (project No 21-73-20031-P).
Abstract
Imidazoles are considered the merit heterocyclic moiety in medicinal chemistry and drug design. Here, we report on a convenient method for the aerobic oxidation of imidazolines under mild conditions using the cheap and available CuSO4∙5H2O as the catalyst. The proposed method allows one to prepare 2-arylimidazoles bearing electron-donating and -withdrawing groups in good and quantitative yields. The developed procedure is applicable for the preparation of labile and oxidation-intolerant heterocyclic moieties.
Publikationsverlauf
Eingereicht: 17. Juni 2025
Angenommen nach Revision: 02. September 2025
Accepted Manuscript online:
22. September 2025
Artikel online veröffentlicht:
21. Oktober 2025
© 2025. Thieme. All rights reserved.
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References
- 1 Hahn FE, Jahnke MC. Angew Chem Int Ed 2008; 47: 3122
- 2 Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
- 3 Makhova NN, Belen’kii LI, Gazieva GA. et al. Russ Chem Rev 2020; 89: 55
- 4 Charushin VN, Verbitskiy EV, Chupakhin ON. et al. Russ Chem Rev 2024; 93: RCR5125
- 5 Sharma S, Kumar D, Singh G, Monga V, Kumar B. Eur J Med Chem 2020; 200: 112438
- 6 Sachdeva H, Khaturia S, Saquib M. et al. Appl Biochem Biotechnol 2022; 194: 6438
- 7 Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. Molecules 1909; 2020: 25
- 8 Mermer A, Keles T, Sirin Y. Bioorg Chem 2021; 114: 105076
- 9 Marcantoni E, Petrini M. Adv Synth Catal 2016; 358: 3657
- 10 Goel KK, Thapliyal S, Kharb R, Joshi G, Negi A, Kumar B. Pharmaceutics 2023; 15
- 11 Sharma D, Narasimhan B, Kumar P. et al. Eur J Med Chem 2009; 44: 2347
- 12 Puratchikody A, Doble M. Bioorg Med Chem 2007; 15: 1083
- 13 Ali I, Lone MN, Aboul-Enein HY. MedChemComm 2017; 8: 1742
- 14 Basanova EI, Kulikova EA, Bormotov NI. et al. RSC Med Chem 2024; 15: 3196
- 15 Bellina F, Calandri C, Cauteruccio S, Rossi R. Tetrahedron 1970; 2007: 63
- 16 Lee DH, Choi M, Yu BW. et al. Adv Synth Catal 2009; 351: 2912
- 17 Kapale SS, Chaudhari HK, Mali SN, Takale BS, Pawar H. J Asian Nat Prod Res 2021; 23: 712
- 18 Fujioka H, Murai K, Ohba Y, Hiramatsu A, Kita Y. Tetrahedron Lett 2005; 46: 2197
- 19 Moghadam M, Mohammadpoor-Baltork I, Mirkhani V. et al. Monatsh Chem 2007; 138: 579
- 20 Nasr-Esfahani M, Montazerozohori M, Mehrizi S. J Heterocycl Chem 2011; 48: 249
- 21 Mohammadpoor-Baltork I, Abdollahi-Alibeik M. Bull Korean Chem Soc 2003; 24: 1354
- 22 Aleksandrov AA, El’Chaninov MM. Russ J Appl Chem 2009; 82: 2161
- 23 Sultanova RM, Khusnutdinova NS, Borisova YG. et al. Russ Chem Bull 2023; 72: 1711
- 24 Martin PK, Matthews HR, Rapoport H, Thyagarajan G. J Org Chem 1968; 33: 3758
- 25 Mohammadpoor-Baltork I, Zolfigol MA, Abdollahi-Alibeik M. Tetrahedron Lett 2004; 45: 8687
- 26 Nicolaou KC, Mathison CJN, Montagnon T. Angew Chem Int Ed 2003; 42: 4077
- 27 Ishihara M, Togo H. Synlett 2006; 227
- 28 Mohammadpoor-Baltork I, Zolfigol M, Abdollahi-Alibeik M. Synlett 2004; 2004: 2803
- 29 Huh DH, Ryu H, Kim YG. Tetrahedron 2004; 60: 9857
- 30 Blum C, Bunke D, Hungsberg M. et al. Sustainable Chem Pharm 2017; 5: 94
- 31 Holme T. Sustainable Chem Pharm 2020; 16: 100234
- 32 Kargar H, Afkhami S, Alikhani F. J Coord Chem 2012; 65: 3502
- 33 Sterckx H, Morel B, Maes BUW. Angew Chem Int Ed 2019; 58: 7946
- 34 Taketoshi A, Tsujimoto A, Maeda S, Koizumi T, Kanbara T. ChemCatChem 2010; 2: 58
- 35 Amemiya Y, Miller DD, Hsu F-L. Synth Commun 1990; 20: 2483
- 36 Aleksandrov AA, El’chaninov MM. Russ J Appl Chem 2010; 83: 1024
- 37 Yusubov MS, Soldatova NS, Postnikov PS. et al. Chem Commun 2019; 55: 7760
- 38 Radulov PS, Mikhaylov AA, Medvedev AG. et al. New J Chem 2024; 48: 4281
- 39 Punniyamurthy T, Rout L. Coord Chem Rev 2008; 252: 134
- 40 Hansch C, Leo A, Taft RW. Chem Rev 1991; 91: 165
- 41 Balboa S, Carballo R, Castiñeiras A, González-Pérez JM, Niclós-Gutiérrez J. Polyhedron 2008; 27: 2921
- 42 Xu L, Wang E, Peng J, Huang R. Inorg Chem Commun 2003; 6: 740
- 43 Zhao K, Jiang Y, Qiu X, Tian J, Li X. J Coord Chem 2011; 64: 1375
- 44 Li S, An Y, Wang L. et al. ACS Omega 2025; 10: 11454
- 45 De Tovar J, Leblay R, Wang Y. et al. Chem Sci 2024; 15: 10308