Copper catalyzed C-N-bond formation and synthesis of Imidazopyridinone derivatives

Year 2022, Volume: 6 Issue: 1, 61 - 65, 06.07.2022

Şengül Dilem Doğan Melike Ongun

https://doi.org/10.32571/ijct.1130734

Abstract

The formation of the C–N bond is critical because it allows for the incorporation of nitrogen into organic molecules. Despite significant advances in this area, the formation of the C–N bond continues to be a challenge for organic chemists owing to the need of severe reaction conditions or costly catalysts in many cases. As a result, developing alternate, milder, and less expensive C–N bonding techniques is a challenge. Herein, a series of novel imidazopyridinone derivatives (8a-8e) were synthesized via copper-mediated C–¬N bond-forming reaction. This reaction takes place under mild conditions with high efficiency, step economy, and tolerance for a wide range of functional groups. All synthesized new compounds were analyzed by 1H NMR, 13C NMR and mass spectrometry.

Keywords

synthesis, imidazopyridinones, Copper-catalyzed, C-N bond formation, urea

References

• Wu, D.; Liu, M.; Li, Z.; Dang, M.; Liu, X.; Li, J.; Huang, L.; Ren, Y.; Zhang, Z.;Liu, W. Heterocycl Commun 2019, 25, 8-14.
• Kuethe, J. T.; Wong, A.;Davies, I. W. J. Org. Chem. 2004, 69, 7752-7754.
• Yutilov, Y. M.; Smolyar, N.;Lomov, D. Russ. J. Org. Chem. 2006, 42, 897-900.
• Wu, D.; Liu, M.; Li, Z.; Dang, M.; Liu, X.; Li, J.; Huang, L.; Ren, Y.; Zhang, Z.;Liu, W. Heterocyclic Communications 2019, 25, 8-14.
• Mamedov, V. A.; Zhukova, N. A.; Zamaletdinova, A. I.; Beschastnova, T. y. N.; Kadyrova, M. S.; Rizvanov, I. d. K.; Syakaev, V. V.;Latypov, S. K. J. Org. Chem. 2014, 79, 9161-9169.
• Yoshida, T.; Kambe, N.; Murai, S.;Sonoda, N. Bull. Chem. Soc. Jpn 1987, 60, 1793-1799.
• Meanwell, N. A.; Sit, S. Y.; Gao, J.; Wong, H. S.; Gao, Q.; Laurent, D. R. S.;Balasubramanian, N. J. Org. Chem. 1995, 60, 1565-1582.
• Beletskaya, I. P.;Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
• Liu, J.; Wei, W.; Zhao, T.; Liu, X.; Wu, J.; Yu, W.;Chang, J. J. Org. Chem. 2016, 81, 9326-9336.
• Sambiagio, C.; Marsden, S. P.; Blacker, A. J.;McGowan, P. C. Chem. Soc. Rev. 2014, 43, 3525-3550.
• Li, Z.; Sun, H.; Jiang, H.;Liu, H. Org. Lett. 2008, 10, 3263-3266.
• Doğan, Ş. D.; Gündüz, M. G.; Uğur, S. B.; Doğan, H.; Özkul, C.;Çetinkaya, Y. ChemistrySelect 2021, 6, 4382-4389.
• McCann, S. D.;Stahl, S. S. Acc. Chem. Res. 2015, 48, 1756-1766.
• Doğan, S. D.; Demirpolat, E.; Aycan, M. B. Y.;Balci, M. Tetrahedron 2015, 71, 252-258.
• Gündüz, M. G.; Uğur, S. B.; Güney, F.; Özkul, C.; Krishna, V. S.; Kaya, S.; Sriram, D.;Doğan, Ş. D. Bioorg. Chem. 2020, 102, 104104.
• Mandal, A. B.; Augustine, J. K.; Quattropani, A.;Bombrun, A. Tetrahedron Lett. 2005, 46, 6033-6036.
• Meier, P.; Legraverant, S.; Mueller, S.;Schaub, J. Synthesis 2003, 2003, 0551-0554.