Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A General Strategy for the Synthesis of Amino-Substituted 2-Pyridones Using a Palladium-Catalyzed Amination Reaction

  • Kim, Young-Ha (Department of Chemistry, Chungnam National University) ;
  • Kim, Yeong-Joon (Department of Chemistry, Chungnam National University) ;
  • Chang, Sung-Youn (Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology) ;
  • Kim, Bum-Tae (Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology) ;
  • Heo, Jung-Nyoung (Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology)
  • Published : 2007.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

A novel library of amino-substituted 2-pyridones has been constructed through a two-step sequence of microwave-promoted Buchwald-Hartwig amination of 2-benzyloxy halopyridines followed by debenzylation. Microwave-promoted amination of 3- or 4-halopyridine in the presence of a suitable palladium catalyst and ligand system provided amino-substituted 2-benzyloxypyridines in excellent yields. Then, debenzylation of 2- benzyloxypyridines afforded the corresponding 2-pyridones with high efficiency.

Keywords

References

  1. For a review, see: Rigby, J. H. Synlett 2000, 1
  2. Kim, E.; Cho, C. H.; Kim, S. Bull. Korean Chem. Soc. 2005, 26, 1869 https://doi.org/10.5012/bkcs.2005.26.11.1869
  3. Hasvold, L. A.; Wang, W.; Gwaltney, II, S. L.; Rockway, T. W.; Nelson, L. T. J.; Mantei, R. A.; Fakhoury, S. A.; Sullivan, G. M.; Li, Q.; Lin, N.-H.; Wang, L.; Zhang, H.; Cohen, J.; Gu, W.-Z.; Marsh, K.; Bauch, J.; Rosenberg, S.; Sham, H. L. Bioorg. Med. Chem. Lett. 2003, 13, 4001 https://doi.org/10.1016/j.bmcl.2003.08.058
  4. Cox, R. J.; O'Hagan, D. J. Chem. Soc., Perkin Trans. 1 1991, 2537
  5. Li, Q.; Mitscher, L. A.; Shen, L. L. Med. Res. Rev. 2000, 20, 231 https://doi.org/10.1002/1098-1128(200007)20:4<231::AID-MED1>3.0.CO;2-N
  6. Fujita, Y.; Oguri, H.; Oikawa, H. Tetrahedron Lett. 2005, 46, 5885 https://doi.org/10.1016/j.tetlet.2005.06.115
  7. Semple, G.; Andersson, B.-M.; Chhajlani, V.; Georgsson, J.; Johansson, M. J.; Rosenquist, A.; Swanson, L. Bioorg. Med. Chem. Lett. 2003, 13, 1141 https://doi.org/10.1016/S0960-894X(03)00033-7
  8. Parreira, R. L. T.; Abrahao, O.; Galembeck, S. E. Tetrahedron 2001, 57, 3243 https://doi.org/10.1016/S0040-4020(01)00193-4
  9. Dragovich, P. S.; Prins, T. J.; Zhou, R.; Brown, E. L.; Maldonado, F. C.; Fuhrman, S. A.; Zalman, L. S.; Tuntland, T.; Lee, C. A.; Patick, A. K.; Matthews, D. A.; Hendrickson, T. F.; Kosa, M. B.; Liu, B.; Batugo, M. R.; Gleeson, J.-P. R.; Sakata, S. K.; Chen, L.; Guzman, M. C.; Meador, III, J. W.; Ferre, R. A.; Worland, S. T. J. Med. Chem. 2002, 45, 1607
  10. Parlow, J. J.; Kurumbail, R. G.; Stegeman, R. A.; Stevens, A. M.; Stallings, W. C.; South, M. S. J. Med. Chem. 2003, 46, 4696 https://doi.org/10.1021/jm0301686
  11. Parlow, J. J.; South, M. S. Tetrahedron 2003, 59, 7695 https://doi.org/10.1016/S0040-4020(03)01239-0
  12. Sanderson, P. E. J.; Lyle, T. A.; Cutrona, K. J.; Dyer, D. L.; Dorsey, B. D.; McDonough, C. M.; Naylor-Olsen, A. M.; Chen, I.-W.; Chen, Z.; Cook, J. J.; Cooper, C. M.; Gardell, S. J.; Hare, T. R.; Krueger, J. A.; Lewis, S. D.; Lin, J. H.; Lucas, Jr., B. J.; Lyle, E. A.; Lynch, Jr., J. J.; Stranieri, M. T.; Vastag, K.; Yan, Y.; Shafer, J. A.; Vacca, J. P. J. Med. Chem. 1998, 41, 4466
  13. Warner, P.; Green, R. C.; Gomes, B.; Strimpler, A. M. J. Med. Chem. 1994, 37, 3090 https://doi.org/10.1021/jm00045a014
  14. Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem. Int. Ed. 2005, 44, 1371 https://doi.org/10.1002/anie.200462629
  15. Urgaonkar, S.; Xu, J.- H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416 https://doi.org/10.1021/jo034994y
  16. Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729 https://doi.org/10.1021/jo010613+
  17. Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Org. Lett. 2002, 4, 3481 https://doi.org/10.1021/ol0265923
  18. Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027 https://doi.org/10.1016/S0040-4020(01)00659-7
  19. Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004, 10, 2983 https://doi.org/10.1002/chem.200306026
  20. Vinter-Pasquier, K.; Jamart-Gregoire, B.; Caubere, P. Heterocycles 1997, 45, 2113
  21. Heo, J.-N.; Song, Y. S.; Kim, B. T. Tetrahedron Lett. 2005, 46, 4621 https://doi.org/10.1016/j.tetlet.2005.04.141
  22. Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250 https://doi.org/10.1002/anie.200400655
  23. Loupy, A. Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim, 2006
  24. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225 https://doi.org/10.1016/S0040-4020(01)00906-1
  25. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131 https://doi.org/10.1007/3-540-45313-X_5
  26. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805
  27. Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046 https://doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L
  28. Shiao, M.-J.; Tarng, K.-Y. Heterocycles 1990, 31, 637
  29. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240 https://doi.org/10.1021/jo9612739
  30. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158 https://doi.org/10.1021/jo991699y

Cited by

  1. Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C–N bond forming reactions with enolizable heterocycles under microwave enhanced conditions vol.38, pp.3, 2014, https://doi.org/10.1039/c3nj01355c
  2. Development of Novel Selective Peptidomimetics Containing a Boronic Acid Moiety, Targeting the 20S Proteasome as Anticancer Agents pp.18607179, 2014, https://doi.org/10.1002/cmdc.201402075
  3. A General Strategy for the Synthesis of Amino-Substituted 2-Pyridones Using a Palladium-Catalyzed Amination Reaction. vol.38, pp.38, 2007, https://doi.org/10.1002/chin.200738145
  4. Biaryl Phosphane Ligands in Palladium-Catalyzed Amination vol.47, pp.34, 2008, https://doi.org/10.1002/anie.200800497
  5. Biarylphosphanliganden in der palladiumkatalysierten Aminierung vol.120, pp.34, 2008, https://doi.org/10.1002/ange.200800497
  6. Solvent-free Microwave-Assisted Ortho-Alkylation of Aromatic Ketimine with Acrylic Acid Derivatives by Rh(I) Catalyst vol.28, pp.11, 2007, https://doi.org/10.5012/bkcs.2007.28.11.2020
  7. Synthetic Studies on the Role of Substituents at C-3 Position on C3-C4 Bond Cleavage of β-Lactam Ring: Convenient Route for Diastereoselective Synthesis of Pyridin-2-ones vol.86, pp.2, 2007, https://doi.org/10.3987/com-12-s(n)83
  8. An efficient one-pot synthesis of 1,4-disubstituted 3-amino-2-pyridone derivatives via three-component reactions of alkynyl aldehydes and amines with ethyl 2-((diphenylmethylene)amino)acetate vol.68, pp.22, 2007, https://doi.org/10.1016/j.tet.2012.03.106
  9. Efficient Use of 1,2‐Dihaloazine Synthons in Transition‐Metal‐Free Preparation of Diverse Heterocycle‐Fused 1,4‐Oxazepines vol.2015, pp.6, 2007, https://doi.org/10.1002/ejoc.201403397
  10. One‐Pot Synthesis of 2‐Amino‐6‐(1,2‐dihydro‐4‐hydroxy‐2‐oxoquinolin‐3‐yl)‐4‐arylpyridine‐3‐carb vol.4, pp.34, 2007, https://doi.org/10.1002/slct.201901866