Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Simple and Efficient Procedure for Synthesis of N'-Arylamidines Using Trimethylaluminum

  • Korbad, Balaji L. (Department of Life Chemistry, Catholic University of Daegu) ;
  • Lee, Sang-Hyeup (Department of Life Chemistry, Catholic University of Daegu)
  • Received : 2012.12.28
  • Accepted : 2013.01.14
  • Published : 2013.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Coles, M. P. Dalton Trans. 2006, 985.
  2. Ikeda, M.; Tanaka, Y.; Hasegawa, T.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 6806. https://doi.org/10.1021/ja0619096
  3. Edwards, P. D.; Albert, J. S.; Sylvester, M.; Aharony, D.; Andisik, D.; Callaghan, O.; Campbell, J. B.; Carr, R. A.; Chessari, G.; Congreve, M.; Frederickson, M.; Folmer, R. H. A.; Geschwindner, S.; Koether, G.; Kolmodin, K.; Krumrine, J.; Mauger, R. C.; Murray, C. W.; Olsson, L.-L.; Patel, S.; Spear, N.; Tian, G. J. Med. Chem. 2007, 50, 5912. https://doi.org/10.1021/jm070829p
  4. Peterlin-Masic, L.; Kikelj, D. Tetrahedron 2001, 57, 7073. https://doi.org/10.1016/S0040-4020(01)00507-5
  5. Sondhi, S. M.; Dinodia, M.; Jain, S.; Kumar, A. Eur. J. Med. Chem. 2008, 43, 2824. https://doi.org/10.1016/j.ejmech.2007.10.005
  6. Boyd, G. V. In The Chemistry of Amidines and Imidates; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1991; Vol. 2, p 367.
  7. Tisler, M. Heterocycles 1983, 20, 1591. https://doi.org/10.3987/R-1983-08-1591
  8. Miocque, M.; Fauran, C.; Le Cloarec, A. Y. Ann. Chim. 1972, 7, 89.
  9. Desset, S. L.; Cole-Hamilton, D. J. Angew. Chem., Int. Ed. 2009, 48, 1472. https://doi.org/10.1002/anie.200804729
  10. Phan, L.; Chiu, D.; Heldebrant, D. J.; Huttenhower, H.; John, E.; Li, X.; Pollet, P.; Wang, R.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. Ind. Eng. Chem. Res. 2008, 47, 539. https://doi.org/10.1021/ie070552r
  11. Pinner, A.; Klein, F. Ber. 1877, 10, 1889. https://doi.org/10.1002/cber.187701002154
  12. Caron, S.; Wei, L.; Douville, J.; Ghosh, A. J. Org. Chem. 2010, 75, 945. https://doi.org/10.1021/jo902159z
  13. Xu, Z. Y.; Yan, W.; Liu, Y. F. Zhejiang Chem. Ind. 1988, 19, 1.
  14. Pedersen, E. B.; Carlsen, D. Chem. Scr. 1984, 23, 123.
  15. van Vliet, P. I.; van Koten, G.; Vrieze, K. J. Organomet. Chem. 1979, 179, 89. https://doi.org/10.1016/S0022-328X(00)87799-2
  16. Forsberg, J. H.; Spaziano, V. T.; Balasubramanian, T. M.; Liu, G. K.; Kinsley, S. A.; Duckworth, C. A.; Poteruca, J. J.; Brown, P. S.; Miller, J. L. J. Org. Chem. 1987, 52, 1017. https://doi.org/10.1021/jo00382a009
  17. Xu, F.; Sun, J.; Shen, Q. Tetrahedron Lett. 2002, 43, 1867. https://doi.org/10.1016/S0040-4039(02)00129-6
  18. Maruoka, K.; Yamamoto, H. Angew. Chem. Int. Ed. Engl. 1985, 24, 668. https://doi.org/10.1002/anie.198506681
  19. Oshima, K., Yamamoto, H., Nozaki, H., Yashida, Z., Eds.; New Synthetic Methodology and Biologically Active Substances; Kodansha-Elsevier: 1981; p 19.
  20. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 48, 4171.
  21. Li, J., Subramaniam, K.; Smith, D.; Qiao, J. X.; Li, J. J.; Qian-Cutrone, J.; Kadow, J. F.; Vite, G. D.; Chen, B.-C. Org. Lett. 2012, 14, 214. https://doi.org/10.1021/ol203007s
  22. Feuvrie, C.; Blanchet, J.; Bonin, M.; Micouin, L. Org. Lett. 2004, 6, 2333. https://doi.org/10.1021/ol049346v
  23. Jeong, J. U.; Chen, X.; Rahman, A.; Yamashita, D. S.; Luengo, J. I. Org. Lett. 2004, 6, 1013. https://doi.org/10.1021/ol049921v
  24. Jackowski, O.; Lecourt, T.; Micouin, L. Org. Lett. 2011, 13, 5664. https://doi.org/10.1021/ol202389u
  25. Hartsel, J. A.; Craft, D. T.; Chen, Q.-H.; Ma, M.; Carlier, P. R. J. Org. Chem. 2012, 77, 3127. https://doi.org/10.1021/jo202371c
  26. Kaim, L. E.; Grimaud, L.; Lee, A.; Perroux, Y.; Tirla, C. Org. Lett. 2004, 6, 381. https://doi.org/10.1021/ol036234f
  27. Koutentis, P. A.; Mirallai, S. I. Tetrahedron 2010, 66, 5134. https://doi.org/10.1016/j.tet.2010.04.103
  28. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969. https://doi.org/10.1016/S0040-4039(00)88891-7
  29. Lee, S.-H.; Yoshida, K.; Matsushita, H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Org. Chem. 2004, 69, 8829. https://doi.org/10.1021/jo048353u
  30. Matsushita, H.; Lee, S.-H.; Yoshida, K.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. Org. Lett. 2004, 6, 4627. https://doi.org/10.1021/ol047933a
  31. Lee, S.-H.; Matsushita, H.; Koch, G.; Zimmermann, J.; Clapham, B.; Janda, K. D. J. Comb. Chem. 2004, 6, 822. https://doi.org/10.1021/cc049916i
  32. Lee, S.-H.; Matsushita, H.; Clapham, B.; Janda, K. D. Tetrahedron 2004, 60, 3439. https://doi.org/10.1016/j.tet.2004.02.034
  33. Matsushita, H.; Lee, S.-H.; Joung, M.; Clapham, B.; Janda, K. D. Tetrahedron Lett. 2004, 45, 313. https://doi.org/10.1016/j.tetlet.2003.10.168
  34. Qi, L.; Meijler, M. M.; Lee, S.-H.; Sun, C.; Janda, K. D. Org. Lett. 2004, 6, 1673. https://doi.org/10.1021/ol049474j
  35. Lee, S.-H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. Org. Lett. 2003, 5, 511. https://doi.org/10.1021/ol020244j
  36. Lee, S.-H.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. J. Comb. Chem. 2003, 5, 188. https://doi.org/10.1021/cc020079z
  37. Clapham, B.; Lee, S.-H.; Koch, G.; Zimmermann, J.; Janda, K. D. Tetrahedron Lett. 2002, 43, 5407. https://doi.org/10.1016/S0040-4039(02)01076-6

Cited by

  1. ChemInform Abstract: Simple and Efficient Procedure for Synthesis of N′-Arylamidines Using Trimethylaluminum. vol.44, pp.39, 2013, https://doi.org/10.1002/chin.201339076
  2. Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes vol.50, pp.64, 2014, https://doi.org/10.1039/C4CC04111A
  3. Promoted Amide Synthesis vol.19, pp.7, 2015, https://doi.org/10.1021/acs.oprd.5b00101
  4. Organophosphorus-mediated N–N bond formation: facile access to 3-amino-2H-indazoles vol.14, pp.36, 2016, https://doi.org/10.1039/C6OB01544A
  5. -[1,2,3]-triazole-4-carbonitriles vol.20, pp.38, 2014, https://doi.org/10.1002/chem.201402074
  6. Synthesis of N,N‐Disubstituted 3‐Amino‐1,4‐diynes and 3‐Amino‐1‐ynes by Addition of Alkynyldimethylaluminum Reagents to N,N‐Disubstituted Formamides and vol.2014, pp.23, 2013, https://doi.org/10.1002/ejoc.201402464
  7. Trimethylaluminium‐Mediated Reaction of Primary Carboxamides with Amines and Indoles: A Convenient Synthesis of Amidines and Indole‐3‐acylimines vol.2014, pp.26, 2014, https://doi.org/10.1002/ejoc.201402386
  8. Adsorption of nickel(II) on polyacrylonitrile nanofiber modified with 2-(2'-pyridyl)imidazole vol.284, pp.None, 2013, https://doi.org/10.1016/j.cej.2015.09.065
  9. 3-Hydroxy-propanamidines, a New Class of Orally Active Antimalarials Targeting Plasmodium falciparum vol.64, pp.6, 2013, https://doi.org/10.1021/acs.jmedchem.0c01744
  10. Palladium‐Catalyzed Regioselective Coupling of Amidines and 1,2,3‐Triiodobenzenes: Facile Synthesis of 2,3‐Diiodinated N ‐Arylbenzimidamides as Potential MDM 2 a vol.6, pp.14, 2021, https://doi.org/10.1002/slct.202100671