A Selective Procedure for 6-Subsituted Pterin Derivatives: Synthesis and Substitution of Pterin 6-Triflate

  • Shizuaki Murata
  • Masato Kujime
  • Kazunari Kudoh


Introduction of a C(6) side chain on the pterin skeleton with regioselective manor is one of most challenging subjects in the field of pteridine chemistry (1). Among procedures for 6-substituted pteridines, substitution reaction of 6-halogenated pteridines by an organic group has succeeded to synthesize valuable naturally occurring pterins and their derivatives (2–6). However, in such halogenated pterins, the general nucleophilic substitution (SN1 or SN2 reaction) by carbon nucleophiles like enolate ions and carbanions did not occur in the absence of accelerators (7). Previously we described that the nucleophilic substitution of lumazine 6-triflate by various carbon reagents proceeded to give 6-substituted pteridine derivatives in high yields (8–10). On the other hand, the selectivity of the oxidation which is the important step in the preparation of a pteridine triflate toward its N-oxide is different, and, in addition, the amino group on the C(2) position is labile under acidic conditions employed to the conversion of N-oxide to the triflate. Therefore, it seemed to be difficult to apply the methodology for lumazine 6-triflate to pterin. We would like to describe in this paper a selective synthesis of the pterin 6-triflate and its application to syntheses of 6-substituted pterins.


Sodium Hydride Selective Synthesis Diethyl Malonate Selective Procedure Yellow Solid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Review for regioselective syntheses of 6- and 7-substituted pteridines: S. Murata, K. Kiguchi, and T. Sugimoto, Heterocycles 48: 1255, 1999.CrossRefGoogle Scholar
  2. 2.
    E. C. Taylor and P. S. Ray, J. Org. Chem. 52: 3997, 1987.CrossRefGoogle Scholar
  3. 3.
    E. C. Taylor and P. S. Ray, J. Org. Chem. 53: 35, 1988.CrossRefGoogle Scholar
  4. 4.
    E. C. Taylor, P. S. Ray, I. S. Darwish, J. L. Johnson, and K. V. Rajagopalan, J. Am. Chem. Soc. 111:7664, 1989.CrossRefGoogle Scholar
  5. 5.
    E. C. Taylor and L. A. Leiter, J. Am. Chem. Soc., 1989, 111: 285.CrossRefGoogle Scholar
  6. 6.
    E. C. Taylor, W. B. Young, and C. Spanka, J. Org. Chem. 61: 1261. 1996.CrossRefGoogle Scholar
  7. 7.
    A. Heckel and W. Pfleiderer, Helv. Chim. Acta 69: 704, 1986.CrossRefGoogle Scholar
  8. 8.
    S. Murata, T. Sugimoto and K. Murakami, Pteridines 8:1, 1997.Google Scholar
  9. 9.
    S. Murata, M. Kujime, T. Sugimoto, K. Murakami, and C. Seo, Heterocycles 50: 117, 1999.CrossRefGoogle Scholar
  10. 10.
    S. Murata, C. Seo, M. Kujime, and T. Sugimoto, Heterocycles 53: 1259, 2000.CrossRefGoogle Scholar
  11. 11.
    K. Kiguchi, S. Murata and T. Sugimoto, Pteridines 6: 160, 1995.Google Scholar

Copyright information

© Springer Science+Business Media New York 2002

Authors and Affiliations

  • Shizuaki Murata
    • 1
    • 2
  • Masato Kujime
    • 1
  • Kazunari Kudoh
    • 1
  1. 1.Graduate School of Environmental StudiesNagoya UniversityNagoyaJapan
  2. 2.CREST JST (Japan Science and Technology)Japan

Personalised recommendations