A novel method for introduction of carbon substituents into pteridine

Heterocycles

Volumn 50, Issue 1, 1999, Pages 117-124

  Murata, Shizuaki ^a   Kujime, Masato ^a   Sugimoto, Takashi ^a   Murakami, Katsuhiko ^a   Seo, Chihiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; FLUOROFORM; LUMAZINE; MALONIC ACID DERIVATIVE; PTERIDINE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; MOLECULAR STABILITY; REACTION ANALYSIS;

EID: 0032837318     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-S(H)12     Document Type: Article

References (25)

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2. M. Akino and K. Iwai, Pteridine, Kodansha: Tokyo, 1981.
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9. D. J. Brown, "The Chemistry of Heterocyclic Compounds", Vol. 24, Part 3, eds by E. C. Taylor and A. Weissberger, Wiley, New York, 1988, Chap. 2 and Chap. 3.
10. S. Murata, K. Kiguchi, and T. Sugimoto, Heterocycles, 1998, 48, 1255.
11. S. Murata, T. Sugimoto, and K. Murakami, Pteridines, 1997, 8, 1.
12. 1,3-Dimethyl-2,4(1H,3H)-pteridinedione: 2,4(1H,3H)-Pteridinedione is abbreviated as lumazine. Compound 1 is prepared by the procedures described in ref. 11.
13. Although we do not have any evidences, we suppose that the formation of 4f proceeded through the mechanism illustrated in the following scheme. Since lumazine and the ester group have strong electron withdrawing characters, 4f could stabilize its carbanion (4f-enolate) very well. Base induced elimination of ketene from initially produced 2f might be occurred to give 4f-enolate. See: W. E. Hanford and J. C. Sauer, "Organic Reactions", Vol. 3, eds by R. Adams, W. E. Bachmann, J. R. Johnson, L. F. Fieser, and H. R. Snyder, Robert E. Krieger Publishing Co., Malabar Florida, 1975, Chap. 3. (equation presented)
14. 5: C 48.24, H 3.52, N 28.13. Found: C 48.07, H 3.64, N 28.34. (equation presented)
15. S. Murata, K. Murakami, C. Seo, T. Sugimoto, and M. Kujime, "Chemistry and Biology of Pteridine and Folates 1997", eds by W. Pfleiderer and H. Rokos, Blackwell Science, Berlin, 1997, pp. 17-22.
16. Reaction of 6-chloro-1,3-dimethyllumazine with the sodium enolate of ethyl cyanoacetate was carried out in the presence of trimethyloxonium tetrafluoroborate. See: A. Heckel and W. Pfleiderer, Helv. Chim. Acta, 1986, 69, 704.
17. S. Murata, T. Sugimoto, S. Ogiwara, K. Mogi, and H. Wasada, Synthesis, 1992, 303.
18. S. Murata, K. Kiguchi, and T. Sugimoto, Heterocycles, 1993, 35, 639.
19. K. Kiguchi, S. Murata, and T. Sugimoto, Pteridines, 1995, 6, 160.
20. PM3 Calculations were carried out using a HyperChem® program running. Atomic coordinates of the optimized (most stable) structure of 2d are cited in Table 3, where hydrogen atoms are omitted.
21. Those reactions afforded significant amounts of 6-hydroxy-1,3-dimethyllumazine (ref. 16), which was produced by alkaline hydrolysis of 1 (ref. 11).
22. 1,2-Bis(triphenylphosphino)ethane (dppe) and 1,3-bis(triphenylphosphino)propane (dppp).
23. 2 column chromatography.
24. T. Sugimoto, C. Seo, S. Murata, and W. Pfleiderer, Pteridines, 1997, 8, 188.
25. R. B. Angier, J. Org. Chem., 1963, 28, 1398.