A facile synthesis of (imidazo[1,2-a]pyrimidin-2-yl)sugars by a modified maillard reaction

Chemistry Letters

Volumn , Issue 4, 1997, Pages 367-368

  Kolar, Patrik ^a   Tišler, Miha ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039449832     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.367     Document Type: Article

References (13)

1. A term "imidazolosugar" refers to imidazoles substituted with a sugar-derived polyolic chain (see Ref. 6), and a term "imidazosugar" refers to bicyclic or polycyclic azasugars containing a fused imidazole ring according to the nomenclature of fused heterocyclic systems.
2. S. Harusawa, Y. Murai, H. Moriyama, H. Ohishi, R. Yoneda, and T. Kurihara, Tetrahedron Lett., 36, 3165 (1995) and references cited therein.
3. K. Tatsuta, S. Miura, S. Ohta, and H. Gunji, Tetrahedron Lett., 36, 1085 (1995).
4. T. Yasuzawa, M. Yoshida, M. Ichimura, K. Shirahata, and H. Sano, J. Antibiot., 40, 727 (1987).
5. See, for example: J. P. Ferris, S. S. Badesha, W. Y. Ren, H. C. Huang, and R. J. Sorcek, J. Chem. Soc., Chem. Commun., 1981, 110.
6. J. Streith, A. Boiron, A. Frankowsky, D. Le Nouen, H. Rudyk, and T. Tschamber, Synthesis, 1995, 944, and references cited therein.
7. According to the recommended IUPAC nomenclature compounds 3 should be named as 2-(triitol-1-yl)-and 2-(tetritol-1-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidin-7(8H)-ones.
8. As a "Maillard reaction" are usually regarded non-enzymatic sugar-amine transformations in aqueous media at physiological pH. 9 A similar cyclization between aminoacetaldehyde diethyl acetal and cyanamide resulted in the formation of 2-amino-imidazole; see : A. Lawson, J. Chem. Soc., 1956, 307.
9. 4: 47.57 %C, 5.77 %H, 18.49 %N. Found: 47.82 %C, 5.80 %H, 18.84 %N.
10. Identical in all respects (mp, mixed mp, optical rotation and NMR).
11. For recent reviews on the chemistry of the Maillard reaction, see: R. Ikan (Ed.), "The Maillard Reaction", J. Wiley, New York (1996); F. Ledl and E. Schleicher, Angew. Chem., 102, 597 (1990); F. Ledl, J. Beck, M. Sengl, H. Osiander, S. Estendorfer, T. Severin, and B. Huber, Prog. Clin. Biol. Res., 304, 23 (1989).
12. For recent reviews on the chemistry of the Maillard reaction, see: R. Ikan (Ed.), "The Maillard Reaction", J. Wiley, New York (1996); F. Ledl and E. Schleicher, Angew. Chem., 102, 597 (1990); F. Ledl, J. Beck, M. Sengl, H. Osiander, S. Estendorfer, T. Severin, and B. Huber, Prog. Clin. Biol. Res., 304, 23 (1989).
13. For recent reviews on the chemistry of the Maillard reaction, see: R. Ikan (Ed.), "The Maillard Reaction", J. Wiley, New York (1996); F. Ledl and E. Schleicher, Angew. Chem., 102, 597 (1990); F. Ledl, J. Beck, M. Sengl, H. Osiander, S. Estendorfer, T. Severin, and B. Huber, Prog. Clin. Biol. Res., 304, 23 (1989).