A short and efficient synthesis of 2′-deoxybenzo- and pyridoimidazole C-nucleosides

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5807-5810

  Jazouli, Mohamed ^a   Guianvarc'h, Dominique ^c   Soufiaoui, Mohamed ^a   Bougrin, Khalid ^a   Vierling, Pierre ^b   Benhida, Rachid ^b  

^a FACULTÉ DES SCIENCES   (Morocco)

^b UNIVERSITÉ CÔTE D'AZUR   (France)

^c MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZIMIDAZOLE; C NUCLEOSIDE; IMIDAZOLE DERIVATIVE; NUCLEIC ACID BASE; NUCLEOSIDE DERIVATIVE;

ARTICLE; CYCLIZATION; DEHYDRATION; DRUG SYNTHESIS; EPIMERIZATION; METHODOLOGY;

EID: 0038303341     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01401-1     Document Type: Article

References (41)

1. For reviews on the chemistry and biochemistry of C-nucleoside analogs, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65; (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; (c) Watanabe, K. A. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, 421-535; (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-716.
2. For reviews on the chemistry and biochemistry of C-nucleoside analogs, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65; (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; (c) Watanabe, K. A. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, 421-535; (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-716.
3. For reviews on the chemistry and biochemistry of C-nucleoside analogs, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65; (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; (c) Watanabe, K. A. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, 421-535; (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-716.
4. For reviews on the chemistry and biochemistry of C-nucleoside analogs, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65; (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; (c) Watanabe, K. A. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, 421-535; (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-716.
5. For reviews on the chemistry and biochemistry of C-nucleoside analogs, see: (a) Hacksell, U.; Daves, G. D., Jr. Prog. Med. Chem. 1985, 22, 1-65; (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599; (c) Watanabe, K. A. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, 421-535; (d) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20; (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-716.
6. For recent articles, see: (a) Franchetti, P.; Marchetti, S.; Cappellaci, L.; Jayaram, H. N.; Yalowitz, J. A.; Goldstein, B. M.; Barascut, J.-L.; Dukhan, D.; Imbach, J.-L.; Grifantini, M. J. Med. Chem. 2000, 43, 1264-1270; (b) Bojack, G.; Earnshaw, C. G.; Klein, R.; Lindell, S. D.; Lowinski, C.; Preuss, R. Org. Lett. 2001, 3, 839-842.
7. For recent articles, see: (a) Franchetti, P.; Marchetti, S.; Cappellaci, L.; Jayaram, H. N.; Yalowitz, J. A.; Goldstein, B. M.; Barascut, J.-L.; Dukhan, D.; Imbach, J.-L.; Grifantini, M. J. Med. Chem. 2000, 43, 1264-1270; (b) Bojack, G.; Earnshaw, C. G.; Klein, R.; Lindell, S. D.; Lowinski, C.; Preuss, R. Org. Lett. 2001, 3, 839-842.
8. Millican T.A., Mock G.A., Chauncey M.A., Patel T.P., Eaton M.A.W., Gunning J., Cutbush S.D., Neidele S., Mann J. Nucleic Acids Res. 12:1984;7435-7453.
9. Kool E.T. Acc. Chem. Res. 35:2002;936-943. and references cited therein.
10. Ogawa A.K., Wu Y., McMinn D.L., Liu J., Schultz P., Romesberg F.E. J. Am. Chem. Soc. 122:2000;3274-3287.
11. Morales-Rojas H., Kool E.T. Org. Lett. 4:2003;4377-4380.
12. Li J.-S., Fan Y.-H., Zhang Y., Marky L.A., Gold B. J. Am. Chem. Soc. 125:2003;2084-2093.
13. Harusawa S., Imazu T., Takashima S., Araki L., Ohishi H., Kurihara T., Sakamoto Y., Yamamoto Y., Yamatodani A. J. Org. Chem. 64:1999;8606-8615.
14. Parsch J., Engels J.W. J. Am. Chem. Soc. 124:2000;5664-5672.
15. Wenska G., Skalski B., Gdaniec Z., Adamiak R.W., Matulic-Adamic J., Beigelman L. J. Photochem. Photobiol. 133:2000;169-176.
16. Tanaka K., Tasaka M., Cao H., Shionoya M. Eur. J. Pharm. Sci. 13:2001;77-83.
17. Wichai U., Woski S.A. Org. Lett. 1:1999;1173-1175.
18. Franchetti P., Cappellaci L., Marchetti S., Martini C., Costa B., Varani K., Borea P.A., Grifantini M. Bioorg. Med. Chem. 8:2000;2367-2373.
19. Ramasamy K.S., Bandaru R., Averett D. J. Org. Chem. 65:2000;5849-5851.
20. Franchetti P., Marchetti S., Cappellaci L., Yalowitz J.A., Jayaram H.N., Goldstein B.M., Grifantini M. Bioorg. Med. Chem. Lett. 11:2001;67-69.
21. Chun B.K., Song G.Y., Chu C.K. J. Org. Chem. 66:2001;4852-4858.
22. Manferdini M., Morelli C.F., Veronese A.C. Tetrahedron. 58:2002;1005-1010.
23. Calter M.A., Zhu C. J. Org. Chem. 64:1999;1415-1419.
24. Chen D.-W., Beuscher A.E. IV, Stevens R.C., Wirsching P., Lerner R.A., Janda K.D. J. Org. Chem. 66:2001;1725-1732.
25. Griesang N., Richert C. Tetrahedron Lett. 43:2002;8755-8758.
26. Takase M., Morikawa T., Abe H., Inouye M. Org. Lett. 5:2003;625-628.
27. For recent examples, see: (a) Tanaka, K.; Shionoya, M. J. Org. Chem. 1999, 64, 5002-5003; (b) Seela, F.; Debelak, H. J. Org. Chem. 2001, 66, 3303-3312.
28. For recent examples, see: (a) Tanaka, K.; Shionoya, M. J. Org. Chem. 1999, 64, 5002-5003; (b) Seela, F.; Debelak, H. J. Org. Chem. 2001, 66, 3303-3312.
29. See for example: Aketani S., Tanaka K., Yamamoto K., Ishihama A., Cao H., Tengeiji A., Hiraoka S., Shiro M., Shionoya M. J. Med. Chem. 45:2002;5594-5603. and also Refs. 7b and 7c.
30. Guianvarc'h D., Benhida R., Fourrey J.-L., Maurisse R., Sun J.S. J. Chem. Soc., Chem. Commun. 2001;1814-1815.
31. Guianvarc'h D., Fourrey J.-L., Maurisse R., Sun J.S., Benhida R. Org. Lett. 4:2002;4209-4212.
32. Guianvarc'h D., Fourrey J.-L., Maurisse R., Sun J.S., Benhida R. Bioorg. Med. Chem. 11:2003;2751-2759.
33. Kolb A., Huynh Dinh T., Igolen J. Bull. Soc. Chim. Fr. 1973;3447.
34. Iyer R.P., Phillips L.R., Egan W. Synth. Commun. 21:1991;2053.
35. Mukaiyama T., Usui M., Shimada E., Saigo K. Chem. Lett. 1975;1045-1048.
36. 1H NMR (2D COSY-NOESY experiments).
37. Guianvarc'h D., Benhida R., Fourrey J.-L. Tetrahedron Lett. 42:2001;647-650.
38. Guianvarc'h D., Fourrey J.-L., Tran Huu Dau M.-E., Guérineau V., Benhida R. J. Org. Chem. 67:2002;3724-3732.
39. For the conversion of α to β anomer, see: (a) Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341-347; (b) Jiang, Y. L.; Stivers, J. T. Tetrahedron Lett. 2003, 44, 85-88.
40. For the conversion of α to β anomer, see: (a) Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341-347; (b) Jiang, Y. L.; Stivers, J. T. Tetrahedron Lett. 2003, 44, 85-88.
41. abstract