Regioselective ribosylation of 6,7-dichloroimidazo[4,5-b]quinolin-2-one

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3263-3266

  Zhu, Zhijian ^a   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

imidazo 4,5 b quinolin 2 one; nucleoside analog; regioselective ribosylation

Indexed keywords

IMIDAZO[4,5 B]QUINOLINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029886321     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00529-1     Document Type: Article

References (19)

1. a). Townsend, L. B.; Drach, J. C.; et.al Fifth Internat. Conf. Antiviral Res., Vancouver, BC, Abstracts 12, 105, 107, 108, 110.
2. b). Townsend, L. B.; Devivar, R. V.; Turk, S. R.; Nassiri, M. R.; Drach, J. C. J. Med. Chem. 1995, 38, 4098-4105.
3. c). Devivar, R. V.; Kawashima, E.; Revankar, G. R.; Breitenbach, J. M.; Freske, E. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1994, 37, 2942-2949.
4. a). Leonard, N.J.; Hiremath, S.P. Tetrahedron 1986, 42, 1917-1961.
5. b). Leonard, N.J. Acc. Chem. Res. 1982, 15, 128-135.
6. Zhu, Z.; Lippa, B. S.; Townsend, L. B. Tetrahedron Lett., in press.
7. a). For a general review on the glycosylation of imidazo[4,5-b]pyridine derivatives: Revankar, G.R.; Robins, R.K. The Synthesis and Chemistry of Heterocyclic Analogs of Purine Nucleosides and Nucleotides. In The Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.;Plenum Press: New York and London, 1991; Vol. 2, pp 161-398.,
8. b). Itoh, T.; Mizumo, Y. Heterocycles 1976, 5, 285-292.
9. c). Cristalli, G.; Franchetti, P.; Grifantini, M.; Vittori, S.; Bordoni, T.; Geroni, C. J. Med. Chem. 1987, 30, 1686-1688.
10. d). Itoh, T.; Sugawara, T.; Mizumo, Y. Heterocycles 1982, 17, 305-309.
11. For a general review on the Hilbert-Johnson glycosylations: Pliml, J.; Prystas, M. Adv. Heterocycl. Chem. 1967, 5, 115-142.
12. Compound 6 was silylated by N,O-bis(trimethylsilyl)acetamide (BSA). It was found that when either acetonitrile or 1,2-dichloroethane was used alone as a solvent, a homogeneous solution cannot be generated when 6 was silylated with BSA. However, 6 was silylated by BSA (2eq) in a mixture of 1,2-dichloroethane/acetonitrile (3/1) at room temperature for one hour to give a clear solution. Most silylations of 6 were conducted under these conditions. A more polar solvent system for the subsequent ribosylation was obtained by the addition of more acetonitrile after the silylation. When acetonitrile was used as the only solvent, 6 was treated with BSA (2eq) at room temperature for one hour and the suspension was then used for the subsequent ribosylation.
13. For the leading references on the Vorbruggen type of ribosylation: a). Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber., 1981 114, 1234-1255.
14. b). Vorbruggen, H.; Bennua, B. Chem. Ber. 1981, 114, 1279-1286.
15. c). Dudycz, L.; Wright, G. E. Nucleosides Nucleotides 1984, 3, 33-44.
16. 2: C, 61.89; H, 3.58; N, 6.02; Found: C, 61.94; H, 3.74; N, 5.94.
17. 2: C, 61.89; H, 3.58; N, 6.02; Found: C, 61.65; H, 3.77; N, 5.80.
18. 1H-nOe was observed for compound 4 between H1′and H4′ which confirmed the β-configurations.
19. For a similar transglycosylation of imidazo[4,5-b]pyridine, see reference 4b.