Highly efficient AgNO3-catalyzed preparation of substituted furano-pyrimidine nucleosides

Synlett

Volumn , Issue 13, 2004, Pages 2406-2408

  Aucagne, Vincent ^a   Amblard, Franck ^a   Agrofoglio, Luigi A ^a  

^a Université d'Orléans   (France)

Author keywords

AgNO3; Cyclization; Furanopyrimidines

Indexed keywords

BICYCLO COMPOUND; FURAN DERIVATIVE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; SILVER NITRATE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; ROOM TEMPERATURE; SONOGASHIRA REACTION; STRUCTURE ANALYSIS;

EID: 8644219601     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831330     Document Type: Article

References (26)

1. Agrofoglio, L. A.; Gillaizeau, S.; Saito, Y. Chem. Rev. 2003, 103, 1875; and references cited therein.
2. (a) McGuigan, C.; Yarnold, C. J.; Jones, G.; Velasquez, S.; Barucki, H.; Brancale, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 4479.
3. (b) McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Erischen, J. T.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 2000, 43, 4993.
4. (c) Srinivasan, S.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Bioorg. Med. Chem. Lett. 2001, 11, 391.
5. (d) McGuigan, C.; Brancale, A.; Barucki, H.; Srinivasan, S.; Jones, G.; Pathirana, R.; Blewett, S.; Alvarez, R.; Yarnold, C. J.; Carangio, A.; Velazquez, S.; Andrei, G.; Snoeck, R.; De Clercq, E. Drugs Future 2000, 25, 1151.
6. (e) Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antivir. Chem. Chemother. 2001, 12, 187.
7. Mansour, T. S.; Evans, C. A.; Charron, M.; Korba, B. E. Bioorg. Med. Chem. Lett. 1997, 7, 303.
8. (a) Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854.
9. (b) Robins, M. J.; Barr, P. J. Tetrahedron Lett. 1981, 22, 421.
10. Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org. Chem. 1966, 31, 4071.
11. Bleackley, R. C.; Jones, A. S.; Walker, R. T. Tetrahedron 1976, 32, 2795.
12. Aucagne, V.; Berteina-Raboin, S.; Guenot, P.; Agrofoglio, L. A. J. Comb. Chem. 2004, in press.
13. For electrophilic cyclization using NIS or NBS, see: (a) Rao, M. S.; Esho, N.; Sergeant, C.; Dembinski, R. J. Org. Chem. 2003, 68, 6788.
14. (b) Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Babrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
15. Jong, T.-T.; Leu, S.-J. J. Chem. Soc., Perkin Trans, 1 1990, 423.
16. Marshall, J. A.; Wang, X. J. J. Org. Chem. 1990, 55, 2995.
17. Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854.
18. Kelly, J. L.; Kelsey, J. E.; Hull, W. R.; Krochmal, M. P.; Schaeffer, H. J. J. Med. Chem. 1981, 24, 753.
19. Amblard, F.; Nolan, S. P.; Gillaizeau, I.; Agrofoglio, L. A. Tetrahedron Lett. 2003, 44, 9177.
20. 2 (0.003 mmol) were added. The reaction was stirred at r.t. until complete conversion was reached. After evaporation of volatiles the crude residue was purified by flash chromatography.
21. +. Found: 411.2259.
22. 13C NMR) to be subjected to the next reaction without further purification.
23. +. Found: 445.5182.
24. 2O (10 mL/5 mL). After evaporation of volatiles the crude residue was purified by flash chromatography.
25. + form) then filtered through a fritted glass funnel. Solvents were evaporated in vacuo and the oily residue was submitted to a flash column chromatography using an appropriate eluent (typically hexanes-EtOAc 25:75, EtOAc, and MeOH-EtOAc 1%) to furnish the desired nucleosides.
26. +. Found: 405.1791.