Novel pyrrole C-nucleosides by nitrogen extrusion from pyridazine C-nucleosides

Tetrahedron Letters

Volumn 45, Issue 5, 2004, Pages 1031-1033

  Joshi, Uday ^a   Josse, Solen ^a   Pipelier, Muriel ^a   Chevallier, Floris ^a   Pradère, Jean Paul ^a   Hazard, Roland ^b   Legoupy, Stéphanie ^c   Huet, François ^c   Dubreuil, Didier ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b CNRS   (France)

^c UNIVERSITÉ DU MAINE   (France)

Author keywords

Pyridazine C nucleosides; Pyrrole C nucleosides; Ring contraction

Indexed keywords

ALKYNYL GROUP; C NUCLEOSIDE; NITROGEN; PYRIDAZINE DERIVATIVE; PYRROLE DERIVATIVE; TETRAZINE DERIVATIVE;

ARTICLE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; GRIGNARD REACTION; REDUCTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; TECHNIQUE;

EID: 0346392193     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.088     Document Type: Article

References (14)

1. Petrie C.R., Revankar G.R., Dalley N.K., George R.D., McKernan P.A., Hamill R.L., Robins R.K. J. Med. Chem. 29:1986;268-278.
2. Hammerschmidt F., Peric B., Ohler E. Monatsh. Chem. 128:1997;183-190.
3. Franchetti P., Marchetti S., Cappellacci L., Yalowitz J.A., Jayaram H.N., Goldstein B.M., Grifantini M. Bioorg. Med. Chem. Lett. 11:2001;67-69.
4. Hungerford N.L., Armitt D.J., Banwell M.G. Synthesis. 2003;1837-1843.
5. Fernandez-Bolanos J., Mota J.F., Ramirez I.R. An. Quim., Ser. C: Quim. Org. Bioquim. 80:1984;123-126. and references cited therein.
6. Lam, K. S.; Glersaye, S.; Patel, K.; Najmi, S.; Burnham, B. S. Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, United States, March 23-27, 2003.
7. Anderson W.K., Heider A.R. J. Med. Chem. 29:1986;2392-2395.
8. Manh G.T., Hazard R., Pradère J.P., Tallec A., Raoult E., Dubreuil D. Tetrahedron Lett. 41:2000;647-650.
9. Boger D.L., Coleman R.S., Panek J.S., Yohannes D. J. Org. Chem. 49:1984;4405-4409.
10. Richter M., Seitz G. Arch. Pharm. (Weinheim). 327:1994;365-370.
11. Boger D.L., Coleman R.S., Panek J.S., Huber F.X., Sauer J. J. Org. Chem. 50:1985;5377-5379.
12. 6 Even in the case of 4a the yield was about 35% when Seitz's conditions were followed.
13. Manh G.T., Hazard R., Tallec A., Pradère J.P., Dubreuil D., Thiam M., Toupet L. Electrochim. Acta. 47:2002;2833-2841.
14. 8: C, 58.31; H, 5.41; N, 3.58. Found: C, 58.63; H, 5.32; N, 3.39.