A new and efficient route to the synthesis of pyrazole and pyrimidine C- nucleoside derivatives

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3853-3856

  Veronese, Augusto C ^a   Morelli, Carlo F ^a  

^a Dipto di Scienze Farmaceutiche   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

C NUCLEOSIDE; HETEROCYCLIC COMPOUND; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRIMIDINE NUCLEOSIDE;

ARTICLE; CATALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0032575208     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00631-5     Document Type: Article

References (17)

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11. 2).
12. 2), 4.65-4.80 (m, 1H, H-4), 4.95 (d, J=4.6 Hz, 1H, H-1), 5.67 (m, 1H, H-2 or H-3), 5.90 (m, 1H, H-2 or H-3), 7.4-7.7 (m, 10 H, Ph), 7.8-8.1 (m, 5H, Ph). Similar C-glycosyl-β-ketoester has been previously prepared: a) by the reductive hydrolysis of an isoxazole C-nucleoside, obtained in a dipolar cycloaddition reaction from a C-ribofuranosyl nitrileoxide and ethoxyacetylene (Kozikowski A. P.; Goldstein S. J. Org. Chem., 1983, 48, 1141);
13. b) by a Michael addition reaction of pyrrolidine on ribofuranosyl ethylpropiolate followed by hydrolysis of the obtained enaminoester (Tam S. Y-K.; Klein R. S.; De las Heras F. G.; Fox J. J. J. Org. Chem. 1979, 44, 4854).
14. 2O + H-4), 5.65 (d, J=1.0 Hz, 1H, H-1), 5.74 (m, 1H, H-3 ), 6.05 (m, 1H, H-2), 6.62 (br, 1H, NH), 7.23-7.60 (m, 9H, Ph), 7.82 (d, 2H, J=7.5, Ph), 8.01 (d, 4H, J=7.5, Ph), 10.65 (s, br, NH); minor isomer shows absorptions at δ: 1.48 (s, 9H, t.Bu), 5.34 (d, 1H, J=1.5 Hz, H-1), 5.95 (br, 1H, NH), 8.73 (s, br, 1H, NH).
15. 2Ph), 5.75-5.86 (m, 2H, H-2 and H-3), 5.90 (d, 1H, J=7.3 Hz, H-1), 7.08-7.62 (m, 14H, Ph), 7.90-7.96 (m, 4H, Ph), 8.09-8.12 (m, 2H, Ph).
16. 12. a) Chen X.; Sauer D. R.; Schneller S. W. Current Medicinal Chemistry, 1994, 1, 105.
17. b) Petrie C. R.; Revankar G. R.; Dalley N. K.; George R. D.; McKernan P. A.; Hamill R. L.; Robins R. K. J. Med. Chem., 1986, 29, 268.