Dye-sensitized photooxygenation of furanosyl furans: Synthesis of a new pyridazine C-nucleoside

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6503-6505

  Cermola, Flavio ^a   Iesce, M Rosaria ^a   Buonerba, Gianluca ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN RESINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

C-NUCLEOSIDE; FURANOSYL FURANS; PHOTOOXYGENATION; PYRIDAZINE;

DYES;

1,4 DIOXOAGLYCONE DERIVATIVE; C NUCLEOSIDE; DYE; FURAN DERIVATIVE; FURANOSYL FURAN DERIVATIVE; GLYCOSIDE; PYRIDAZINE; RIBOFURANOSYL FURAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CIS ISOMER; PHOTOOXIDATION; PHOTOSENSITIVITY; SYNTHESIS;

COLORING AGENTS; FURANS; MOLECULAR STRUCTURE; NUCLEOSIDES; OXYGEN; PHOTOCHEMISTRY; PYRIDAZINES;

EID: 23044511491     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0504159     Document Type: Article

References (32)

1. (a) Suhadolnik, R. J. Nucleoside as Biological Probes; John Wiley & Sons: New York, 1979;
2. (b) Suhadolnik, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1979.
3. Simons, C. Nucleoside Mimetics Their Chemistry and Biological Properties; Gordon and Breach Science Publisher: Australia, Canada, 2001.
4. Peasley, K, Med. Hypotheses 2000, 55, 408.
5. Townsend, L. B. Chemistry of Nucleosides and Nucleotides; Plenum Press: New York, 1994; pp 421-535.
6. Miller, P. S. Antisense/Antigene Oligonucleotides. In Bioorganic Chemistry-Nucleic Acids; Hecht, S. M., Ed.; Oxford Univerisity Press: New York, 1996; pp 347-274.
7. (a) Postema, H. D. M. C-Glycoside Synthesis; CRC Press: London, 1995.
8. (b) Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913.
9. (c) Wu, Q.; Simons, C. Synthesis 2004, 1533.
10. (a) Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc. 1989, 111, 2193 and references therein.
11. (b) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484.
12. (a) Maeba, L; Iijima, T.; Matsuda, Y.; Ito, C. J. Chem. Soc., Perkin Trans, 1 1990, 73.
13. (b) Maeba, I.; Takeuchi, T.; Iijima, T.; Kitaori, K.; Muramatsu, H. J. Chem. Soc., Perkin Trans. 1 1989, 649.
14. (c) Maeba, L; Kitaori, K.; Ito, C. J. Org. Chem. 1989, 54, 3927.
15. (d) Maeba, I.; Takeuchi, T.; Iijima, T.; Furukawa, H. J. Org. Chem. 1988, 53, 1401.
16. (e) Maeba, I.; Hara, O.; Suzuki, M.; Furukawa, H. J. Org. Chem. 1987, 52, 2368.
17. (f) Maeba, L; Iwata, K.; Usami, F.; Furukawa, H. J. Org. Chem. 1983, 48, 2998.
18. Cermola, F.; Iesce, M. R.; Montella, S. Lett. Org. Chem. 2004, 1, 271.
19. C-Glycosides 1 were synthesized using 6 equiv (for 1a,c) and 1 equiv (for 1a) of the related furan. The use of a large amount of 2-methylfuran for 1b has to be avoided. Indeed, when 6 equiv of the 2-methylfuran was used, the reaction afforded only an open-chain product deriving from a further furan addition to the furanoside ring (unpublished results).
20. 1H COSY experiments. The heteronuclear chemical shift correlations were determined by HMQC and HMBC pulse sequences.
21. 13C chemical shifts of the anomeric-H1 and C1 and by comparison with the data reported in the literature for α- and β-glycoside derivatives: (a) Mizutani, K.; Kasai, R.; Nakamura, M.; Tanak, O. Carbohydr. Res. 1989, 185, 27.
22. (b) Agrawal, P. K. Phytochemistry 1992, 37, 3307.
23. Methanol as a solvent is particularly attractive for α, α′-disubstituted furans, for example 1b, since it adds to the corresponding endoperoxides leading to 5-hydroperoxy-2,5-dihydrofurans (below), which are more stable than the parent peroxides. Moreover, these hydroperoxides are readily deoxygenated by alkyl sulfides to the cis-α,β-unsaturated 1,4-dicarbonyl compounds, and the reduction can be carried out on the crude methanolic solution. (diagram presented) In the other cases, when alcohol addition fails, e.g., with endoperoxides of α,α′- or α-unsubstituted furans as 1a, methanol can also be used while maintaining the temperature at low values to avoid thermal rearrangement of the endoperoxide intermediate (Iesce, M. R.; Cermola, F.; Temussi, F Curr. Org. Chem. 2005, 9, 109-139).
24. 9 It is reasonable that it occurs for unsubstituted unsaturated 1,4-dicarbonyl derivatives.
25. Thermal stability of endoperoxides of 2,5-dialkylfurans has been reported: Graziano, M. L.; Iesce, M. R.; Scarpati, R. J. Chem. Soc., Chem. Commun. 1981, 720.
26. On the other hand, the lack of the 0-glycoside starting from 1c was expected; indeed the Baeyer-Villiger-type rearrangement is reported not to occur for endoperoxides of 2,5-dialkylfurans. It has been demonstrated only for monosubstituted endoperoxides with an acyl group at C1 (Bloodworth, A. J.; Eggelte, H. J. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. II, p 165)
27. 2OCOR groups (Kuo, Y.-H.; Shih, K-S.; Lee, S.-M. J. Photochem. Photobiol, A: Chem. 1988, 97). Thus, as for the C-glucoside analogues, the formation of 2 is probably due to the electrophilicity of the anomeric carbon of the sugar, which promotes this pathway also for both mono- and disubstitued 1a,b.
28. 1H NMR spectrum showed the disappearance of these two signals together with the appearance of the signals of 5c. The cis relationship of the carbonyl groups in 5c was unambiguously related to the bicyclic structure of the parent endoperoxides 3c.
29. (a) Borowski, P.; Lang, M.; Haag, A.; Schmitz, H.; Choe, J.; Chen, H.-M.; Hosmane, R. S. Antimicrob. Agents Chemother. 2002, 46, 1231.
30. (b) Cook, P. D.; Dea, P.; Robins, R. K. J. Heterocycl. Chem. 1978, 15, 1.
31. (c) Joshi, U.; Josse, S.; Pipelier, M.; Chevallier, F.; Pradere, J.-P.; Hazard, R.; Legoupy, S.; Huet, F.; Dubreuil, D. Tetrahedron Lett. 2004, 45, 1031.
32. 3 solution is changed. This is probably due to strong nonbonded intermolecular interactions between one of the heterocyclic nitrogens with the sufficiently acidic hydrogen at C5′ (δ = 7.41 ppm).