Mild and regioselective nitration of 1-deazapurine nucleosides using TBAN/TFAA

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 569-573

  Deghati, Paymaneh Y F ^a   Bieräugel, Hans ^a   Wanner, Martin J ^a   Koomen, Gerrit Jan ^a  

^a Univ A   (Netherlands)

Author keywords

Nitration; Nucleosides

Indexed keywords

1 DEAZAADENOSINE; PURINE NUCLEOSIDE DERIVATIVE; TETRABUTYLAMMONIUM; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG STRUCTURE; NITRATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343339952     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02073-0     Document Type: Article

References (20)

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13. 5/bisulfite via a different mechanism: (a) Bakke, J. M.; Ranes, E. Synthesis 1997, 281; (b) Bakke, J. M.; Ranes, E.; Riha, J. Tetrahedron Lett. 1998, 39, 911; (c) Bakke, J. M.; Ranes, E.; Riha, J.; Svenson, H. Acta Chem. Scand. 1999, 53, 141.
14. 5/bisulfite via a different mechanism: (a) Bakke, J. M.; Ranes, E. Synthesis 1997, 281; (b) Bakke, J. M.; Ranes, E.; Riha, J. Tetrahedron Lett. 1998, 39, 911; (c) Bakke, J. M.; Ranes, E.; Riha, J.; Svenson, H. Acta Chem. Scand. 1999, 53, 141.
15. Protected inosine gives N-1 nitration: Ariza, X.; Bou, V.; Vilarrasa, J. J. Am. Chem. Soc. 1995, 117, 3665.
16. Uridine is nitrated at N-3 and at C-5: (a) Ariza, X.; Farràs, J.; Serra, C.; Vilarrasa, J. J. Org. Chem. 1997, 62, 1547. (b) Giziewicz, J.; Wnuk, S. F.; Robins, M. J. J. Org. Chem. 1999, 64, 2149.
17. Uridine is nitrated at N-3 and at C-5: (a) Ariza, X.; Farràs, J.; Serra, C.; Vilarrasa, J. J. Org. Chem. 1997, 62, 1547. (b) Giziewicz, J.; Wnuk, S. F.; Robins, M. J. J. Org. Chem. 1999, 64, 2149.
18. Probably the unstable 2-nitro isomer is formed, which is hydrolyzed during work-up.
19. 3 and extracted with DCM. Chromatographic separation gave the pure nitro compounds.
20. 1H NMR correlation studies showed coupling between carbon and hydrogen atoms through three bonds (J=10 Hz). In the 5,7-dinitro compound for instance, the following correlation's were observed: H-1′⇆C-2, H-2⇆C-1a, H-6⇆C-1a.