Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine

Authors
Deghati, PYF Wanner, MJ Koomen, GJ
Citation
Pyf. Deghati et al., Regioselective nitration of purine nucleosides: synthesis of 2-nitroadenosine and 2-nitroinosine, TETRAHEDR L, 41(8), 2000, pp. 1291-1295
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
8
Year of publication
2000
Pages
1291 - 1295
Database
ISI
SICI code
0040-4039(20000219)41:8<1291:RNOPNS>2.0.ZU;2-1
Abstract
Nitration reactions of 6-substituted purine nucleosides with tetrabutylammo nium nitrate/trifluoroacetic anhydride (TBAN/TFAA) have been studied. This nitrating mixture selectively nitrates C-6 substituted purines at the 2-pos ition, but the method is limited to substrates without NH or OH substituent s. Acetylated 6-chloropurine riboside was cleanly nitrated (DCM, 0 degrees C, 71%) and converted to nitro substituted adenosine and inosine in a few s imple steps. (C) 2000 Elsevier Science Ltd. All rights reserved.