Azido/Tetrazole Tautomerism in 2‐Azidoadenine β‐ D ‐Pentofuranonucleoside Derivatives

The β‐D‐ribofuranoside derivative of 2‐azidoadenine and its 2′‐deoxy‐, 2′,3′‐dideoxy‐ and 2′,3′‐dideoxy‐2′,3′‐didehydro counterparts have been synthesized. All these compounds were obtained through the preparation of their 2‐chloro precursors. These were converted into their 2‐hydrazino derivatives, which upon treatment with sodium nitrate in acid medium gave the target nucleosides. The azido/tetrazole tautomerism observed in such nucleoside analogues was studied in detail. The compounds were also tested for their activity against HIV and HBV, but did not show significant antiviral effects. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)