Purines. LXVI. Adenine 7-oxide: Its synthesis, chemical properties, and X-ray molecular structure

Article abstract of DOI:10.1248/cpb.43.53

A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H₂O as an equilibrated mixture of the NO-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H₂O₂ in MeOH in the presence of MeCN and KHCO₃ at 30°C produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.

Full text of DOI:10.1248/cpb.43.53

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