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Communication | Regular issue | Vol 31, No. 9, 1990, pp.1593-1596
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5505
Synthesis of the 1-N-Oxides and 1-Methoxy and N6-Methoxy Derivatives of 2-Deuterioadenines Substituted or Unsubstituted at the 9-Position

Tohru Saito, Hiromi Hayashibara, Yukinari Kumazawa, Tetsunori Fujisawa, and Tozo Fujii*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


Peracid oxidations of adenine-2-d (1a) and its 9-substituted derivatives (1b-e) produced the corresponding 1-N-oxides (3a-e) in fair yields. Methylations of 9-methyl- (3b) and 9-benzyladenine-2-d 1-oxide (3d) and adenosine-2-d 1-oxide (3e) with MeI in AcNMe2 afforded the corresponding 1-methoxy derivatives 5b,d and 11e in good yields. Dimroth rearrangement of 5b, 5d, and 11e gave the N6-isomers 9b, 9d, and 9e, but their isotopic purities were unsatisfactory. Unambiguous assignments of the purine-ring proton signals in the nmr spectra of the unlabeled adenines (4a-e, 6b,d, and 12e) have been made by comparison with those of the labeled species (3a-e, 5b,d, and 11e).