Purines. LXVII. An Alternative Synthesis of Adenine 7-Oxide : N-Oxidation of the Adenine Ring Utilizing Blocking/Deblocking at the 1-Position

Tozo FUJII; Kazuo OGAWA; Tohru SAITO; Taisuke ITAYA; Tadamasa DATE; Kimio OKAMURA

doi:10.1248/cpb.43.321

Tozo FUJII, Kazuo OGAWA, Tohru SAITO, Taisuke ITAYA, Tadamasa DATE, Kimio OKAMURA

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Keywords: 1-benzyladenine 7-oxide, X-ray analysis, adenine 7-oxide synthesis, m-chloroperoxybenzoic acid oxidation, 1-benzyladenine N-oxidation, debenzylation nonreductive

JOURNAL FREE ACCESS

1995 Volume 43 Issue 2 Pages 321-324

DOI https://doi.org/10.1248/cpb.43.321

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Abstract

Oxidation of 1-benzyladenine (12) with m-chloroperoxybenzoic acid in MeOH or in MeOH-0.5 M phosphate buffer (pH 6.6) has been found to afford 1-benzyladenine 7-oxide (13) as the main product. Nonreductive debenzylation of 13 gave adenine 7-oxide (14) in 63% yield. The structure of 13 was unequivocally established by an X-ray crystallographic analysis.

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