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Synlett 1997; 1997(12): 1409-1410
DOI: 10.1055/s-1997-1073
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A New Synthesis of Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-diones by Oxidative N-N Bond Formation of 6-Amino-5-(N-aryliminomethyl)uracils Using Iodobenzene Diacetate

Hironao Sajiki, Kazuyuki Hattori, Magoichi Sako, Kosaku Hirota*
  • *Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Gifu 502, Japan, FAX +81-58-237-5979, E-mail hirota@gifu-pu.ac.jp
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Publication Date:
31 December 2000 (online)

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The intramolecular cyclizations of 6-amino-5-(N-aryliminomethyl)-1,3-dimethyluracils (2) involving the N-N bond formation were effected via a hypervalent iodine oxidation using iodobenzene diacetate. This method enabled a facile synthesis of 2-aryl-5,7-dimethylpyrazolo[3,4-d]pyrirnidine-4,6(5H,7H)-diones (3) in moderate to excellent yields. The primary advantage of this N-N bond formation method is that various 2-aryl-substituted pyrazolo[3,4d]pyrimidines can be provided under mild oxidative conditions.

pyrazolo[3,4-d]pyrimidine - N-N bond formation - iodobenzene diacetate - 6-amino-5-(N-aryliminomethyl)uracil - synthesis