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Synthesis 1999; 1999(4): 655-663
DOI: 10.1055/s-1999-3437
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Facile and General Syntheses of 3- and/or 5-Substituted 7-β-d-Ribofuranosyl-7H-[1,2,4]triazolo[3,4-i]purines as a New Class of Potential Xanthine Oxidase Inhibitors

Tomohisa Nagamatsu* , Hiroo Yamasaki, Toshihiko Akiyama, Sachiko Hara, Kenya Mori, Hitoshi Kusakabe
  • *Faculty of Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700-8530, Japan; Fax +81(86)2 51 79 26; E-mail: nagamatsu@pheasant.pharm.okayama-u.ac.jp
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Publication Date:
31 December 1999 (online)

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Novel, general, and facile syntheses of 3- and/or 5-substituted 7-β-d-ribofuranosyl-7H-[1,2,4]triazolo[3,4-i]purines (5-8) via compounds 4 as a new class of potential xanthine oxidase inhibitors are described. The key intermediates 4b-j were prepared by oxidative cyclization of the aldehyde hydrazones 3a-i, derived from 6-hydrazino-2-iodo-9-(2′,3′,5′-tri-O-acetyl-β-d-ribofuranosyl)-9H-purines (2) and an appropriate aldehyde, with diethyl azodicarboxylate (DEAD) (Method A) or lead tetraacetate (Method B) in good yields. The intermediates 4a-j were also synthesized from heating of 2 with triethyl orthoesters (Method C) or with aldehydes and DEAD in one-pot reactions (Method D).

purine nucleosides - s-triazolo[3,4-i]purine nucleosides - oxidative cyclization - xanthine oxidase inhibitor

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