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Paper | Regular issue | Vol 60, No. 12, 2003, pp.2677-2684
Published online, 25th September, 2003
DOI: 10.3987/COM-03-9884
Synthesis of 2H-1,2,3-Triazolo[4,5-d]pyrimidine-5,7-diones from Uracils Using Cyclization Reaction of β-Azo-α,β-unsaturated Sulfilimines

Nobuaki Matsumoto and Masahiko Takahashi*

*Department of Materials Sciences, Faculty of Engineering, Ibaraki University, 4-12-1 Nakanarusawamachi, Hitachi, Ibaraki 316-8511, Japan


N-(Uracil-6-yl)-S,S-diphenylsulfilimine (1) prepared from uracils reacted with aryldiazonium salts to give N-(5-arylazouracil-6-yl)-S,S-diphenylsulfilimines (2), β-azo-α,β-unsaturated sulfilimines, in good yields. The azo sulfilimines (2) were converted on thermolysis into the corresponding 2H-1,2,3-triazolo[4,5-d]pyrimidine-5,7-diones (3) in good yields.