Pyrazine nucleoside analogs. Synthesis and reactions of some 5-thio-substituted pyrazines

5-Benzylthio-1,2-dihydro-2-oxopyrazine (8) was prepared from 2-amino-5-bromopyrazine by sequential treatment with sodium thiobenzylate and diazotization. Condensation of the silyl derivative of 8 with a protected 2-deoxyribofuranosyl chloride gave α and β anomers of 5-benzylthiopyrazine nucleosides. Reaction of 2,5-dichloropyrazine 4-oxide with sodium thiobenzylate followed by hydrolysis gave 5-benzylthio-1,2-dihydro-2-oxopyrazine 4-oxide (16).

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