Pyrazine nucleoside analogs. Synthesis and reactions of some 5‐thio‐substituted pyrazines | Zendy

Tuntiwachwuttikul Pittaya | Zendy; Bardos Thomas J. | Zendy; Bobek Miroslav | Zendy

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

Author(s) -

Tuntiwachwuttikul Pittaya,

Bardos Thomas J.,

Bobek Miroslav

Publication year - 1991

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570280450

Subject(s) - chemistry , pyrazine , thio , hydrolysis , derivative (finance) , organic chemistry , silylation , sodium , phosphoryl chloride , oxide , benzoyl chloride , nucleoside , medicinal chemistry , stereochemistry , catalysis , financial economics , economics

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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