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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 ).