A general synthesis of 4-substituted 1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridines
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 125-129
- https://doi.org/10.1039/p19750000125
Abstract
The trimethylsilyl derivative (I) of 4,6-dichloroimidazo[4,5-c]pyridine was condensed with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (II) to afford, after removal of protecting groups, the isomeric 1- and 3-(β-D-ribofuranosyl) derivatives [(V) and (VI)]. The reaction of the nucleoside (V) with a variety of nucleophiles afforded various 4-substituted 6-chloro-derivatives. Removal of the 6-chloro-group by catalytic hydrogenation provided a general synthesis of 4-substituted 1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridines, including the 4-amino-compound (3-deaza-adenosine).Keywords
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