SYNTHESIS AND REACTION OF SOME 6‐SUBSTITUTED PYRIMIDINE NUCLEOSIDES*
- 1 August 1975
- journal article
- Published by Wiley in Annals of the New York Academy of Sciences
- Vol. 255 (1) , 121-130
- https://doi.org/10.1111/j.1749-6632.1975.tb29218.x
Abstract
Treatment of 5-bromouridines with sodium cyanide afforded 6-cyanouridines. Further treatment of the 6-cyano derivatives with cyanide ion at higher temperature gave the 5-cyanouridines. The 6-cyano group was transformed to thioamido, carboxy, chloromethyl cyanomethyl, carboxymethyl, and methyl group, respectively. 5-Bromocytidines were also converted to the 6-cyanocytidines, from which cytidine 6-carboxylic acid was derived. The cyano group of 6-cyanocytidines has a leaving ability toward nucleophilic substitution reactions. The circular dichroic spectra of various 6-substituted pyrimidine nucleosides showed positive Cotton effect at B2u region, which were in contrast to the reported negative bands in 6-methyl-uridine or-cytidine.Keywords
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