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SYNTHESIS AND REACTION OF SOME 6‐SUBSTITUTED PYRIMIDINE NUCLEOSIDES *
Author(s) -
Ueda Tohru,
Inoue Hideo,
Matsuda Akira
Publication year - 1975
Publication title -
annals of the new york academy of sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.712
H-Index - 248
eISSN - 1749-6632
pISSN - 0077-8923
DOI - 10.1111/j.1749-6632.1975.tb29218.x
Subject(s) - library science , christian ministry , citation , computer science , political science , law
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.