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Studies on the preparation and exchange reactions of 5‐deuterated uracils
Author(s) -
Santi Daniel V.,
Brewer Curtis F.,
Farber Debora
Publication year - 1970
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.5570070425
Subject(s) - chemistry , hydrogen–deuterium exchange , deuterium , uracil , base (topology) , catalysis , medicinal chemistry , organic chemistry , hydrogen , biochemistry , quantum mechanics , dna , mathematical analysis , physics , mathematics
Abstract The mechanism of base catalyzed proton exchange at the 5‐position of uracil and its N ‐methylated derivatives has been studied. These reactions proceed by addition — elimination across the 5,6‐double bond when the 1‐nitrogen is substituted with a methyl group, or with anchimeric assistance of the N ‐1 anion if the 1‐position is unsubstituted. The base catalyzed hydrolyses of 1,3‐dimethyluracil and 3‐methyluracil also appear to proceed through hydrated intermediates. A facile method for an acid catalyzed preparation of 5‐deuterated uracils is described as well as a simple and accurate method for analysis of deuterium content.