Studies on the preparation and exchange reactions of 5‐deuterated uracils

Daniel V. Santi, Curtis F. Brewer, Debora Farber

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28 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)903-910
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume7
Issue number4
DOIs
Publication statusPublished - 1970
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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