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

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

Research output: Contribution to journalArticle

28 Citations (Scopus)

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
StatePublished - 1970
Externally publishedYes

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Uracil
Deuterium
Anions
Protons
Hydrolysis
Derivatives
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Studies on the preparation and exchange reactions of 5‐deuterated uracils. / Santi, Daniel V.; Brewer, Curtis F.; Farber, Debora.

In: Journal of Heterocyclic Chemistry, Vol. 7, No. 4, 1970, p. 903-910.

Research output: Contribution to journalArticle

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