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

Santi Daniel V. | Zendy; Brewer Curtis F. | Zendy; Farber Debora | Zendy

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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

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.

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