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 language | English (US) |
|---|---|
| Pages (from-to) | 903-910 |
| Number of pages | 8 |
| Journal | Journal of Heterocyclic Chemistry |
| Volume | 7 |
| Issue number | 4 |
| DOIs | |
| State | Published - 1970 |
| Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry