Deuterium exchange of C-methyl protons in lumazine derivatives
- 15 January 1970
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 48 (2) , 263-270
- https://doi.org/10.1139/v70-041
Abstract
Proton magnetic resonance spectroscopy has been used to examine the deuterium exchange of the methyl protons in two lumazine derivatives. The exchange occurs at the C-7 methyl group in 6,7,8-trimethyllumazine (2) and at the C-6 methyl group in 1,7-dihydro-6,7,8-trimethyllumazine (3). The former reaction is subject to both general acid- and general base-catalysis but the latter only to general acid-catalysis. Plausible mechanisms for the reactions of both compounds are advanced, involving in the case of 3, acid-catalyzed addition of water across the C6—N5 double bond.Keywords
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