N. Jacobsen, S. Rose
1987
Citations
0
Influential Citations
8
Citations
Journal
Australian Journal of Chemistry
Abstract
The methylation of various 3- and 6-substituted l, 2, 4-triazin-5(2H)-one derivatives yield new zwitterionic N 1 methylation products in addition to the previously reported 2-, 4- and O-methyl isomers. Specifically, 3-phenyl-l, 2, 4-triazin-5(2H)one and hs 6-methyl and 6-phenyl derivatives gave l-methyl-3-phenyl-l, 2, 4-triazinium-5-olate, 1, 6-dimethyl-3-phenyl-1, 2, 4-triazinium-5-olate and 1-methyl-3, 6-diphenyl-1, 2, 4-triazinium-5-olate, respectively, upon methylation. A new hindered derivative, 3, 6-di-t-butyl-l, 2, 4-triazin-5(2H)-one, did not yield a zwitterion upon methylation but instead gave the 2- and O-methyl isomers. In all cases, carbon-13 nuclear magnetic resonance spectroscopy employing both proton-coupled and -decoupled spectra was used to identify the sites of methylation.