
TY  - JOUR
A1  - Collins, David J. 
A1  - Hughes, Timothy C. 
A1  - Johnson, Wynona M. 
T1  - Dihydro-1,2,4-triazin-6(1<emph type="2">H</emph>)-ones. III. Oxidation Products of 1-Methyl-3-phenyl- 4,5-dihydro-1,2,4-triazin-6(1<emph type="2">H</emph>)-one
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1999
VL  - 52
IS  - 10
SP  - 971
EP  - 976
KW  - 
UR  - https://doi.org/10.1071/CH99047 
N2  - 1-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (1) undergoes aerial oxidation to give a mixture of 1- methyl-3-phenyl-1,2,4-triazin-6(1H)-one (2) and 1-methyl-3-phenyl-1,4-dihydro-1,2,4-triazine-5,6-dione (3). The dehydro derivative (2) was cleanly prepared by the oxidation of (1) with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (ddq). The dehydro derivative (2) underwent a surprising rearrangement to the triazole (12) upon oxidation with OxoneR. Several attempts at unambiguous synthesis of the &#945;-dicarbonyl derivative (3) were unsuccessful; it was obtained, together with the 1,4-dimethyl derivative (13) by methylation of 3-phenyl-1,4- dihydro-1,2,4-triazine-5,6-dione (4) with sodium hydride and methyl iodide. 
ER  -

