R. Milcent et al., NEW GENERAL-SYNTHESIS OF TETRAHYDRO-1,2,4,5-TETRAZIN-3(2H)-ONE DERIVATIVES AND STABLE 3,4-DIHYDRO-3-OXO-1,2,4,5-TETRAZIN-1(2H)-YL RADICAL DERIVATIVES, Journal of heterocyclic chemistry, 31(2), 1994, pp. 319-324
Reactions of 2-chloroformylhydrazones of aromatic aldehydes or ketones
2 with various hydrazines were converted to monocarbonohydrazone deri
vatives 3 or 5 and/or tetrahydro-1,2,4,5-tetrazin-3(2H)-one derivative
s 6, 7. By oxidation with lead dioxide, compounds 6 were transformed i
nto stable 3,4-dihydro-3-oxo-1,2, 4,5-tetrazin-1(2H)-yl radical deriva
tives 8.