Reactions of triacetylmethane with monosubstituted hydrazines and amidine analogues. Syntheses of 4-acetyl-3,5-dimethylpyrazole amidinohydrazone and 1,3,5-triazine derivatives

Triacetylmethane ( 1 ) reacts with amidinohydrazines in acidic medium to afford 4-acetyl-3,5-dimethylpyrazole amidinohydrazone derivatives 2,4 . However, a similar reaction of 1 with thiosemicarbazide or semicarbazide led mainly to 3,5-dimethylpyrazole ( 6 ). The great propensity of 1 to hydrolysis accounts for this last transformation, as well as for the fact that with guanidine it led to 2-amino-4,6-dimethylpyrimidine ( 10 ) and with S-methylisothiourea it provided the unexpected 2-amino-4-methyl-6-methylthio-1,3,5-triazine ( 11 ).