Reactions with Halogenated Compound: Synthesis of Several New Pyrazolo[3,2-c] triazine and 2-Benzenesulfonylglyoxal arylhydrazone Derivatives

Diazotized primary artomatic amines 4 coupled with the ketosulfones 1-3 in ethanol in the presence of sodium acetate at $0^\circ{C}$ to afford the corresponding bydrazones 5-7. Also diazotized 3-aminopyrazoles 14 coupled with 1-3 in ethanolic sodium acetate to give the pyrazolotriazines 18-20 in good yields. Compounds 5-7 and 18 can also be obtained from the reaction of hydraziodoyl halides 8-10 and 21 with sodium benzenesultinate. The hydrazones 11-13 can easy be oxidized to the hydrazones 5-7, using hydrogen peroxide in acetic acid.