5-Chloro-3-methyl-1-phenyl-1-pyrazole-carboxaldehyde(1
) was reacted with hydrazine hydrate and thiosemicarbazide to afford the corresponding hydrazones 2 and thiosemicarbazones 4. The latter compounds were used to obtain the pyrazole derivatives
3, 5-7. A series of azines 8a-e were obtained by reacting 2 with aromatic aldehydes. Potassium permanganate oxidation of1 gave the acid 9, which was transformed into the corresponding acid azide 11 then used to prepare diverse urea derivatives 13-18 via Curtius reaction