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Coupling of dimedone with the diazonium salt of 4‐aminoantipyrine afforded 2,3‐dimethyl‐4‐[2‐(5,5‐dimethyl‐ 2,6‐dioxocyclohex‐2‐ylidend)‐hydrazino]‐5‐oxo‐1‐phenylpyrazoline (3). Reaction of 3 with excess phenylhydrazine gave the mixed trishydrazone derivative 4. Treatment of 3 with hydroxylamine produced the bisoxime 5 which upon dehydrative cyclization with acetic anhydride gave the corrsponding tetrahydrobenzo[d][1,2,3]triazole derivative 7. A one‐pot synthesis of 7 was done by reacting 3 with hydroxylamine hydrochloride in pyridine, followed by heatment with acetic anhydride.

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Two derivatives of 2-(4-acetylanilino)quinolines (IIIa, b) were synthesized as scaffolds for synthesis of open chalcone analogues (Va-f) through Claisen-Schmidt condensation with a set of aromatic aldehydes (IVa-d). Derivatives (Va, b) were further manipulated into cyclic alpha,beta-unsaturated ketones by Michael-addition of acetylacetone and ethylacetoacetate affording derivatives (VI-VII). Deethoxycarboxylation of derivatives (VIIa, b) afforded cyclohexenons (VIIIa, b) allowing formation of a mini library of alpha,beta-unsaturated ketones for screening their anticancer and synergistic anticancer effect with doxorubicin using colon cancer cell line (Caco-2). Two open enones, (Vb) and (Ve), showed significant anticancer activity with IC50 of 5.0 and 2.5 microM respectively. Only one cyclic enone, (VIa) showed synergistic anticancer activity with doxorubicin at 10 microM.

Coupling of dimedone with the diazonium salt of 4-aminoantipyrine afforded 2,3-dimethyl-4-[2-(5,5-dimethyl-2,6-dioxocyclohex-2-ylidend)-hydrazino]-5-oxo-1-phenylpyrazoline (3). Reaction of 3 with excess phenylhydrazine gave the mixed trishydrazone derivative 4. Treatment of 3 with hydroxylamine produced the bisoxime 5 which upon dehydrative cyclization with acetic anhydride gave the corrsponding tetrahydrobenzo [d][1,2,3]triazole derivative 7. A one-pot synthesis of 7 was done by reacting 3 with hydroxylamine hydrochloride in pyridine, followed by heatment with acetic anhydride.