Table 2.

The one-pot pseudo-five-component production of bis (pyrazolyl)methanes catalyzed by ZnFe₂O₄@SiO₂@APTES@DHBS-Cu.

Entry	Ar	Product	Time (min)	Yield (%)b	TON	TOF (h−1)	M.P. (°C)
							Measured	Literature
1	C6H5		45	92	102	136	169–176	171–17755
2	4-ClC6H5		60	96	106	106	214–217	213–21855
3	2,6-ClC6H5		50	70	77.7	97	247–251	248–25356
4	2,4-ClC6H5		45	84	93.3	124	220–226	223–22757
5	2-BrC6H5		60	92	102	102	197–205	198–20655
6	4-MeC6H5		60	93	155	155	200–207	203–20955
7	4-MeOC6H5		65	89	98.8	91.4	170–178	173–17955
8	4-OHC6H5		55	91	101	112	151–158	153–15855
9	3,4-MeOHC6H5		95	91	101	67	192–195	193–19755
10	2-NO2C6H5		45	88	97.7	129	223–227	225–22855
11	3-NO2C6H5		70	85	94.4	85.4	150–154	151–15455

^aIsolated yield.

^bReaction conditions: phenylhydrazine (2 mmol), ethyl acetoacetate (2 mmol), aromatic aldehydes (1 mmol), ZnFe₂O₄@SiO₂@APTES@DHBS-Cu in EtOH (2 mL) under reflux conditions.