SHARGHI ET AL.
9 of 10
azide and amines as starting materials using the
heterogeneous nanocatalyst. Herein, we examined the
synthesis of 2‐(4‐methoxyphenyl)‐2H‐indazole using
2‐bromobenzaldehyde (1.0 mmol), p‐anisidine (1.1 mmol)
and sodium azide (2.0 mmol) in DMSO (1.0 ml) in the
presence of 5.0 mol% catalyst at 120°C (Scheme 2).
The progress of the reaction was monitored by TLC.
The product (2‐(4‐methoxyphenyl)‐2H‐indazole) could
be isolated in good yield after 12 h.
During our optimization studies, the effect of tempera-
ture, solvent and amount of catalyst for this three‐
component reaction was investigated. We found that the
temperature, solvent and amount of catalyst play a signif-
icant role in terms of the isolated yield and the reaction
rate. Among various conditions used, the best result was
obtained using 5.0 mol% of catalyst in DMSO as a solvent
at 120°C (Table 3).
In the next step, we studied the scope of the reaction
with various anilines for the synthesis of 2H‐indazoles
under the optimized conditions (Table 4). The presented
protocol has the ability to tolerate other functional
groups, such as methyl, methoxy and halogen, on the ani-
lines. The results are presented in Table 4. Also, aliphatic
amines such as tert‐butylamine are applicable for the syn-
thesis of 2H‐indazoles using the presented procedure
(Table 4, entry 8).
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ORCID