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. 2022 Apr 29;12(21):13087–13092. doi: 10.1039/d2ra00331g

Substrate scope of the synthesis of multi-substituted pyrazolesa.

graphic file with name d2ra00331g-u2.jpg
Entry 1 (R1, R2) 2 (Ar) Product, yieldb
1 Ph, Ph 4-BrC6H4 3a, 54%; 4a, 29%
2 Ph, Ph 4-ClC6H4 3b, 59%; 4b, 28%
3 Ph, Ph 4-OMeC6H4 3c, 48%; 4c, 27%
4 3-FC6H4, Ph 4-BrC6H4 3d, 57%; 4d, 24%
5 3-FC6H4, Ph 4-ClC6H4 3e, 59%; 4e, 22%
6 3-FC6H4, Ph 4-OMeC6H4 3f, 50%; 4f, 25%
7 4-FC6H4, Ph 4-ClC6H4 3g, 55%; 4g, 27%
8 4-FC6H4, Ph 4-BrC6H4 3h, 50%; 4h, 27%
9 3-ClC6H4, Ph 4-ClC6H4 3i, 54%; 4i, 27%
10 3-ClC6H4, Ph 4-BrC6H4 3j, 44%; 4j, 29%
11 3-ClC6H4, 4-OMeC6H4 4-OMeC6H4 3k, 52%; 4k, 29%
12 2-BrC6H4, 4-OMeC6H4 4-ClC6H4 3l, 48%; 4l, 47%
13 2-Np, 4-OMeC6H4 4-ClC6H4 3m, 56%; 4m, 30%
14 2-Np, 4-OMeC6H4 4-OMeC6H4 3n, 54%; 4n, 32%
15 2-Np, Ph 4-ClC6H4 3o, 54%; 4o, 31%
16 3-FC6H4, 2,4,6-triMeC6H2 4-ClC6H4 3p, 67%; 4p, 29%
17 4-FC6H4, 2,4,6-triMeC6H2 4-ClC6H4 3q, 65%; 4q, 30%
18 4-FC6H4, 2,4,6-triMeC6H2 4-OMeC6H4 3r, 60%; 4r, 28%
19 2-Thiophenyl, Ph 4-ClC6H4 3s, 59%; 4s, 21%
20 Ph, Ph 4-NO2C6H4 3t, 52%; 4t, 24%
21 Ph, 3-CF3C6H4 4-NO2C6H4 3u, 45%; 4u, 29%
a

The reaction of 1 (0.2 mmol) with 2 (0.24 mmol) was carried out in the presence of K2CO3 (0.5 mmol) in EtOH (2.5 mL) at room temperature for 12 h.

b

Isolated yield.