Synthesis of 1,2,4,5-tetrasubstituted imidazole derivatives using the ZSM-11 zeolite (48 h) catalyst under solvent-free conditionsa.
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Entry | R1 | R2 | Product | Yieldb (%) | M.p. (obsd) (°C) | M.p. (lit.) (°C) |
1 | 4-CH3 | C6H5 | 5a | 92 | 184–186 | 185–187 ref. 58 |
2 | 2-OMe | C6H5 | 5b | 94 | 208–210 | 207–211 ref. 59 |
3 | C6H5 | 4-CH3 | 5c | 95 | 284–285 | 285–289 ref. 6 |
4 | 4-OH | C6H5 | 5d | 92 | 280–282 | 282–284 ref. 11 |
5 | 4-Cl | C6H5 | 5e | 93 | 160–161 | 160–163 ref. 60 |
6 | C6H5 | C6H5 | 5f | 95 | 215–217 | 216–218 ref. 61 |
7 | 4-OCH3 | C6H5 | 5g | 92 | 182–184 | 183–185 ref. 58 |
8 | 4-NO2 | 4-Me | 5h | 95 | 220–222 | 219–220 ref. 51 |
9 | 4Cl | 4-OCH3 | 5i | 94 | 182–184 | 180–183 ref. 62 |
10 | 4Cl | 2,4-Dichloro | 5j | 92 | 264–66 | — |
Reaction conditions: synthesis of 1,2,4,5-tetrasubstituted imidazole derivatives using benzil (1.0 mmol), aldehyde (1.0 mmol), aniline (1.0 mmol), NH4OAc (3.0 mmol), ZSM-11 zeolite catalyst of time 48 h (0.05 g).
Isolated yield in 30 minutes.