Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by Fe3O4/SO3H@zeolite-Ya.
Entry | R | Product | Time (min) | Yieldb (%) | mprep/mplit. (°C) |
---|---|---|---|---|---|
1 | H | 4a | 45 | 98 | 270–272 (271–273)11 |
2 | 2-NO2 | 4b | 65 | 97 | 226–228 (226–227)37 |
3 | 3-NO2 | 4c | 20 | 85 | 268–270 (267–268)11 |
4 | 3-OH, 4-OMe | 4d | 45 | 93 | 215–217 (215–217)11 |
5 | 2-OMe | 4e | 65 | 97 | 200–202 (209–211)38 |
6 | 3,4-OMe | 4f | 45 | 98 | 214–216 (214–216)11 |
7 | 3-OH | 4g | 35 | 97 | 259–261 (259–260)11 |
8 | 4-OMe | 4h | 60 | 95 | 226–228 (230–231)11 |
9 | 2-Cl | 4i | 65 | 95 | 168–170 (196–199)37 |
10 | 2,3-Cl | 4j | 50 | 98 | 254–256 (194–197)37 |
11 | 2,4-Cl | 4k | 50 | 98 | 168–170 (175–178)37 |
12 | 4-Cl | 4l | 35 | 97 | 260–262 (260–262)11 |
13 | 3-Br | 4m | 30 | 98 | 301–303 (302–303)11 |
14 | 4-Me | 4n | 45 | 96 | 231–233 (230–232)11 |
Reaction conditions: benzil (1 mmol), aldehyde (1 mmol), ammonium acetate (2 mmol) and Fe3O4/SO3H@zeolite-Y (0.020 g) in EtOH at 80 °C.
Isolated yield.