One-pot synthesis of trisubstituted imidazoles in the presence of MC–SO3H catalysta.
Comp. | α-Diketone | R | Yield (%) | Mp (°C) | Ref. |
---|---|---|---|---|---|
3a | 1a | 4-Br–C6H4 | 96 | 251–253 | 249–251 (ref. 49) |
3b | 1a | 4-F–C6H4 | 95 | 187–189 | 189–190 (ref. 50) |
3c | 1a | 3-F–C6H4 | 91 | >260 | 284–285 (ref. 50) |
3d | 1a | 2,6-diCl–C6H4 | 83 | 231–232 | 229–230 (ref. 51) |
3e | 1a | 4-CN–C6H4 | 97 | >260 | 259–261 (ref. 49) |
3f | 1a | 3-NO2–C6H4 | 90 | >260 | 301–303 (ref. 49) |
3g | 1a | 4-OMe–C6H4 | 89 | 222–224 | 219–221 (ref. 49) |
3h | 1a | 2-Thiophene | 87 | 254–256 | 257–259 (ref. 49) |
3i | 1b | C6H4 | 89 | >260 | 311–313 (ref. 52) |
3j | 1b | 4-Br–C6H4 | 95 | >260 | 280–282 (ref. 52) |
3k | 1b | 4-Cl–C6H4 | 93 | >260 | 274–276 (ref. 52) |
3l | 1b | 2-Cl–6-F–C6H4 | 87 | >260 | — |
3m | 1b | 4-NO2–C6H4 | 93 | >260 | 335–337 (ref. 52) |
3n | 1b | 2-NO2–C6H4 | 94 | >260 | 267 (ref. 53) |
3o | 1b | 4-iPr–C6H4 | 90 | >260 | — |
3p | 1b | 4-Ph–C6H4 | 94 | >260 | 258–259 (ref. 54) |
3q | 1b | 2-OH–5-NO2–C6H4 | 88 | >260 | 259–260 (ref. 55) |
3r | 1b | 4-OMe–C6H4 | 91 | 252–254 | 254–255 (ref. 56) |
Reaction conditions: 4-bromobenzaldehyde (1 mmol), benzil (1 mmol), ammonium acetate (3 mmol), EtOH (4 mL).