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. 2018 May 3;8(29):16392–16399. doi: 10.1039/c8ra02755b

Synthesis of 2,4,5-trisubstituted imidazoles (6a–p) via the reaction of benzil (5a), aldehydes (4a–p) and NH4OAc catalyzed by 3aa.

graphic file with name c8ra02755b-u1.jpg
Entry Ar Time (min) Yield (%) mp
Found Reported
1 C6H5 5 99 272–273 272–274 (ref. 18)
2 4-CH3O–C6H4 4 99 230–232 229–231 (ref. 18)
3 4-HO–C6H4 4 98 234–236 232–234 (ref. 18)
4 4-Me2N–C6H4 7 97 255–227 255–256 (ref. 18)
5 2-HO–C6H4 6 95 202–204 201–203 (ref. 18)
6 3,4-(MeO)2C6H3 6 98 214–216 213–216 (ref. 19)
7 4-CH3–C6H4 8 95 230–232 226–227 (ref. 18)
8 4-F–C6H4 8 96 260–262 262–264 (ref. 20)
9 4-Br–C6H4 5 98 265–266 261–263 (ref. 21)
10 2-Cl–C6H4 5 98 192–193 199–201 (ref. 21)
11 4-Cl–C6H4 7 97 263–265 262–263 (ref. 22)
12 2,4-Cl2C6H3 6 96 171–173 172–173 (ref. 20)
13 4-NO2–C6H4 7 96 242–243 239–242 (ref. 21)
14 2-Thienyl 5 99 255–257 254–256 (ref. 18)
15 2-Furyl 5 98 201–202 201–203 (ref. 21)
16 CH3 6 99 244–246 243–245 (ref. 23)
a

The mixture of 4a–p (1 mmol), 5a (1 mmol), NH4OAc (2.5 mmol) and 3a (5 mol%) in water (5 mL) was sonicated at 60 °C.