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

Preparation of 1,2,4,5-tetrasubstituted imidazoles (8a–j) via the reaction of benzil (5a), aldehydes (4a–f), amines (7a–e) and NH4OAc catalyzed by 3aa.

graphic file with name c8ra02755b-u2.jpg
Entry Ar Ar′ Time (min) Yield (%) mp
Found Reported
1 C6H5 C6H5 5 98 220–222 219–221 (ref. 18)
2 4-CH3–C6H4 C6H5 7 96 188–189 185–187 (ref. 18)
3 4-CH3O–C6H4 C6H5 5 96 183–185 183–185 (ref. 18)
4 4-Cl–C6H4 C6H5 6 95 161–162 160–163 (ref. 24)
5 4-Br–C6H4 C6H5 7 96 209–211 207–211 (ref. 18)
6 C6H5 C6H4–CH2 5 98 160–164 160–164 (ref. 24)
7 C6H5 4-CH3O–C6H4–CH2 5 98 150–153 150–154 (ref. 24)
8 4-CH3–C6H4 4-CH3–C6H4–CH2 5 98 132–135 132–135 (ref. 24)
9 4-F–C6H4 4-F–C6H4–CH2 6 96 158–161 158–162 (ref. 24)
10 4-CH3O–C6H4 4-CH3O–C6H4–CH2 6 96 152–154 152–154 (ref. 24)
a

The mixture of 4a–f (1 mmol), 7a–e (1 mmol), 5a (1 mmol), NH4OAc (1 mmol) and 3a (5 mol%) in water (5 mL) was sonicated at 60 °C.