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T. S. Chundawat et al.
Letter
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(38) General Procedure for the Synthesis of Substituted 2,4,5-
Triphenylimidazoles
A mixture of benzil (1, 2.3 mmol), benzaldehyde (2, 2.3 mmol),
NH4OAc (3, 2.8 mmol), and the catalytic amount of Ni-C (10
mol%) in EtOH (2 mL) were taken in a microwave tube (10 mL)
and exposed to microwave irradiation for 15–30 min. The com-
pletion of reaction was monitored by TLC. After completion of
reaction, EtOAc was added to the reaction mixture, and the cat-
alyst was recovered by filtration. After that organic layer was
washed with H2O, dried over Na2SO4, and concentrated under
reduced pressure. The obtained residues were purified by
column chromatography using silica gel (100–200 mesh size) in
20% EtOAc–hexane as eluent to provide the desired compound 4.
Representative Spectroscopic Data
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Compound 4g: 1H NMR (400 MHz, DMSO): δ = 12.98 (s, 1 H),
8.29–8.27 (d, J = 8.79 Hz, 2 H), 7.85–7.83 (d, J = 8.05 Hz, 2 H),
7.55–7.36 (m, 7 H), 7.32–7.30 (t, J = 7.32 Hz, 2 H), 7.23–7.21 (t,
J = 7.32 Hz, 1 H). 13C NMR (100 MHz, DMSO): δ = 144.01, 137.76,
134.84, 133.99, 130.76, 129.25, 128.76, 127.93, 127.14, 126.78,
125.80, 125.60, 123.00. IR (KBr): ν = 3432, 3025, 1621, 1325,
1131, 1064, 697 cm–1. ESI-MS: m/z = 365.54 [M + 1]. Anal. Calcd
for C22H15F3N2: C, 72.52, H, 4.15; N, 7.69. Found: C, 72.31; H,
3.94; N, 7.64.
Compound 4i: 1H NMR (400 MHz, DMSO): δ = 12.63 (s, 1 H),
7.97–7.94 (dd, 1 H), 7.74–7.71 (dd, 1 H), 7.49–7.38 (m, 7 H),
7.28–7.26 (t, J = 7.32 Hz, 2 H), 7.19–7.17 (t, J = 7.32 Hz, 2 H).
13C NMR (100 MHz, DMSO): δ = 155.47, 152.99, 150.29, 139.13,
137.43, 134.71, 130.50, 128.66, 127.14, 126.74, 116.99, 115.65,
107.31. IR (KBr): ν = 3442, 3068, 1614, 1604, 1490, 1185, 1061,
696 cm–1. ESI-MS: m/z = 351.29 [M + 1]. Anal. Calcd for
C
21H13F3N2: C, 71.99; H, 3.74; N, 8.00. Found: C, 71.63; H, 3.78;
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N, 7.71.
Compound 4r: 1H NMR (400 MHz, DMSO): δ = 12.89 (s, 1 H),
7.76–7.74 (d, J = 6.59 Hz, 2 H), 7.54–7.38 (m, 8 H), 7.32–7.28 (t,
J = 7.32 Hz, 2 H), 7.24–7.21 (m, 1 H). 13C NMR (100 MHz,
DMSO): δ = 163.95, 161.65, 143.23, 137.58, 134.70, 133.50,
130.65, 128.78, 127.15, 108.12, 103.42. IR (KBr): ν = 3425, 3076,
1626, 1467, 1213, 1074, 693 cm–1. ESI-MS: m/z = 333.14 [M + 1].
Anal. Calcd for C21H14F2N2: C, 75.89; H, 4.25; N, 8.43. Found: C,
75.61; H, 3.89; N, 8.20.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, 404–408