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Organic & Biomolecular Chemistry
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ARTICLE
Journal Name
4,5-diphenyl-2-m-tolyl-1H-imidazole(5f)25: Colourless Solid. H NMR 55.15, 20.81, 20.74. HRMS (ESI) Calcd for C24H22N2O [M+H]+
1
DOI: 10.1039/C8OB02785D
(400 MHz, DMSO-d6) δ, ppm: 12.65 (s, 1H), 7.93 (s, 1H), 7.88 355.1810; found, 355.1806.
(d, J = 8.0 Hz, 1H), 7.56–7.18 (m, 12H), 2.38 (s, 3H). 13C NMR (100 2-(4-chlorophenyl)-4,5-dip-tolyl-1H-imidazole(5o): Colourless Solid.
MHz, DMSO-d6): 145.59, 137.80, 137.01, 130.17, 128.92, 128.61, 1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.67 (s, 1H), 8.09 (d, J = 8.4
128.35, 128.16, 127.72, 127.06, 126.50, 125.70, 122.34, 21.06.
Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 7.44 (d, J = 8.0 Hz, 2H), 7.39
2-(3-fluorophenyl)-4,5-diphenyl-1H-imidazole(5g): Colourless Solid. (d, J = 8.0 Hz, 2H), 7.25 (d, J = 8.0 Hz, 2H), ), 7.12 (d, J = 7.6 Hz, 2H),
1H NMR (400 MHz, DMSO-d6) δ, ppm: δ 12.85 (s, 1H), 8.10-7.19 (m, 2.35 (s, 3H), 2.29 (s, 3H). 13C NMR (100 MHz, DMSO-d6): 144.06,
14H). 13C NMR (100 MHz, DMSO-d6): 166.31, 163.14, 160.70, 137.09, 135.61, 132.55, 132.20, 129.23, 129.17, 128.75, 128.71,
144.25, 144.22, 132.50, 130.72, 128.41, 125.38, 121.16, 119.54, 128.16, 128.01, 126.96, 126.73, 20.82, 20.74. HRMS (ESI) Calcd for
115.79, 114.75, 111.72. HRMS (ESI) Calcd for C21H15FN2 [M+H]+ C23H20N2 [M+H]+ 359.1315; found, 359.1276.
315.1297; found, 315.1300.
2-(2-methoxyphenyl)-4,5-diphenyl-1H-imidazole(5h)26: Colourless (400 MHz, DMSO-d6) δ, ppm: 12.58 (s, 1H), 7.92 (m, 2H), 7.44-7.32
Solid. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 11.90 (s, 1H), 8.05 (m, 5H), 7.23-7.10 (m, 5H), 2.38 (s, 3H), 2.35 (s, 3H), 2.29 (s, 3H). 13
2-m-tolyl-4,5-dip-tolyl-1H-imidazole(5p): Colourless Solid. 1H NMR
C
(d, J = 7.6 Hz, 1H), 7.54–7.05 (m, 13H), 3.92 (s, 3H). 13C NMR (100 NMR (100 MHz, DMSO-d6): 145.24, 137.72, 129.12, 128.74, 128.51,
MHz, DMSO-d6): 115.96, 143.12, 136.37, 135.23, 131.21, 129.74, 128.15, 126.97, 125.63, 122.28, 21.07. HRMS (ESI) Calcd for
128.53, 128.11, 127.04, 120.55, 118.86, 111.55, 55.5.
C24H22N2 [M+H]+ 339.1861; found, 339.1857.
2-(2-bromophenyl)-4,5-diphenyl-1H-imidazole(5i): Pale white solid. 2-(3-fluorophenyl)-4,5-dip-tolyl-1H-imidazole(5q): Colourless Solid.
1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.65 (s, 1H), 7.79 (d, J = 8.0 1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.72 (s, 1H), 7.94-7.85 (m,
Hz, 1H), 7.56-7.21(m, 11H). 13C NMR (100 MHz, DMSO-d6): 144.61, 2H), 7.54-7.40 (m, 6H), 7.25-7.12 (m, 5H), 2.35 (s, 3H), 2.29 (s, 3H).
136.63, 135.10, 133.33, 131.78, 128.67, 128.18, 128.07, 127.62, 13C NMR (100 MHz, DMSO-d6): 163.65, 161.23, 143.92, 137.13,
127.13, 126.53, 121.61. HRMS (ESI) Calcd for C21H15BrN2 [M+H]+ 135.69, 132.70, 132.62, 130.80, 130.71, 129.14, 128.77, 128.18,
375.0496; found, 375.0494.
2-(benzo[d][1,3]dioxol-5-yl)-4,5-diphenyl-1H-imidazole(5j)27:
127.02, 121.12, 114.80, 114.60, 111.63, 111.40, 79.15, 20.78. HRMS
(ESI) Calcd for C23H19FN2 [M+H]+ 343.1610; found, 343.1619.
Colourless Solid. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.51 (s, 2-(2-bromophenyl)-4,5-dip-tolyl-1H-imidazole(5r): Pale white solid.
1H), 7.63-7.01 (m, 13H), 6.08 (s, 1H). 13C NMR (100 MHz, DMSO-d6): 1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.53 (s, 1H), 7.78-7-70 (m,
147.59, 147.37, 145.37, 128.26, 127.60, 127.02, 126.47, 124.61, 2H), 7.52-7.37 (m, 6H), 7.23 (d, J = 8 Hz, 2H), 7.12 (d, J = 8 Hz, 2H),
119.27, 108.52, 105.51, 101.67, 101.23.
2.34 (s, 3H), 2.29 (s, 3H). 13C NMR (100 MHz, DMSO-d6): 144.27,
4,5-diphenyl-2-(thiophen-2-yl)-1H-imidazole(5k): Colourless Solid. 136.89, 136.40, 135.50, 133.30, 132.38, 132.27, 131.76, 130.35,
1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.80 (s, 1H), 7.69-7.14 (m, 129.19, 128.73, 128.08, 127.88, 127.57, 127.41, 127.05, 121.59,
13H). 13C NMR (100 MHz, DMSO-d6):141.58, 133.86, 128.22, 79.15, 20.80, 20.75. HRMS (ESI) Calcd for C23H19BrN2 [M+H]+
127.91, 127.08, 126.60, 126.23, 124.25. HRMS (ESI) Calcd for 403.0809; found, 403.0846.
C19H14N2S [M+H]+ 303.0955; found, 303.0949.
2-phenyl-1H-phenanthro[9,10-d]imidazoles(5s)28: Colourless Solid.
2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole(5l): Yellow Solid. 1H 1H NMR (400 MHz, DMSO-d6) δ, ppm: 13.54 (s, 1H), 8.90-8.64 (m,
NMR (400 MHz, DMSO-d6) δ, ppm: 13.16 (s, 1H), 8.37 (m, 4H), 7.62 4H), 8.39-8.36 (m, 2H), 7.80-7.70 (m, 2H), 7.68-7.56 (m, 4H),
(m, 4H), 7.49 (m, 2H), 7.43 (d, J = 7.2 Hz, 1H), 7.35(m, 2H), 7.27 (d, J 7.55(m, 1H). 13C NMR (100 MHz, DMSO-d6): 149.08, 136.91, 132.82,
= 6.8 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): δ 147.02, 143.86, 130.30, 129.23, 128.93, 128.54, 127.63, 127.50, 127.12, 126.12,
138.93, 136.58, 135.07, 130.97, 130.55, 129.22, 129.01, 128.77, 125.36, 125.16, 124.06, 123.72, 122.36, 121.96.
127.61, 127.38, 126.22, 124.76. HRMS (ESI) Calcd for C21H15N3O2 2-(4-methoxyphenyl)-1H-phenanthro[9,10-d]imidazoles(5t)29:
[M+H]+ 342.1242; found, 342.1236.
Colourless Solid. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 13.33 (s,
2-phenyl-4,5-dip-tolyl-1H-imidazole(5m): Colourless Solid. 1H NMR 1H), 8.83 (m, 2H), 8.57 (m, 2H), 8.28 (m, 2H), 7.91-7. 61 (m, 4H),
(400 MHz, DMSO-d6) δ, ppm: 12.49 (s, 1H), 7.99 (m, 2H), 7.39–7.22 7.02(m, 2H). 3.86(s, 3H) 13C NMR (100 MHz, DMSO-d6): 160.15,
(m, 8H), 7.16 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 7.6 Hz, 2H), 2.26 (s, 3H), 149.26, 131.32, 127.69, 127.42, 127.00, 125.01, 123.79, 122.99,
2.20 (s, 3H). 13C NMR (100 MHz, DMSO-d6): 145.14, 136.96, 136.85, 121.84, 114.32, 113.75, 55.28.
135.48, 132.39, 130.39, 129.15, 128.72, 128.61, 128.20, 128.07,
127.84, 126.96, 125.08. HRMS (ESI) Calcd for C23H20N2 [M+H]+
325.1704; found, 325.1700.
Acknowledgements
S. S. would like to thank the Department of Science and
2-(4-methoxyphenyl)-4,5-dip-tolyl-1H-imidazole(5n):
Colourless
Technology (DST), Govt. of India for DST-INSPIRE fellowship
(IF150745). The authors thank DST-FIST for the instruments facilities
at School of Chemistry, Bharathidasan University, India.
Solid. 1H NMR (400 MHz, DMSO-d6) δ, ppm: 12.41 (s, 1H), 8.01
(d, J = 8.8 Hz, 2H), 7.44 (d, J = 8.0 Hz, 2H), 7.38 (d, J = 8.0 Hz, 2H),
7.24 (d, J = 7.6 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 7.04 (d, J = 8.8 Hz,
2H), 3.81 (s, 3H), 2.34 (s, 3H), 2.28 (s, 3H). 13C NMR (100 MHz,
DMSO-d6): 159.27, 145.26, 136.77, 136.48, 135.34, 132.54, 129.12,
128.69, 128.35, 128.10, 127.22, 126.94, 126.59, 123.20, 114.01,
Notes and references
1
(a) M. R. Grimmett, in Comprehensive Heterocyclic
Chemistry, eds. A. R. Katritzky and C. W. Rees, Pergamon,
6 | J. Name., 2012, 00, 1-3
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