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128.2, 127.8, 127.5, 126.8, 126.8, 34.6; HRMS (ESI) m/z: calcd for
5-(2-Chlorophenyl)-4-(3,4-dimethoxyphenyl)-2-phenyl-1H-
imidazole (4g). White solid (117.2 mg, 91% yield); mp 205–
207 ꢀC; 1H NMR (500 MHz, CDCl3): d (ppm) 10.81 (br s, 1H, NH),
7.85 (d, J ¼ 6.7 Hz, 2H, ArH), 7.38 (d, J ¼ 7.9 Hz, 1H, ArH), 7.31–
7.27 (m, 4H, ArH), 7.21 (td, J ¼ 1.6, 15.5 Hz, 1H, ArH), 7.14 (td, J
¼ 0.9, 15.0 Hz, 1H, ArH), 6.91 (d, J ¼ 7.4 Hz, 2H, ArH), 6.65 (d, J
C
22H19N2 [M + H]+ 311.1543, found 311.1543.
4,5-Diphenyl-1H-imidazole (3ab).91 White solid (63.3 mg,
61% yield); mp 231–233 ꢀC; 1H NMR (500 MHz, DMSO-d6):
d (ppm) 12.48 (s, 1H, NH), 7.78 (s, 1H, H-2), 7.49–7.20 (m, 10H,
ArH); 13C NMR (75 MHz, DMSO-d6): d (ppm) 136.6, 136.1, 136.0,
131.8, 129.2, 128.7, 128.3, 128.0, 127.5, 126.8, HRMS (ESI) m/z:
calcd for C15H13N2 [M + H]+ 221.1073, found 221.1071.
¼ 8.4 Hz, 1H, ArH), 3.75 (s, 3H, OCH3), 3.50 (s, 3H, OCH3); 13
C
NMR (125 MHz, CDCl3): d (ppm) 148.6, 148.0, 146.2, 134.2,
132.7, 130.0, 129.9, 129.5, 128.8, 128.7, 126.9, 125.6, 119.1,
111.1, 110.1, 55.8, 55.4; HRMS (ESI) m/z: calcd for C23H20N2O2Cl
[M + H]+ 391.1208, found 391.1199.
4,5-Bis(4-uorophenyl)-2-phenyl-1H-imidazole (4a).92 White
solid (116.2 mg, 86% yield); mp 271–273 ꢀC; 1H NMR (500 MHz,
DMSO-d6): d (ppm) 12.73 (br s, 1H, NH), 8.08 (d, J ¼ 7.4 Hz, 2H,
ArH), 7.57–7.52 (m, 4H, ArH), 7.48 (t, J ¼ 7.6 Hz, 2H, ArH), 7.38
(t, J ¼ 7.4 Hz, 1H, ArH), 7.30 (t, J ¼ 8.6 Hz, 2H, ArH), 7.15 (t, J ¼
9.0 Hz, 2H, ArH); 13C NMR (125 MHz, DMSO-d6): d (ppm) 162.9
(d, J ¼ 245.2 Hz), 160.9 (d, J ¼ 243.4 Hz), 146.0, 136.8, 132.0 (d, J
¼ 2.1 Hz), 131.1 (d, J ¼ 8.1 Hz), 130.7, 129.4 (d, J ¼ 8.0 Hz), 129.2,
128.8, 127.9 (d, J ¼ 2.4 Hz), 116.2 (d, J ¼ 21.6 Hz), 115.6 (d, J ¼
21.3 Hz); HRMS (ESI) m/z: calcd for C21H15N2F2 [M + H]+
333.1198, found 333.1193.
4,5-Bis(4-chlorophenyl)-2-phenyl-1H-imidazole (4b).35 White
solid (114.4 mg, 87% yield); mp 292–294 ꢀC; 1H NMR (500 MHz,
DMSO-d6): d (ppm) 12.79 (br s, 1H, NH), 8.07 (d, J ¼ 7.5 Hz, 2H,
ArH), 7.54–7.38 (m, 11H, ArH); 13C NMR (125 MHz, DMSO-d6):
d (ppm) 146.5, 130.6, 129.2, 129.0, 125.8; HRMS (ESI) m/z: calcd
for C21H15N2Cl2 [M + H]+ 365.0607, found 365.0598.
4,5-Di(thiophen-2-yl)-2-phenyl-1H-imidazole (4h). White
solid (119.0 mg, 86% yield); mp 269–271 ꢀC; 1H NMR (500 MHz,
DMSO-d6): d (ppm) 12.87 (br s, 1H, NH), 8.05–8.03 (m, 2H, ArH),
7.71 (d, J ¼ 4.6 Hz, 1H, ArH), 7.50–7.47 (m, 2H, ArH), 7.43–7.38
(m, 3H, ArH), 7.22 (dd, J ¼ 3.6, 5.0 Hz, 1H, ArH), 7.17 (d, J ¼
3.0 Hz, 1H, ArH), 7.02 (dd, J ¼ 3.7, 4.9 Hz, 1H, ArH); 13C NMR
(125 MHz, DMSO-d6): d (ppm) 148.2, 137.9, 134.1, 131.2, 130.2,
129.2, 129.1, 129.0, 128.1, 127.9, 127.8, 125.8, 125.3, 123.9,
121.2; HRMS (ESI) m/z: calcd for C17H13N2S2 [M + H]+ 309.0515,
found 309.0513.
4,5-Di(furan-2-yl)-2-phenyl-1H-imidazole (4i).94 Brown solid
(45.1 mg, 31% yield); mp 192–194 ꢀC; 1H NMR (500 MHz,
CDCl3): d (ppm) 7.89 (dd, J ¼ 1.4, 8.5 Hz, 2H, ArH), 7.47 (d, J ¼
0.9 Hz, 2H, ArH), 7.42–7.39 (m, 2H, ArH), 7.37–7.34 (m, 1H,
ArH), 6.95 (br s, 2H, ArH), 6.50 (dd, J ¼ 1.8, 3.3 Hz, 2H, ArH); 13
C
4,5-Bis(4-bromophenyl)-2-phenyl-1H-imidazole (4c).78 White
solid (114.4 mg, 87% yield); mp 314–316 ꢀC; 1H NMR (500 MHz,
DMSO-d6): d (ppm) 12.79 (br s, 1H, NH), 8.07 (dd, J ¼ 1.3, 8.5 Hz,
NMR (125 MHz, CDCl3): d (ppm) 146.3, 141.6, 129.4, 129.3,
129.0, 125.6, 111.9, 110.1, 107.7; HRMS (ESI) m/z: calcd for
2H, ArH), 7.65–7.46 (m, 10H, ArH), 7.41–7.38 (m, 1H, ArH); 13
C
C
17H13N2O2 [M + H]+ 277.0972, found 277.0971.
4,5-Di(pyrid-2-yl)-2-phenyl-1H-imidazole (4j).95 Pale yellow
NMR (125 MHz, DMSO-d6): d (ppm) 146.6, 136.8, 134.6, 131.9,
130.5, 129.2, 129.0, 125.8, 121.6, 120.3; HRMS (ESI) m/z: calcd
for C21H15N2Br2 [M + H]+ 452.9597, found 452.9602.
solid (61.6 mg, 44% yield); mp 181–183 ꢀC; 1H NMR (500 MHz,
CDCl3): d (ppm) 11.24 (br s, 1H, NH), 8.58 (br s, 3H, ArH), 8.19–
8.13 (m, 1H, ArH), 7.98 (dd, J ¼ 1.5, 8.5 Hz, 2H, ArH), 7.77–7.67
(m, 2H, ArH), 7.43–7.40 (m, 2H, ArH), 7.37–7.33 (m, 1H, ArH),
7.18 (br s, 2H, ArH); 13C NMR (125 MHz, CDCl3): d (ppm) 148.6,
146.3, 136.8, 129.7, 129.2, 129.0, 125.7, 122.3; HRMS (ESI) m/z:
calcd for C19H14N4Na [M + Na]+ 321.1111, found 321.1109.
4,5-Dimethyl-2-phenyl-1H-imidazole (4k).35 Pale yellow solid
(73.7 mg, 52% yield); mp 171–173 ꢀC; 1H NMR (500 MHz,
CDCl3): d (ppm) 7.81 (dd, J ¼ 1.3, 8.5 Hz, 2H, ArH), 7.36–7.33 (m,
2H, ArH), 7.05 (d, J ¼ 7.2 Hz, 1H), 2.19 (s, 6H, CH3); 13C NMR
(125 MHz, CDCl3): d (ppm) 144.1, 131.3, 130.5, 128.9, 128.0,
124.8, 11.9; HRMS (ESI) m/z: calcd for C11H13N2 [M + H]+
173.1073, found 173.1069.
4-Ethyl-5-methyl-2-phenyl-1H-imidazole (4l).96 Pale yellow
solid (135.8 mg, 73% yield); mp 151–153 ꢀC; 1H NMR (500 MHz,
CDCl3): d (ppm) 7.76 (dd, J ¼ 1.4, 8.6 Hz, 2H, ArH), 7.33 (t, J ¼
7.2 Hz, 2H, ArH), 7.26 (dt, J ¼ 1.1, 7.3 Hz, 1H, ArH), 2.56 (q, J ¼
7.6 Hz, 2H, CH2), 2.19 (s, 3H, CH3), 1.19 (t, J ¼ 7.5 Hz, 3H, CH3);
13C NMR (125 MHz, CDCl3): d (ppm) 144.1, 130.7, 128.9, 128.1,
124.9, 14.6; HRMS (ESI) m/z: calcd for C11H13N2 [M + H]+
187.1230, found 187.1225.
4,5-Bis(4-methylphenyl)-2-phenyl-1H-imidazole (4d).54 White
1
ꢀ
solid (135.4 mg, quantitative yield); mp 275–277.5 C; H NMR
(500 MHz, DMSO-d6): d (ppm) 12.57 (br s, 1H, NH), 8.07 (dd, J ¼
1.2, 8.4 Hz, 2H, ArH), 7.48–7.35 (m, 7H, ArH), 7.24 (br s, 2H,
ArH), 7.12 (br s, 2H, ArH), 2.34 (br s, 3H, CH3), 2.30 (br s, 3H,
CH3); 13C NMR (125 MHz, DMSO-d6): d (ppm) 145.6, 137.5,
137.4, 136.0, 132.9, 130.9, 129.6, 129.2, 129.1, 129.0, 128.9,
128.7, 128.6, 128.3, 127.5, 125.6, 21.3; HRMS (ESI) m/z: calcd for
C
23H21N2 [M + H]+ 325.1699, found 325.1691.
4,5-Bis(4-methoxyphenyl)-2-phenyl-1H-imidazole
(4e).93
White solid (119.0 mg, 90% yield); mp 200–202 ꢀC; 1H NMR (500
MHz, CDCl3): d (ppm) 7.83 (dd, J ¼ 1.5, 8.5 Hz, 2H, ArH), 7.40–
7.33 (m, 6H, ArH), 7.31–7.28 (m, 1H, ArH), 6.82 (d, J ¼ 8.7 Hz,
4H, ArH), 3.78 (s, 6H, OCH3); 13C NMR (125 MHz, CDCl3):
d (ppm) 159.0, 145.7, 130.2, 129.2, 128.9, 128.6, 125.4, 114.1,
55.4; HRMS (ESI) m/z: calcd for C23H21N2O2 [M + H]+ 357.1598,
found 357.1589.
4,5-Bis(3-methoxyphenyl)-2-phenyl-1H-imidazole (4f). White
solid (109.2 mg, 83% yield); mp 196–197.5 ꢀC; 1H NMR (400
MHz, CDCl3): d (ppm) 9.98 (br s, 1H, NH), 7.85 (d, J ¼ 7.6 Hz, 2H,
ArH), 7.38–7.30 (m, 3H, ArH), 7.18 (t, J ¼ 7.8 Hz, 2H, ArH), 7.07
(br s, 4H, ArH), 6.79 (d, J ¼ 7.3 Hz, 2H, ArH), 3.68 (s, 6H, OCH3);
13C NMR (100 MHz, CDCl3): d (ppm) 159.7, 146.1, 130.0, 129.6,
129.0, 128.9, 125.5, 120.5, 113.7, 113.1, 55.3; HRMS (ESI) m/z:
calcd for C23H21N2O2 [M + H]+ 357.1598, found 357.1590.
5-Methyl-4-propyl-2-phenyl-1H-imidazole (4m). Yellow sticky
paste (123.2 mg, 70% yield); 1H NMR (500 MHz, CDCl3): d (ppm)
7.82 (dd, J ¼ 1.4, 8.6 Hz, 2H, ArH), 7.29 (t, J ¼ 7.2 Hz, 2H, ArH),
7.24–7.20 (m, 1H, ArH), 2.47 (t, J ¼ 7.5 Hz, 2H, CH2), 2.15 (s, 3H,
28068 | RSC Adv., 2021, 11, 28061–28071
© 2021 The Author(s). Published by the Royal Society of Chemistry