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B. Li et al. / C. R. Chimie 15 (2012) 784–792
3017, 2917, 2853, 1599, 1530, 1493, 1433, 1374, 1262,
1200, 1021, 912, 823, 732, 590. 1H NMR (300 MHz, CDCl3):
for C17H11N3O4: C, 63.55; H, 3.45; N, 13.08. Found: C,
63.25; H, 3.52; N, 12.98.
d
(ppm) 7.79 (d, J = 8.1 Hz, 2H), 7.45 (d, J = 1.2 Hz, 2H),
7.19(s, 2H), 6.97 (d, J = 3.2 Hz, 2H), 6.64–6.35 (m, 2H),
2.34(s, 3H). 13C NMR (125 MHz, CDCl3):
(ppm) 146.74,
3-(4,5-di(furan-2-yl)-1H-imidazol-2-yl)pyridine (3h)
Mp: 244–246 8C. Yield: 82.5%. IR (KBr):
3150, 3106, 3045, 1600, 1545, 1523, 1474, 1450, 1373,
1264, 1210, 1091, 1010, 962, 909, 884, 731, 594. 1H NMR
n
(cmÀ1) 3440,
d
139.70, 129.98, 126.84, 125.80, 112.16, 107.89, 21.77. MS,
m/z: (M + H)+ 291.2 (Calcd 291.31). Anal. calcd for
(300 MHz, DMSO):
d (ppm) 9.27 (s, 1H), 8.61 (d, J = 3.5 Hz,
C
18H14N2O2: C, 74.47; H, 4.86; N, 9.65. Found: C, 74.52;
1H), 8.47–8.42 (m, 1H), 7.80 (d, J = 1.1 Hz, 2H), 7.55 (dd,
J = 8.1, 4.9 Hz, 1H), 6.89 (d, J = 3.0 Hz, 2H), 6.64 (dd, J = 3.3,
H, 4.76; N, 9.95.
4,5-di(furan-2-yl)-2-(4-chlorophenyl)-1H-imidazole
1.8 Hz, 2H). 13C NMR (125 MHz, DMSO):
d (ppm): 149.82,
(3c) Mp: 216–218 8C. Yield: 81.6%. IR (KBr):
3052, 1598, 1525, 1483, 1432, 1374, 1260, 1201, 1011, 835,
736, 590. 1H NMR (300 MHz, CDCl3):
(ppm): 7.87 (d,
J = 8.6 Hz, 2H), 7.51 (d, J = 1.7 Hz, 2H), 7.42 (d, J = 8.6 Hz,
2H), 7.01 (d, J = 3.2 Hz, 2H), 6.54 (dd, J = 3.4, 1.8 Hz, 2H). 13
NMR (125 MHz, DMSO): (ppm) 145.44, 141.99, 135.56,
n
(cmÀ1) 3115,
147.17, 144.41, 143.32, 134.14, 126.65, 124.83, 112.57,
108.86. MS, m/z: (M + H)+ 278.8 (Calcd 278.29). Anal. calcd
for C16H11N3O2: C, 69.31; H, 4.00; N, 15.15. Found: C,
69.05; H, 4.12; N, 15.30.
4,5-di (furan-2-yl)-2-undecyl-1H-imidazole (3i) Mp:
80–82 8C. Yield: 56.0%. IR (KBr): n
(cmÀ1) 3423, 3120, 3024,
d
C
d
129.53, 127.97, 127.15, 112.22, 108.25. MS, m/z:
(M + 2 + H)+ 313.8, (M + 2)+ 312.8, (M + H)+ 311.8, (M)+
310.8 (Calcd 310.7). Anal. calcd for C17H11ClN2O2: C, 65.71;
H, 3.57; N, 9.02. Found: C, 65.46; H, 3.65; N, 8.83.
4,5-di(furan-2-yl)-2-(2-furylvinyl)-1H-imidazole
2920, 2850, 1600, 1550, 1512, 1470, 1415, 1380, 1270,
1210, 1194, 1160, 1080, 1020, 912, 883, 806, 733, 660, 593.
1H NMR (300 MHz, DMSO):
d
(ppm) 12.30 (s, 1H), 7.72 (s,
2H), 6.74 (s, 2H), 6.58 (s, 2H), 2.63 (s, 2H), 1.67 (s, 2H), 1.24
(s, 16H), 0.85 (s, 3H). 13C NMR (125 MHz, DMSO):
(ppm)
d
(3d) Mp: 213–215 8C. Yield: 89.7%. IR (KBr):
3027, 1625, 1482, 1425, 1370, 1255, 1201, 1021, 885, 733,
589. 1H NMR (300 MHz, CDCl3):
(ppm) 7.46 (d, J = 1.7 Hz,
n
(cmÀ1) 3121,
150.11, 142.52, 132.58, 129.53, 112.39, 107.33, 32.16,
30.88, 29.87, 29.79, 29.57, 29.47, 28.81, 28.46, 19.52, 14.81.
MS, m/z: (M + H)+ 355.1. (Calcd 354.49). Anal. calcd for
d
2H), 7.37–7.29 (m, 2H), 7.00 (d, J = 3.4 Hz, 2H), 6.83 (d,
J = 16.2 Hz, 1H), 6.49 (dd, J = 3.4, 1.8 Hz, 2H), 6.40–6.34 (m,
C22H30N2O2: C, 74.54; H, 8.53; N, 7.90. Found: C, 74.26; H,
8.48; N, 7.70.
2H).13C NMR (125 MHz, CDCl3):
d
(ppm) 152.38, 147.03,
2,4,5-tri (furan-2-yl)-1H-imidazole (3j) Mp: 196–
145.58, 143.54, 142.00, 120.98, 113.11, 112.34, 112.19,
111.49, 108.31. MS, m/z: (M)+ 292.9, (M + H)+ 293.9 (Calcd
293.30). Anal. calcd for C17H12N2O3: C, 69.86; H, 4.14; N,
9.58. Found: C, 69.68; H, 4.29; N, 9.30.
197 8C. Yield: 73.3%. IR (KBr):
1400, 1200, 1420, 1540, 885, 733, 590. 1H NMR
(500 MHz, CDCl3): (ppm) 10.48 (s, 1H),7.42 (s, 2H),
n
(cmÀ1) 3110, 3420,
d
7.36 (s, 1H, furan-5H), 6.92 (d, J = 3.3 Hz, 3H), 6.46 (dd,
J = 3.0, 1.7 Hz, 2H), 6.41 (dd, J = 3.1, 1.6 Hz, 1H). 13C NMR
4,5-di(furan-2-yl)-2-(1-chloro-2,2-dimethylethyl)-
1H-imidazole (3e) Mp: 186–187 8C. Yield: 48.9%. IR (KBr):
(125.5 MHz, CDCl3)
d (ppm) 147.2, 145.2, 143.1, 141.9,
n
(cmÀ1) 3444, 3130, 3026, 2983, 2940, 2815, 1602, 1544,
139.5, 112.4, 112.1, 108.9, 108.1. MS, m/z: (M + H)+
267.3, (M)+ 266.9, (Calcd 266.25). Anal. calcd for
1517, 1473, 1410, 1367, 1215, 1190, 1074, 1011, 976, 885,
812, 738, 593. 1H NMR (300 MHz, CDCl3):
(ppm) 7.48 (s,
2H), 6.88 (s, 2H), 6.50 (dd, J = 3.4, 1.8 Hz, 2H), 3.81 (s, 2H),
1.56 (s, 6H). 13C NMR (125 MHz, DMSO):
(ppm) 152.23,
d
C15H10N2O3: C, 67.67; H, 3.79; N, 10.52. Found: C, 67.57;
H, 3.73; N, 10.46.
4,5-di(furan-2-yl)-2-styryl-1H-imidazole (3k) Mp:
209–211 8C. Yield: 90.3%. IR (KBr): n
(cmÀ1) 3420, 3110,
2970, 2920, 1626, 1540, 1501, 1430, 1372, 1260, 1200,
1160, 1070, 1020, 987, 962, 912, 883, 806, 733, 685, 590. 1H
d
141.73, 112.29, 111.77, 107.60, 54.85, 38.51, 25.45. MS, m/
z: (M + H)+ 291.8 (M)+ 290.8 (Calcd 290.74); Anal. calcd for
C15H15ClN2O2: C, 61.97; H, 5.20; N, 9.64. Found: C, 61.77;
H, 5.18; N, 9.66.
NMR (500 MHz, DMSO): d (ppm) 12.75 (s, 1H), 7.78 (d,
4,5-di(furan-2-yl)-2-methyl-1H-imidazole (3f) Mp:
164–166 8C. Yield: 60.4%. IR (KBr):
3000, 2902, 2786, 1610, 1560, 1430, 1272, 1216, 1159,
1091, 1022, 927, 886, 912, 813, 724, 594. 1H NMR
J = 48.9 Hz, 2H), 7.59 (d, J = 7.5 Hz, 2H), 7.52 (d, J = 16.5 Hz,
1H), 7.41 (t, J = 7.6 Hz, 2H), 7.32 (t, J = 7.3 Hz, 1H), 7.06 (d,
J = 16.5 Hz, 1H), 6.97 (s, 1H), 6.66 (dd, J = 44.5, 31.3 Hz, 3H).
n
(cmÀ1) 3415, 3131,
13C NMR (125 MHz, DMSO):
d (ppm): 146.66, 137.09,
(300 MHz, CDCl3):
(d, J = 3.3 Hz, 2H), 6.50 (dd, J = 3.3, 1.8 Hz, 2H), 2.47 (s, 3H).
13C NMR (125 MHz, DMSO):
(ppm) 147.73, 145.36,
141.55, 123.55, 111.99, 107.20, 14.19. MS, m/z: (M)+ 214.8
(Calcd 214.22). Anal. calcd for C12H10N2O2: C, 67.28; H,
4.71; N, 13.08. Found: C, 67.43; H, 4.65; N,13.10.
d
(ppm) 7.45 (d, J = 1.1 Hz, 2H), 6.90
129.78, 127.45, 117.37, 112.86, 112.32, 108.86, 107.61. MS,
m/z: (M + H)+ 303.0 (Calcd 303.34). Anal. calcd for
C19H14N2O2: C, 75.58; H, 4.67; N, 9.27. Found: C, 75.82;
d
H, 4.81; N, 9.45.
4,5-di(phenyl)-2-(2-furylvinyl)-1H-imidazole
(3l)
Mp: 194–196 8C. Yield: 83.3%. IR (KBr)
1600, 1580, 1480, 1450, 1320, 1260, 1200, 1070, 1010, 968,
883, 764, 696, 592 cmÀ1. 1H NMR (CDCl3, 500 MHz)
: 7.51
n: 3060, 2960,
4,5-di(furan-2-yl)-2-(4-nitrophenyl)-1H-imidazole
(3g) Mp: 208–210 8C (lit. [21] 208 8C). Yield: 86.2%. IR
d
(KBr):
1201, 1110, 1080, 991, 906, 886, 850, 798, 731, 629. 1H
NMR (300 MHz, CDCl3): (ppm) 8.29 (d, J = 8.9 Hz, 2H),
8.09 (d, J = 8.9 Hz, 2H), 7.53 (d, J = 1.3 Hz, 2H), 7.04 (s, 2H),
6.56 (dd, J = 3.5, 1.8 Hz, 2H). 13C NMR (125 MHz, DMSO):
n
(cmÀ1) 3428, 3095, 3032, 1600, 1510, 1340, 1250,
(d, J = 7.2 Hz, 4H), 7.39 (d, J = 1.1 Hz, 1H), 7.32 (t, J = 7.3 Hz,
4H), 7.28 (d, J = 7.2 Hz, 2H), 7.22 (d, J = 16.1 Hz, 1H), 6.85 (d,
J = 16.1 Hz, 1H), 6.41 (dd, J = 3.2, 1.8 Hz, 1H), 6.38 (d,
d
J = 3.3 Hz, 1H); 13 C NMR (DMSO, 126 MHz)
d: 152.29,
d
145.16, 142.80, 132.50, 129.15, 128.56, 127.84, 127.47,
119.36, 113.69, 111.87, 110.39; HRMS, m/z: (M + H)+
313.1334 (Calcd 313.1335).
(ppm) 147.71, 144.93, 136.31, 127.12, 125.05, 112.63. MS,
m/z: (M + H)+ 322.9, (M)+ 321.8 (Calcd 321.29). Anal. calcd