LAMIE ET AL.
9 of 11
|
benzoxazole H-5), 7.80, 7.81 (dd, J = 3.6 Hz, 6.8 Hz, 1H, benzoxazole
H-6), 8.26 (d, J = 8.4 Hz, 2H, imidazole-1-phenyl H-3, H-5), 8.33 (d,
J = 8.4 Hz, 2H, p-chlorobenzylidene H-2, H-6); 13C NMR (100 MHz,
CDCl3, δ = ppm) δ = 21.62 (CH3), 110.70 (benzoxazole C-7), 120.20
(benzoxazole C-5), 126.89 (imidazole-1-phenyl C-4), 127.61 (imidazole
C-4), 127.64 (imidazole-1-phenyl C-3, C-5), 128.59 (p-chlorobenzyli-
dene C-3, C-5), 129.11 (p-chlorobenzylidene C-2, C-6), 129.24 (p-tolyl
C-3, C-5), 129.31 (p-tolyl C-2, C-6), 132.83 (p-chlorobenzylidene C-1),
133.73 (imidazole-1-phenyl C-2, C-6), 136.57 (p-tolyl C-1), 137.34 (p-
chlorobenzylidene C-4), 138.69 (imidazole-1-phenyl C-1), 142.04 (p-
tolyl C-4), 142.53 (benzoxazole C-3a), 150.86 (benzoxazole C-7a),
127.64 (phenyl C-2, C-6), 128.46 (phenyl C-3, C-5), 128.51 (p-
methoxybenzylidene C-2, C-6), 128.86 (imidazole-1-phenyl C-4),
129.16 (imidazole-1-phenyl C-3, C-5), 130.07 (benzothiazole C-5),
131.30 (phenyl C-4), 133.14 (imidazole C-4), 134.78 (imidazole-1-
phenyl C-2, C-6), 135.60 (benzothiazole C-7a), 136.50 (phenyl C-1),
137.03 (imidazole-1-phenyl C-1), 154.12 (benzothiazole C-3a),
(
CH), 124.42 (benzoxazole C-4), 125.49 (benzoxazole C-6), 125.56
158.78 (imidazole C-2), 161.84 (p-methoxybenzylidene C-4),
+.
166.77 (benzothiazole C-2), 170.13 (C O); EIMS (m/z) 487 (M ,
31.53%), 105 (100%). Anal. calcd. for C30H21N3O2S (487.57): C,
73.90; H, 4.34; N, 8.62. Found: C, 73.87; H, 4.28; N, 8.66.
(ZE)-1-[4-(Benzo[d]thiazol-2-yl)phenyl]-4-(4-chlorobenzylidene)-
2-phenyl-1H-imidazol-5(4H)-one (4i)
Green solid; yield 87%; m.p. 299–301°C; IR (KBr, cm−1) 3055 (aromatic
CH), 2924 (aliphatic CH), 1716 (CO); 1H NMR (400 MHz, DMSO-d6,
160.48 (imidazole C-2), 162.02 (benzoxazole C-2), 170.00 (C O);
EIMS (m/z) 491 (M+2+., 29.78), 489 (M+., 77.86%), 119 (100%). Anal.
calcd. for C30H20ClN3O2 (489.12): C, 73.54; H, 4.11; N, 8.58. Found: C,
73.38; H, 4.09; N, 8.45.
δ = ppm) δ = 7.32–7.54 (m, 10H, CH, phenyl H-2, H-3, H-4, H-5, H-6,
imidazole-1-phenyl H-2, H-6 and benzothiazole H-5, H-6), 7.64 (d,
J = 8 Hz, 2H, p-chlorobenzylidene H-3, H-5), 7.95 (d, J = 8 Hz, 1H,
benzothiazole H-7), 8.04 (d, J = 8 Hz, 1H, benzothiazole H-4), 8.18 (d,
J = 8 Hz, 2H, imidazole-1-phenyl H-3, H-5), 8.27 (d, J = 8 Hz, 2H, p-
chlorobenzylidene H-2, H-6); 13C NMR (100 MHz, DMSO-d6, δ = ppm)
(ZE)-1-[4-(Benzo[d]thiazol-2-yl)phenyl]-4-benzylidene-2-phenyl-
1H-imidazol-5(4H)-one (4g)
Yellow solid; yield 86%; m.p. 282–284°C; IR (KBr, cm−1) 3063
(aromatic CH), 2924 (aliphatic CH), 1717 (C O); 1H NMR
(400 MHz, DMSO-d6, δ = ppm) δ = 7.34 (s, 1H, CH), 7.43–7.61 (m,
δ = 122.97 ( CH), 123.50 (benzothiazole C-4), 126.27 (benzothiazole C-
12 H, phenyl H-2, H-3, H-4, H-5, H-6, benzylidene H-2, H-3, H-4, H-5,
H-6 and imidazole-1-phenyl H-2, H-6), 8.10 (d, J = 8 Hz, 1H,
benzothiazole H-6), 8.19–8.21 (m, 3H, benzothiazole H-4, H-5, H-7),
8.39 (d, 2H, imidazole-1-phenyl H-3, H-5); 13C NMR (100 MHz,
7), 127.01 (imidazole-1-phenyl C-4), 127.30 (benzothizole C-6), 128.53
(phenyl C-2, C-6), 128.87 (phenyl C-3, C-5), 129.01 (imidazole C-4),
129.05 (p-chlorobenzylidene C-3, C-5), 129.11 (imidazole-1-phenyl C-2,
C-6), 129.54 (p-chlorobenzylidene C-2, C-6), 130.07 (benzothiazole C-5),
131.30 (p-chlorobenzylidene C-1), 132.23 (imidazole-1-phenyl C-3, C-5),
133.07 (benzothiazole C-7a), 134.39 (phenyl C-1), 135.00 (p-chloroben-
zylidene C-4), 135.03 (phenyl C-4), 137.31 (imidazole-1-phenyl C-1),
152.03 (benzothiazole C-3a), 159.02 (imidazole C-2), 166.17 (benzothia-
DMSO-d6, δ = ppm) δ = 115.05 ( CH), 124.50 (benzothiazole C-4),
125.30 (benzothiazole C-7), 127.90 (benzothizole C-6), 128.25
(benzothiazole C-5), 128.36 (benzylidene C-4), 128.52 (benzylidene
C-2, C-6), 128.80 (benzylidene C-3, C-5), 129.10 (phenyl C-2, C-6),
129.40 (phenyl C-3, C-5), 129.50 (imidazole-1-phenyl C-4), 130.43
(imidazole-1-phenyl C-3, C-5), 132.89 (imidazole C-4), 133.01
(imidazole-1-phenyl C-2, C-6), 133.23 (benzothiazole C-7a), 135.14
(phenyl C-1), 135.20 (imidazole-1-phenyl C-1), 137.69 (benzylidene C-
1), 151.90 (benzothiazole C-3a), 159.59 (imidazole C-2), 167.04
zole C-2), 169.13 (C O). Anal. calcd. for C29H18ClN3OS (491.99): C,
70.80; H, 3.69; N, 8.54. Found: C, 70.75; H, 3.63; N, 8.47.
(ZE)-1-[4-(Benzo[d]thiazol-2-yl)phenyl]-4-benzylidene-2-(p-
tolyl)-1H-imidazol-5(4H)-one (4j)
Yellow solid; yield 85%; m.p. 288–290°C; IR (KBr, cm−1) 3059
(benzothiazole C-2), 171.62 (C O). Anal. calcd. for C29H19N3OS
(457.55): C, 76.13; H, 4.19; N, 9.18. Found: C, 75.99; H, 4.17; N, 9.20.
(aromatic CH), 2920 (aliphatic CH), 1717 (C O); 1H NMR
(400 MHz, DMSO-d6, δ = ppm) δ = 2.33 (s, 3H, CH3), 7.26 (d,
(ZE)-1-[4-(Benzo[d]thiazol-2-yl)phenyl]-4-(4-
J = 8 Hz, 2H, p-tolyl H-3, H-5), 7.30 (s, 1H, CH), 7.48–7.60 (m, 9H,
methoxybenzylidene)-2-phenyl-1H-imidazol-5(4H)-one (4h)
Yellow solid; yield 84%; m.p. 304–306°C; IR (KBr, cm−1) 3059
benzylidene H-2, H-3, H-4, H-5, H-6, p-tolyl H-2, H-6 and imidazole-1-
phenyl H-2, H-6), 8.10 (d, J = 8 Hz, 1H, benzothiazole H-6), 8.18–8.21
(m, 3H, benzothiazole H-4, H-5, H-7), 8.38 (d, J = 7.6 Hz, 2H, imidazole-
1-phenyl H-3, H-5); 13C NMR (100 MHz, DMSO-d6, δ = ppm) δ = 21.55
1
(aromatic CH), 2859 (aliphatic CH), 1717 (C O); H NMR (400 MHz,
CDCl3, δ = ppm) δ = 3.91 (s, 3H, OCH3), 7.02 (d, J = 8.8 Hz, p-
methoxybenzylidene H-3, H-5), 7.33–7.39 (m, 5H, CH, imidazole-
(CH3), 114.60 ( CH), 122.97 (benzothiazole C-4), 123.50 (benzothia-
1-phenyl H-2, H-6 and phenyl H-3, H-5), 7.42–7.49 (m, 2H,
benzothiazole H-5, H-6), 7.54 (t, J = 8 Hz, 1H, phenyl H-4), 7.63 (d,
J = 7.6 Hz, 2H, phenyl H-2, H-6), 7.95 (d, J = 8.4 Hz, 1H, benzothia-
zole H-7), 8.10 (d, J = 8 Hz, 1H, benzothiazole H-4), 8.17 (d,
J = 8.4 Hz, 2H, imidazole-1-phenyl H-3, H-5), 8.32 (d, J = 8.8 Hz, p-
methoxybenzylidene H-2, H-6); 13C NMR (100 MHz, CDCl3, δ = ppm)
δ = 55.44 (OCH3), 114.47 (p-methoxybenzylidene C-3, C-5), 121.71
zole C-7), 125.30 (benzothizole C-6), 127.90 (benzthiazole C-5),
128.01 (imidazole-1-phenyl C-1), 128.54 (benzylidene C-4), 128.80
(imidazole C-4), 129.12 (benzylidene C-2, C-6), 129.38 (benzylidene C-
3, C-5), 129.49 (p-tolyl C-3, C-5), 129.64 (imidazole-1-phenyl C-3, C-
5), 131.05 (imidazole-1-phenyl C-2, C-6), 132.00 (p-tolyl C-1), 132.81
(p-tolyl C-2, C-6), 133.05 (benzothiazole C-7a), 135.03 (phenyl C-1),
137.07 (imidazole-1-phenyl C-4), 139.31 (p-tolyl C-4), 154.02
(
CH), 123.37 (benzothiazole C-4), 125.51 (benzothiazole C-7),
(benzothiazole C-3a), 157.09 (imidazole C-2), 168.02 (benzothiazole
+.
126.55 (benzothizole C-6), 127.27 (p-methoxybenzylidene C-1),
C-2), 169.18 (C O). EIMS (m/z) 471 (M , 87.55%), 119 (100%). Anal.