Molecules 2017, 22, 213
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4-(1-Ethyl-1H-benzo[d]imidazol-2-yl)thiazole (AI-18). Off-white solid; yield 71%; m.p. 140–142 C;
1H-NMR (400 MHz, CDCl3) δ 8.92 (d, J = 1.9 Hz, 1H), 8.31 (d, J = 2.0 Hz, 1H), 7.80 (dd, J = 5.6, 3.2 Hz,
1H), 7.44 (dd, J = 5.9, 3.0 Hz, 1H), 7.36–7.27 (m, 2H), 4.79 (q, J = 7.1 Hz, 2H), 1.47 (t, J = 7.1 Hz, 3H);
13C-NMR (101 MHz, CDCl3)
109.96, 40.23, 15.49.
δ
152.96, 148.09, 146.53, 143.05, 135.55, 123.05, 122.65, 121.13, 119.79,
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4-(1-Allyl-1H-imidazo[4,5-c]pyridin-2-yl)thiazole (AI-19). Brown solid; yield 78%; m.p. 112–114 C;
1H-NMR (400 MHz, DMSO-d6)
δ 9.36 (d, J = 1.9 Hz, 1H), 9.03 (d, J = 17.8 Hz, 1H), 8.62 (d, J = 2.0 Hz, 1H),
8.38 (d, J = 5.6 Hz, 1H), 7.68 (t, J = 16.9 Hz, 1H), 6.02 (ddd, J = 22.3, 10.3, 5.2 Hz, 1H), 5.44 (d, J = 5.1 Hz,
2H), 5.09 (d, J = 10.3 Hz, 1H), 4.93 (dd, J = 17.2, 1.0 Hz, 1H); 13C-NMR (101 MHz, DMSO-d6)
δ 155.68,
147.88, 145.98, 141.62, 141.57, 140.34, 139.64, 133.25, 123.91, 116.92, 106.49, 47.00.
1-Ethyl-2-phenyl-1H-imidazo[4,5-c]pyridine (AI-20). Orange solid; yield 66%; 1H-NMR (400 MHz, CDCl3)
9.15 (s, 1H), 8.48 (s, 1H), 7.73 (s, 2H), 7.56 (s, 3H), 7.39 (d, J = 4.0 Hz, 1H), 4.31 (d, J = 6.8 Hz, 2H), 1.47
δ
(t, J = 6.4 Hz, 3H).
4-(1-Ethyl-1H-imidazo[4,5-c]pyridin-2-yl)thiazole (AI-21). Off-white solid; yield 86%; m.p. 171–172 ◦C;
1H-NMR (400 MHz, CDCl3)
(
δ
9.08 (s, 1H), 8.93 (d, J = 1.7 Hz, 1H), 8.41 (t, J = 10.2 Hz, 1H), 8.35
d, J = 1.8 Hz, 1H), 7.35 (d, J = 5.6 Hz, 1H), 4.77 (q, J = 7.1 Hz, 2H), 1.45 (t, J = 7.1 Hz, 3H); 13C-NMR
(101 MHz, CDCl3) δ 153.36, 148.00, 147.26, 142.78, 142.15, 140.42, 140.27, 122.41, 105.32, 40.67, 15.46;
HR-EI-MS: Calcd. for C11H11N4S [M + H]+: 231.06980; found: 231.06989.
4-(1-Benzyl-5-nitro-1H-benzo[d]imidazol-2-yl)thiazole (AI-22). Orange solid; yield 47%; m.p. >200 ◦C;
1H-NMR (400 MHz, DMSO-d6)
δ
9.35 (d, J = 1.7 Hz, 1H), 8.70 (d, J = 1.7 Hz, 1H), 8.57 (d, J = 1.8 Hz, 1H),
8.15 (dd, J = 8.9, 1.9 Hz, 1H), 7.78 (d, J = 9.0 Hz, 1H), 7.24 (dq, J = 14.1, 7.0 Hz, 3H), 7.13 (d, J = 7.1 Hz, 2H),
6.20 (s, 2H); 13C-NMR (101 MHz, DMSO-d6)
156.03, 150.22, 145.70, 143.41, 141.73, 140.06, 136.74,
δ
128.69, 127.57, 126.64, 124.91, 118.45, 115.20, 111.79, 48.11; HR-EI-MS: Calcd. for C17H12N4O2S
[M + H]+: 337.07145; found: 337.07550.
4-(1-Benzyl-6-nitro-1H-benzo[d]imidazol-2-yl)thiazole (AI-23). Orange solid; yield 40%; m.p. 183–185 ◦C;
1H-NMR (400 MHz, DMSO-d6)
δ
9.35 (d, J = 1.5 Hz, 1H), 8.72 (t, J = 8.2 Hz, 1H), 8.54 (d, J = 1.6 Hz, 1H),
8.13 (dd, J = 8.8, 1.8 Hz, 1H), 7.87 (d, J = 8.9 Hz, 1H), 7.31–7.21 (m, 3H), 7.14 (d, J = 7.2 Hz, 2H), 6.28
(s, 2H); 13C-NMR (101 MHz, DMSO-d6)
δ 156.11, 151.20, 147.10, 145.76, 142.94, 136.86, 135.08, 128.70,
127.54, 126.57, 125.38, 119.39, 118.27, 108.10, 47.96; HR-EI-MS: Calcd. for C17H12N4O2S [M + H]+
337.07145; found: 337.07526.
:
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2-(1H-Indol-3-yl)-1H-benzo[d]imidazole (AI-24). Yellow solid; yield 73%; m.p. 233–235 C; 1H-NMR
(400 MHz, DMSO-d6)
δ 12.98 (s, 1H), 12.01 (s, 1H), 7.69–7.57 (m, 3H), 7.48 (d, J = 8.1 Hz, 1H), 7.22
(d, J = 5.6 Hz, 3H), 7.18 (t, J = 7.6 Hz, 1H), 7.05 (t, J = 7.4 Hz, 1H); 13C-NMR (101 MHz, DMSO)
δ 146.6,
137.1, 129.1, 128.3, 123.3, 121.3, 120.2, 112.4, 102.1.
2-(1H-Indol-2-yl)-1H-benzo[d]imidazole (AI-25). Yellow solid; yield 71%; 1H-NMR (400 MHz, DMSO-d6)
12.14 (s, 1H), 9.00 (s, 1H), 8.32 (t, J = 23.5 Hz, 1H), 7.64 (dd, J = 22.2, 6.3 Hz, 2H), 7.52 (d, J = 8.0 Hz,
1H), 7.36 (s, 1H), 7.21 (t, J = 7.3 Hz, 1H), 7.06 (t, J = 7.2 Hz, 1H).
δ
1
3-(Ethylthio)-2-phenylimidazo[1,2-a]pyridine (AI-26). Brown oil; yield 71%; H-NMR (400 MHz, CDCl3)
8.52 (d, J = 6.9 Hz, 1H), 8.32 (d, J = 7.3 Hz, 2H), 7.67 (d, J = 9.0 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.37
t, J = 7.3 Hz, 1H), 7.31–7.26 (m, 1H), 6.91 (t, J = 6.5 Hz, 1H), 2.69 (q, J = 7.4 Hz, 2H), 1.11 (t, J = 7.4 Hz, 3H).
δ
(
3-Ethyl-2-phenylimidazo[1,2-a]pyridine (AI-27). Yellow solid; yield 68%; 1H-NMR (400 MHz, CDCl3)
7.90–7.87 (m, 1H), 7.79–7.72 (m, 2H), 7.62 (d, J = 9.1 Hz, 1H), 7.43 (dd, J = 10.3, 5.1 Hz, 2H), 7.34–7.29
δ
(m, 1H), 7.10 (ddd, J = 9.0, 6.7, 1.2 Hz, 1H), 6.75 (td, J = 6.8, 1.1 Hz, 1H), 3.03 (q, J = 7.5 Hz, 2H), 1.29
(dd, J = 9.9, 5.2 Hz, 3H).