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137.12, 141.16, 141.88, 147.90, 148.99, 165.49. Anal. calcd for
4.2.13 (E)-2-(5-Nitro-2-(3-nitrostyryl)-1H-imidazol-1-yl)ethyl
isoquinoline-1-carboxylate (3k). Yield 65.7%. m.p. 186–188 C;
ꢁ
C
24H20N4O4: C, 67.28; H, 4.71; N, 13.08 (%); found: C, 67.42; H,
1H NMR (DMSO-d6, 300 MHz) d: 8.25 (d, J ¼ 3.6 Hz, 1H), 8.19 (t, J
¼ 5.1 Hz, 2H), 7.96–7.82 (m, 2H), 7.75 (d, J ¼ 5.1 Hz, 1H) 7.68 (t, J
¼ 6.9 Hz, 1H), 7.55 (t, J ¼ 5.1 Hz, 2H), 7.43 (t, J ¼ 3.3 Hz, 1H),
7.26 (d, J ¼ 5.4 Hz, 2H), 7.13 (d, J ¼ 5.1 Hz, 1H), 5.06 (t, J ¼ 4.2
Hz, 2H), 4.83 (t, J ¼ 6.3 Hz, 2H), ESI-MS: 460.12 [M + H]+. 13C
NMR (DMSO-d6, 75 MHz) d: 45.07, 66.22, 114.13, 123.05, 124.01,
125.09, 126.02, 127.00, 127.35, 128.63, 129.02, 129.93, 130.29,
131.68, 134.51, 135.65, 136.40, 137.73, 140.21, 141.32, 146.69,
150.66, 165.98. Anal. calcd for C23H17N5O6: C, 60.13; H, 3.73; N,
15.24 (%); found: C, 60.01; H, 3.84; N, 15.30 (%).
4.2.14 (E)-2-(5-Nitro-2-(4-nitrostyryl)-1H-imidazol-1-yl)ethyl
isoquinoline-1-carboxylate (3l). Yield 62.3%. m.p. 187–188 ꢁC;
1H NMR (DMSO-d6, 300 MHz) d: 8.26 (d, J ¼ 3.9 Hz, 1H), 8.17 (t, J
¼ 4.2 Hz, 2H), 7.95–7.68 (m, 4H), 7.55 (t, J ¼ 5.4 Hz, 2H), 7.36–
7.25 (m, 2H), 7.17 (d, J ¼ 7.4 Hz, 2H), 5.06 (t, J ¼ 3.3 Hz, 2H), 4.86
(t, J ¼ 3.6 Hz, 2H), ESI-MS: 460.12 [M + H]+. 13C NMR (DMSO-d6,
75 MHz) d: 45.41, 65.61, 116.36, 124.78, 125.10, 126.65, 127.08,
127.51, 128.83, 129.12, 129.38, 130.80, 132.99, 134.47, 136.01,
137.15, 140.56, 142.77, 146.82, 151.30, 167.74. Anal. calcd for
4.83; N, 13.27 (%).
4.2.18 (E)-2-(2-(2-Methoxystyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3p). Yield 62.4%. m.p. 187–
188 ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.45 (d, J ¼ 4.5 Hz, 1H),
8.32 (d, J ¼ 5.4 Hz, 1H), 8.17–7.98 (m, 4H), 7.82 (t, J ¼ 7.5 Hz,
2H), 7.62 (d, J ¼ 4.5 Hz, 1H), 7.49–7.26 (m, 3H), 7.17 (d, J ¼ 7.5
Hz, 1H), 5.05 (t, J ¼ 6.0 Hz, 2H), 4.83 (t, J ¼ 3.3 Hz, 2H), 3.55 (d, J
¼ 4.2 Hz, 3H), ESI-MS: 445.14 [M + H]+. 13C NMR (DMSO-d6, 75
MHz) d: 45.30, 56.01, 67.39, 113.62, 123.92, 124.53, 125.14,
126.09, 126.55, 127.36, 128.18, 129.19, 130.00, 130.44, 132.11,
134.89, 135.46, 136.15, 138.34, 140.48, 141.74, 146.79, 151.22,
165.01. Anal. calcd for C24H20N4O5: C, 64.86; H, 4.54; N, 12.61
(%); found: C, 64.61; H, 4.31; N, 12.55 (%).
4.2.19 (E)-2-(2-(3-Methoxystyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3q). Yield 64.4%. m.p. 187–
188 ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.35 (d, J ¼ 4.5 Hz, 1H),
8.22 (d, J ¼ 5.1 Hz, 1H), 8.11–7.93 (m, 2H), 7.81 (t, J ¼ 7.5 Hz,
2H), 7.57 (d, J ¼ 4.2 Hz, 2H), 7.46–7.24 (m, 2H), 7.12 (d, J ¼ 7.5
Hz, 1H), 5.02 (t, J ¼ 6.3 Hz, 2H), 4.81 (t, J ¼ 3.3 Hz, 2H), 3.51 (d, J
¼ 4.2 Hz, 3H), ESI-MS: 445.14 [M + H]+. 13C NMR (DMSO-d6, 75
MHz) d: 46.60, 54.82, 66.35, 116.66, 122.81, 123.05, 124.95,
126.75, 127.16, 128.20, 129.10, 129.73, 130.15, 131.89, 132.52,
133.30, 135.40, 136.41, 139.70, 140.56, 142.92, 145.44, 153.78,
166.47. Anal. calcd for C24H20N4O5: C, 64.86; H, 4.54; N, 12.61
(%); found: C, 64.93; H, 4.67; N, 12.43 (%).
4.2.20 (E)-2-(2-(4-Methoxystyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3r). Yield 62.4%. m.p. 186–188
ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.38 (d, J ¼ 4.2 Hz, 1H), 8.25
(t, J ¼ 5.1 Hz, 1H), 8.13–7.95 (m, 4H), 7.82 (t, J ¼ 7.5 Hz, 1H),
7.54–7.43 (m, 2H), 7.46–7.24 (m, 3H), 7.12 (d, J ¼ 7.5 Hz, 1H),
5.02 (t, J ¼ 6.3 Hz, 2H), 4.81 (t, J ¼ 3.3 Hz, 2H), 3.45 (d, J ¼ 4.2 Hz,
3H), ESI-MS: 445.14 [M + H]+. 13C NMR (DMSO-d6, 75 MHz) d:
46.33, 55.59, 64.86, 115.58, 123.95, 125.76, 126.71, 127.45,
127.52, 128.37, 128.94, 129.80, 130.41, 135.72, 136.07, 136.27,
138.31, 142.59, 143.75, 148.91, 151.03, 167.20. Anal. calcd for
C
23H17N5O6: C, 60.13; H, 3.73; N, 15.24 (%); found: C, 60.20; H,
3.65; N, 15.39 (%).
4.2.15 (E)-2-(2-(2-Methylstyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3m). Yield 65.4%. m.p. 186–
188 ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.35 (d, J ¼ 4.5 Hz, 1H),
8.27 (d, J ¼ 5.4 Hz, 1H), 8.07–7.94 (m, 4H), 7.75 (t, J ¼ 7.5 Hz,
1H), 7.62 (d, J ¼ 14.5 Hz, 1H), 7.45–7.27 (m, 4H), 7.14 (d, J ¼ 7.5
Hz, 1H), 5.09 (t, J ¼ 4.5 Hz, 2H), 4.87 (t, J ¼ 6.3 Hz, 2H), 2.45 (d, J
¼ 4.2 Hz, 3H), ESI-MS: 429.15 [M + H]+. 13C NMR (DMSO-d6, 75
MHz) d: 19.55, 44.72, 64.47, 114.76, 124.48, 125.87, 125.89,
126.29, 126.48, 127.69, 129.25, 129.55, 130.86, 131.20, 134.37,
135.32, 135.64, 136.61, 136.79, 139.26, 141.69, 148.49, 151.08,
165.66. Anal. calcd for C24H20N4O4: C, 67.28; H, 4.71; N, 13.08
(%); found: C, 67.03; H, 4.53; N, 13.20 (%).
4.2.16 (E)-2-(2-(3-Methylstyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3n). Yield 65.9%. m.p. 187–
189 ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.32 (d, J ¼ 4.2 Hz, 1H),
8.26 (d, J ¼ 5.4 Hz, 1H), 8.12–7.95 (m, 2H), 7.75 (t, J ¼ 7.5 Hz,
1H), 7.69–7.60 (m, 2H), 7.51 (t, J ¼ 4.5 Hz, 2H), 7.44–7.26 (m,
3H), 7.14 (d, J ¼ 7.5 Hz, 1H), 5.05 (s, 2H), 4.85 (s, 2H), 2.36 (d, J ¼
4.2 Hz, 3H), ESI-MS: 429.15 [M + H]+. 13C NMR (DMSO-d6, 75
MHz) d: 20.94, 46.19, 64.45, 115.72, 123.23, 124.58, 125.62,
126.12, 126.26, 127.54, 128.68, 129.68, 130.07, 130.98, 132.63,
134.37, 135.85, 136.32, 137.65, 139.02, 140.76, 145.93, 154.09,
167.00. Anal. calcd for C24H20N4O4: C, 67.28; H, 4.71; N, 13.08
(%); found: C, 67.35; H, 4.65; N, 12.91 (%).
C
24H20N4O5: C, 64.86; H, 4.54; N, 12.61 (%); found: C, 64.72; H,
4.49; N, 12.78 (%).
4.2.21 (E)-2-(2-(2,4-Dichlorostyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl-7-1-carboxylate (3s). Yield 65.1%. m.p. 187–189 ꢁC; 1H NMR
(DMSO-d6, 300 MHz) d: 8.27 (d, J ¼ 4.2 Hz, 1H), 8.18 (t, J ¼ 6.2 Hz,
1H), 7.84–7.56 (m, 5H), 7.42 (d, J ¼ 4.5 Hz, 2H), 7.22–7.07 (m,
3H), 5.07 (t, J ¼ 6.3 Hz, 2H), 4.84 (t, J ¼ 3.3 Hz, 2H), ESI-MS:
485.07 [M + H]+. 13C NMR (DMSO-d6, 75 MHz) d: 45.91, 66.48,
116.11, 121.17, 122.57, 124.61, 125.33, 126.71, 127.83, 128.18,
129.55, 129.69, 131.13, 131.50, 134.97, 135.03, 136.39, 137.80,
139.06, 140.42, 145.79, 153.14, 166.46. Anal. calcd for
C23H16Cl2N4O4: C, 59.17; H, 3.35; N, 12.00 (%); found: C, 59.31;
H, 3.23; N, 11.93 (%).
4.2.22 (E)-2-(2-(4-Chloro-2-uorostyryl)-5-nitro-1H-imida-
zol-1-yl)ethyl isoquinoline-1-carboxylate (3t). Yield 67.1%. m.p.
187–189 ꢁC; 1H NMR (DMSO-d6, 300 MHz) d: 8.29 (d, J ¼ 4.2 Hz,
1H), 8.17 (d, J ¼ 6.3 Hz, 2H), 7.85–7.58 (m, 4H), 7.42 (d, J ¼ 4.2
Hz, 2H), 7.24–7.09 (m, 3H), 5.05 (t, J ¼ 6.3 Hz, 2H), 4.81 (t, J ¼ 3.3
Hz, 2H), ESI-MS: 467.08 [M + H]+. 13C NMR (DMSO-d6, 75 MHz)
d: 43.64, 66.36, 115.67, 125.08, 125.86, 126.53, 126.87, 127.38,
4.2.17 (E)-2-(2-(4-Methylstyryl)-5-nitro-1H-imidazol-1-yl)-
ethyl isoquinoline-1-carboxylate (3o). Yield 67.9%. m.p. 187–
189 ꢁC. 1H NMR (DMSO-d6, 300 MHz) d: 8.39–8.32 (m, 1H), 8.22
(d, J ¼ 8.4 Hz, 1H), 8.00–7.92 (m, 2H), 7.79 (t, J ¼ 7.5 Hz, 1H),
7.71–7.64 (m, 2H), 7.54 (d, J ¼ 14.5 Hz, 1H), 7.42–7.24 (m, 4H),
7.11 (d, J ¼ 7.5 Hz, 1H), 5.02 (s, 2H), 4.84 (s, 2H), 2.32 (d, J ¼ 7.2
Hz, 3H), ESI-MS: 429.15 [M + H]+. 13C NMR (DMSO-d6, 75 MHz)
d: 22.34, 43.56, 66.24, 114.85, 124.08, 125.43, 126.96, 127.17,
127.26, 128.54, 129.64, 129.77, 130.82, 135.97, 136.05, 136.47,
20390 | RSC Adv., 2014, 4, 20382–20392
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