Molecules 2011, 16
5534
1
23.5 (CH), 121.8 (CH), 102.7 (CH), 66.1 (OCH ), 40.3 (NCH ); HRMS m/z: 314.0963 found
2
2
+
(
calculated for C16
15 3 2
H N O S, [M+H] requires 314.0957).
(
Z)-4-(Benzo[b]thiophen-3-ylmethylene)-2-(3-methylpiperidin-1-yl)-1H-imidazol-5(4H)-one (5c). This
−1
compound was obtained as white solid. m.p.: 242–244 °C; IR (KBr) ν (cm ): 3206, 1692, 1616, 1426,
1
1
2
407; H-NMR (DMSO-d
6
) δ: 11.15 (brs, 1H, NH), 8.66 (s, 1H, Ar–CH), 7.99 (dd, J = 4.3 Hz, 7.9 Hz,
), 3.01 (dd,
H, Ar–CH), 7.42–7.37 ( m, 2H, Ar–CH), 6.62 (s, 1H, vinylic proton), 4.25 (brs, 2H, CH
2
J = 10 Hz, 10.5 Hz, 1H, CH ), 2.70 (brs, 1H, CH ), 1.76–1.44 (m, 4H, CH × 2), 1.17–1.13 (m, 1H,
2
2
2
13
CH), 0.87 (d, J = 4.5 Hz, 3H, CH
3
); C-NMR (DMSO-d
6
) δ: 172.3 (C), 159.5 (C), 139.4 (C), 138.7 (C),
1
2
31.4 (C), 127.9 (CH), 125.1 (CH), 125.0 (CH), 123.4 CH), 121.7 (CH), 101.4 (CH), 51.2 (NCH ),
4
5.3 (NCH ), 32.6 (CH ), 31.0 (CH), 24.9 (CH ), 18.9 (CH ); HRMS m/z: 326.1334 found (calculated
2
2
2
3
+
for C18
H
19
3
N OS, [M+H] requires 326.1322).
(
Z)-4-(Benzo[b]thiophen-3-ylmethylene)-1-methyl-2-(piperidin-1-yl)-1H-imidazol-5(4H)-one (5d). This
−
1
compound was obtained as light yellow solid. m.p.: 165–168 °C; IR (KBr) ν (cm ): 1713, 1638, 1560,
1
1
7
1
1
3
451; H-NMR (DMSO-d
6
) δ: 8.77 (s, 1H, Ar-CH), 8.02 (dd, J = 7.2 Hz, 7.8 Hz, 2H, Ar–CH),
× 2), 3.17 (s, 3H, NCH ),
) δ: 171.5 (C), 161.7 (C), 140.3 (C), 139.4 (C), 138.6 (C),
31.1 CH), 129.5 (CH), 125.2 (CH), 125.1 (CH), 123.5 (CH), 121.9 (CH), 105.3 (CH), 48.3 (NCH ),
OS,
.43–7.38 (m, 2H, Ar–CH), 6.84 (s, 1H, vinylic proton), 3.55 (s, 4H, CH
2
3
1
3
2 6
.62 (s, 6H, CH × 3); C-NMR (DMSO-d
2
0.4 (NCH
3
), 25.6 (CH
2
), 24.2 (CH
2
); HRMS m/z: 326.1335 found (calculated for C18
H
19
N
3
+
[M+H] requires 326.1322).
(
Z)-4-(Benzo[b]thiophen-3-ylmethylene)-2-(3,5-dimethylmorpholino)-1H-imidazol-5(4H)-one (5e). This
−1
compound was obtained as bright yellow solid. m.p.: 240–242 °C. IR (KBr) ν (cm ): 3112, 1696,
1
1
7
3
640, 1584, 1452; H-NMR (DMSO-d
6
) δ: 11.30 (brs, 1H, NH), 8.74 (s, 1H, Ar-CH), 7.99 (dd, J = 4.1 Hz,
.8 Hz, 2H, Ar–CH), 7.42–7.37 (m, 2H, Ar–CH), 6.66 (s, 1H, vinylic proton). 4.01–3.98 (m, 2H, CH),
13
2 2 3 6
.61–3.60 (m, 2H, CH ), 2.71 (brs, 2H, CH ), 1.13–1.11 (m, 6H, CH × 2); C-NMR (DMSO-d )
δ: 172.0 (C), 158.8 (C), 142.3 (C), 139.4 (C), 138.7 (C), 131.2 CH), 128.7 (CH), 125.1 (CH), 123.5
(
(
CH), 121.7 (CH), 102.7 (CH), 71.3 (OCH
3
), 60.1 (CH) 19.0 (CH
3
); HRMS m/z: 342.1282 found
+
calculated for C18
H
19
N O
3 2
S, [M+H] requires 342.1271).
(
Z)-4-(Benzo[b]thiophen-3-ylmethylene)-1-methyl-2-morpholino-1H-imidazol-5(4H)-one (5f). This
−1
compound was obtained as bright yellow solid. m.p.: 154–156 °C. IR (KBr) ν (cm ): 1717, 1641,
1
1
7
4
1
6
561, 1465; H-NMR (DMSO-d
6
) δ: 8.79 (s, 1H, Ar–CH), 8.05 (dd, J = 7.45 Hz, 7.7 Hz, 2H, Ar–CH),
.43–7.38 (m, 2H, Ar–CH), 6.89 (s, 1H, vinylic proton), 3.72–3.70 (m, 4H, CH × 2), 3.62–3.60 (m,
2
1
3
H, CH
2 3 6
× 2), 3.18 (s, 3H, NCH ); C-NMR (DMSO-d ) δ: 171.2 (C), 161.5 (C), 139.9 (C), 139.3 (C),
38.6 (C), 130.9 (CH), 130.1 (CH), 125.3 (CH), 125.2 (CH), 123.5 (CH), 121.9 (CH), 106.2 (CH),
6.1 (OCH
2
), 40.3 (NCH
2
), 30.2 (NCH
3
); HRMS m/z: 328.1123 found (calculated for C17
H N
17 3
O
2
S,
+
[M+H] requires 328.1114).
(
Z)-4-(Benzo[b]thiophen-3-ylmethylene)-1-methyl-2-(3-methylpiperidin-1-yl)-1H-imidazol-5(4H)-one
−1
(
5g). This compound was obtained as light yellow solid. m.p.: 150–152 °C; IR (KBr) ν (cm ): 1709,
1
1
637, 1561, 1457, 1439; H-NMR (DMSO-d
6
) δ: 8.75 (s, 1H, Ar–CH), 8.05 (dd, J = 7.2 Hz, 7.8 Hz,