6
Journal of Chemical Research 00(0)
(DCM/MeOH=100:1): a yellowish solid (1.16g, 84%),
m.p.=236.2°C–237.0°C; 1H NMR (400MHz, DMSO-d6):
δ 10.57 (s, 1H), 9.75 (s, 1H), 8.54 (d, J=8.0Hz, 1H), 8.34
(t, J=8.0Hz, 1H), 8.27 (d, J=8.0Hz, 1H), 8.20 (d,
J=8.0Hz, 1H), 8.00 (d, J=8.0Hz, 1H), 7.85–7.79 (m, 2H),
7.63 (t, J=8.0Hz, 2H), 7.39 (t, J=8.0Hz, 1H), 6.95 (d,
J=8.0Hz, 1H), 4.61 (t, J=7.2Hz, 2H), 2.06 (sext, J=7.2Hz,
2H), 1.02 (t, J=7.2Hz, 3H), ppm; 13C NMR (100MHz,
DMSO-d6): δ 158.00, 156.30, 147.15, 142.38, 141.50,
138.25, 131.70, 130.18, 129.51, 127.83, 127.12, 121.10,
117.68, 117.17, 115.77, 115.43, 114.16, 113.55, 48.72,
22.06, 10.79, ppm; HRMS (MALDI): m/z [M–I]+ calcd
for C21H20N3O: 330.1601; found: 330.1606.
Data for 1-(6-(2-hydroxyphenyl)pyridin-2-yl)-3-propyl-
1H-benzo[d]imidazol-3-ium iodide 1e are as follows:
Purification by column chromatography on silica gel
(DCM/MeOH=30:1): a yellowish solid (1.206g, 88%),
m.p.=254.5°C–255.1°C; 1H NMR (400MHz, DMSO-d6):
δ 10.59 (s, 1H), 10.55 (s, 1H), 8.49–8.47 (m, 1H), 8.33 (d,
J=5.2Hz, 2H), 8.28–8.26 (m, 1H), 8.01–7.96 (m, 2H),
7.81–7.76 (m, 2H), 7.35 (t, J=6.0Hz, 1H), 7.06–6.99 (m,
2H), 4.62 (t, J=8.0Hz, 2H), 2.06 (sext, J=7.2Hz, 2H),
1.02 (t, J=7.2Hz, 3H), ppm; 13C NMR (100MHz,
DMSO-d6): δ 156.04, 155.80, 146.28, 142.27, 140.71,
131.64, 131.17, 129.94, 129.53, 127.72, 127.07, 124.53,
123.13, 119.60, 116.94, 115.52, 114.95, 114.14, 48.71,
22.03, 10.78, ppm; HRMS (MALDI): m/z [M–I]+ calcd
for C21H20N3O: 330.1601; found: 330.1597.
Data for 1-(6-(4-carboxyphenyl)pyridin-2-yl)-3-propyl-
1H-benzo[d]imidazol-3-ium iodide 1f are as follows:
Purification by column chromatography on silica gel
(DCM/MeOH=30:1): a yellowish solid (1.321g, 91%),
m.p.=236.3°C–236.7°C; 1H NMR (400MHz, DMSO-d6):
δ 13.18 (s, 1H), 10.61 (s, 1H), 8.54 (d, J=8.0Hz, 1H),
8.44–8.35 (m, 4H), 8.28 (d, J=8.0Hz, 1H), 8.15–8.09 (m,
3H), 7.86–7.79 (m, 2H), 4.62 (t, J=8.0Hz, 2H), 2.07 (sext,
J=7.2Hz, 2H), 1.03 (t, J=7.2Hz, 3H), ppm; 13C NMR
(100MHz, DMSO-d6): δ 166.91, 155.16, 147.29, 142.51,
141.85, 140.73, 132.00, 131.72, 130.03, 129.51, 127.96,
127.15, 121.87, 116.38, 115.69, 114.19, 48.75, 22.09,
10.80, ppm; HRMS (MALDI): m/z [M–I]+ calcd for
C22H20N3O2: 358.1550; found: 358.1544.
δ 10.19 (s, 1H), 9.67 (s, 1H), 8.63 (s, 1H), 8.26 (t, J=8.0Hz,
1H), 8.12 (d, J=8.0Hz, 2H), 7.95 (d, J=8.0Hz, 1H), 7.69
(d, J=8.0Hz, 1H), 7.62 (s, 1H), 7.35 (t, J=8.0Hz, 1H),
6.94 (d, J=8.0Hz, 1H), 4.30 (t, J=7.2Hz, 2H),1.94 (sext,
J=7.2Hz, 2H), 0.94 (t, J=8.0Hz, 3H), ppm; 13C NMR
(100MHz, DMSO-d6): δ 157.92, 155.89, 146.11, 141.49,
137.94, 135.02, 129.96, 123.55, 121.02, 119.35, 117.80,
117.16, 113.75, 112.42, 51.00, 22.75, 10.47, ppm; HRMS
(MALDI): m/z [M–I]+ calcd for C17H18N3O: 280.1444;
found: 280.1445.
Data for 1-(6-(2-hydroxyphenyl)pyridin-2-yl)-3-propyl-
1H-imidazol-3-ium iodide 1i are as follows: Purification by
columnchromatographyonsilicagel(DCM/MeOH=100:1):
a yellowish solid (1.102g, 90%), m.p.=154.1°C–154.9°C;
1H NMR (400MHz, DMSO-d6): δ 10.40 (s, 1H), 10.14 (s,
1H), 8.61 (t, J=2.0Hz, 1H), 8.31 (d, J=8.0Hz, 1H), 8.22 (t,
J=8.0Hz, 1H), 8.10–8.06 (m, 2H), 7.91 (d, J=8.0Hz, 1H),
7.33 (t, J=8.0Hz, 1H), 7.04–6.97 (m, 2H), 4.30 (t, J=8.0Hz,
2H), 1.93 (sext, J=7.2Hz, 2H), 0.93 (t, J=7.2Hz, 3H),
ppm; 13C NMR (100MHz, DMSO-d6): δ 156.01, 155.16,
145.72, 140.59, 134.96, 131.17, 130.41, 124.86, 123.52,
123.11, 119.48, 119.42, 116.78, 111.78, 50.96, 22.74, 10.46,
ppm; HRMS (MALDI): m/z [M–I]+ calcd for C17H18N3O:
280.1444; found: 280.1439.
Data for 1-(6-(4-carboxyphenyl)pyridin-2-yl)-3-propyl-
1H-imidazol-3-ium iodide 1j are as follows: Purification by
column chromatography on silica gel (DCM/MeOH=50:1):
a yellowish solid (873mg, 67%), m.p.=213.7°C–214.4°C;
1H NMR (400MHz, DMSO-d6): δ 10.42 (s, 1H), 8.72 (s,
1H), 8.45 (s, 1H), 8.32–8.23 (m, 4H), 8.13 (s, 1H), 8.06 (d,
J=8.0Hz, 3H), 4.32 (t, J=7.2Hz, 2H), 1.94 (sext, J=7.2Hz,
2H), 0.94 (t, J=7.2Hz, 3H), ppm; 13C NMR (100MHz,
DMSO-d6): δ 167.10, 154.50, 146.26, 141.80, 140.13,
135.07, 132.40, 129.76, 127.14, 123.61, 121.58, 119.39,
113.21, 51.04, 22.78, 10.49, ppm; HRMS (MALDI): m/z
[M–I]+ calcd for C18H18N3O2: 308.1394; found: 308.1390.
Data for 1-(6-(4-methoxyphenyl)pyridin-2-yl)-3-pro-
pyl-1H-benzo[d]imidazol-3-ium iodide 1k are as follows:
Purification by column chromatography on silica gel
(DCM/MeOH=30:1): a yellowish solid (1.278g, 90%),
m.p.=247.5°C–248.2°C; 1H NMR (400MHz, DMSO-d6):
δ 10.59 (s, 1H), 8.51 (d, J=8.0Hz, 1H), 8.33–8.26 (m, 2H),
8.20 (d, J=8.0Hz, 3H), 7.95 (d, J=8.0Hz, 1H), 7.85–7.78
(m, 2H), 7.13 (d, J=8.0Hz, 2H), 4.62 (t, J=7.2Hz, 2H),
3.85 (s, 3H), 2.06 (sext, J=7.2Hz, 2H), 1.03 (t, J=7.2Hz,
3H), ppm; 13C NMR (100MHz, DMSO-d6): δ 160.94,
156.07, 147.00, 142.30, 141.36, 131.69, 129.45, 129.23,
128.41, 127.81, 127.09, 120.23, 115.63, 114.48, 114.16,
55.40, 48.70, 22.07, 10.78, ppm; HRMS (MALDI): m/z
[M–I]+ calcd for C22H22N3O: 344.1757; found: 344.1762.
Data for 1-(6-(4-hydroxyphenyl)pyridin-2-yl)-2-me-
thyl-3-propyl-1H-benzo[d]imidazol-3-ium iodide 1l are as
follows: Purification by column chromatography on silica
gel (DCM/MeOH=50:1): a yellowish solid (1.296g, 92%),
m.p.=232.8°C–233.5°C; 1H NMR (400MHz, DMSO-d6):
δ 10.18 (s, 1H), 8.30–8.20 (m, 3H), 8.01 (d, J=8.0Hz, 2H),
7.77–7.64 (m, 4H), 6.95 (d, J=8.0Hz, 2H), 4.60 (t,
J=7.2Hz, 2H), 2.96 (s, 3H), 1.94 (sext, J=7.2Hz, 2H),
1.05 (t, J=7.2Hz, 3H), ppm; 13C NMR (100MHz,
DMSO-d6): δ 159.73, 157.30, 151.88, 145.46, 141.28,
Data for 1-(6-(4-hydroxyphenyl)pyridin-2-yl)-3-propyl-
1H-imidazol-3-ium iodide 1g are as follows: Purification
by column chromatography on silica gel (DCM/
MeOH=30:1):
a
yellowish solid (1.014g, 83%),
m.p.=192.0°C–192.8°C; 1H NMR (400MHz, DMSO-d6):
δ 10.20 (s, 1H), 9.96 (s, 1H), 8.65 (s, 1H), 8.20–8.14 (m,
3H), 8.08 (t, J=8.0Hz, 2H), 7.85 (d, J=8.0Hz, 1H), 6.92
(d, J=8.0Hz, 2H), 4.30 (t, J=8.0Hz, 2H), 1.94 (sext,
J=7.2Hz, 2H), 0.94 (t, J=7.2Hz, 3H), ppm; 13C NMR
(100MHz, DMSO-d6): δ 159.61, 155.98, 146.00, 141.26,
134.93, 128.66, 127.38, 123.55, 119.71, 119.32, 115.69,
110.85, 51.02, 22.78, 10.50, ppm; HRMS (MALDI): m/z
[M–I]+ calcd for C17H18N3O: 280.1444; found: 280.1441.
Data for 1-(6-(3-hydroxyphenyl)pyridin-2-yl)-3-propyl-
1H-imidazol-3-ium iodide 1h are as follows: Purification
by column chromatography on silica gel (DCM/
MeOH=100:1):
a yellowish solid (1.007g, 80%),
m.p.=190.4°C–191.0°C; 1H NMR (400MHz, DMSO-d6):