DMSO) δ 13.53 (s, 1H), 10.49 (s, 1H), 8.36 (s, 1H), 8.12 (d, J = 16.1 Hz, 1H), 7.95 (d,
J = 16.0 Hz, 1H), 7.88 (d, J = 8.1 Hz, 2H), 7.60 (d, J = 8.1 Hz, 1H), 7.57 (d, J = 7.7
Hz, 1H), 7.53 (d, J = 7.2 Hz, 1H), 7.48 (t, J = 7.9 Hz, 1H), 7.42 (t, J = 7.3 Hz, 2H),
7.53 (m, 3H), 2.44 (s, 3H); 13C NMR (101 MHz, DMSO) δ 181.25, 168.58, 149.45,
144.49, 143.52, 140.49, 137.41, 135.82, 135.32, 135.16, 131.06, 130.27, 130.11,
127.75, 126.30, 126.14, 125.81, 123.68, 122.79, 122.03, 121.64, 118.06, 113.38,
19.85; HRMS calcd for C24H20N3O2 (M+H)+ 382.15500, found 382.15477.
(E)-N-(3-(3-(1H-benzo[d]imidazol-2-yl)-3-oxoprop-1-en-1-yl)phenyl)-3-methylbenza
1
mide (6i). Yellow solid; yield: 56%; m.p.: 225.4–227.2 °C; H NMR (400 MHz,
DMSO) δ 10.42 (s, 1H), 8.38 (s, 1H), 8.18 (d, J = 16.1 Hz, 1H), 8.01 (d, J = 7.8 Hz,
1H), 7.94 (d, J = 16.1 Hz, 1H), 7.83(t, J = 7.4 Hz, 2H), 7.74 (dd, J = 5.8, 3.1 Hz, 2H),
7.55 (d, J = 7.4 Hz, 1H), 7.48 (t, J = 7.8 Hz, 1H), 7.44 (d, J = 6.4 Hz, 2H), 7.34 (dd, J
= 6.0, 3.0 Hz, 2H), 2.42 (s, 3H); 13C NMR (101 MHz, DMSO) δ 181.58, 166.31,
150.31, 144.13, 140.46, 138.23, 135.18, 132.78, 129.98, 128.80, 128.64, 125.96,
125.35, 124.61, 123.27, 122.32, 119.08, 21.46; HRMS calcd for C24H20N3O2 (M+H)+
382.15500, found 382.15494.
(E)-N-(3-(3-(1H-benzo[d]imidazol-2-yl)-3-oxoprop-1-en-1-yl)phenyl)-4-methylbenza
1
mide (6j). Yellow solid; yield: 52%; m.p.: 264.4–266.2 °C; H NMR (400 MHz,
DMSO) δ 10.36 (s, 1H), 8.38 (s, 1H), 8.15 (d, J = 16.1 Hz, 1H), 8.02–7.94 (m, 4H),
7.76 (s, 2H), 7.55 (d, J = 7.6 Hz, 1H), 7.49 (t, J = 7.8 Hz, 1H), 7.38 (m, 4H), 2.40 (s,
3H); 13C NMR (101 MHz, DMSO) δ 181.19, 166.01, 149.42, 144.57, 142.28, 140.50,
135.07, 132.26, 129.98, 129.44 , 128.21, 125.98, 123.41, 121.95, 119.13, 21.50;
HRMS calcd for C24H20N3O2 (M+H)+ 382.15500, found 382.15500.
(E)-N-(3-(3-(1H-benzo[d]imidazol-2-yl)-3-oxoprop-1-en-1-yl)phenyl)-2-(trifluoromet
1
hyl)benzamide (6k). Yellow solid; yield: 51%; m.p.: 200.4–202.1 °C; H NMR (400
MHz, DMSO) δ 10.65 (s, 1H), 8.36 (d, J = 0.88 Hz, 2H), 8.33 (d, J = 8.0 Hz, 1H),
8.16 (d, J = 16.1 Hz, 1H), 8.01–7.96 (m, 3H), 7.83 (t, J = 7.8 Hz, 1H), 7.75 (s, 2H),
7.59 (d, J = 7.7 Hz, 1H), 7.51 (t, J = 7.8 Hz, 1H), 7.38 (dd, J = 6.1, 3.1 Hz, 2H); 13C
NMR (101 MHz, DMSO) δ 181.21, 164.69, 149.44, 144.37, 140.05, 136.03, 135.17,
132.35, 130.24, 130.08, 126.39, 124.79, 124.75, 124.71, 123.56, 122.10, 119.37;
HRMS calcd for C24H17F3N3O2 (M+H)+ 436.12674, found 436.12696.
(E)-N-(3-(3-(1H-benzo[d]imidazol-2-yl)-3-oxoprop-1-en-1-yl)phenyl)-2-methoxybenz
1
amide (6l). Yellow solid; yield: 58%; m.p.: 225.9–227.4 °C; H NMR (400 MHz,
DMSO) δ 10.29 (s, 1H), 8.33 (s, 1H), 8.11 (d, J = 16.1 Hz, 1H), 7.94 (d, J = 16.1 Hz,
1H), 7.86 (d, J = 8.0 Hz, 1H), 7.75 (s, 2H), 7.66 (d, J = 7.4 Hz, 1H), 7.56–7.44 (m,
3H), 7.36 (dd, J = 5.9, 2.9 Hz, 2H), 7.17 (d, J = 8.4 Hz, 1H), 7.07 (t, J = 7.4 Hz, 1H),
3.91 (s, 3H); 13C NMR (101 MHz, DMSO) δ 181.25, 165.32, 156.96, 149.42, 144.53,
140.25, 135.18, 132.61, 130.12, 130.06, 125.56, 125.26, 122.87, 122.05, 120.94,
118.91, 112.43, 56.36; HRMS calcd for C24H20N3O3 (M+H)+ 398.14992, found
398.17975.