From: Synthesis and biological profile of substituted benzimidazoles
Comp. | Molecular structures with stereochemistry | M. formula and CHN analyses | M. wt. | Rf value | % Yield | M. Pt. (°C) |
---|---|---|---|---|---|---|
1 |
(E)-N-((E)-3-(4-(Dimethylamino)phenyl) allylidene)-1H-benzo[d]imidazol-2-amine | C18H18N4: Anal calcd: C, 74.46; H, 6.25; N, 19.30; Found: C, 74.43; H, 6.27; N, 19.33 | 290.40 | 0.76a | 76 | 228–230 |
2 |
(E)-1-(((1H-Benzo[d]imidazol-2-yl)imino)methyl)naphthalen-2-ol | C18H13N3O: Anal calcd: C, 75.25; H, 4.56; N, 14.63; Found: C, 75.27; H, 4.59; N, 14.60 | 287.34 | 0.79a | 74 | 255–257 |
3 |
(E)-N-(3,4-Dimethoxybenzylidene)-1H-benzo[d]imidazol-2-amine | C16H15N3O2: Anal calcd: C, 68.31; H, 5.37; N, 14.94; Found: C, 68.34; H, 5.35; N, 14.97 | 281.34 | 0.77a | 78 | 225–227 |
4 |
(E)-4-(((1H-Benzo[d]imidazol-2-yl)imino)methyl)phenol | C14H11N3O: Anal calcd: C, 70.87; H, 4.67; Cl, 17.71; Found: C, 70.88; H, 4.65; Cl, 17.73 | 237.28 | 0.75a | 67 | 220–222 |
5 |
(E)-N-(4-Nitrobenzylidene)-1H-benzo[d]imidazol-2-amine | C14H10N4O2: Anal calcd: C, 63.15; H, 3.79; N, 21.04; Found: C, 63.13; H, 3.77; N, 21.07 | 266.28 | 0.72a | 72 | 236–238 |
6 |
(E)-N-(4-(Dimethylamino)benzylidene)-1H-benzo[d]imidazol-2-amine | C16H16N4: Anal calcd: C, 72.70; H, 6.10; N, 21.20; Found: C, 72.73; H, 6.12; N, 21.22 | 264.36 | 0.79a | 82 | 238–240 |
7 |
(E)-N-(3-Nitrobenzylidene)-1H-benzo[d]imidazol-2-amine | C14H10N4O2: Anal calcd: C, 63.15; H, 3.79; N, 21.04; Found: C, 63.18; H, 3.77; N, 21.05 | 266.28 | 0.76a | 76 | 190–192 |
8 |
(E)-N-Ethylidene-1H-benzo [d]imidazol-2-amine | C9H9N3: Anal calcd: C, 67.90; H, 5.70; N, 26.40; Found: C, 67.88; H, 5.72; N, 26.42 | 159.21 | 0.72a | 80 | 172–175 |
9 |
(E)-N-(4-Methoxybenzylidene)-1H-benzo[d]imidazol-2-amine | C15H13N3O: Anal calcd: C, 71.70; H, 5.21; N, 16.72; Found: C, 71.73; H, 5.22; N, 16.74 | 251.31 | 0.71a | 75 | 198–200 |
10 |
(E)-5-((1H-Benzo[d]imidazol-2-yl)imino)pentanal | C12H13N3O: Anal calcd: C, 66.96; H, 6.09; N, 19.52; Found: C, 66.94; H, 6.11; N, 19.55 | 215.28 | 0.75a | 78 | 265–267 |
11 |
(E)-N-(3,4,5-Trimethoxybenzylidene)-1H-benzo[d]imidazol-2-amine | C17H17N3O3: Anal calcd: C, 65.58; H, 5.50; N, 13.50; Found: C, 65.61; H, 5.53; N, 13.52 | 311.37 | 0.72a | 84 | 242–245 |
12 |
(E)-1-(2-(Ethylideneamino)-1H-benzo[d]imidazol-1-yl)ethanone | C11H11N3O: Anal calcd: C, 65.66; H, 5.51; N, 20.88; Found: C, 65.65; H, 5.54; N, 20.86 | 201.22 | 0.63b | 74 | 262–265 |
13 |
(E)-(3,5-Dinitrophenyl)(2-((4-methoxy-benzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C22H15N5O6: Anal calcd: C, 59.33; H, 3.39; N, 15.72; Found: C, 59.35; H, 3.42; N, 15.75 | 445.38 | 0.58b | 68 | 243–245 |
14 |
(E)-5-((1-(3,5-Dinitrobenzoyl)-1H-benzo[d]imidazol-2-yl)imino)pentanal | C14H11N3O2: Anal calcd: C, 55.75; H, 3.69; N, 17.11; Found: C, 55.78; H, 3.71; N, 17.14 | 253.26 | 0.66b | 65 | 162–164 |
15 |
(E)-5-((1-Acetyl-1H-benzo[d]imidazol-2-yl)imino)pentanal | C14H15N3O2: Anal calcd: C, 65.35; H, 5.88; N, 16.33; Found: C, 65.37; H, 5.90; N, 16.36 | 257.29 | 0.62b | 72 | 226–228 |
16 |
(E)-(3,5-Dinitrophenyl)(2-((4-hydroxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C21H13N5O6: Anal calcd: C, 58.47; H, 3.04; N, 16.24; Found: C, 58.49; H, 3.05; N, 16.25 | 431.36 | 0.64b | 70 | 175–177 |
17 |
(E)-(2-((2,4-Dimethoxybenzylidene)amino) -1H-benzo[d]imidazol-1-yl)(naphthalen-2-yl)methanone | C27H21N3O3: Anal calcd: C, 74.47; H, 4.86; N, 9.65; Found: C, 74.49; H, 4.88; N, 9.68 | 435.47 | 0.54b | 67 | 120–122 |
18 |
(E)-Naphthalen-2-yl(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C28H23N3O4: Anal calcd: C, 72.24; H, 4.98; N, 9.03; Found: C, 72.27; H, 4.95; N, 9.05 | 465.5 | 0.65b | 75 | 210–212 |
19 |
(E)-(3,5-Dinitrophenyl)(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C24H19N5O8: Anal calcd: C, 57.03; H, 3.79; N, 13.86; Found: C, 57.07; H, 3.76; N, 13.88 | 505.44 | 0.66b | 66 | 141–143 |
20 |
(E)-1-(2-((3,4,5-trimethoxybenzylidene)amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one | C33H47N3O4: Anal calcd: C, 72.10; H, 8.62; N, 7.64; Found: C, 72.11; H, 8.65; N, 7.67 | 549.74 | 0.62b | 78 | 136–138 |
21 |
(E)-(3-Nitrophenyl)(2-((4-(pyridin-2-yl)benzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C26H17N5O3: Anal calcd: C, 69.79; H, 3.83; N, 15.65; Found: C, 69.77; H, 3.86; N, 15.68 | 447.44 | 0.57b | 67 | 142–144 |
22 |
(2-((E)-((E)-3-(4-(Dimethylamino)phenyl) allylidene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone | C25H21N5O3: Anal calcd: C, 68.33; H, 4.82; N, 15.94; Found: C, 68.37; H, 4.80; N, 15.97 | 439.47 | 0.59b | 82 | 126–128 |
23 |
(E)-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone | C23H19N5O3: Anal calcd: C, 66.82; H, 4.63; N, 16.94; Found: C, 66.83; H, 4.66; N, 16.97 | 413.43 | 0.63b | 76 | 131–133 |
24 |
(E)-(2-(((2-hydroxynaphthalen-1-yl)-methylene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl)methanone | C25H16N4O4: Anal calcd: C, 68.80; H, 3.70; N, 12.84; Found: C, 68.83; H, 3.72; N, 12.87 | 436.42 | 0.64b | 65 | 134–136 |
25 |
(E)-(2-((4-Nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)(3-nitrophenyl) methanone | C21H13N5O5: Anal calcd: C, 60.72; H, 3.15; N, 16.86; Found: C, 60.75; H, 3.17; N, 16.89 | 415.36 | 0.66b | 74 | 119–121 |
26 |
(E)-Naphthalen-2-yl(2-((4-nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)methanone | C25H16N4O3: Anal calcd: C, 71.42; H, 3.84; N, 13.33; Found: C, 71.43; H, 3.87; N, 13.37 | 420.42 | 0.52b | 62 | 176–178 |
27 |
(E)-(2-((3,4-Dimethoxybenzylidene)amino) -1H-benzo[d]imidazol-1-yl)(3-nitro phenyl)methanone | C23H18N4O5: Anal calcd: C, 64.18; H, 4.22; N, 13.02; Found: C, 64.21; H, 4.25; N, 13.04 | 430.41 | 0.63b | 65 | 235–237 |
28 |
(E)-1-(2-((4-Nitrobenzylidene)amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one | C30H40N4O3: Anal calcd: C, 71.40; H, 7.99; N, 11.10; Found: C, 71.39; H, 7.97; N, 11.12 | 504.66 | 0.59b | 66 | 126–128 |
29 |
(E)-1-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)hexadecan-1-one | C34H48N4O: Anal calcd: C, 77.23; H, 9.15; N, 10.60; Found: C, 77.21; H, 9.16; N, 10.63 | 528.77 | 0.64b | 68 | 131–133 |
30 |
(E)-(2-((4-(Dimethylamino)benzylidene) amino)-1H-benzo[d]imidazol-1-yl)(naphthalen-2-yl)methanone | C27H22N4O: Anal calcd: C, 77.49; H, 5.30; N, 13.39; Found: C, 77.51; H, 5.32; N, 13.42 | 418.49 | 0.62b | 76 | 192–195 |