Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles containing…
1-[[1-(3-Phenylpropyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-
benzo[d]imidazole (3c, C19H19N5)
127.4 (C5 triazole), 131.3, 134.1, 134.8, 142.6, 143.5 (C4
triazole), 166.3 (C=O) ppm; IR (KBr): vꢀ = 3134 (C–H str.,
triazole ring), 3078 (C–H str., aromatic), 1720 (C=O str.),
1654 (C=N str., aromatic), 1612, 1492 (C=C str., aromatic)
cm-1; MS: m/z for C19H14N6O2: 359.0 [M?], 360.0 [M??1].
Brown solid; yield: 72 %; m.p.: 96–98 °C; 1H NMR
(300 MHz, CDCl3): d = 2.12 (p, J = 10.5 Hz, 2H, CH2),
2.53 (t, J = 10.5 Hz, 2H, CH2), 4.18 (t, J = 10.5 Hz, 2H,
CH2), 5.41 (s, 2H, CH2), 7.01–7.05 (m, 3H, Ar–H), 7.17 (t,
J = 12 Hz, 3H, Ar–H), 7.24-7.28 (m, 3H, Ar–H), 7.77 (s,
1H, C–H triazole), 7.84 (s, 1H, C2–H benzimidazole) ppm;
13C NMR (75 MHz, CDCl3): d = 31.3, 32.3, 40.7, 49.5,
109.9, 120.5, 121.8, 123.2, 126.3 (C5 triazole), 128.2,
128.5, 139.6, 142.8 (C4 triazole) ppm; IR (KBr): vꢀ = 3113
(C–H str., triazole ring), 3082 (C–H str., aromatic), 1670
(C=N str., aromatic), 1615, 1525, 1438 (C=C str., aromatic)
cm-1; MS: m/z for C19H19N5: 318.0 [M?], 319.0 [M??1].
1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]-
[1,2,3]triazole (6a, C16H14N6)
Light brown crystalline solid; yield: 74 %; m.p.:
156–160 °C (Ref. [29] 158–160 °C).
1-[(1-Phenethyl-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]-
[1,2,3]triazole (6b, C17H16N6)
Light yellow solid; yield: 70 %; m.p.: 120–124 °C; 1H
NMR (400 MHz, CDCl3): d = 3.12 (t, J = 7.2 Hz, 2H,
CH2), 4.51 (t, J = 7.2 Hz, 2H, CH2), 5.91 (s, 2H, CH2),
6.93 (d, J = 8.4 Hz, 2H, Ar–H), 7.07–7.16 (m, 4H, Ar–H),
7.37 (t, J = 8.4 Hz, 1H, Ar–H), 7.47 (s, 1H, C–H triazole),
7.66 (d, J = 8.4 Hz, 1H, Ar–H), 8.04 (d, J = 8.4 Hz, 1H,
Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 36.6, 43.8,
51.9, 110.1, 119.9, 123.2, 124.1, 127.2 (C5 triazole), 127.6,
128.5, 132.6, 136.6, 141.7 (C4 triazole), 146.2 ppm; IR
(KBr): vꢀ = 3142 (C–H str., triazole ring), 3026 (C–H str.,
1-[[1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-
benzo[d]imidazole (3d, C18H17N5)
Light yellow solid; yield: 74 %; m.p.: 150–154 °C; 1H
NMR (400 MHz, CDCl3): d = 2.00 (s, 3H, CH3), 5.50 (s,
2H, CH2), 5.57 (s, 2H, CH2), 7.27–7.29 (m, 2H, Ar–H),
7.36 (t, J = 8.8 Hz, 3H, Ar–H), 7.40–7.43 (m, 1H, Ar–H),
7.80 (s, 1H, C–H triazole), 7.99 (s, 1H, C2–H benzimida-
zole), 8.17 (d, J = 8.8 Hz, 2H, Ar–H) ppm; 13C NMR
(75 MHz, CDCl3): d = 21.1, 40.5, 54.0, 109.8, 120.4,
121.6, 122.3, 123.1, 128.0 (C5 triazole), 129.8, 131.1,
138.7, 143.1, 143.7 (C4 triazole) ppm; IR (KBr): vꢀ = 3118
(C–H str., triazole ring), 3072 (C–H str., aromatic), 1658
(C=N str., aromatic), 1614, 1550, 1431 (C=C str., aromatic)
cm-1; MS: m/z for C18H17N5: 304.0 [M?], 305.0 [M??1].
aromatic), 1612, 1494, 1450 (C=C str., aromatic) cm-1
MS: m/z for C17H16N6: 305.0 [M?], 306.0 [M??1].
;
1-[[1-(3-Phenylpropyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-
benzo[d][1,2,3]triazole (6c, C18H18N6)
Creamy white solid; yield: 72 %; m.p.: 92–96 °C; 1H NMR
(400 MHz, CDCl3): d = 2.19 (p, J = 7.2 Hz, 2H, CH2),
2.60 (t, J = 7.2 Hz, 2H, CH2), 4.28 (t, J = 7.2 Hz, 2H,
CH2), 5.97 (s, 2H, CH2), 7.08 (d, J = 7.2 Hz, 2H, Ar–H),
7.16 (d, J = 7.2 Hz, 1H, Ar–H), 7.25 (t, J = 7.2 Hz, 2H,
Ar–H), 7.36 (t, J = 7.2 Hz, 1H, Ar–H), 7.45 (s, 1H, C–H
triazole), 7.48 (d, J = 7.2 Hz, 1H, Ar–H), 7.71 (d,
J = 8.4 Hz, 1H, Ar–H), 8.04 (d, J = 8.4 Hz, 1H, Ar–H)
ppm; 13C NMR (100 MHz, CDCl3): d = 31.4, 32.4, 43.8,
49.7, 110.1, 119.9, 122.8, 124.2, 126.4, 127.7 (C5 triazole),
128.4, 128.6, 132.7, 139.8, 142.1 (C4 triazole), 146.2 ppm;
IR (KBr): vꢀ = 3134 (C–H str., triazole ring), 3070 (C–H
str., aromatic), 1604, 1494, 1448 (C=C str., aromatic)
cm-1; MS: m/z for C18H18N6: 319.0 [M?], 320.0 [M??1].
1-[[1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-
benzo[d]imidazole (3e, C17H14N6O2)
Light yellow solid; yield: 70 %; m.p.: 144–148 °C; 1H
NMR (400 MHz, DMSO-d6): d = 5.59 (s, 2H, CH2), 5.75
(s, 2H, CH2), 7.19–7.26 (m, 2H, Ar–H), 7.50 (d,
J = 8.8 Hz, 2H, Ar–H), 7.64 (t, J = 8.8 Hz, 2H, Ar–H),
8.20-8.23 (m, 2H, Ar–H), 8.26 (s, 1H, C–H triazole), 8.33
(s, 1H, C2–H benzimidazole) ppm; 13C NMR (100 MHz,
DMSO-d6): d = 40.6, 52.4, 111.1, 119.9, 122.1, 122.8,
124.6, 127.1 (C5 triazole), 129.5, 131.1, 143.6, 143.8 (C4
triazole), 147.7 ppm; IR (KBr): vꢀ = 3113 (C–H str.,
triazole ring), 3082 (C–H str., aromatic), 1656 (C=N str.,
aromatic), 1606, 1555, 1492 (C=C str., aromatic), 1523 (N–
O str., asym., NO2), 1348 (N–O str., sym., NO2) cm-1; MS:
m/z for C17H14N6O2: 335.0 [M?], 336.0 [M??1].
1-[[1-(4-Methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl]-1H-
benzo[d][1,2,3]triazole (6d, C17H16N6)
Light brown solid; yield: 70 %; m.p.: 152–156 °C; 1H
NMR (400 MHz, CDCl3): d = 2.32 (s, 3H, CH3), 5.40 (s,
2H, CH2), 5.92 (s, 2H, CH2), 7.09–7.15 (m, 4H, Ar–H),
7.35 (t, J = 8.0 Hz, 1H, Ar–H), 7.42 (s, 1H, C–H triazole),
7.46 (t, J = 8.0 Hz, 1H, Ar–H), 7.71 (d, J = 8.0 Hz, 1H,
Ar–H), 8.01 (d, J = 8.0 Hz, 1H, Ar–H) ppm; 13C NMR
(100 MHz, CDCl3): d = 21.2, 43.8, 54.2, 110.2, 119.8,
122.7, 124.1, 127.0, 127.6 (C5 triazole), 128.5, 131.0,
132.7, 139.0, 142.3 (C4 triazole), 146.1 ppm; IR (KBr):
vꢀ = 3134 (C–H str., triazole ring), 3072 (C–H str.,
2-[[4-[(1H-Benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-tria-
zol-4-yl]methyl]isoindoline-1,3-dione (3f, C19H14N6O2)
Dark brown solid; yield: 55 %; m.p.: 152–156 °C; 1H
NMR (300 MHz, CDCl3): d = 5.45 (s, 2H, CH2), 6.11 (s,
2H, phthalimide NCH2), 7.23–7.27 (m, 3H, Ar–H), 7.73–
7.77 (m, 4H, Ar–H), 7.85–7.89 (m, 2H, Ar–H), 7.99 (s, 1H,
C2–H benzimidazole) ppm; 13C NMR (75 MHz, CDCl3):
d = 40.3, 49.7, 109.9, 120.4, 122.5, 123.2, 123.3, 124.2,
123