Journal of the Iranian Chemical Society
9,9‑Dimethyl‑8,10,17‑triazatetracyclo[8.7.0 2,
7.011,16]heptadeca‑1(17),2,4,6,11 (16),12, 14‑hep‑
taene (I)
reaction mixture was allowed to stand for two weeks.
The light yellow solid formed was fltered at the pump to
obtain a yellow solid which recrystallized as yellow crys-
tals from DMSO/toluene (1:1), yield = (2.39 g) 50.93%;
mp = 124–125 °C. IR (νmax, cm−1): 3232 (N–H), 3006
(N–H), 2932 (C–H), 1611 (C=N), 1531 (C=C), 1505, 1492
2-(2′-Aminophenyl)-1H-benzimidazole (0.015 mol) was
heated under refux in acetone (10 mL) for 6 h. The solvent
was removed by rotary evaporation to obtain a yellow solid
which was recrystallized as a yellow crystal from DMSO/
toluene (1:1), yield = (2.89 g) 77.45%; mp = 209–211 °C.
IR (νmax, cm−1): 3221 (N–H), 2956 (C–H), 1582 (C=N),
1
(C–N). H NMR (400 MHz) δ (ppm): 7.95 (dd, J = 7.6,
8.0 Hz, 2H, Ar–H), 7.66–7,62 (m, 1H, Ar–H), 7.55–7.51
(m, 2H,Ar–H), 7.35 (s, 5H, Ar–H), 7.24 (t, J=7.2, 8.4 Hz,
1H, Ar–H), 7.18 (t, J=7.6 Hz, 1H, Ar–H), 7.03 (t, J=7.2,
7.6 Hz, 1H, Ar–H), 6.95 (d, J = 8.0 Hz, 1H, Ar–H), 6.85
(d, J=8.0 Hz, 1H, Ar–H), 6.81 (t, J=7.6 Hz, 1H, Ar–H),
3.35 (s, 3H), 1.85 (s, 2H). 13C NMR (100 MHz) δ (ppm):
147.7 (C), 143.9 (C), 143.4 (C), 143.1, 136.8 (C), 133.2
(CH), 133.1 (CH) 131.6 (C), 128.7 (CH), 128.5 (CH), 128.1
(CH), 125.8 (C), 124.7 (CH), 122.1 (CH), 121.2 (CH), 118.9
(CH), 118.3 (CH), 114.7 (CH), 111.7 (CH), 74.8 (C), 26.8
(CH3). Anal. calcd. for C21H17N3: C, 81.00; H, 5.50; N,
13.49. Found: C, 80.93; H, 5.42; N, 13.30. LRMS (m/z,
M+): Found for C21H17N3 =311.10, expected mass=311.38.
1
1513 (C=C), 1477 (C–N). H NMR (400 MHz) δ (ppm):
8.12–8.10 (m, 1H, Ar–H), 7.93 (d, J=8.0 Hz, 1H, Ar–H),
7.83 (d, J=6.4 Hz, 1H, Ar–H), 7.62–7.53 (m, 2H, Ar–H),
7.49 (t, J = 7.6, 8.4 Hz, 1H, Ar–H), 6.97–6.90 (m, 2H,
Ar–H), 2.00 (s, 6H). 13C NMR (100 MHz) δ (ppm): 144.7
(C), 144.3 (C), 135.3 (CH), 125.2 (CH), 118.3 (CH), 114.6
(CH), 74.4 (C), 28.0 (CH3). Anal. calcd. for C16H15N3: C,
77.08; H, 6.06; N, 16.85. Found: C, 77.24; H, 6.13; N, 16.89.
GC–MS (m/z, M+): Found for C16H15N3 =249.20, expected
mass=249.31.
9‑Ethyl‑9‑methyl‑8,10,17‑triazatetracyclo[8.7.0 2,
7.011,16]heptadeca‑1(17),2,4,6,11(16), 12,14‑hep‑
taene (II)
9‑Methyl‑9‑propyl‑8,10,17‑triazatetracy‑
clo[8.7.02,7.011,16]heptadeca‑1(17),2,4,6,11 (16),
12,14‑heptaene (IV)
2-(2′-Aminophenyl)-1H-benzimidazole (0.015 mol) was
heated under refux in 2-pentanone (10 mL) for 6 h. The
reaction mixture was allowed to stand overnight. The white
solid formed was fltered at the pump and recrystallized
as white crystals from THF/ethanol (1:1), yield=(2.56 g)
61.68%; mp=165–166 °C). IR (νmax, cm−1): 3249 (N–H),
3110 (N–H), 2968 (C–H), 1610 (C=N), 1528 (C=C), 1481
(C–N). 1H NMR (400 MHz) δ (ppm): 7.92 (d, J =7.6 Hz,
1H, Ar–H), 7.65 (d, J=7.2 Hz, 2H, Ar–H), 7.23–7.15 (m,
3H, Ar–H), 6.81 (d, J=8.4 Hz, 1H, Ar–H), 6.73 (t, J=7.2,
7.6 Hz, 1H, Ar–H), 1.42–1.39 (br, 2H, CH2), 1.10–1.07
(br, 2H, CH2), 0.76 (t, J=6.8, 7.2 Hz, 3H, CH3). 13C NMR
(100 MHz) δ (ppm): 147.4 (C), 144.0 (C), 143.4 (C), 132.4
(CH), 131.6 (C), 128.8 (C), 128.1 (C), 125.2 (CH), 122.1
(CH), 121.8 (CH), 118.8 (CH), 117.3 (CH), 113.9 (CH),
111.8 (CH), 110.7 (C), 74.0 (C), 42.6 (CH2), 27.4 (CH3),
16.5 (CH2), 13.6 (CH3). Anal. calcd. for C18H19N3: C, 77.95;
H, 6.90; N, 15.50. Found: C, 77.98; H, 6.75; N, 15.45.
LRMS (m/z, M+): Found for C18H19N3 =277.65, expected
mass=277.36.
2-(2′-Aminophenyl)-1H-benzimidazole (0.015 mol) was
heated under refux in 2-butanone (10 mL) for 6 h. The
solvent was removed by rotary evaporation to obtain a
white solid which was recrystallized as a white crys-
tal from DMSO/toluene (1:1), yield = ( 3.39 g) 85.76%;
mp = 210–211 °C. IR (νmax, cm−1): 3221 (N–H), 3024
(N–H), 2956 (C–H), 1611 (C=N), 1582 (C=N), 1513
1
(C=C), 1477 (C–N). H NMR (400 MHz) δ (ppm): 7.90
(dd, J=6.8 Hz, 1H, Ar–H), 7.73 (d, J=7.2 Hz, 1H), 7.67 (d,
J=7.2 Hz, 1H, Ar–H), 7.65–7.62 (m, 2H, Ar–H), 7.28–7.16
(m, 4H, Ar–H), 6.92 (s, 1H, Ar–H), 6.81 (t, J=7.6, 8.0 Hz,
3H, Ar–H), 6.74 (t, J = 7.2, 8.0 Hz, 1H, Ar–H), 3.42 (s,
3H) 1.85 (d, J= 6.4 Hz, 2H) 0.80 (t, J= 7.2 Hz, 2H,). 13
C
NMR (100 MHz) δ (ppm): 147.4 (C), 147.0 (C), 144.1 (C),
143.4 (C), 143.0 (C), 132.3 (C), 131.5 (CH), 124.6 (CH),
122.0 (CH), 121.8 (CH), 118.8 (CH), 117.9 (C), 117.3
(C), 114.5 (CH), 113.9 (CH), 111.8 (CH), 110.8 (C), 74.7
(C), 71.6 (C), 33.2 (CH2), 27.6 (CH3), 7.9 (CH3). Anal.
calcd. for C17H17N3: C, 77.54; H, 6.51; N, 15.96. Found:
C, 77.38; H, 6.37; N, 15.81. GC–MS (m/z, M+): Found for
C17H17N3 =263.15, expected mass=263.14.
9‑Butyl‑9‑methyl‑8,10,17‑triazatetracy‑
clo[8.7.0.02,7.011,16]heptadeca‑(17),2,4,6,11(16),
12,14‑heptaene (V)
9‑Methyl‑9‑phenyl‑8,10,17‑triazatetracyclo[8.7.0
2, 7.011,16]heptadeca‑(17),2,4,6,11(16), 12, 14‑hep‑
taene (III)
2-(2′-Aminophenyl)-1H-benzimidazole (0.015 mol) was
heated under refux in 2-hexanone (10 mL) for 6 h. The reac-
tion mixture was allowed to stand overnight. The white solid
2-(2′-Aminophenyl)-1H-benzimidazole (0.015 mol) was
heated under refux in acetophenone (10 mL) for 6 h. The
1 3