Molecules 2016, 21, 23
10 of 15
1-Butyl-2-[(3-methyl-1,3-benzoxazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6a); Yield 0.43 g, 69%;
˝
mp > 260 C; 1H-NMR (DMSO-d6):
δ ppm 0.95 (t, J = 7.1 Hz, 3H), 1.44–1.49 (m, 2H), 1.82–1.85 (m, 2H),
4.04 (s, 3H), 4.48 (t, J = 7.3 Hz, 2H), 6.14 (s, 1H), 7.55–7.67 (m, 3H), 7.73 (t, J = 8.6 Hz, 1H), 7.82–7.89 (m,
2H), 8.04 (t, J = 7.3 Hz, 1H), 8.15 (d, J = 7.1 Hz, 1H), 8.39 (d, J = 7.6 Hz, 1H), 9.17 (d, J = 7.6 Hz, 1H);
13C-NMR (DMSO-d6):
δ ppm 14.3, 20.1, 30.2, 32.0, 75.5, 110.1, 112.3, 112.6, 126.6, 127.2, 129.7, 129.7,
130.3, 130.4, 131.8, 132.9, 141.1, 146.8, 155.6, 162.0; HRMS (ESI): Calcd for C24H23N2O+ m/z 355.1805,
obsd m/z 355.1791.
1-Butyl-2-[(3-methyl-1,3-benzothiazol-2(3H)-ylidene)methyl]benzo[c,d]indolium iodide (6b); Yield 0.37 g, 57%;
mp 249–251 ˝C; 1H-NMR (DMSO-d6):
δ ppm 0.96 (t, J = 7.3 Hz, 3H), 1.43–1.49 (m, 2H), 1.75–1.92 (m,
2H), 4.16 (s, 3H), 4.37 (t, J = 7.2 Hz, 2H), 6.47 (s, 1H), 7.55 (d, J = 7.3Hz, 1H), 7.59–7.72 (m, 2H), 7.74–7.81
(m, 2H), 7.89 (t, J = 7.8 Hz, 1H), 8.04 (d, J = 8.3 Hz, 1H), 8.20 (d, J = 7.8 Hz, 1H), 8.32 (d, J = 8.1 Hz,
1H), 9.25 (d, J = 7.6 Hz, 1H); 13C-NMR (DMSO-d6):
δ ppm 13.8, 19.7, 29.7, 35.4, 43.4, 87.0, 109.0, 115.0,
122.0, 123.6, 124.7, 126.8, 128.8, 129.2, 129.6, 129.7, 132.3, 141.0, 141.2, 154.0, 165.9; HRMS (ESI): Calcd
for C24H23N2S+ m/z 371.1576, obsd m/z 371.1566.
1-Butyl-2-[(1-methylquinolin-2(1H)-ylidene)methyl]benzo[c,d]indolium iodide (6c); Yield 0.44 g, 69%; mp
225–227 ˝C; 1H-NMR (DMSO-d6):
δ
ppm 0.95 (t, J = 7.2 Hz, 3H), 1.40–1.54 (m, 2H), 1.79–1.85 (m, 2H),
4.25 (t, J = 7.3 Hz, 2H), 4.37 (s, 3H), 6.35 (s, 1H), 7.31 (d, J = 7.3 Hz, 1H), 7.55–7.62 (m, 2H), 7.65 (t,
J = 7.7 Hz, 1H), 7.82 (t, J = 7.4 Hz, 1H), 8.07 (t, J = 7.7 Hz, 1H), 8.12 (d, J = 8.1 Hz, 1H), 8.21 (d, J = 7.8 Hz
1H), 8.35 (d, J = 8.1 Hz, 2H), 8.58–8.71 (m, 2H); 13C-NMR (DMSO-d6):
ppm 13.9, 19.7, 29.7, 42.9, 93.6,
,
δ
106.4, 118.4, 120.0, 123.7, 127.5, 128.9, 129.5, 129.7, 130.4, 133.9, 141.2, 152.1, 157.0; HRMS (ESI): Calcd
for C26H25N2+ m/z 365.2012, obsd m/z 365.1999.
1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-2H-benzo[e]indol-2-ylidene)methyl]benzo[c,d]indolium iodide (6d);
˝
Yield 0.52 g, 72%; mp 190–192 C; 1H-NMR (DMSO-d6):
δ ppm 0.95 (t, J = 7.3 Hz, 3H), 1.45 (q, J = 7.3 Hz,
2H), 1.80–1.97 (m, 8H), 3.60 (s, 3H) 4.46 (t, J = 7.3 Hz, 2H), 6.43 (s, 1H), 7.60 (t, J = 7.5 Hz, 1H), 7.67–7.78
(m, 3H), 7.81 (d, J = 7.3 Hz, 1H), 7.84–7.93 (m, 3H), 8.14 (d, J = 8.0 Hz, 1H), 8.21 (d, J = 8.7 Hz, 1H), 8.35
(d, J = 8.2 Hz, 2H); 13C-NMR (DMSO-d6):
δ ppm 13.7, 19.7, 25.2, 29.8, 43.8, 53.2, 54.9, 82.9, 110.4, 113.1,
122.9, 123.0, 124.1, 125.8, 127.7, 128.0, 128.6, 129.3, 129.6, 129.8, 130.0, 130.2, 130.3, 132.1, 132.3, 133.6,
140.8, 141.3, 156.5, 181.1; HRMS (ESI): Calcd for C31H31N2+ m/z 431.2482, obsd m/z 431.2469.
1-Butyl-2-[(1,1,3-trimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d]indolium iodide (10a); Yield
0.42 g, 63%; mp 238–240 ˝C; 1H-NMR (DMSO-d6):
δ ppm 0.95 (t, J = 7.08 Hz, 3H), 1.42–1.47 (m, 2H),
1.65 (s, 6H), 1.85–1.88 (m, 2H), 3.47 (s, 3H), 4.46 (t, J = 7.0 Hz, 2H), 6.31 (s, 1H), 7.44 (t, J = 7.3 Hz, 1H),
7.51–7.63 (m, 2H), 7.69–7.85 (m, 4H), 7.88–7.96 (m, 2H), 8.38 (d, J = 8.0 Hz, 1H); 13C-NMR (DMSO-d6):
δ
ppm 13.6, 19.6, 25.6, 29.7, 43.8, 45.7, 51.4, 82.9, 110.9, 113.3, 122.7, 123.2, 123.9, 126.4, 128.6, 129.1,
+
129.1, 129.5, 130.0, 130.2, 132.5, 140.1, 140.6, 143.9, 156.9, 179.5; HRMS (ESI): Calcd for C27H29N2 m/z
381.2325, obsd m/z 381.2313.
1-Butyl-2-[(3-ethyl-5-methoxy-1,1-dimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d] indolium iodide
(
10b); Yield 0.65 g, 90%; mp 187–189 ˝C; 1H-NMR (DMSO-d6):
δ ppm 0.92 (t, J = 7.2 Hz, 3H), 1.14 (t,
J = 6.7 Hz, 3H), 1.37–1.43 (m, 2H), 1.61 (s, 6H), 1.79–1.83 (m, 2H), 3.85 (s, 3H), 4.20 (q, J = 6.3 Hz, 2H),
4.39 (t, J = 6.1 Hz, 2H), 6.23 (s, 1H), 7.10 (d, J = 9.9 Hz, 1H), 7.40 (s, 1H), 7.58–7.67 (m, 2H), 7.70 (t,
J = 7.9 Hz, 1H), 7.77–7.87 (m, 2H), 7.87–7.94 (m, 1H), 7.91 (d, J = 7.5 Hz, 1H), 8.30 (d, J = 8.0 Hz, 2H);
13C-NMR (DMSO-d6):
δ ppm 13.3, 13.7, 19.5, 25.1, 29.7, 43.4, 45.6, 51.9, 56.0, 83.4, 109.5, 109.9, 113.8,
115.3, 122.4, 124.1, 127.3, 129.4, 129.5, 129.9, 130.1, 132.1, 134.8, 140.9, 142.8, 154.9, 158.9, 179.4; HRMS
(ESI): Calcd for C29H33N2O+ m/z 425.2587, obsd m/z 425.2576.
1-Butyl-2-[(5-chloro-3-ethyl-1,1-dimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d] indolium iodide
˝
1
(
10c); Yield 0.25 g, 34%; mp 152–154 C; H-NMR (DMSO-d6): δ ppm 0.91 (t, J = 7.2 Hz, 3H), 1.08
(t, J = 6.7 Hz, 3H), 1.37–1.43 (m, 2H), 1.63 (s, 6H), 1.81–1.84 (m, 2H), 4.16 (q, J = 6.7 Hz, 2H), 4.47 (t,
J = 6.3 Hz, 2 H), 6.29 (s, 1H), 7.59 (d, J = 8.7 Hz, 1H), 7.67 (d, J = 8.7 Hz, 1H), 7.71–7.81 (m, 2H), 7.85–7.95
(m, 3H), 8.10 (d, J = 7.3 Hz, 1H), 8.39 (d, J = 8.2 Hz, 1H); 13C-NMR (DMSO-d6):
δ ppm 13.0, 13.7,