A. Ouach et al. / Tetrahedron 64 (2008) 1962e1970
1969
123.8, 125.2, 125.5, 126.5, 127.1, 127.4, 127.6, 129.0, 129.9,
137.3, 142.0, 145.9, 147.3, 152.6, 165.9. HRMS (FAB)
[C29H32N3O4][Cl]: calculated 486.2392, found: 486.2384 (Cþ).
J1¼2.0 Hz, J2¼6.4 Hz), 7.99 (d, 2H, J¼8.7 Hz), 8.27 (d, 2H,
J¼8.9 Hz), 8.64 (d, 1H, J¼8.2 Hz), 8.96 (s, 1H), 13C NMR
(75 MHz, acetonitrile-d3): 22.5, 38.4, 52.6 (t, J¼4.0 Hz),
63.5, 64.5, 114.8, 123.2, 125.1, 125.3, 125.4, 127.8, 130.8,
131.1, 132.4, 133.8, 135.8, 137.6, 139.4, 147.1, 150.6, 152.1,
160.8. HRMS (FAB) [C29H28N2OCl][BF4]: calculated
443.1890, found: 443.1892 (Cþ).
4.4. Quinolines
4.4.1. {3-[4-(7H-Indeno[2,1-c]quinolin-6-yl)phenoxy]-
propyl}trimethylammonium tetrafluoroborate 7a
Following procedure C using 4, aniline, and indene, a pale
greenish solid was obtained in 60% yield. Mp 220e222 ꢂC. 1H
NMR (300 MHz, acetonitrile-d3): 2.24e2.34 (m, 2H), 3.09 (s,
9H), 3.47e3.59 (m, 2H), 4.21 (t, 2H, J¼5.7 Hz), 4.36 (s, 2H),
7.19 (d, 2H, J¼8.7 Hz), 7.71e7.80 (m, 2H), 7.88 (dd, 1H,
J1¼3.4 Hz, J2¼8.2 Hz), 8.00e8.09 (m, 3H), 8.14 (t, 1H,
J¼8.3 Hz), 8.75e8.78 (m, 1H), 8.83 (d, 1H, J¼8.5 Hz), 9.09
(d, 1H, J¼8.7 Hz), 13C NMR (75 MHz, DMSO-d6): 22.5,
38.6, 52.6 (t, J¼4.0 Hz), 63.5, 64.6, 115.0, 121.2, 122.5,
123.6, 124.5, 125.4, 125.8, 128.0, 129.0, 131.2, 131.3, 133.2,
134.9, 137.6, 138.7, 147.8, 150.9, 153.4, 161.1. HRMS (FAB)
[C28H29N2O][BF4]: calculated 409.2279, found: 409.2265 (Cþ).
4.4.5. {3-[4-(2-Bromo-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7e
Following procedure C using 4, 4-bromoaniline, and in-
dene, a yellow solid was obtained in 56% yield. Mp 258e
260 ꢂC. 1H NMR (300 MHz, acetone-d6): 2.56e2.63 (m,
2H), 3.43 (s, 9H), 3.85e3.93 (m, 2H), 4.36 (t, 2H, J¼5.7 Hz),
4.37 (s, 2H), 7.28 (d, 2H, J¼8.7 Hz), 7.64e7.72 (m, 2H), 7.82
(dd, 1H, J1¼2.0 Hz, J2¼6.4 Hz), 7.99 (d, 2H, J¼8.6 Hz), 8.27
(d, 2H, J¼8.9 Hz), 8.64 (d, 1H, J¼8.2 Hz), 8.96 (s, 1H), 13C
NMR (75 MHz, acetonitrile-d3): 23.8, 38.6, 53.8 (t, J¼4.0 Hz),
64.9, 66.2, 115.8, 122.0, 125.0, 125.6, 126.4, 126.9, 128.8,
129.7, 129.9, 130.8, 131.8, 134.6, 136.6, 139.5, 144.2, 147.1,
148.4, 155.2, 161.1. HRMS (FAB) [C29H28N2OBr][BF4]: calcu-
lated 487.1385, found: 487.1382 (Cþ).
4.4.2. {3-[4-(2-Methyl-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7b
Following procedure C using 4, 4-methylaniline, and in-
dene, a yellow solid was obtained in 62% yield. Mp 208e
210 ꢂC. 1H NMR (300 MHz, acetone-d6): 2.36e2.52 (m,
2H), 2.78 (s, 3H), 3.25 (s, 9H), 3.58e3.74 (m, 2H), 4.32 (t,
2H, J¼5.7 Hz), 4.37 (s, 2H), 7.34 (d, 2H, J¼8.6 Hz), 7.69e
7.79 (m, 2H), 7.84e7.82 (m, 1H), 8.01 (m, 3H), 8.26 (d,
1H, J¼8.7 Hz), 8.82 (d, 1H, J¼8.7 Hz), 8.89 (s, 1H), 13C
NMR (75 MHz, acetonitrile-d3): 20.6, 22.5, 38.5, 52.6 (t,
J¼4.0 Hz), 63.5, 64.6, 115.0, 120.6, 122.7, 123.2, 123.4,
125.4, 126.1, 128.0, 131.2, 135.3, 137.0, 137.6, 140.2, 147.7,
149.8, 153.0, 161.1. HRMS (FAB) [C29H31N2O][BF4]: calcu-
lated 423.2436, found: 423.2436 (Cþ).
4.4.6. {3-[4-(2-Nitro-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7f
Following procedure C using 4, 4-nitroaniline, and indene,
a yellow solid was obtained in 50% yield. Mp 258e260 ꢂC. 1H
NMR (300 MHz, methanol-d4): 2.36e2.50 (m, 2H), 3.27 (s,
9H), 3.64e3.75 (m, 2H), 4.35 (t, 2H, J¼5.6 Hz), 4.50 (s,
2H), 7.38 (d, 2H, J¼8.6 Hz), 7.76e7.86 (m, 2H), 7.89e7.99
(m, 1H), 8.14 (d, 2H, J¼8.6 Hz), 8.57 (d, 1H, J¼9.4 Hz),
8.72e8.80 (m, 1H), 8.86 (d, 1H, J¼9.4 Hz), 9.89 (s, 1H),
13C NMR (75 MHz, methanol-d4): 22.3, 53.7 (t, J¼4.0 Hz),
65.4, 66.2, 116.2, 121.8, 123.1, 125.5, 126.1, 126.8, 127.2,
128.1, 128.7, 129.4, 132.1, 132.6, 137.7, 139.3, 146.6, 147.1,
148.5, 157.4, 162.6. HRMS (FAB) [C29H28N3O3][BF4]: calcu-
lated 454.2130, found: 454.2135 (Cþ).
4.4.3. {3-[4-(2-Methoxy-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7c
Following procedure C using 4, 4-methoxyaniline, and in-
dene, a yellow solid was obtained in 60% yield. Mp 198e
200 ꢂC. 1H NMR (300 MHz, acetone-d6): 2.42e2.61 (m,
2H), 3.51 (s, 9H), 3.84e3.95 (m, 2H), 4.18 (s, 3H), 4.28e4.41
(m, 4H), 7.18 (d, 2H, J¼8.7 Hz), 7.47e7.68 (m, 3H), 7.87 (d,
1H, J¼7.2 Hz), 8.05e8.21 (m, 4H), 8.62 (d, 1H, J¼7.2 Hz),
13C NMR (75 MHz, acetonitrile-d3): 24.0, 38.3, 53.6 (t, J¼
4.0 Hz), 56.1, 64.9, 65.7, 102.8, 115.3, 122.5, 125.1, 125.2,
126.0, 128.3, 129.4, 131.0, 131.3, 132.4, 135.4, 140.7, 143.1,
146.2, 146.3, 152.5, 159.3, 160.3. HRMS (FAB) [C29H31N2O2]
[BF4]: calculated 439.2385, found: 439.2375 (Cþ).
4.4.7. {3-[4-(2-Fluoro-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7g
Following procedure C using 4, 4-fluoroaniline, and indene,
a brown solid was obtained in 62% yield. Mp 218e220 ꢂC. 1H
NMR (300 MHz, acetonitrile-d3): 2.25e2.41 (m, 2H), 3.14 (s,
9H), 3.49e3.63 (m, 2H), 4.27 (t, 2H, J¼5.7 Hz), 4.37 (s, 2H),
7.28 (d, 2H, J¼8.7 Hz), 7.69e7.80 (m, 2H), 7.84e7.91 (m,
1H), 7.97 (d, 1H, J¼8.6 Hz), 8.01 (d, 2H, J¼8.8 Hz), 8.42
(d, 1H, J¼5.4 Hz), 8.67 (m, 2H), 13C NMR (75 MHz, ace-
tone-d6): 23.7, 38.4, 53.8 (t, J¼4.0 Hz), 64.8, 65.9, 109.7,
116.3, 123.3, 123.7, 124.5, 125.7, 126.3, 126.6, 126.8, 129.2,
132.2, 132.4, 136.8, 138.4, 138.7, 148.4, 152.7, 162.3 (d,
J¼250 Hz), 162.1. HRMS (FAB) [C29H28N2OF][BF4]: calcu-
lated 427.2185, found: 427.2191 (Cþ).
4.4.4. {3-[4-(2-Chloro-7H-indeno[2,1-c]quinolin-6-yl)-
phenoxy]propyl}trimethylammonium tetrafluoroborate 7d
Following procedure C using 4, 4-chloroaniline, and in-
dene, a yellow solid was obtained in 57% yield. Mp 224e
226 ꢂC. 1H NMR (300 MHz, acetone-d6): 2.30e2.51 (m,
2H), 3.25 (s, 9H), 3.59e3.73 (m, 2H), 4.24e4.35 (m, 4H),
7.28 (d, 2H, J¼8.7 Hz), 7.64e7.72 (m, 2H), 7.82 (dd, 1H,
4.4.8. {3-[4-(2-Chloro-7H-indeno[2,1-c]quinolin-6-yl)-
benzoloxy]propyl}trimethylammonium tetrafluoroborate 8a
Following procedure C using 3, 4-chloroaniline, and in-
dene, a yellow solid was obtained in 60% yield. Mp