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Med Chem Res (2015) 24:1568–1577
8-(3-methoxybenzyloxy)-quinoline (2a)
115.66 (C, Ar–C), 120.09 (C, Ar–C), 121.67 (C, Ar–C),
126.52 (C, Ar–C), 129.13 (C, Ar–C), 129.55 (C, Ar–C),
132.68 (C, Ar–C), 135.93 (C, Ar–C), 140.52 (C, Ar–C),
149.46 (C, Ar–C), 154.22 (C, Ar–C), 161.25 (C, Ar–C),
163.70 (C, Ar–C); HRMS (ESI): Calcd. for C16H13NOF
[M?H]?, 254.0981. found 254.0968. Melting Point =
101.4–103.1 °C; Yield = 74 %.
1H NMR (400 MHz, CDCl3): d 3.80 (s, 3H, OCH3), 5.46
(s, 2H, OCH2), 6.85-6.87 (m, 1H, Ar–H), 7.04–7.06 (m,
1H, Ar–H), 7.11–7.13 (m, 2H, Ar–H), 7.38-7.40 (m, 3H,
Ar–H), 7.44–7.48 (m, 1H, Ar–H), 8.15 (dd, 1H,
J = 6.8 Hz, 1.6 Hz, Ar–H), 8.99–9.00 (m, 1H, Ar–H); 13
C
NMR (100 MHz, CDCl3): d 55.25 (C, CH3), 70.70 (C,
OCH2), 109.99 (C, Ar–C), 112.43 (C, Ar–C), 113.47 (C,
Ar–C), 119.29 (C, Ar–C), 119.89 (C, Ar–C), 121.61 (C,
Ar–C), 126.59 (C, Ar–C), 129.69 (C, Ar–C), 135.89 (C,
Ar–C), 138.68 (C, Ar–C), 149.37 (C, Ar–C), 159.93 (C,
Ar–C); HRMS (ESI): Calcd. for C17H16NO2 [M?H]?,
266.1181. found 266.1178. Yield = 36 %.
8-(3-bromobenzyloxy)-quinoline (2e)
1H NMR (400 MHz, CDCl3): d 5.43 (s, 2H, OCH2), 7.03
(dd, 1H, J = 4.8 Hz, 2.0 Hz, Ar–H), 7.24–7.26 (m, 1H,
Ar–H), 7.41–7.49 (m, 5H, Ar–H), 7.71 (s, 1H, Ar–H), 8.17
(dd, 1H, J = 6.8 Hz, 1.6 Hz, Ar–H), 9.01 (dd, 1H,
J = 2.4 Hz, 1.6 Hz, Ar–H); 13C NMR (100 MHz, CDCl3):
d 69.98 (C, OCH2), 109.94 (C, Ar–C), 120.25 (C, Ar–C),
121.71 (C, Ar–C), 122.76 (C, Ar–C), 125.74 (C, Ar–C),
126.54 (C, Ar–C), 129.55 (C, Ar–C), 130.14 (C, Ar–C),
130.24 (C, Ar–C), 130.99 (C, Ar–C), 135.97 (C, Ar–C),
139.30 (C, Ar–C), 140.38 (C, Ar–C), 149.45 (C, Ar–C),
154.06 (C, Ar–C); HRMS (ESI): Calcd. for C16H13NOBr
[M?H]?, 314.0181. found 314.0169. Melting Point =
50.7–52.3 °C; Yield = 67 %.
8-(benzyloxy)-quinoline (2b)
1H NMR (400 MHz, CDCl3): d 5.48 (s, 2H, OCH2), 7.05–7.07
(m, 1H, Ar–H), 7.32–7.41 (m, 5H, Ar–H), 7.45–7.48 (m,1H,
Ar–H), 7.55 (d, 2H, J = 7.2 Hz, Ar–H), 8.15 (dd, 1H,
J = 6.8 Hz, 1.6 Hz, Ar–H), 9.00 (dd, 1H,, J = 2.8 Hz,
1.6 Hz, Ar–H); 13C NMR (100 MHz, CDCl3): d 70.73 (C,
OCH2), 109.90 (C, Ar–C), 119.86 (C, Ar–C), 121.61 (C, Ar–
C), 126.58 (C, Ar–C), 127.13 (C, Ar–C), 127.82 (C, Ar–C),
128.64(C, Ar–C), 129.51(C, Ar–C), 135.90(C, Ar–C), 136.97
(C, Ar–C), 149.38 (C, Ar–C), 154.34 (C, Ar–C); HRMS (ESI):
Calcd. for C16H14NO [M?H]?, 236.1075. found 236.1067.
Melting Point = 62.0–64.2 °C; Yield = 40 %.
8-(3-methylbenzyloxy)-quinoline (2f)
1H NMR (400 MHz, CDCl3): d 2.37 (s, 3H, CH3), 5.43 (s,
2H, OCH2), 7.06 (t, 1H, J = 4.4 Hz, Ar–H), 7.12–7.14 (m,
1H, Ar–H), 7.27–7.28 (m, 1H, Ar–H), 7.29–7.40 (m, 4H,
Ar–H), 7.44–7.48 (m, 1H, Ar–H), 8.15 (dd, 1H,
J = 6.4 Hz, 1.6 Hz, Ar–H), 9.00 (dd, 1H, J = 2.8 Hz,
1.6 Hz, Ar–H); 13C NMR (100 MHz, CDCl3): d 21.44 (C,
CH3), 70.83 (C, OCH2), 109.86 (C, Ar–C), 119.78 (C, Ar–
C), 121.60 (C, Ar–C), 124.27 (C, Ar–C), 126.63 (C, Ar–C),
127.87 (C, Ar–C), 128.52 (C, Ar–C), 128.62 (C, Ar–C),
129.51 (C, Ar–C), 135.95 (C, Ar–C), 136.87 (C, Ar–C),
138.30 (C, Ar–C), 140.45 (C, Ar–C), 149.32 (C, Ar–C),
154.42 (C, Ar–C); HRMS (ESI): Calcd. for C17H16NO
[M?H]?, 250.1232. found 250.1226. Yield = 87 %.
8-(3,5-bis-(trifluoromethyl)benzyloxy)-quinoline (2c)
1H NMR (400 MHz, CDCl3): d 5.54 (s, 2H, OCH2), 7.07 (d,
1H, J = 7.6 Hz, Ar–H), 7.43–7.52 (m, 3H, Ar–H), 7.87 (s,
1H, Ar–H), 8.05 (s, 2H, Ar–H), 8.19 (dd, 1H, J = 6.8 Hz,
1.6 Hz, Ar–H), 9.01 (dd, 1H, J = 2.8 Hz, 1.6 Hz, Ar–H);
13C NMR (100 MHz, CDCl3): d 69.92 (C, OCH2), 110.46
(C, Ar–C), 121.10 (C, Ar–C), 121.89 (C, Ar–C), 121.97 (C,
Ar–C), 122.01 (C, Ar–C), 124.59 (C, Ar–C), 126.43 (C, Ar–
C), 127.47 (C, Ar–C), 129.68 (C, Ar–C), 131.51 (C, Ar–C),
131.85 (C, Ar–C), 132.18 (C, Ar–C), 132.51 (C, Ar–C),
136.01 (C, Ar–C), 140.50 (C, Ar–C), 149.71 (C, Ar–C),
153.88 (C, Ar–C); HRMS (ESI): Calcd. for C18H12NOF6
[M?H]?, 372.0823. found 372.0805. Melting Point =
106.3–108.6 °C; Yield = 81 %.
8-(3-phenylbenzyloxy)-quinoline (2g)
1H NMR (400 MHz, CDCl3): d 5.53 (s, 2H, OCH2), 7.10
(d, 1H, J = 4.0 Hz, Ar–H), 7.40–7.46 (m, 7H, Ar–H),
7.55–7.61 (m, 4H, Ar–H), 7.77 (s, 1H, Ar–H), 8.14–8.16
(m, 1H, Ar–H), 9.00 (s, 1H, Ar–H); 13C NMR (100 MHz,
CDCl3): d 70.77 (C, OCH2), 110.00 (C, Ar–C), 119.95 (C,
Ar–C), 121.51 (C, Ar–C), 125.93 (C, Ar–C), 126.24 (C,
Ar–C), 126.51 (C, Ar–C), 126.61 (C, Ar–C), 127.07 (C,
Ar–C), 127.35 (C, Ar–C), 128.73 (C, Ar–C), 129.09 (C,
Ar–C), 129.40 (C, Ar–C), 135.74 (C, Ar–C), 137.54 (C,
Ar–C), 140.45 (C, Ar–C), 140.69 (C, Ar–C), 141.39 (C,
Ar–C), 149.21 (C, Ar–C), 154.33 (C, Ar–C); HRMS (ESI):
8-(4-fluorobenzyloxy)-quinoline (2d)
1H NMR (400 MHz, CDCl3): d 5.42 (s, 2H, OCH2),
7.05–7.10 (m, 3H, Ar–H), 7.41–7.42 (m, 2H, Ar–H),
7.45–7.48 (m, 1H, Ar–H), 7.51-7.55 (m, 2H, Ar–H), 8.16
(dd, 1H, J = 4.4 Hz, 1.6 Hz, Ar–H), 8.99 (dd, 1H,
J = 2.8 Hz, 1.6 Hz, Ar–H); 13C NMR (100 MHz, CDCl3): d
70.14 (C, OCH2), 109.90 (C, Ar–C), 115.44 (C, Ar–C),
123