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HETEROCYCLES, Vol. 75, No. 10, 2008
reaction, the mixture was poured in ice-water (20 mL), and neutralized with saturated aqueous NaHCO3.
Then, the precipitates were filtered and recrystallized from n-hexane/ EtOAc to give corresponding
quinoline derivatives.
1
(3a): H NMR (500 MHz, DMSO-d6): δ 0.85 (t, 3H, J= 7.0 Hz), 2.66 (s, 3H), 4.01 (q, 2H, J= 7.0 Hz),
13
7.31-7.34 (m, 2H), 7.46-7.53 (m, 5H), 7.78 (t, 1H, J= 8.2 Hz), 8.03 (d, 1H, J= 8.3 Hz). C NMR (125
MHz, DMSO-d6): δ 13.84, 23.76, 61.48, 124.78, 126.44, 127.36, 128.80, 129.00, 129.09, 129.55, 130.98,
135.42, 145.91, 147.56, 154.30, 167.98.
(3b): 1H NMR (500 MHz, DMSO-d6): δ 2.67 (s, 3H), 3.55 (s, 3H), 7.34-7.35 (m, 2H), 7.50-7.54 (m, 5H),
7.81 (t, 1H, J= 6.9 Hz), 8.05 (d, 1H, J= 8.2 Hz). 13C NMR (125 MHz, DMSO-d6): δ 24.19, 53.08, 125.15,
126.89, 127.75, 127.84, 129.30, 129.53, 129.56, 129.86, 131.48, 135.76, 146.39, 148.04, 154.70, 168.98.
1
(3c): H NMR (500 MHz, DMSO-d6): δ 2.15 (p, 2H, J= 6.3 Hz), 2.65 (t, 2H, J= 6.5 Hz), 3.29 (t, 2H, J=
6.2 Hz), 7.19 (m, 2H), 7.33 (d, 1H, J= 8.3 Hz), 7.46-7.51 (m, 4H), 7.84 (t, 1H, J= 7.2 Hz), 8.03 (d, 1H, J=
8.3 Hz). 13C NMR (125 MHz, DMSO-d6): δ 21.68, 34.69, 40.90, 124.71, 127.50, 127.57, 128.14, 128.27,
128.77, 129.09, 129.19, 132.57, 138.28, 148.77, 150.80, 163.23, 198.30.
(3d): 1H NMR (500 MHz, DMSO-d6): δ 1.07 (s, 6H), 2.55 (s, 2H), 3.22 (s, 2H), 7.16-7.18 (m, 2H), 7.30-
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7.33 (m, 1H), 7.46-7.54 (m, 5H), 7.80-7.85 (m, 1H), 8.02 (m, 1H). C NMR (125 MHz, DMSO-d6): δ
28.31, 32.35, 47.85, 53.86, 127.15, 127.95, 128.38, 128.64, 128.79, 128.97, 131.33, 132.15, 134.69,
137.87, 148.77, 150.13, 161.62, 197.79.
(3e): 1H NMR (500 MHz, DMSO-d6): δ 1.09 (m, 2H), 2.11 (m, 2H), 2.86 (t, 2H, J= 7.0 Hz), 3.23 (t, 2H,
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J= 7.20 Hz), 7.40-7.42 (m, 2H), 7.53-7.60 (m, 5H), 7.77 (t, 1H, J= 8.1 Hz), 8.05 (d, 1H, J= 8.1 Hz). C
NMR (125 MHz, DMSO-d6): δ 22.76, 22.89, 27.96, 34.51, 126.39, 126.51, 126.77, 127.67, 129.56,
129.64, 129.88, 130.61, 135.67, 136.02, 144.78, 145.73, 167.20.
1
(3f): H NMR (500 MHz, DMSO-d6): δ 2.08 (p, 2H, J= 7.4 Hz), 2.83 (t, 2H, J= 7.3 Hz), 3.11 (t, 2H, J=
7.6 Hz), 7.40-7.45 (m, 3H), 7.49-7.58 (m, 4H), 7.65 (t, 1H, J= 7.5 Hz), 7.98 (d, 1H, J= 8.3 Hz). 13C NMR
(125 MHz, DMSO-d6): δ 23.84, 30.66, 35.27, 125.93, 126.33, 126.50, 128.99, 129.01, 129.50, 129.57,
130.01, 134.23, 136.90, 142.49, 148.41, 167.96.
1
(3g): H NMR (500 MHz, DMSO-d6): δ 7.58-7.65 (m, 6H), 7.84 (t, 1H, J= 7.6 Hz), 7.88 (d, 1H, J= 8.3
Hz), 8.14 (s, 1H), 8.20 (d, 1H, J= 8.3 Hz), 8.34 (d, 2H, J= 8.9 Hz), 8.59 (d, 2H, J= 8.9 Hz). 13C NMR (125
MHz, DMSO-d6): δ 120.05, 124.73, 126.18, 126.33, 128.53, 129.39, 129.60, 130.40, 130.49, 130.83,
131.09, 138.09, 145.29, 148.86, 148.94, 149.98, 154.26.
1
(3h): H NMR (500 MHz, DMSO-d6): δ 0.85 (t, 3H, J= 7.0 Hz), 2.64 (s, 3H), 4.02 (q, 2H, J= 7.0 Hz),
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7.32-7.37 (m, 3H), 7.53-7.54 (m, 3H), 7.79 (d, 1H, J= 8.9 Hz), 8.03 (d, 1H, J= 8.9 Hz). C NMR (125
MHz, DMSO-d6): δ 13.83, 23.73, 61.66, 124.91, 125.70, 128.16, 128.99, 129.41, 129.52, 131.34, 131.46,
131.85, 134.67, 145.17, 145.96, 155.03, 167.60.