SYNTHESIS OF QUINOLINE DERIVATIVES
1755
trans-7-Methyl-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano-[3,2-c]-
quinoline (5j). Solid, mp 130–131 ꢁC. IR (KBr): n 3340, 2975, 2840, 1615, 1504,
1085 cmꢂ1.1H NMR (CDCl3): d 1.25–1.35 (m, 3H), 1.60–1.65 (m, 1H), 1.80–1.85
(m, 1H), 2.10 (s, 3H), 3.70, (dt, 1H, J ¼ 11.5 & 2.5 Hz), 3.90 (brs, 1H, NH), 4.10
(m, 1H), 4.40 (d, 1H, J ¼ 2.8 Hz), 4.78 (d, 1H, J ¼ 10.5 Hz), 6.64 (t, 1H, J ¼ 8.0 Hz),
7.00 (dd, 1H, J ¼ 8.0 & 0.8 Hz,), 7.10 (dd, 1H, J ¼ 8.0 & 1.5 Hz), 7.30–7.40 (m, 3H),
7.44 (m, 2H). 13C NMR (CDCl3): d 17.2, 22.1, 24.3, 38.7, 55.3, 68.7, 74.5, 117.0,
120.0, 121.3, 127.8, 128.0, 128.5, 128.9, 130.5, 142.5, 142.9.
cis-9-Methoxy-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano-[3,2-c]-
quinoline (4k). Solid, mp 145–146 ꢁC. IR (KBr): n 3340, 2970, 2855, 1610, 1520,
1
1065 cmꢂ1. H NMR (CDCl3). d 1.30–1.60 (m, 4H), 2.15 (m, 1H), 3.42 (m, 1H),
3.58 (m, 1H), 3.60 (brs, 1H, NH), 3.80 (s, 3H), 4.62 (d, 1H, J ¼ 2.0 Hz), 5.25
(d, 1H, J ¼ 5.2 Hz), 6.50 (d, 1H, J ¼ 8.0 Hz), 6.70 (dd, J ¼ 8.2, 2.7 Hz, 1H), 7.05
(d, 1H, J ¼ 2.7 Hz), 7.30–7.45 (m, 5H). EIMS: m=z: 295 m,þ 237, 225, 160, 91.
trans-9-Methoxy-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano-[3,2-c]-
quinoline (5k). Solid, mp 98–99 ꢁC. IR (KBr): n 3325, 3059, 2961, 2868, 1605, 1515,
1457, 1324, 1279, 1163, 1070, 928, 861, 741 cmꢂ1. 1H NMR (CDCl3): d 1.20–1.26 (m,
1H), 1.30–1.45 (m, 1H), 1.52–1.62 (m, 1H), 1.68–1.78 (m, 1H), 1.95–2.05 (m, 1H),
3.40–3.50 (m, 1H), 3.60 (s, 3H, OCH3), 3.90–4.10 (m, 1H), 4.30 (d, 1H, J ¼ 2.7 Hz),
4.55 (d, 1H, J ¼ 10.5 Hz), 6.38 (d, 1H, J ¼ 8.0 Hz), 6.60 (dd, 1H, J ¼ 8.1, 2.7 Hz), 6.65
(d, 1H, J ¼ 2.7 Hz), 7.20–7.30 (m, 5H). 13C NMR (CDCl3): d 22.0, 24.5, 39.0, 55.4,
55.9, 68.5, 74.5, 114.9, 115.5, 116.7, 121.4, 127.9, 128.5, 139.0, 142.4, 152.3.
cis-9-Fluoro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano-[3,2-c]-
quinoline (4l). Solid, mp 174–175 ꢁC. IR (KBr). n 3326, 3063, 2945, 2847, 1618,
1582, 1505, 1492, 1356, 1251, 1163, 1089, 1006, 931, 847, 739 cmꢂ1 1H NMR
.
(CDCl3): d 1.24–1.32 (m, 1H), 1.38–1.60 (m, 3H), 2.05–2.15 (m, 1H), 3.40 (dt, 1H,
J ¼ 11.5, 2.5 Hz), 3.58 (dd, 1H, J ¼ 11.5, 2.5 Hz), 3.68 (brs, 1H, NH), 4.60 (d, 1H,
J ¼ 2.7 Hz), 5.20 (d, 1H, J ¼ 5.7 Hz), 6.44 (d, 1H, J ¼ 8.4 Hz), 6.78 (dd, 1H, J ¼ 8.4,
2.8 Hz), 7.10 (d, 1H, J ¼ 2.8 Hz), 7.25–7.40 (m, 5H). EIMS m=z: 283 m,þ 239, 225,
198, 150, 148, 91.
trans-9-Fluoro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano-[3,2-c]-
quinoline (5l). Viscous oil. IR (KBr): n 3325, 3062, 2945, 2853, 1612, 1589, 1495,
1
1367, 1250, 1153, 1080, 927, 831, 743 cmꢂ1. H NMR (CDCl3): d 1.30–1.40 (m,
1H), 1.45–1.52 (m, 1H), 1.55–1.65 (m, 1H), 1.75–1.90 (m, 1H), 2.05–2.15 (m, 1H),
3.68 (dt, 1H, J ¼ 11.5, 2.8 Hz), 3.90 (brs, 1H, NH), 4.10 (d, 1H, J ¼ 2.8 Hz), 4.32
(d, 1H, J ¼ 2.8 Hz), 4.65 (d, 1H, J ¼ 10.5 Hz), 6.45 (d, 1H, J ¼ 8.4 Hz), 6.80 (dd,
1H, J ¼ 8.4, 2.8 Hz), 6.95 (d, 1H, J ¼ 2.8 Hz), 7.30–7.40 (m, 5H).
cis-12-Phenyl-2,3,4a,11,12,12a-hexahydro-1H-benzo[H]pyrano-[3,2-c]-
quinoline (4m). Solid, mp 163–163 ꢁC. IR (KBr): n 3375, 3054, 2941, 2861, 1667,
1574, 1510, 1465, 1371, 1081, 1012, 962, 873, 741 cmꢂ1 1H NMR (CDCl3):
.
1.35–1.45 (m, 3H), 1.60–1.70 (m, 1H), 2.25–2.35 (m, 1H), 3.40 (dt, 1H, J ¼ 11.5,
2.5 Hz), 3.62 (dd, 1H, J ¼ 11.5, 2.5 Hz), 4.50 (brs, 1H, NH), 4.88 (d, 1H, J ¼ 2.7 Hz),
5.50 (d, 1H, J ¼ 5.7 Hz), 7.22–7.31 (m, 2H), 7.35–7.50 (m, 4H), 7.58–7.68 (m, 3H),
7.75–7.85 (m, 2H). EIMS m=z: 316 m,þ 256, 206, 180, 155, 141, 115, 69, 43.