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TETRAHYDROQUINOLINES CATALYZED BY Dy(OTf )3
2547
(100); 131 (13.49); 130 (11.97); Anal. calcd. for C12H15NO: C, 76.19; H, 7.94;
N, 7.40. Found C, 76.00; H, 7.63; N, 7.41.
Pyrano[3,2-c]quinoline: Colorless oil; 1H-NMR(300 MHz, CDCl3):
ꢀ 1.45 (m, 1H); 1.72–1.95 (m, 3H); 2.15 (m, 1H); 2.90 (s, 3H); 2.93 (dd,
J ¼ 4.0 and 1.2Hz), 3.51 (t, J ¼ 11.1 Hz, 1 Hz); 3.64 (td, J ¼ 10.4 and
2.4 Hz, 1H); 3.92 (m, 1H); 4.40 (d, J ¼ 3.0 Hz, 1H); 6.62(t, J ¼ 8.3 Hz,
1H); 6.65 (dd, J ¼ 1.0 Hz and 7.4 Hz, 1H); 6.65 (dd, J ¼ 1.0 and 7.4 Hz,
1H); 7.12–7.20 (m, 2H); IR (neat, cmÀ1): 3068, 3028, 2933, 2855, 1607,
1572, 1503, 1478, 1452, 1359, 1322, 1294, 1271, 1245, 1208, 1162, 1141,
1091, 1065, 1052, 1043, 1023, 1002, 977, 934, 911, 884, 865, 850, 746, 727,
703, 663, 642, 574, 541; MS: 203(Mþ, 48.46); 190 (24.19); 158 (28.61); 146
(33.16); 145 (27.52); 144 (100); 131 (13.49); 130 (11.97); Anal. calcd. for
C13H17NO: C, 76.84; H, 8.37; N, 6.90; Found C, 76.73; H, 7.93; N, 6.90.
1
1-Methyl-4-methoxy-1,2,3,4-tetrahydroquinoline: Colorless oil; H-NMR
(300 MHz, CCl4): ꢀ: 1.73–2.20 (m, 2H); 2.90 (s, 3H); 3.23 (s, 3H); 3.06–3.57
(m, 2H); 4.03 (t, 1H, J ¼ 3 Hz), 6.30–7.23 (m, 4H); IR (neat, cmÀ1): 3058,
3020, 1600, 1500, 1200, 1090, 742; Anal. calcd for C11H15NO: C, 74.54; H,
8.53; N, 7.90. Found: C, 74.21; H, 8.77; N, 7.74.
1-Methyl-4-ethoxy-1,2,3,4-tetrahydroquinoline: Colorless oil; 1H-NMR
(300 MHz, CCl4): ꢀ: 1.15 (t, 3H, J ¼ 7 Hz); 1.73–2.11 (m, 2H ); 2.88 (s, 1H);
2.96–3.63 (m, 2H); 3.60 (q, 2H, J ¼ 7.0 Hz); 4.15 (t, 1H, J ¼ 3.4 Hz),
6.30–7.21 (m, 4H); IR (neat, cmÀ1): 3058, 3020, 1600, 1500, 1325, 1220,
1080, 742; Anal. calcd. for C12H17NO: C, 75.37; H, 8.96; N, 7.32. Found:
C, 75.03; H, 9.06; N, 7.16.
1
1-Methyl-4-hexyl-1,2,3,4-tetrahydroquinoline: Colorless oil: H-NMR
(300 MHz, CCl4): ꢀ: 0.85 (t, 3H, J ¼ 4.0 Hz); 1.07–2.11 (m, 12H ); 2.43–
2.98 (m, 1H); 2.83 (s, 1H); 2.96–3.63 (m, 2H); 6.23–7.06 (m, 2H); IR
(neat, cmÀ1): 3058, 3020, 1600, 1501, 1320, 742; Anal. calcd. for C16H25N:
C, 83.06; H, 10.89; N, 6.05. Found: C, 83.01; H, 11.08; N, 5.95
1
1-Methyl-4-phenyl-1,2,3,4-tetrahydroquinoline: Colorless oil; H-NMR
(90MHz, CCl4): ꢀ: 1.94–2.41 (m, 2H); 2.79 (s, 3H); 3.01 (t, 2H, J ¼ 4.8 Hz);
3.85 (t, 1H, J ¼ 5.9 Hz); 6.15–7.50 (m, 9H); IR (neat, cmÀ1): 3058, 3019,
1600, 1500, 1320, 740, 700; Anal. calcd. for C16H17N: C, 86.06; H, 7.67;
N, 6.27. Found: C, 86.01; H, 7.75; N, 6.29.
ACKNOWLEDGMENTS
Financial support from the State Key Project of Basic Research
(Project 973, No. G 2000048007) and National Natural Sciences
Foundation of China are grateful acknowledged.