Molecules 2013, 18
827
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2-Methyl-12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline (3Ga). H-NMR (400 MHz,
CDCl3) δ 7.31 (d, J = 8.0 Hz, 1H), 7.26–7.19 (m, 5H), 7.07–7.03 (m, 2H), 7.00 (s, 1H), 6.92 (t,
J = 7.6Hz, 1H), 6.78 (t, J = 7.6Hz, 1H), 6.22 (d, J = 8.4 Hz, 1H), 6.07 (s, 1H), 5.90 (s, 1H), 5.26 (d,
J =14.8 Hz,1H), 5.09 (d, J =14.4 Hz,1H), 2.36 (s, 3H). 13C-NMR (125 MHz, CDCl3) δ 140.81, 140.05,
138.74, 137.11, 132.24, 128.65, 128.52, 127.97, 127.79, 126.94, 126.78, 125.69, 124.79, 124.70,
124.12, 123.88, 122.54, 105.59, 85.00, 68.00, 21.40. LRMS (EI) m/z 325 (M+); HRMS (EI) m/z calcd
C23H19NO (M+) 325.1467, found 325.1463
8-Chloro-2-methyl-12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline (3Gc). 1H-NMR
(400 MHz, CDCl3) δ 7.32–7.25 (m, 4H), 7.23–7.21 (m, 2H), 7.08 (d, J = 8.0 Hz, 1H), 7.04 (d, J = 1.6 Hz,
1H), 7.01 (s, 1H), 6.75 (dd, J = 8.8, 2.4 Hz, 1H), 6.13 (d, J = 8.8 Hz, 1H), 6.02 (s, 1H), 5.95 (s, 1H),
5.18 (d, J =14.8 Hz,1H), 5.04 (d, J =14.8 Hz,1H), 2.34 (s, 3H). 13C-NMR (125 MHz, CDCl3) δ 140.27,
138.87, 138.51, 136.68, 132.07, 129.69, 128.56, 128.21, 128.05, 127.60, 127.21, 126.58, 125.99,
124.95, 124.67, 124.23, 106.49, 85.14, 67.49, 21.41. LRMS (EI) m/z 359 (M+); HRMS (EI) m/z calcd
C23H18ClNO (M+) 359.1077, found 359.1058.
2,8-Dimethyl-12-phenyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline (3Gf). 1H-NMR
(400 MHz, CDCl3) δ 7.31–7.28 (d, J = 8.0 Hz, 1H), 7.26–7.18 (m, 5H), 7.04 (d, J = 7.6 Hz, 1H), 6.99
(s, 1H), 6.85 (s, 1H), 6.59 (d, J = 7.6 Hz, 1H), 6.12 (d, J = 8.0 Hz, 1H), 6.04 (s, 1H), 5.81 (s, 1H), 5.25
(d, J = 14.8 Hz,1H), 5.06 (d, J = 14.8 Hz,1H), 2.36 (s, 3H), 2.24(s, 3H). 13C-NMR (125 MHz, CDCl3)
δ 141.11, 138.76, 137.73, 137.30, 132.43, 132.29, 128.82, 128.52, 127.89, 127.69, 127.14, 126.73,
126.36, 125.10, 124.69, 124.08, 123.59, 104.46, 84.99, 68.06, 21.42, 20.87. LRMS (EI) m/z 339 (M+);
HRMS (EI) m/z calcd C24H21NO (M+) 339.1623, found 339.1617.
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2-Methyl-14-phenyl-4b,6-dihydronaphtho[2',3':4,5][1,3]oxazino[2,3-a]isoquinoline (3Gh). H-NMR
(400 MHz, CDCl3) δ 7.68 (d, J = 8.4 Hz,1H), 7.54 (s, 1H), 7.42–7.36 (m, 3H), 7.27–7.25 (m, 6H), 7.10
(d, J = 7.6 Hz, 1H), 7.07 (s, 1H), 6.51 (s, 1H), 6.31 (s, 1H), 6.21 (s, 1H), 5.28 (d, J = 13.6 Hz, 1H),
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5.22 (d, J = 14.0 Hz, 1H), 2.39 (s, 3H). C-NMR (125 MHz, CDCl3) δ 140.27, 138.34, 137.00,
136.43, 132.78, 132.32, 128.77, 128.33, 128.17, 128.10, 128.03, 127.60, 127.20, 126.88, 126.53,
125.76, 124.98, 124.87, 124.12, 123.19, 118.14, 109.99, 85.88, 67.63, 21.39. LRMS (EI) m/z 375
(M+); HRMS (EI) m/z calcd C27H21NO (M+) 375.1623, found 375.1617.
12-Hexyl-4b,6-dihydrobenzo[4,5][1,3]oxazino[2,3-a]isoquinoline (3Ha). 1H-NMR (400 MHz, CDCl3)
δ 7.35– 7.31 (m, 3H), 7.27–7.09 (m, 5H), 5.83(s, 1H), 5.75(s, 1H), 5.23 (d, J = 15.6 Hz, 1H), 5.00 (d,
J = 15.2 Hz, 1H), 2.57–2.36 (m, 2H), 1.46–1.31 (m, 2H), 1.25–1.13 (m, 6H), 0.85 (t, J = 6.4 Hz, 3H).
13C-NMR (100 MHz, CDCl3) δ 142.63, 140.91, 132.49, 130.91, 129.23, 127.63, 125.91, 125.31,
125.15, 125.00, 124.92, 124.85, 123.62, 100.42, 84.85, 67.74, 32.88, 31.52, 28.75, 27.57, 22.43, 14.02.
LRMS (EI) m/z 319 (M+); HRMS (EI) m/z calcd C22H25NO (M+) 319.1936, found 319.1935.
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12-Hexyl-8-iodo-4b,6-dihydrobenzo[4,5][1,3]oxa-zino[2,3-a]isoquinoline (3Hi). H-NMR (300 MHz,
CDCl3) δ 7.54 (d, J =8.7 Hz, 1H), 7.43 (s, 1H), 7.34–7.27 (m, 2H), 7.19–7.10 (m, 2H), 6.92 (d, J = 8.4 Hz,
1H), 5.74 (s, 2H), 5.14 (d, J = 15.3 Hz,1H), 4.91 (d, J =15.9 Hz, 1H), 2.43–2.40 (m, 2H), 1.30–1.17
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(m, 8H), 0.88–0.84 (m, 3H). C-NMR (125 MHz, CDCl3) δ 141.92, 140.66, 134.94, 134.27, 133.07,