Molecular Diversity
12-(3-Chlorophenyl)-1,2,3,4,7,8,9,10-
(CDCl3, 75 MHz) δ/ppm: 22.3, 22.6, 23.1, 23.7, 27.7, 32.6,
34.2, 107.4, 111.1, 123.9, 127.1, 128.1, 131.4, 132.2, 140.9,
144.0, 150.2, 151.5, 159.0, 162.1. LC–MS (m/z): 408.1
[MH]+. Anal. Calcd. for C22H22BrN3: C, 64.71; H, 5.43; N,
10.29; found: C, 64.88; H, 5.56; N, 10.34.
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine (4b)
Cream powder, 60% yield; mp. 225–227 °C; IR: 3440, 3380,
2937, 2857, 1638, 1561, 1542, 1431, 1302, 1146, 1078, 800,
1
673 cm−1; H NMR (CDCl3, 300 MHz) δ/ppm: 1.73–1.77
(2H, m), 1.85–1.89 (6H, m), 2.32–2.39 (4H, m), 3.01 (2H, t,
J=6.1 Hz), 3.12 (2H, t, J=6.4 Hz), 4.10 (2H, s), 7.20 (1H,
t, J=4.1 Hz), 7.30 (1H, s), 7.47 (2H, d, J=4.6 Hz); 13C
NMR (CDCl3, 75 MHz) δ/ppm: 22.8, 23.0, 23.3, 23.9, 27.8,
34.3, 107.8, 111.1, 126.8, 127.1, 128.7, 130.9, 135.6, 141.6,
143.5, 148.1, 153.6, 160.9. LC–MS (m/z): 364.1 [MH]+.
Anal. Calcd. for C22H22ClN3: C, 72.62; H, 6.09; N, 11.55;
found: C, 72.50; H, 6.00; N, 11.78.
12-(4-Bromophenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine
(4f)
Light brown powder, 40% yield; mp. 227–229 °C; IR: 3480,
3410, 2930, 2860, 1698, 1608, 1565, 1542, 1426, 1313,
1
1069, 1011, 929, 834 cm−1; H NMR (CDCl3, 300 MHz)
δ/ppm: 1.69–1.77 (2H, m), 1.84–1.91 (6H, m), 2.30–2.34
(4H, m), 3.01 (2H, t, J=5.8 Hz), 3.12 (2H, t, J=6.4 Hz), 4.15
(2H, s), 7.20 (2H, d, J=8.4 Hz), 7.67 (2H, d, J=8.4 Hz);
13C NMR (CDCl3, 75 MHz) δ/ppm: 22.8, 23.0, 23.3, 23.9,
27.8, 34.2, 34.3, 107.8, 111.0, 122.9, 127.2, 130.3, 132.8,
138.5, 143.9, 148.2, 153.4, 160.7, 160.9. LC–MS (m/z):
408.1 [MH]+. Anal. Calcd. for C22H22BrN3: C, 64.71; H,
5.43; N, 10.29; found: C, 64.82; H, 5.60; N, 10.40.
12-(4-Chlorophenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine (4c)
Light brown powder, 67% yield; mp. 142–145 °C; IR: 3430,
3400, 2930, 2857, 1625, 1563, 1541, 1491, 1428, 1304,
1088, 1015, 863 cm−1; 1H NMR (CDCl3, 300 MHz) δ/ppm:
1.64–1.74 (2H, m), 1.80–2.01 (6H, m), 2.28–2.32 (4H, m),
2.99 (2H, t, J=5.8 Hz), 3.10 (2H, t, J=6.4 Hz), 4.13 (2H,
s), 7.23 (2H, d, J=8.2 Hz), 7.50 (2H, d, J=7.9 Hz); 13C
NMR (CDCl3, 75 MHz) δ/ppm: 22.8, 23.0, 23.3, 23.9, 25.2,
27.8, 34.3, 42.2, 107.9, 111.0, 123.8, 127.3, 129.8, 130.1,
134.8, 136.0, 138.1, 143.8, 148.2, 153.5, 160.7, 160.9.
LC–MS (m/z): 364.0 [MH]+. Anal. Calcd. for C22H22ClN3:
C, 72.62; H, 6.09; N, 11.55; found: C, 72.70; H, 6.12; N,
11.65.
12-(4-Methoxyphenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine (4g)
Yellow powder, 86% yield; mp. 209–211 °C; IR: 3460, 3400,
2928, 2857, 1633, 1563, 1541, 1510, 1435, 1284, 1243,
1
1177, 1030, 930, 835 cm−1; H NMR (CDCl3, 300 MHz)
δ/ppm: 1.67–1.75 (2H, m), 1.82–1.84 (6H, m), 2.31–2.35
(4H, m), 2.98 (2H, s, br), 3.09 (2H, t, J=6.4 Hz), 3.86
(3H, s), 4.26 (2H, s), 7.03 (2H, d, J=8.7 Hz), 7.16 (2H, d,
J=8.4 Hz); 13C NMR (CDCl3, 75 MHz) δ/ppm: 22.8, 23.0,
23.4, 23.8, 27.7, 34.1, 34.3, 55.5, 108.4, 110.7, 115.0, 127.9,
129.7, 131.3, 145.1, 148.7, 153.5, 159.7, 160.4, 160.8.
LC–MS (m/z): 360.2 [MH]+. Anal. Calcd. for C23H25N3O:
C, 76.85; H, 7.01; N, 11.69; found: C, 77.00; H, 7.21; N,
11.52.
12-(3,4-Dichlorophenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine (4d)
Brown powder, 67% yield; mp. 201–203 °C; IR: 3470, 3380,
2931, 2857, 1632, 1563, 1541, 1433, 1315, 1135, 1031, 938,
1
822 cm−1; H NMR (CDCl3, 300 MHz) δ/ppm: 1.71–1.77
(2H, m), 1.85–1.88 (6H, m), 2.26–2.39 (4H, m), 3.01 (2H, t,
J=5.8 Hz), 3.11 (2H, t, J=6.1 Hz), 4.14 (2H, s), 7.17 (1H,
dd, J=8.7, 1.7 Hz), 7.40 (1H, s), 7.61 (1H, d, J=8.2 Hz); 13C
NMR (CDCl3, 75 MHz) δ/ppm: 22.7, 22.9, 23.2, 23.9, 27.8,
34.2, 34.3, 107.7, 111.3, 127.3, 128.1, 130.6, 131.6, 133.2,
134.0, 139.6, 142.4, 148.0, 153.4, 160.9, 161.0. LC–MS
(m/z): 398.0 [MH] +. Anal. Calcd. for C22H21Cl2N3: C,
66.34; H, 5.31; N, 10.55; found: C, 66.42 H, 5.55; N, 10.62.
12-(2,3-Dimethoxyphenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine(4h)
Light brown powder, 72% yield; mp. 162–164 °C; IR: 3480,
3410, 2938, 2856, 1622, 1558, 1540, 1512, 1436, 1284„
1
1277, 1030, 930, 837 cm−1; H NMR (CDCl3, 300 MHz)
δ/ppm: 1.67–1.76 (2H, m), 1.80–1.84 (6H, m), 2.24–2.38
(4H, m), 2.99 (2H, s, br), 3.10 (2H, t, J=6.4 Hz), 3.59
(3H, s), 3.92 (3H, s), 4.32 (2H, s), 6.68 (1H, d, J=7.9 Hz),
7.08 (2H, d, J=7.9 Hz), 7.18 (1H, t, J=8.2 Hz); 13C NMR
(CDCl3, 75 MHz) δ/ppm: 22.8, 22.9, 23.0, 23.3, 23.9, 27.2,
27.4, 34.3, 56.0, 60.0, 108.5, 110.7, 112.9, 121.1, 125.3,
127.7, 133.7, 141.7, 145.8, 148.5, 153.6, 160.4, 160.8.
LC–MS (m/z): 390.2 [MH]+. Anal. Calcd. for C24H27N3O2:
C, 74.01; H, 6.99; N, 10.79; found: C, 74.66; H, 7.20; N,
11.00.
12-(3-Bromophenyl)-1,2,3,4,7,8,9,10-
octahydrodibenzo[b,g][1,8]naphthyridin-11-amine
(4e)
Light brown powder, 57% yield; mp. 174–176 °C; IR: 3420,
3380, 2932, 2858, 1618, 1563, 1543, 1431, 1326, 1169,
1
1143, 1071, 967, 693 cm−1; H NMR (CDCl3, 300 MHz)
δ/ppm: 1.61–1.74 (4H, m), 1.85–2.13 (6H, m), 2.30–2.35
(4H, m), 3.04–3.09 (2H, m), 4.58 (2H, s), 7.19–7.25 (1H,
m), 7.40–7.45 (2H, m), 7.64 (1H, d, J=7.9 Hz); 13C NMR
123