4
J.-jia Jin et al. / Tetrahedron xxx (2013) 1e6
CDCl3):
d
161.0, 146.0, 143.4, 134.9, 131.4, 130.2, 130.1, 128.4, 127.8,
138.7,135.5, 133.7,131.3,130.2,128.5,128.3,127.8,127.4,126.4,124.1,
127.2, 126.5, 126.0, 122.9, 46.1, 45.5; HRMS: calcd for C27H20Cl2N2Na
44.9, 44.0; HRMS: calcd for C27H21N4O4 [MþH]þ 465.1557, found
[MþNa]þ 465.0896, found 465.0900; IR (NaCl)
n
/cmꢁ1: 3059, 2923,
465.1565; IR (KBr) n
/cmꢁ1: 3065, 2922, 1601, 1500, 1431, 1380, 751.
1597, 1489, 1452, 765.
4.3.11. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-fluoroquinoline) (3ja).
Yellow liquid. 1H NMR (400 MHz, CDCl3):
4.3.4. 2,20-(2-Phenylpropane-1,3-diyl)bis(8-chloroquinoline)
(3ca). Yellow liquid. 1H NMR (400 MHz, CDCl3):
d
8.00 (q, J¼4.8 Hz, 2H),
d
7.86 (d, J¼8.4 Hz,
7.78 (d, J¼8.4 Hz, 2H), 7.43e7.34 (m, 2H), 7.28e7.25 (m, 2H),
2H), 7.75 (d, J¼7.6 Hz, 2H), 7.55 (d, J¼8.0 Hz, 2H), 7.33e7.29 (m, 4H),
7.20e7.07 (m, 7H), 4.03e3.95 (m, 1H), 3.48e3.35 (m, 4H); 13C NMR
7.26e7.18 (m, 4H), 7.11 (t, J¼7.2 Hz, 1H), 4.33e4.26 (m, 1H),
(100 MHz, CDCl3):
d 160.0, 144.6, 143.5, 135.3, 135.2, 131.0, 130.9,
3.61e3.44 (m, 4H); 13C NMR (100 MHz, CDCl3):
d
161.7, 144.2, 143.8,
129.9, 128.3, 127.8, 127.2, 127.1, 126.4, 122.9, 119.5, 119.2, 110.5, 110.3,
135.9,133.0,129.2,128.2,128.0,127.9,126.5,126.3,125.4,123.1, 45.2,
46.2, 45.3; HRMS: calcd for C27H21F2N2 [MþH]þ 411.1667, found
45.0; HRMS: calcd for C27H20Cl2N2Na [MþNa]þ 465.0896, found
411.1666; IR (KBr) n
/cmꢁ1: 3059, 2933, 1605, 1503, 1476, 1228, 698.
465.0899; IR (KBr) n
/cmꢁ1: 3059, 2912, 2882, 1598, 1496, 1424, 759.
4.3.12. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-(trifluoromethyl)quino-
line) (3ka). Yellow liquid. 1H NMR (400 MHz, CDCl3):
8.09 (d,
4.3.5. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-methoxyquinoline)
(3da). Dark yellow liquid. 1H NMR (400 MHz, CDCl3):
7.89 (d,
d
d
J¼8.4 Hz, 2H), 7.94e7.90 (m, 4H), 7.81e7.78 (m, 2H), 7.20e7.11 (m,
J¼9.2 Hz, 2H), 7.75 (d, J¼8.4 Hz, 2H), 7.30e7.26 (m, 2H), 7.20e7.02
7H), 4.10e4.03 (m, 1H), 3.55e3.42 (m, 4H); 13C NMR (100 MHz,
(m, 7H), 6.93 (d, J¼2.8 Hz, 2H), 3.97e3.91 (m, 1H), 3.88 (s, 6H),
CDCl3):
d 163.1, 148.5, 143.3, 136.5, 129.9, 129.7, 128.4, 128.3, 127.8,
3.44e3.31 (m, 4H); 13C NMR (100 MHz, CDCl3):
d
158.1, 157.1, 143.9,
127.7, 127.5, 126.6,125.5,125.4,125.3,125.3,125.0,123.3,122.7, 46.0,
143.8, 134.6, 130.1, 128.2, 127.9, 127.5, 126.2, 122.3, 121.7, 105.0, 55.4,
45.6; HRMS: calcd for
511.1610; IR (NaCl) n
C
29H21F6N2 [MþH]þ 511.1603, found
46.3, 45.4; HRMS: calcd for C29H27N2O2 [MþH]þ 435.2067, found
/cmꢁ1: 3062, 2924, 1604, 1483, 1453, 1120, 700.
435.2071; IR (NaCl)
1232, 732.
n
/cmꢁ1: 3059, 2936, 2836, 1600, 1500, 1462,
4.3.13. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-bromoquinoline) (3la).
Yellow liquid. 1H NMR (400 MHz, CDCl3):
7.86 (d, J¼8.8 Hz, 2H),
7.77 (s, 2H), 7.86 (q, J¼8.0 Hz, 4H), 7.17e7.05 (m, 7H), 4.03e3.96 (m,
1H), 3.48e3.35 (m, 4H); 13C NMR (100 MHz, CDCl3):
161.1, 146.1,
d
4.3.6. 2,20-(2-Phenylpropane-1,3-diyl)bis(8-methoxyquinoline)
(3ea). Yellow liquid. 1H NMR (400 MHz, CDCl3):
2H), 7.34 (t, J¼8.0 Hz, 2H), 7.26e7.24 (m, 2H), 7.20 (d, J¼7.2 Hz, 2H),
7.14 (t, J¼7.2 Hz, 2H), 7.08 (d, J¼8.4 Hz, 3H), 6.99 (d, J¼6.8 Hz, 2H),
4.06 (s, 6H), 4.01e3.96 (m, 1H), 3.57e3.43 (m, 4H); 13C NMR
d
7.80 (d, J¼8.4 Hz,
d
143.4, 134.8, 132.6, 130.4, 129.4, 128.4, 127.8, 127.7, 126.5, 122.9,
119.5, 46.1, 45.5; HRMS: calcd for
522.9885, found 522.9886; IR (KBr)
1456, 833, 699.
C
27H20Br2N2Na [MþNa]þ
n
/cmꢁ1: 3054, 2925, 1595, 1486,
(100 MHz, CDCl3):
d 159.7, 155.0, 143.7, 139.7, 135.5, 128.2, 128.1,
127.8, 126.2, 125.6, 122.6, 119.4, 107.7, 56.1, 46.0, 45.7; HRMS: calcd
for C29H27N2O2 [MþH]þ 435.2067, found 435.2068; IR (NaCl)
n
/
4.3.14. 2,20-(2-Phenylpropane-1,3-diyl)bis(benzo[h]quinoline)
(3ma). Yellow liquid. 1H NMR (400 MHz, CDCl3):
9.41e9.39 (m,
cmꢁ1: 3057, 2933, 2834, 1602, 1504, 1471, 1259, 731.
d
2H), 7.89e7.87 (m, 4H), 7.72e7.65 (m, 6H), 7.56 (d, J¼8.8 Hz, 2H),
4.3.7. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-methylquinoline)
(3fa). Dark yellow liquid. 1H NMR (400 MHz, CDCl3):
7.94 (d,
7.33e7.21 (m, 2H), 7.22e7.18 (m, 4H), 7.13e7.09 (m, 1H), 4.49e4.42
d
(m, 1H), 3.66e3.49 (m, 4H); 13C NMR (100 MHz, CDCl3):
d 159.5,
J¼8.4 Hz, 2H), 7.76 (d, J¼8.4 Hz, 2H), 7.48e7.46 (m, 2H), 7.41 (s, 2H),
145.9, 135.4, 133.6, 131.5, 128.2, 128.0, 127.8, 127.5, 126.6, 126.6,
126.0, 125.2, 124.7, 124.3, 122.5, 45.7, 45.3; HRMS: calcd for
C
7.21e7.12 (m, 4H), 7.09e7.03 (m, 3H), 4.03e3.95 (m, 1H), 3.50e3.36
(m, 4H), 2.47 (s, 6H); 13C NMR (100 MHz, CDCl3):
d
159.8, 146.1,
35H27N2 [MþH]þ 475.2169, found 475.2175; IR (KBr)
n
/cmꢁ1: 3049,
143.7, 135.5, 135.3, 131.5, 128.2, 127.9, 126.7, 126.3, 122.1, 46.4, 45.4,
2921, 1595, 1505, 1449, 1395, 843.
21.5; HRMS: calcd for C29H27N2 [MþH]þ 403.2169, found 403.2172;
IR (NaCl)
n
/cmꢁ1: 3058, 2917, 1600, 1496, 1451, 829.
4.3.15. 4-(1,3-Di(quinolin-2-yl)propan-2-yl)benzonitrile
(4ab). Yellow liquid. 1H NMR (400 MHz, CDCl3):
d
7.99 (d, J¼8.4 Hz,
4.3.8. 2,20-(2-Phenylpropane-1,3-diyl)bis(8-methylquinoline) (3ga).
Yellow liquid. 1H NMR (400 MHz, CDCl3):
2H), 7.91 (d, J¼8.4 Hz, 2H), 7.71e7.64 (m, 4H), 7.48e7.40 (m, 4H),
7.30 (d, J¼8.0 Hz, 2H), 7.09 (d, J¼8.4 Hz, 2H), 4.23e4.15 (m, 1H),
d
7.87 (d, J¼8.4 Hz, 2H),
7.52 (q, J¼8.0 Hz, 4H), 7.33 (t, J¼7.2 Hz, 2H), 7.27e7.25 (m, 2H),
3.53e3.34 (m, 4H); 13C NMR (100 MHz, CDCl3):
d 159.7, 149.6, 147.8,
7.19e7.07 (m, 5H), 4.30e4.22 (m, 1H), 3.55e3.38 (m, 4H), 2.81 (s,
136.0, 132.0, 129.4, 128.8, 127.5, 126.6, 125.9, 121.8, 119.0, 110.0, 45.9,
6H); 13C NMR (100 MHz, CDCl3):
d
159.6, 146.8, 144.7, 136.9, 135.7,
45.0; HRMS: calcd for C28H22N3 [MþH]þ 400.1808, found 400.1800;
129.1, 128.0, 126.5, 126.0, 125.3, 125.2, 121.8, 45.3, 18.0; HRMS: calcd
IR (KBr) n
/cmꢁ1: 3041, 2924, 2224, 1598, 1504, 1426, 827.
for C29H27N2 [MþH]þ 403.2169, found 403.2167; IR (KBr)
n :
/cmꢁ1
3041, 2951, 2915, 2882, 1600, 1500, 1426, 760.
4.3.16. 2,20-(2-(4-(Trifluoromethyl)phenyl)propane-1,3-diyl)diquino-
line (4ac). Yellow liquid. 1H NMR (400 MHz, CDCl3):
8.05 (d,
d
4.3.9. 2,20-(2-Phenylpropane-1,3-diyl)bis(6-nitroquinoline)
(3ha). Red solid. 1H NMR (400 MHz, CDCl3):
J¼9.2 Hz, 2H), 7.88 (d, J¼8.4 Hz, 2H), 7.71e7.64 (m, 4H), 7.47e7.39
d
8.65 (d, J¼2.4 Hz,
(m, 4H), 7.33 (d, J¼8.0 Hz, 2H), 7.10 (d, J¼8.4 Hz, 2H), 4.21e4.13 (m,
2H), 8.42e8.39 (m, 2H), 8.08 (q, J¼8.0 Hz, 4H), 7.23 (d, J¼8.4 Hz,
1H), 3.57e3.40 (m, 4H); 13C NMR (100 MHz, CDCl3):
d 160.0, 147.9,
2H), 7.17e7.09 (m, 5H), 4.12e4.04 (m, 1H), 3.56e3.43 (m, 4H); 13C
147.4, 136.3, 130.2, 129.6, 128.3, 128.2, 127.5, 126.7, 126.0, 125.2,
NMR (100 MHz, CDCl3):
d
164.7, 149.8, 144.9, 142.8, 137.3, 130.5,
125.2, 122.0, 46.0, 44.9; HRMS: calcd for C28H22F3N2 [MþH]þ
128.5, 127.7, 126.7, 125.3, 124.2, 123.9, 122.7, 45.8, 45.7; HRMS: calcd
443.1730, found 443.1729; IR (KBr)
1426, 1326, 837.
n
/cmꢁ1: 3058, 2926, 1600, 1506,
for C27H21N4O4 [MþH]þ 465.1557, found 465.1562; IR (KBr)
n :
/cmꢁ1
3097, 2920, 1610, 1490, 1465, 1341, 702.
4.3.17. 2,20-(2-(4-Fluorophenyl)propane-1,3-diyl)diquinoline
(4ad). Yellow liquid. 1H NMR (400 MHz, CDCl3):
4.3.10. 2,20-(2-Phenylpropane-1,3-diyl)bis(8-nitroquinoline) (3ia).
Gray solid. 1H NMR (400 MHz, CDCl3):
d
8.01 (d, J¼8.0 Hz,
d
7.94 (d, J¼8.8 Hz, 2H), 7.89
2H), 7.88 (d, J¼8.4 Hz, 2H), 7.70e7.63 (m, 4H), 7.44 (t, J¼7.6 Hz, 2H),
7.15e7.07 (m, 4H), 6.82 (t, J¼8.8 Hz, 2H), 4.08e4.00 (m, 1H),
(d, J¼7.2 Hz, 2H), 7.80 (d, J¼8.0 Hz, 2H), 7.50e7.41 (m, 3H), 7.32 (d,
J¼8.8 Hz, 2H), 7.28(s, 1H), 7.23e7.10 (m, 3H), 4.27e4.18 (m, 1H),
3.50e3.33 (m, 4H); 13C NMR (100 MHz, CDCl3):
d 160.4, 147.8, 139.3,
3.51e3.36 (m, 4H); 13C NMR (100 MHz, CDCl3):
d
163.6, 147.9, 144.0,
139.3, 135.9, 129.3, 129.2, 128.8, 127.5, 126.7, 125.8, 122.0, 115.1,