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The Journal of Organic Chemistry
61% (141.5 mg, 0.46 mmol); Yellow solid; mp: 255ꢀ257°C; TLC : R f 0.81 (cꢀhexane/EtOAc
50/50); IR(neat):ν(cmꢀ1) 2998, 2837, 1716, 1628, 1610, 1601, 1582, 1552, 1510, 1487, 1452,
1437, 1407, 1374, 1348, 1320, 1301, 1268, 1249, 1210, 1194, 1163, 1137, 1096, 1067, 1036,
1022; 1H NMR (300 MHz, CDCl3) δ 8.89 (s, 1H), 8.60 (d, J = 1.3 Hz, 1H), 7.84 (s, 1H), 7.60 (s,
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1H), 7.46 (d, J = 8.7 Hz, 1H), 7.39 – 6.82 (m, 7H), 3.83 (dd, J = 12.3, 1.2 Hz, 6H). C NMR
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(75 MHz, CDCl3) δ 175.0 (C), 160.5 (C), 160.2 (C), 156.9 (C), 151.6 (C), 144.3 (2CH), 140.2
(CH), 135.0 (C), 134.0 (C), 133.5 (CH), 130.3 (CH), 128.54 (CH), 127.7 (C), 122.7 (2CH),
121.6 (C), 121.4 (C), 119.3 (CH), 117.7 (CH), 116.9 (C), 115.2 (CH), 111.7 (C), 105.9 (CH),
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55.8 (CH3), 55.7 (CH3). HRMS (ESI): m/z calc. for C26H18NO5 Br (M+H) 504.0447, found:
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504.0446 and m/z calc. for C26H18NO5 Br (M+H) + 506.0426, found: 506.0432.
1-methyl-1'-phenyl-[3,3'-biquinoline]-2,4'(1H,1'H)-dione (3l): The reaction was carried out
from 4ꢀoxoꢀ1ꢀphenylꢀ1,4ꢀdihydroquinolineꢀ3ꢀcarboxylic acid 1a11c and 3ꢀbromoꢀ1ꢀ
methylquinolinꢀ2(1H)ꢀone 2d12b. Yield: 66% (139.8 mg, 0.56 mmol); white solid; mp: 218ꢀ
220°C; TLC : R f 0.26 (cꢀhexane/EtOAc 50/50); IR (neat): ν (cmꢀ1) 2923, 1621, 1583, 1548,
1493, 1476, 1452, 1401, 1372, 1333,1318, 1292, 1236, 1198, 1165, 1104, 1062; 1H NMR (300
MHz, CDCl3) δ 8.79 (d, J = 8.8 Hz, 2H), 8.58 (dt, J = 12.3, 6.1 Hz, 1H), 7.68 (dd, J = 7.8, 1.3
Hz, 1H), 7.64 – 7.46 (m, 7H), 7.38 (ddd, J = 15.6, 11.3, 4.8 Hz, 2H), 7.23 (dd, J = 10.9, 3.7 Hz,
1H), 7.06 (d, J = 8.0 Hz, 1H), 3.76 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 176.0 (C), 161.9 (C),
144.9 (CH), 141.6 (C), 140.3 (C), 139.3 (CH), 139.1 (C), 131.7 (CH), 130.3 (2CH), 130.2 (CH),
129.5 (CH), 129.4 (CH), 127.7 (2CH), 127.3 (CH), 126.9 (C), 124.1 (CH), 123.9 (C), 122.3
(CH), 121.0 (C), 117.4 (CH), 115.2 (C), 113.9 (CH), 30.2 (CH3). HRMS (ESI): m/z calc. for
C25H18N2O2 (M+H) + 379.1447, found: 379.1450.
6'-methoxy-1'-(4-methoxyphenyl)-1-methyl-[3,3'-biquinoline]-2,4'(1H,1'H)-dione
(3m):
The reaction was carried out from 6ꢀmethoxyꢀ1ꢀ(4ꢀmethoxyphenyl)ꢀ4ꢀoxoꢀ1,4ꢀdihydroquinolineꢀ
3ꢀcarboxylic acid 1d11c and 3ꢀbromoꢀ1ꢀmethylquinolinꢀ2(1H)ꢀone 2d12b. Yield: 70% (141.1 mg,
0.46 mmol); White solid; mp: 231ꢀ233°C; TLC : R f 0.18 (cꢀhexane/EtOAc 50/50); IR (neat): ν
(cmꢀ1) 3117, 3079, 3010, 2934, 2837, 1630, 1612, 1584, 1547, 1512, 1490, 1458, 1435, 1414,
1374, 1350, 1328, 1292, 1267, 1252, 1232, 1212, 1187 ,1163, 1099, 1060, 10221H NMR (300
MHz, CDCl3) δ 8.84 (s, 1H), 8.75 (s, 1H), 8.01 (d, J = 2.9 Hz, 1H), 7.66 (t, J = 12.7 Hz, 1H),
7.62 – 7.50 (m, 1H), 7.40 (dt, J = 13.9, 5.9 Hz, 3H), 7.27 (dd, J = 13.5, 5.9 Hz, 1H), 7.21 – 6.98
(m, 4H), 3.96 (s, 3H), 3.91 (s, 3H), 3.78 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 175.3 (C), 161.9
(C), 160.1 (C), 156.5 (C), 144.4 (CH), 139.1 (CH), 139.0 (C), 135.3 (C), 134.4 (C), 130.0 (CH),
129.2 (CH), 128.7 (2CH), 127.9 (C), 124.2 (C), 122.3 (CH), 122.2 (CH), 121.0 (C), 119.2
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