Experimental

Melting points were determined in open capillaries and are uncorrected. IR spectra were recorded on a TENSOR 27 spectrometer in KBr pellet. 1H NMR spectra were obtained from solution in DMSO-d6 with Me4Si as internal standard using a Bruker-400 spectrometer. HRMS analyses were carried out using Bruker-microTOF-Q-MS analyzer.

General procedure for the syntheses of 1,3-diarylbenzo[f]quinoline derivatives4.

A dry 50 mL flask was charged with aromatic aldehyde (2.0 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol), phenylacetylene (0.204 g, 2.0 mmol), AgOTf (0.026 g, 0.1 mmol)andtoluene (10 mL). The reaction mixture was stirred at 100 C for 10-14 h. A little amount (5 mL) of DMF was added to the mixture, and then the un-dissolvedmaterial was removed by hot filtration.The desired products 4 were obtained as good crystals, when the filtratewas cooled down to room temperature.

3-(4-Bromophenyl)-1-phenylbenzo[f]quinoline (4a, C25H16BrN)

M.p. 182~183 C, Lit.[12] 183~184 C; 1H NMR (DMSO-d6, 400 MHz): H 7.18~7.23 (m, 1H, ArH), 7.51~7.61 (m, 7H, ArH), 7.73~7.76 (m, 2H, ArH), 8.01~8.06 (m, 3H, ArH), 8.17 (d, J = 9.2 Hz, 1H, ArH), 8.31~8.34 (m, 2H, ArH). IR (KBr, , cm-1): 3052, 3030, 1578, 1544, 1489, 1475, 1450, 1387, 1354, 1257, 1166, 1075, 1008, 834, 814, 772, 754, 701. HRMS (ESI, m/z): Calcd for C25H17BrN (M+H+) 410.0544, found 410.0566.

3-(4-Chlorophenyl)-1-phenylbenzo[f]quinoline (4b, C25H16ClN)

M.p. 171~172 C,Lit. [13] 164~165 C;1H NMR (DMSO-d6, 400 MHz): H 7.19~7.23 (m, 1H, ArH), 7.52~7.62 (m, 9H, ArH), 8.02~8.07 (m, 3H, ArH), 8.17 (d, J = 9.2 Hz, 1H, ArH), 8.40 (d, J = 8.4 Hz, 2H, ArH).IR (KBr, , cm-1): 3052, 3030, 1578, 1546, 1491, 1476, 1451, 1390, 1356, 1257, 1090, 1011, 836, 773, 754, 701. HRMS (ESI, m/z): Calcd for C25H17ClN (M+H+) 366.1050, found 366.1044.

3-(4-Fulorophenyl)-1-phenylbenzo[f]quinoline (4d, C25H16FN)

M.p. 170~172 C, Lit. [14] 171~172 C; 1H NMR (DMSO-d6, 400 MHz): H 7.18~7.22 (m, 1H, ArH), 7.36~7.40 (m, 2H, ArH), 7.51~7.62 (m, 7H, ArH), 7.99~8.06 (m, 3H, ArH), 8.16 (d, J = 8.8 Hz, 1H, ArH), 8.40~8.44 (m, 2H, ArH). IR (KBr, , cm-1): 3052, 3030, 1602, 1577, 1547, 1508, 1478, 1450, 1358, 1284, 1228, 1152, 1028, 838, 799, 770, 753, 701. HRMS (ESI, m/z): HRMS (ESI, m/z): Calcd for C25H17FN (M+H+) 350.1345, found 350.1330.

3-(4-Methoxyphenyl)-1-phenylbenzo[f]quinoline (4g, C26H20NO)

M.p. 154~155 C, Lit. [15] 154~155 C; 1H NMR (DMSO-d6, 400 MHz): H 3.85 (s, 3H, CH3O), 7.10 (d, J = 8.8 Hz, 2H, ArH), 7.17~7.21 (m, 1H, ArH), 7.50~7.61 (m, 7H, ArH), 7.91 (s, 1H, ArH), 8.00~8.04 (m, 2H, ArH), 8.14 (d, J = 9.2 Hz, 1H, ArH), 8.32 (d, J = 8.4 Hz, 2H, ArH). IR (KBr, , cm-1): 3048, 3003, 2836, 1605, 1580, 1545, 1523, 1511, 1467, 1453, 1441, 1391, 1360, 1306, 1292, 1249, 1175, 1113, 1031, 872, 837, 806, 770, 760, 702. HRMS (ESI, m/z): Calcd for C26H20NO (M+H+) 362.1545, found 362.1543.

3-(3-Nitrophenyl)-1-phenylbenzo[f]quinoline (4h,C25H16N2O2)

M.p. 232~233 C; 1H NMR (DMSO-d6, 400 MHz): H 7.20~7.24 (m, 1H, ArH), 7.54~7.61 (m, 7H, ArH), 7.84 (t, J = 8.0 Hz, 1H, ArH), 8.05 (d, J = 7.6 Hz, 1H, ArH), 8.10 (d, J = 8.8 Hz, 1H, ArH), 8.16~8.21 (m, 2H, ArH), 8.35 (d, J = 8.0 Hz, 1H, ArH), 8.80 (d, J = 8.0 Hz, 1H, ArH), 9.16 (s, 1H, ArH). 13C NMR (DMSO-d6, 100 MHz): C152.5, 149.9, 149.8, 148.9, 142.6, 140.8, 133.15, 133.14, 132.1, 129.8, 129.6, 129.4, 128.9, 128.7, 128.4, 128.3, 128.2, 126.9, 125.8, 123.8, 123.5, 122.2, 121.4. IR (KBr, , cm-1): 3052, 1580, 1528, 1481, 1451, 1344, 1256, 1153, 1110, 1070, 872, 834, 801, 745, 708, 683. HRMS (ESI, m/z): Calcd for C25H17N2O2 (M+H+) 377.1290, found 377.1293.

3-(4-Nitrophenyl)-1-phenylbenzo[f]quinoline (4i, C25H17 N2O2)

M.p. 256~258 C, Lit. [16] 254C;1H NMR (DMSO-d6, 400 MHz): H 7.17~7.22 (m, 1H, ArH), 7.47~7.58 (m, 6H, ArH), 7.69 (d, J = 8.8 Hz, 1H, ArH), 7.86 (s, 1H, ArH), 7.90 (dd, J = 8.0 Hz, J’ = 1.6 Hz, 1H, ArH), 8.04 (d, J = 9.2 Hz, 1H, ArH), 8.12 (d, J = 9.2 Hz, 1H, ArH), 8.36~8.39 (m, 2H, ArH), 8.41~8.44 (m, 2H, ArH). IR (KBr, , cm-1): 3053, 3031, 1599, 1577, 1547, 1511, 1493, 1476, 1441, 1340, 1257, 1166, 1106, 1079, 1008, 860, 849, 832, 774, 755, 699. HRMS (ESI, m/z): Calcd for C25H17 N2O2 (M+H+) 377.1290, found 377.1273.

3-(2-Thienyl)-1-phenylbenzo[f]quinoline (4j, C23H15NS)

M.p. 177~178 C; 1H NMR (DMSO-d6, 400 MHz): H 7.17~7.23 (m, 2H, ArH), 7.49~7.54 (m, 4H, ArH), 7.59~7.62 (m, 3H, ArH), 7.75 (dd, J = 8.8 Hz, J’ = 1.2 Hz, 1H, ArH), 7.95~7.97 (m, 2H, ArH), 8.01~8.03 (m, 1H, ArH), 8.06 (dd, J = 8.0 Hz, J’ = 1.2 Hz, 1H, ArH), 8.14 (d, J = 8.8 Hz, 1H, ArH). 13C NMR (DMSO-d6, 100 MHz): C149.1, 148.5, 142.0, 132.6, 131.8, 131.2, 129.4, 128.89, 128.86, 128.5, 128.4, 128.0, 127.3, 127.0, 125.8, 125.0, 124.9, 122.1, 116.5, 116.3, 112.7.IR (KBr, , cm-1): 3052, 3026, 1580, 1543, 1475, 1451, 1438, 1421, 1361, 1351, 1319, 1255, 1239, 1067, 1028, 880, 832, 799, 772, 755, 703. HRMS (ESI, m/z): Calcd for C23H16NS (M+H+) 338.1003, found 338.1019.

References

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13. Wang XS, Li Q, Zhou J, Tu SJ(2009) J Heterocycl Chem 46:1222.

14. Kozlov NS, Isaeva RK (1965)KhimGeterotsiklicheskikh Soed379.

15. Kozlov NS, ShurIA (1958)Doklady Akademii Nauk SSSR123:102.

16. Kozlov NS, ShurIA (1960) Izvestiya Vysshikh Uchebnykh Zavedenii Khimiya i Khimicheskaya Tekhnologiya 3:675.