7094
W. Luo et al. / Tetrahedron 67 (2011) 7090e7095
d
160.2, 149.9, 147.4, 139.3, 133.7, 133.3, 130.2, 129.4, 129.2, 129.0,
145.8, 137.3, 134.7, 132.8, 132.0, 130.9, 129.9, 129.3 (2CH), 129.2,
127.9, 127.0, 119.8, 113.4, 113.2, 55.4.
128.4, 127.5 (2CH), 120.9.
4.3.4. 3-(2-Methoxyphenyl)quinoline (4d)14. Yellow oil; 76% yield;
4.3.11. 3-Methylquinoline (4k)17. Yellow oil; 67% yield; IR (KBr):
n
mp: 62e63 ꢀC; IR (KBr):
n
3062, 3030, 3009, 2977, 2936, 2835, 1595,
1493, 1461, 1438, 1243, 1181, 1056, 1022, 952, 908, 790, 753 cmꢁ1
1H NMR (CDCl3, 400 MHz)
3064, 3031, 2921, 2857, 1495,1400, 1328, 1123, 977, 887, 785,
;
749 cmꢁ1 1H NMR (CDCl3, 500 MHz) :
;
d
8.76 (s, 1H), 8.06 (d,
d
9.12 (1H, d, J¼2.2 Hz), 8.25 (1H, d,
J¼8.4 Hz, 1H), 7.89 (s, 1H), 7.72 (d, J¼8.1 Hz, 1H), 7.65 (m, 1H), 7.49
J¼2.2 Hz), 8.13 (1H, d, J¼8.0 Hz), 7.84 (1H, d, J¼8.0 Hz), 7.72e7.68
(m, 1H), 2.50 (s, 3H). 13C NMR (CDCl3, 125 MHz):
134.6, 130.4, 129.1, 128.4, 128.1, 127.1, 126.5, 18.7.
d 152.4, 146.5,
(1H, m), 7.56e7.52 (1H, m), 7.43e7.38 (2H, m), 7.12e7.03 (2H, m),
3.83 (3H, s). 13C NMR (CDCl3, 100 MHz)
d 156.7, 152.0, 146.8, 135.4,
131.6, 130.9, 129.6, 129.1, 129.1, 127.9, 127.1, 126.5, 121.1 (2CH), 111.2,
55.5.
4.3.12. 6-Nitro-3-phenylquinoline (4l). White solid; 34% yield; mp:
159e161 ꢀC; IR (KBr):
3055, 3037, 2956, 2924, 2853, 1606, 1518,
1489, 1440, 1420, 1348, 1085, 934, 911, 826, 751, 690 cmꢁ1; 1H NMR
(CDCl3, 500 MHz):
9.35 (d, J¼2.5 Hz, 1H), 8.86 (d, J¼2.5 Hz, 1H),
8.49e8.47 (m, 2H), 8.29e8.27 (m, 1H), 7.74e7.73 (m, 2H), 7.59e7.56
(m, 2H), 7.52e7.49 (m, 1H); 13C NMR (CDCl3, 125 MHz):
153.5,
n
4.3.5. 3-(4-Tolyl)quinoline (4e)15. White solid; 77% yield; mp:
d
81e81.5 ꢀC; IR (KBr):
n
3063, 3022, 2953, 2923, 2853, 1491, 1340,
953, 908, 815, 786, 749 cmꢁ1; 1H NMR (CDCl3, 400 MHz)
d
9.17 (1H,
d
d, J¼2.0 Hz), 8.27 (1H, s), 8.13 (1H, d, J¼8.0 Hz), 7.86 (1H, d,
149.2, 146.0, 136.7, 135.8, 134.6, 131.2, 129.5, 129.0, 127.6, 127.05,
124.8, 122.8. HRMS (ESI) for C15H11N2O2 [MþH]þ: calcd 251.0815,
found 251.0812.
J¼8.0 Hz), 7.72e7.54 (4H, m), 7.34e7.32 (2H, m), 2.43 (3H, s). 13C
NMR (CDCl3,100 MHz) d 150.0, 147.3, 138.1, 135.1, 133.9, 132.9, 130.0,
129.3 (2CH), 129.2, 128.2, 128.0, 127.3 (2CH), 127.0, 21.1. HRMS (ESI):
[MþH]þ calcd for C16H14N: 220.1121; found: 220.1105.
4.3.13. (E)-2-(3-Oxo-2,3-diphenylprop-1-enylamino)benzaldehyde
(E-3a) with (Z)-2-(3-oxo-2,3-diphenylprop-1-enylamino)benzalde-
4.3.6. 3-(4-Bromophenyl)quinoline (4f). White solid; 77% yield;
hyde (Z-3a). Yellowsolid.1H NMR (CDCl3, 500 MHz)
d 13.38 (0.3H, d,
mp: 141e141.5 ꢀC; IR (KBr):
n
3059, 3030, 1492, 1431, 1354, 1078,
1006, 954. 906, 823, 785, 750 cmꢁ1 1H NMR (CDCl3, 400 MHz)
9.13 (1H, d, J¼2.2 Hz), 8.26 (1H, d, J¼2.2 Hz), 8.14 (1H, d, J¼8.0 Hz),
7.87 (1H, d, J¼8.0 Hz), 7.75e7.71 (1H, m), 7.66e7.63 (2H, m),
7.60e7.56 (3H, m). 13C NMR (CDCl3, 100 MHz)
149.4, 147.5, 136.8,
J¼12.5 Hz, NH of Z-Configuration),10.78 (0.7H, d, J¼13.0 Hz, NH of E-
Configuration), 10.5 (0.3H, s, CHO of Z-Configuration), 9.75 (0.7H, s,
CHO of E-Configuration), 8.01 (0.7H, d, J¼13.0 Hz, ]CHeN of E-
Configuration), 7.71 (0.3H, d, J¼8.0 Hz, ]CHeN of Z-Configuration),
7.66e7.63 (2.1H, m,), 7.58e7.55 (0.9H, m), 7.53e7.42 (4H, m), 7.38
(3H, t, J¼7.5 Hz), 7.30 (0.3H, t, J¼7.5 Hz), 7.25e7.11 (3H, m), 7.05 (0.7H,
;
d
d
133.1, 132.6 (2CH), 132.3, 129.6, 129.3, 129.0 (2CH), 128.0, 127.9,
127.2, 122.5. HRMS (ESI): [MþH]þ calcd for C15H11BrN: 284.0075;
found: 284.0088.
t, J¼7.5 Hz). 13C NMR (CDCl3, 100 MHz)
d 194.7 (0.7C, C]O of E-
Configuration), 194.6 (0.3C, C]O of Z-Configuration), 194.3 (0.7C,
CHO of E-Configuration),193.2 (0.3C, CHO of E-Configuration),142.9
(0.7C), 142.2 (0.3C), 141.1 (0.3C), 140.2 (0.7C), 140.1 (0.3C), 139.5
(0.7C), 136.6 (0.3C), 136.5 (0.7C), 136.0 (0.7C), 135.5 (0.3C), 134.2
(0.7C), 130.8 (0.6C), 130.6 (0.3C), 130.2 (0.6C), 129.5 (0.6C), 129.3
(0.6C), 129.2 (1.4C), 129.1 (1.4C), 128.4 (1.4C), 128.1 (1.4C), 128.0
(1.4C), 127.5 (0.6C), 126.3 (0.7C), 122.2 (0.3C), 121.6 (0.3C), 121.0
(0.7C),120.4 (0.7C),116.1 (0.3C),113.2 (0.3C),112.8 (0.7C). HRMS (ESI)
for C22H17NO2Na [MþNa]þ: calcd 350.1175, found 350.1187.
4.3.7. 3-(4-Fluorophenyl)quinoline (4g)12. White solid; 75% yield;
mp: 105e105.4 ꢀC; IR (KBr):
n
3065, 3047, 3025, 1603, 1518, 1494,
1237, 1166, 951, 905, 832, 747 cmꢁ1 1H NMR (CDCl3, 400 MHz)
9.13 (1H, d, J¼2.2 Hz), 8.25 (1H, d, J¼2.2 Hz), 8.14 (1H, d, J¼8.0 Hz),
7.87 (1H, d, J¼8.0 Hz), 7.74e7.65 (3H, m), 7.60e7.56 (1H, m),
7.23e7.19 (2H, m). 13C NMR (CDCl3, 100 MHz)
164.3, 161.8, 149.8,
;
d
d
147.4, 134.1, 133.1, 133.0, 129.5, 129.3, 129.2, 129.1, 128.0, 127.2, 116.3,
116.1. HRMS (ESI): [MþH]þ calcd for C15H11FN: 224.0876; found:
224.0897.
Acknowledgements
4.3.8. 3-(Thiophen-2-yl)quinoline (4h). White solid; 61% yield;
This research was financially supported by the National Nature
Science Foundation of China (Grant No. 20772032), Shanghai Key
Laboratory of Green Chemistry and Chemical Processes and
Shanghai Science and Technology Council (Nos. 09142200800 and
10142200800 (gs3)). We also thank the Laboratory of Organic
Functional Molecules, Sino-French Institute of ECNU for support.
mp: 70e70.3 ꢀC; IR (KBr):
n
3065, 3034, 2983, 2920, 1492, 1429,
1346, 824, 782, 749, 692 cmꢁ1 1H NMR (CDCl3, 400 MHz)
;
d
9.21
(1H, d, J¼2.2 Hz), 8.27 (1H, d, J¼2.2 Hz), 8.10 (1H, d, J¼8.0 Hz),
7.83 (1H, d, J¼8.0 Hz), 7.71e7.67 (1H, m), 7.57e7.49 (2H, m),
7.40e7.39 (1H, m), 7.17e7.15 (1H, m). 13C NMR (CDCl3, 100 MHz)
d
148.6, 147.3, 140.7, 131.3, 129.3, 129.3, 128.4, 127.9, 127.8, 127.5,
127.2, 126.1, 124.4.
Supplementary data
4.3.9. 6-Methoxy-3-phenylquinoline (4i)16. White solid; 67% yield;
Supplementary data associated with this article can be found, in
mp: 120e122 ꢀC; IR (KBr):
n
3056, 2996, 2964, 2923, 2851, 1621,
1502, 1456, 1246, 1216, 1027, 901, 829, 700 cmꢁ1 1H NMR (CDCl3,
400 MHz)
;
d
9.02 (1H, d, J¼2.2 Hz), 8.19 (1H, d, J¼2.2 Hz), 8.03e8.01
References and notes
(1H, m), 7.71e7.69 (2H, m), 7.54e7.50 (2H, m), 7.45e7.41 (1H, m),
7.38e7.35 (1H, m), 7.13e7.12 (1H, m), 3.95 (3H, s). 13C NMR (CDCl3,
1. (a) Gildchrist, T. L. Heterocyclic Chemistry, 1st ed.; Pitman Publishing LTD:
London, 1985; (b) Joshi, A. A.; Narkhede, S. S.; Viswanathan, C. L. Bioorg. Med.
Chem. Lett. 2005, 15, 73e76; (c) Roma, G.; Di Braccio, M.; Grossi, G.; Mattioli, F.;
Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021e1035; (d) Narender, P.; Srinivas, U.;
Ravinder, M.; Rao, B. A.; Ramesh, C.; Harakishore, K.; Gangadasu, B.; Murthy, U.
S. N.; Rao, V. J. Bioorg. Med. Chem. 2006, 14, 4600e4609; (e) Martirosyan, A. R.;
Rahim-Bata, R.; Freeman, A. B.; Clarke, C. D.; Howard, R. L.; Strobl, J. S. Biochem.
Pharmacol. 2004, 68, 1729e1738.
100 MHz) d 158.2, 147.5, 138.1, 134.2, 132.1, 130.7, 129.2 (2CH), 129.1
(2CH), 128.1, 127.5 (2CH), 122.2, 105.3, 55.5.
4.3.10. 6-Bromo-3-phenylquinoline (4j). White solid; 76% yield;
mp: 114e114.5 ꢀC; IR (KBr):
n
3055, 3037, 2956, 2924, 2853, 1594,
1483, 1451, 1398, 1330, 1059, 954, 891, 826, 757, 700 cmꢁ1; 1H NMR
(CDCl3, 400 MHz)
9.17 (1H, d, J¼2.2 Hz), 8.18 (1H, d, J¼2.2 Hz),
8.03e7.99 (2H, m), 7.79e7.76 (1H, m), 7.70e7.68 (2H, m), 7.55e7.51
(2H, m), 7.47e7.44 (1H, m). 13C NMR (CDCl3, 100 MHz)
150.3,
2. Dube, D.; Blouin, M.; Brideau, C.; Chan, C.; Desmarais, S.; Ethier, D.; Falgueyret,
J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Tagari, P.; Young, R. N. Biorg.
Med. Chem. Lett. 1998, 8, 1255e1260.
d
d
3. Kalluraya, B.; Sreevinasa, S. Farmaco 1998, 53, 399e404.