JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Synthesis of Substituted Quinolines
J = 2.4, 2.4, 9.2 Hz, 2H), 8.24 (ddd, J = 0.6, 0.8, 8.4 Hz,
1H). 13C NMR (CDCl3, 100 MHz) d: 55.3, 114.1, 118.8,
125.4, 125.5, 125.9, 128.3, 128.5, 128.8, 129.4, 129.5,
129.8, 130.1, 132.0, 137.4, 138.4, 148.7, 149.0, 156.3,
160.8. MS (EI) m/z: 311 (M+), 310, 268, 267, 140, 139,
132.
Hz, 1H), 7.42-7.57 (m, 7H), 7.68-7.74 (m, 3H), 7.84 (dd, J
= 0.8, 8.4 Hz, 1H), 8.16 (d, J = 8.8 Hz, 1H). 13C NMR
(CDCl3, 100 MHz) d: 117.8, 125.6, 125.7, 125.8, 126.0,
128.0, 128.4, 128.5, 128.6, 129.4, 129.5, 129.6, 138.0,
145.3, 148.5, 148.7, 151.7. MS (EI) m/z: 287 (M+), 286,
253, 202, 200.
2-(4-Fluorophenyl)-4-phenylquinoline (3d)
2-(4-Nitrophenyl)-4-phenylquinoline (3i)
mp 63-64 °C. IR (KBr) n: 3056, 1593, 1546 cm-1. 1H
NMR (CDCl3) d: 7.19-7.24 (m, 2H), 7.47-7.57 (m, 6H),
7.72-7.76 (m, 1H), 7.78 (s, 1H), 7.91 (dd, J = 1.0, 8.4 Hz,
1H), 8.18-8.24 (m, 3H). 13C NMR (CDCl3, 100 MHz) d:
115.4, 115.7, 118.7, 125.5, 126.2, 128.3, 128.4, 129.2,
129.3, 129.4, 129.5, 129.8, 135.5, 135.6, 138.1, 148.6,
149.1, 155.5, 162.4. MS (EI) m/z: 299 (M+), 298, 220, 202,
201, 139, 125. Anal. Calcd for C12H14NF: C, 84.26, H,
4.71, N, 4.68; Found: C, 84.39, H, 4.54, N, 4.53.
mp 156-157 °C (Lit.,30 mp 162-163 °C). IR (KBr) n:
3055, 1588, 1547 cm-1. 1H NMR (CDCl3) d: 7.52-7.58 (m,
6H), 7.77-7.81 (m, 1H), 7.86 (s, 1H), 7.95 (d, J = 8.0 Hz,
1H), 8.27 (d, J = 8.4 Hz, 1H), 8.37-8.42 (m, 4H). 13C NMR
(CDCl3, 100 MHz) d: 119.0, 120.8, 123.3, 123.9, 125.7,
126.0, 127.2, 128.1, 128.2, 128.6, 129.3, 129.4, 130.0,
130.2, 130.9, 137.8, 145.3, 148.2, 148.7, 149.8, 153.9. MS
(EI) m/z: 326 (M+), 325, 280, 278, 202, 176, 139.
3-Methyl-2,4-diphenylquinoline (3j)
mp 134-135 °C (Lit.,31 mp 145-146 °C). IR (KBr) n:
3048, 1609, 1568 cm-1. 1H NMR (CDCl3) d: 2.17 (s, 3H),
7.32-7.34 (m, 2H), 7.40-7.58 (m, 8H), 7.62-7.68 (m, 3H),
8.20 (d, J = 8.4 Hz, 1H). 13C NMR (CDCl3, 100 MHz) d:
18.5, 115.8, 126.1, 126.5, 126.9, 127.7, 127.9, 128.0,
128.2, 128.4, 128.6, 128.8, 129.2, 129.3, 137.5, 141.3,
146.1, 147.6, 160.6. MS (EI) m/z: 295 (M+), 294, 217, 189,
139.
2-(4-Chlorophenyl)-4-phenylquinoline (3e)
mp 104-105 °C (Lit.,29 mp 106 °C). IR (KBr) n: 3055,
1589, 1542 cm-1. 1H NMR (CDCl3) d: 7.47-7.57 (m, 8H),
7.74-7.77 (m, 1H), 7.79 (s, 1H), 7.91 (d, J = 8.0 Hz, 1H),
8.14-8.18 (m, 2H), 8.23 (d, J = 8.4 Hz, 1H). 13C NMR
(CDCl3, 100 MHz) d: 118.6, 125.6, 125.7, 126.5, 128.4,
128.6, 128.8, 128.9, 129.5, 129.6, 130.0, 136.5, 137.9,
138.2, 148.7, 149.4, 155.4. MS (EI) m/z: 317 (M++2), 315
(M+), 314, 220, 202, 176, 139.
2,3,4-Triphenylquinoline (3k)
2-(4-Bromophenyl)-4-phenylquinoline (3f)
mp 190-191 °C (Lit.,32 mp 189-190 °C). IR (KBr) n:
3052, 1603, 1547 cm-1. 1H NMR (CDCl3) d: 6.88-6.91 (m,
2H), 6.99-7.02 (m, 3H), 7.14-7.16 (m, 2H), 7.21-7.23 (m,
3H), 7.26-7.31 (m, 3H), 7.38-7.40 (m, 2H), 7.46 (ddd, J =
1.2, 6.8, 8.4 Hz, 1H), 7.59 (dd, J = 1.2, 8.4 Hz, 1H), 7.74
mp 111-112 °C (Lit.,30 mp 128-129 °C). IR (KBr) n:
3029, 1584, 1539 cm-1. 1H NMR (CDCl3) d: 7.48-7.57 (m,
6H), 7.64-7.67 (m, 2H), 7.73-7.87 (m, 2H), 7.91 (dd, J =
1.0, 8.4 Hz, 1H), 8.08-8.11 (m, 2H), 8.24 (d, J = 8.4 Hz,
1H). 13C NMR (CDCl3, 100 MHz) d: 118.7, 123.8, 125.5,
125.7, 126.4, 128.4, 128.5, 129.0, 129.4, 129.6, 130.0,
131.8, 138.1, 138.3, 148.6, 149.3, 155.3. MS (EI) m/z: 361
(M++2), 360 (M++1), 359 (M+), 279, 278, 202, 139.
2-(2-Furyl)-4-phenylquinoline (3g)
(ddd, J = 1.2, 6.8, 8.4 Hz, 1H), 8.28 (d, J = 8.4 Hz, 1H). 13
C
NMR (CDCl3, 100 MHz) d: 126.2, 126.4, 126.5, 127.1,
127.2, 127.4, 127.5, 127.6, 129.2, 129.5, 129.8, 130.1,
131.2, 132.8, 136.8, 138.2, 141.0, 147.2, 147.5, 158.8. MS
(EI) m/z: 357 (M+), 356, 278, 176, 171.
mp 98-99 °C (Lit.,28 mp 109-111 °C). IR (KBr) n:
3060, 1594, 1546 cm-1. 1H NMR (CDCl3) d: 6.60 (dd, J =
1.6, 3.6 Hz, 1H), 7.25 (m, 1H), 7.43-7.57 (m, 6H), 7.63 (dd,
J = 0.6, 1.8 Hz, 1H), 7.74 (ddd, J = 1.0, 6.8, 8.4 Hz, 1H),
7.78 (s, 1H), 7.87 (dd, J = 1.2, 8.4 Hz, 1H), 8.21 (d, J = 8.4
Hz, 1H). 13C NMR (CDCl3, 100 MHz) d: 110.1, 112.1,
117.6, 125.6, 125.7, 126.1, 128.3, 128.4, 129.4, 129.5,
129.8, 138.0, 144.0, 148.4, 148.5, 148.9, 153.6. MS (EI)
m/z: 271 (M+), 270, 243, 242, 241, 120.
6-Chloro-2,4-diphenylquinoline (3l)
mp 131-132 °C (Lit.,33 mp 130-132 °C). IR (KBr) n:
3057, 1588, 1541 cm-1, 1H NMR (CDCl3) d: 7.41-7.62 (m,
7H), 7.65-7.84 (m, 2H), 7.84 (s, 1H), 7.87 (d, J = 3.6 Hz,
1H), 8.15-8.20 (m, 3H). MS (EI) m/z: 317 (M++2), 315
(M+), 280, 139. Anal. Calcd for C21H14ClN: C, 79.87, H,
4.47, N, 4.44; Found: C, 79.68, H, 4.56, N, 4.32.
6-Chloro-2-(4-bromophenyl)-4-phenylquinoline (3m)
mp 173-175 °C (Lit.,33 mp 174-176 °C). IR (KBr) n:
3060, 1590, 1542 cm-1, 1H NMR (CDCl3) d: 7.54-7.58 (m,
5H), 7.64-7.70 (m, 3H), 7.80 (s, 1H), 7.86 (d, J = 2.2 Hz,
1H), 8.08 (d, J = 11.2 Hz, 2H), 8.15 (d, J = 12.4 Hz, 1H).
4-Phenyl-2-(2-thienyl)quinoline (3h)
mp 92-93 °C (Lit.,28 mp 89-92 °C). IR (KBr) n: 3054,
1585, 1543 cm-1. 1H NMR (CDCl3) d: 7.16 (dd, J = 3.8, 5.0
J. Chin. Chem. Soc. 2012, 59, 535-539
© 2012 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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