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R. Martınez et al. / Tetrahedron 62 (2006) 8988–9001
8998
one, 2m, C5H4Fe), 7.13 and 7.80 (1H each one, 2d,
J¼15.6 Hz, CH]CHCO), 7.40–7.45 and 7.65–7.70 (3 and
2H, respectively, 2m, Ph); dC 69.7 (2C), 70.1 (5C), 72.75
(2C), 80.6, 122.9, 128.25 (2C), 128.9 (2C), 130.1, 135.1,
140.8, 192.9; m/z 317 (M++1, 23%), 316 (M+, 100), 251
(17), 121 (12).
126.85, 127.2, 127.25 (2C), 128.05, 129.35 (2C), 129.4,
136.4, 136.6, 139.1, 148.05, 156.95; m/z 220 (M++1,
17%), 219 (M+, 100), 218 (51), 217 (20), 204 (21), 108 (13).
4.2.38. 2-(4-Methylphenyl)benzo[h]quinoline (8f). Mp
79–81 ꢀC; tR 23.6; Rf 0.74 (hexane/ethyl acetate: 4/1); n
(KBr) 3049, 2918, 1601, 1558 cmꢂ1 (C]CH); dH 2.39
(3H, s, CH3), 7.28 and 8.17 (2 and 2H, 2d, J¼7.8 Hz,
CH3C6H4), 7.52 (1H, d, J¼8.6 Hz, H6), 7.60–7.70 (3H, m,
H9, H7, and H8), 7.81 (2H, d, J¼8.6 Hz, H5 and H3), 7.98–
8.01 (1H, m, H4), 9.47 (1H, d, J¼7.8 Hz, H10); dC 21.25,
118.45, 124.6, 124.8, 125.0, 126.65, 127.0, 127.15 (2C),
127.6, 127.9, 129.4 (2C), 131.7, 133.75, 136.25, 136.8,
139.05, 146.0, 155.25; m/z 270 (M++1, 22%), 269 (M+,
100), 268 (27), 267 (13). C20H15N: requires C 89.19, H
5.61, N 5.20; found C 89.25, H 5.70, N 5.23.
4.2.32. (E)-1-(1H-3-Indolyl)-3-phenyl-2-propen-1-one
(6v).70 Mp 225–230 ꢀC; tR 26.4; Rf 0.57 (hexane/ethyl ace-
tate: 1/1); n (KBr) 3126 (N–H), 1638 (C]O), 1569 cmꢂ1
(C]CH); dH 7.20–7.90, 8.35–8.40, and 8.70–8.75 (10, 1,
and 1H, respectively, 3m, C]CH), 12.11 (1H, s, NH); dC
113.2, 118.85, 122.85, 122.9, 24.1, 125.7, 127.0, 129.4
(2C), 129.8 (2C), 130.7, 135.7, 136.3, 137.95, 140.55,
184.7; m/z 248 (M++1, 18%), 247 (M+, 100), 246 (50),
219 (22), 218 (50), 217 (19), 144 (46), 117 (11), 116 (18),
89 (16).
4.2.39. 2-(2-Pyridyl)quinoline (8g).37c Mp 95–97 ꢀC; tR
16.1; Rf 0.5 (hexane/ethyl acetate: 4/1); n (KBr) 3060,
1596 cmꢂ1 (C]CH); dH 7.25–7.35 (1H, m, H5-Py), 7.50–
7.55 (1H, m, H6-quinoline), 7.70–7.65 (1H, m, H7-quino-
line), 7.70–7.85 (2H, m, H3,4-Py), 8.17 (1H, d, J¼8.4 Hz,
H5-quinoline), 8.23 (1H, d, J¼8.7 Hz, H4-quinoline), 8.54
(1H, d, J¼8.7 Hz, H3-quinoline), 8.64 (1H, d, J¼8.1 Hz,
H8-quinoline) 8.70–8.75 (1H, m, H6-Py); dC 118.85,
121.75, 123.9, 126.65, 127.5, 128.1, 129.45, 129.65,
136.7, 136.8, 147.75, 149.0, 155.95, 156.1; m/z 207
(M++1, 14%), 206 (M+, 100), 205 (73), 178 (17).
4.2.33. 2-Phenylquinoline (8a).37c Mp 80–82 ꢀC; tR 16.3; Rf
0.61 (hexane/ethyl acetate: 4/1); n (KBr) 3053, 1601,
1546 cmꢂ1 (C]CH); dH 7.35–7.50, 7.60–7.80, and 8.00–
8.20 (4, 3, and 4H, respectively, 3m, ArH); dC 118.8,
126.1, 127.0, 127.3, 127.4 (2C), 128.7 (2C), 129.15, 129.5,
129.55, 136.6, 139.45, 148.1, 157.1; m/z 206 (M++1,
15%), 205 (M+, 100), 204 (95), 203 (12), 102 (15).
4.2.34. 3-Methyl-2-phenylquinoline (8b).37b tR 16.4 min;
Rf 0.48 (hexane/ethyl acetate: 4/1); n (film) 3058, 1605,
1558 cmꢂ1 (C]CH); dH 2.36 (3H, s, CH3), 7.35–7.70
(8H, m, Ph and H5–7-quinoline), 7.87 (1H, s, H4-quinoline),
8.14 (1H, d, J¼8.4 Hz, H8-quinoline); dC 20.3, 126.05,
126.4, 127.2, 127.85, 127.95 (2C), 128.4, 128.55 (2C),
128.8, 128.95, 136.4, 140.5, 146.25, 160.1; m/z 219 (M+,
35%), 218 (100), 217 (28), 108 (12).
4.2.40. 2-(2-Furyl)quinoline (8h).37c Mp 94 ꢀC; tR 14.7;
Rf 0.45 (hexane/ethyl acetate: 4/1); n (KBr) 3143, 1600 cmꢂ1
(C]CH); dH 6.54 (1H, dd, J¼1.9, 3.4 Hz, H4-furyl), 7.19
(1H, dd, J¼0.6, 3.4 Hz, H3-furyl), 7.40–7.75 (5H, m, H5-
furyl and H3,5–7-quinoline), 8.05 (1H, d, J¼4.3 Hz, H4-quin-
oline), 8.13 (1H, d, J¼4.2 Hz, H8-quinoline); dC 110.05,
112.05, 117.25, 126.0, 126.9, 127.4, 129.0, 129.7, 136.5,
143.9, 147.8, 148.75, 153.4; m/z 196 (M++1, 14%), 195
(M+, 100), 194 (26), 167 (30), 166 (23), 140 (12), 139 (14).
4.2.35. 3-Ethyl-2-phenylquinoline (8c).71 tR 16.8; Rf 0.53
(hexane/ethyl acetate: 4/1);
n
(film) 3058, 1626,
1592 cmꢂ1 (C]CH); dH 1.16 (3H, t, J¼7.5 Hz, CH3),
2.77 (2H, q, J¼7.5 Hz, CH2), 7.35–7.65 (7H, m, Ph and
H5,7-quinoline), 7.75–7.80 (1H, m, H6-quinoline), 8.01
(1H, s, H4-quinoline), 8.14 (1H, d, J¼8.4 Hz, H8-quinoline);
dC 14.55, 25.85, 126.2, 126.75, 127.75, 127.95, 128.15 (2C),
128.55 (2C), 128.65, 129.05, 134.8, 135.10, 140.65, 146.1,
160.4; m/z 233 (M+, 43%), 232 (100), 218 (11), 217 (39),
216 (11), 108 (13).
4.2.41. 2-(2-Thienyl)quinoline (8i).37c Mp 131–133 ꢀC; tR
16.6; Rf 0.62 (hexane/ethyl acetate: 4/1); n (KBr) 3103,
3053, 1615, 1597 cmꢂ1 (C]CH); dH 7.10–7.15 (1H, m,
H4-thienyl), 7.40–7.45 (2H, m, H3-thienyl and H3-quino-
line), 7.60–7.75 (4H, m, H5-thienyl, H3,5–7-quinoline), 8.05
(1H, d, J¼8.4 Hz, H4-quinoline), 8.07 (1H, d, J¼7.8 Hz,
H8-quinoline); dC 117.15, 125.75, 125.95, 127.05, 127.4,
128.0, 128.5, 129.0, 129.7, 136.5, 145.25, 147.95, 152.2;
m/z 212 (M++1, 16%), 211 (M+, 100), 210 (29).
4.2.36. 1,2-Dihydrobenzo[c]acridine (8d).37c Mp 62–
64 ꢀC; tR 18.7; Rf 0.78 (hexane/ethyl acetate: 4/1); n (KBr)
3038, 1601 cmꢂ1 (C]CH); dH 2.90–2.95 and 3.00–3.05 (2H
each one, 2m, CH2CH2), 7.15–8.15 and 8.57 (7 and 1H,
respectively, m and d, respectively, J¼1.2 Hz, ArH); dC
28.25, 28.65 125.9, 125.95, 126.8, 127.2, 127.7, 127.85,
128.55, 129.25, 129.55, 130.45, 133.6, 134.55, 139.3,
147.45, 153.2; m/z 232 (M++1, 16%), 183 (M+, 99), 230
(100), 229 (13), 228 (17), 202 (10), 115 (14), 114 (12).
4.2.42. 2-(1-Methyl-1H-2-pyrrolyl)quinoline (8j).72 Mp
61–63 ꢀC; tR 16.2; Rf 0.6 (hexane/ethyl acetate: 4/1); n
(KBr) 3104, 2948, 1609, 1558 cmꢂ1 (C]CH); dH 4.15
(3H, s, CH3), 6.20–6.25 and 6.70–6.75 (1 and 2H, respec-
tively, 2m, CH3NCH]CHCH), 7.35–7.40 (1H, m, H3-quin-
oline), 7.55–7.70 (3H, m, H5–7-quinoline), 7.97 (1H, d,
J¼8.6 Hz, H4-quinoline), 8.00 (1H, d, J¼8.6 Hz, H8-quino-
line); dC 37.6, 107.7, 112.25, 119.95, 125.35, 125.9, 127.35,
127.55, 128.9, 129.95, 132.0, 135.75, 147.5, 152.1; m/z 208
(M+, 51%), 207 (100).
4.2.37. 2-(4-Methylphenyl)quinoline (8e).37c Mp 80–
81 ꢀC; tR 17.2; Rf 0.75 (hexane/ethyl acetate: 4/1); n (KBr)
3058, 1661, 1606 cmꢂ1 (C]CH); dH 2.36 (3H, s, CH3),
7.25 (2H, d, J¼8.1 Hz, 2ꢁCH3CCH), 7.35–7.45 (1H, m,
H3-quinoline), 7.60–7.75 (3H, m, H5–7-quinoline), 8.00–
8.05 (3H, m, H4-quinoline and 2ꢁCH3CCHCH), 8.15 (1H,
d, J¼4.1 Hz, H8-quinoline); dC 21.15, 118.55, 125.8,
4.2.43. 2-Ferrocenylquinoline (8k).73 tR 21.3; Rf 0.52 (hex-
ane/ethyl acetate: 4/1); n (KBr) 3094, 1601 cmꢂ1 (C]CH);
dH 4.05 (5H, s, C5H5Fe), 4.40–4.45 and 5.00–5.05 (2H each