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12 A typical procedure for quinoline 3 is as follows: to a solution of 2-amino-5-chlorobenzophenone 2c (0.2 g, 0.86 mmol) and 2,4-pentanedione 1b (0.13 g, 1.29 mmol) in EtOH (3 mL) NaAuCl4·2H2O
was added at r.t. under nitrogen atmosphere. The reaction mixture
was stirred for 48 h. The solvent was then evaporated under reduced
pressure. The residue, purified by flash chromatography (silica
gel, 95/5 v/v n-hexane/ethyl
acetate), afforded 1-(6-chloro-2-methyl-4-phenyl-quinolin-3-yl)-ethanone 3f (0.23 g, 89% yield); mp 153-155 °C.
IR (KBr): 1715 cm-1. 1H
NMR (CDCl3): δ = 2.00 (s, 3 H), 2.68
(s, 3 H), 7.33-7.96 (m, 8 H). 13C
NMR (CDCl3): δ = 23.8, 31.7, 124.8,
125.7, 128.9, 129.2, 129.8, 130.5, 130.8, 132.3, 134.4, 135.4, 142.9, 145.8,
153.8, 205.1. EI-MS: m/z (relative
intensity) = 295 (39) [M+],
281 (100), 252 (22).
13 Selected data for 3g,
3i, 3j, 3g: Mp 80-81 °C. IR (KBr): 1750
cm-1. 1H NMR (CDCl3): δ = 2.71
(s, 3 H), 7.34-7.67 (m, 9 H). 13C
NMR (CDCl3): δ = 23.8, 115,4 (q, J = 308 Hz), 126.3,
127.1, 127.6, 128.2, 129.1, 129.4, 130.3, 131.3, 131.6, 147.5, 148.3,
153.3, 189.4 (q, J = 38
Hz). EI-MS: m/z (relative intensity) = 315(68) [M+],
247 (100), 218 (27). 3i: Mp 118-120 °C. 1H
NMR (CDCl3): δ = 1.33-1.47
(m, 6 H), 1.90-1.95 (m, 2 H), 2.73 (t, J = 5.6
Hz, 2 H), 3.21 (t, J = 6.1 Hz,
2 H), 7.18-7.26 (m, 4 H), 7.42-7.47 (m, 3 H),
7.52-7.60 (m, 1 H), 8.05-8.09 (m, 1 H). 13C
NMR (CDCl3): δ = 25.6, 26.5, 27.9,
31.0, 31.1, 36.2, 125.2, 125.9, 127.0, 127.4, 128.0, 128.1, 128.4,
129.1, 131.6, 137.4, 146.2, 146.3, 163.2. EI-MS: m/z (relative
intensity) = 287 (100) [M+],
258 (27). 3j: Mp 194-196 °C. 1H
NMR (CDCl3): δ = 2.02-2.06 (m,
2 H), 2.38 (t, J = 6.7 Hz, 2
H), 2.57 (t, J = 6.9 Hz, 2 H), 7.07-8.22
(m, 12 H). 13C NMR (CDCl3): δ = 25.1,
29.6, 31.9, 115.8 (d, J = 22.2
Hz), 126.2, 126.3, 127.2, 127.9, 128.4, 128.6, 129.4, 129.5, 129.7,
130.4, 161.9 (d, J = 244.2 Hz).
EI-MS: m/z (relative intensity) = 339
(100) [M+].
14
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Klug P.
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Möbius G.
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19 Selected data for 4:
IR(neat): 3460, 3350, 1720, 1665 cm-1. 1H
NMR (CDCl3): δ = 2.05 (s, 3 H), 5.43
(s, 1 H), 7.27-7.66 (m, 9 H). 13C
NMR (CDCl3): δ = 20.3, 91.5, 114.4
(q, J = 218
Hz), 126.9, 127.3, 128.5, 129.4, 129.9, 130.7, 131.7, 133.5, 134.4,
137.6, 176.6 (q, J = 33
Hz), 195.3. EI-MS:
m/z (relative
intensity) = 324 (100) [M + 1+],
265 (21), 220 (94), 105 (67).