Synthesis of New Quinoline Derivatives

3586
J. Tóth et al.
5-(6-Methoxy-2-chloro-3-quinolyl)-3-methyl-1,3-oxazolone (3c): pale
yellow oil. 1 H NMR (500 MHz, CDCl 3 ): 8.26 (s, 1H, qui-H-4), 7.89 (d, 1H,
J ¼ 9.2 Hz, qui-H-8), 7.35 (dd, 1H, J ¼ 2.8 and 9.2 Hz, qui-H-7), 7.09
(d, 1H, J ¼ 2.8 Hz, qui-H-5), 5.35 (t, 1H, J ¼ 6.5 Hz, H-5), 4.66 (d, 1H,
J ¼ 5.1 Hz, H-2), 4.53 (d, 1H, J ¼ 5.1 Hz, H-2), 3.92 (s, 3H, OCH 3 ), 3.62
(dd, 1H, J ¼ 6.7 and 11.3 Hz, H-4), 2.85 (dd, 1H, J ¼ 6.7 and 11.3 Hz,
H-4), 2.53 (s, 3H, NCH 3 ); 13 C NMR (125 MHz, CDCl 3 ): 158.2 (CH), 145.5
(q), 142.8 (q), 134.7 (CH), 133.3 (q), 129.5 (CH), 128.4 (q), 122.7 (CH),
105.2 (CH), 89.3 (CH 2 ), 73.6 (CH), 61.4 (CH 2 ), 55.5 (CH 3 ), 41.7 (CH 3 );
IR (neat, cm 21 ): 2955, 2870, 2801, 1671, 1623, 1592, 1498, 1455,
1329, 1228, 1165, 1123, 1056, 1032, 959; HRMS (E.I) [M] þ calcd. for
C 14 H 15 C1 N 2 O 2 ¼ 278.08220; found 278.0852.
5-(6-Methoxy-2-chloro-3-quinolyl)-3-benzyl-1,3-oxazolone (3d): pale yellow
oil. 1 H NMR (500 MHz, CDCl 3 ): 8.25 (s, 1H, qui-H-4), 7.86 (d, 1H, J ¼ 9.2 Hz,
qui-H-8), 7.33–7.25 (m, 6H, Ph and qui-H-7), 7.06 (d, 1H, J ¼ 2.8 Hz, qui-H-
5), 5.33 (t, 1H, J ¼ 6.8 Hz, H-5), 4.66 (d, 1H, J ¼ 5.5 Hz, H-2), 3.87 (s, 3H,
OCH 3 ), 3.81 (s, 2H, NCH 2 ), 3.72 (dd, 1H, J ¼ 6.8 and 11.8 Hz, H-4), 3.57
(dd, 1H, J ¼ 6.8 and 11.8 Hz, H-4); 13 C NMR (125 MHz, CDCl 3 ): 158.0 (q),
145.4 (q), 142.6 (q), 138.2 (q), 134.5 (q), 133.1 (CH), 129.3 (CH), 128.5
(2 CH), 128.3 (2 CH), 128.2 (q), 127.2 (CH), 122.5 (CH), 105.0 (CH),
87.1 (CH 2 ), 73.3 (CH), 59.2 (CH 2 ), 58.2 (CH 2 ), 55.3 (CH 3 ). IR (neat, cm 21 ):
3062, 2935, 2878, 1674, 1594, 1498, 1454, 1329, 1061, 998; HRMS (E.I)
[M] þ calcd. for C 20 H 19 C1 N 2 O 2 ¼ 354.11350; found 354.1147.
5-(2,8-Dichloro-6-methyl-3-quinolyl)-3-methyl-1,3-oxazolone (3e): pale
yellow oil. 1 H NMR (500 MHz, CDCl 3 ): 8.23 (s, 1H, qui-H-4), 7.65 (d, 1H,
J ¼ 2.1 Hz, qui-H-5), 7.49 (d, 1H, J ¼ 2.1 Hz, qui-H-7), 5.35 (t, 1H,
J ¼ 6.5 Hz, H-5), 4.65 (d, 1H, J ¼ 5.1 Hz, H-2), 4.53 (d, 1H, J ¼ 5.1 Hz,
H-2), 3.56 (dd, 1H, J ¼ 6.5 and 11.5 Hz, H-4), 2.84 (dd, 1H, J ¼ 6.5 and
11.5 Hz, H-4), 2.73 (s, 3H, CH 3 ), 2.52 (s, 3H, CH 3 ); 13 C NMR (125 MHz,
CDCl 3 ): 147.4 (q), 144.6 (q), 138.6 (q), 135.5 (q), 133.8 (CH), 132.4 (q),
130.8 (CH), 128.0 (q), 124.0 (CH), 89.4 (CH 2 ), 73.5 (CH), 61.3 (CH 2 ), 41.6
(CH 3 ), 17.6 (CH 3 ); IR (KBR, cm 21 ): 3694, 2963, 2794, 1654, 1522, 1322,
1263, 1099, 1022; HRMS (E.I) [M] þ calcd. for C 14 H 14 C1 2 N 2 O ¼ 296.04831;
found 296.0499.
5-(2,8-Dichloro-6-methyl-3-quinolyl)-3-benzyl-1,3-oxazolone (3f): pale
yellow oil. 1 H NMR (500 MHz, CDCl 3 ): 8.24 (s, 1H, qui-H-4), 7.65 (s, 1H,
qui-H-5), 7.49 (s, 1H, qui-H-7), 7.36–7.25 (m, 5H, Ph), 5.35 (t, 1H,
J ¼ 7.0 Hz, H-5), 4.67 (d, 1H, J ¼ 5.6 Hz, H-2), 4.63 (d, 1H, J ¼ 5.6 Hz,
H-2), 3.83 (s, 2H, NCH 2 ), 3.76 (dd, 1H, J ¼ 7.0 and 11.8 Hz, H-4), 3.73
(dd, 1H, J ¼ 7.0 and 11.8 Hz, H-4), 2.72 (s, 3H, CH 3 );
13 C NMR
(125 MHz, CDCl 3 ): 147.4 (q), 144.6 (q), 138.6 (q), 138.3 (q), 135.4 (q),
133.8 (CH), 132.4 (q), 130.8 (CH), 128.7 (2 CH), 128.5 (2 CH), 127.9