Organic & Biomolecular Chemistry
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IR (CHCl3): νmax 3400, 2919, 1716, 1620, 1585, 1497, 1472, 1714, 1619, 1553, 1463, 1249, 1028 cm−1; ESI-MS: m/z 338.10
1253, 1105 cm−1; ESI-MS: m/z 322.00 [M + H]+; HRMS: m/z [M + H]+; HRMS: m/z 338.1391 (ESI) calcd for C20H19NO4 + H+
322.1445 (ESI) calcd for C20H19NO3 + H+ (322.1438).
Ethyl 6-methoxy-4-(thiophen-3-yl)quinoline-2-carboxylate
(338.1387).
Ethyl 6-methoxy-4-m-tolylquinoline-2-carboxylate (1h).28
(1c). Brown solid; m.p. 153–154 °C; 1H NMR (CDCl3, Pale yellow solid; m.p. 139–140 °C; 1H NMR (CDCl3, 400 MHz):
400 MHz): δ 8.26 (d, J = 8.0 Hz, 1H), 8.14 (s, 1H), 7.60 (s, 1H), δ 8.28 (d, J = 8.0 Hz, 1H), 8.09 (s, 1H), 7.45–7.42 (m, 2H),
7.55–7.53 (m, 1H), 7.44 (d, J = 8.0 Hz, 1H), 7.40–7.37 (m, 2H), 7.36–7.31 (m, 3H), 7.24 (s, 1H), 4.58–4.53 (m, 2H), 3.81 (s, 3H),
4.58–4.53 (m, 2H), 3.86 (s, 3H), 1.49 (t, J = 4.0 Hz, 3H); 13C 2.47 (s, 3H), 1.49 (t, J = 8.0 Hz, 3H); 13C NMR (CDCl3,
NMR (CDCl3, 100 MHz): δ 165.6, 159.6, 145.4, 144.4, 142.8, 100 MHz): δ 165.7, 159.5, 148.2, 145.4, 144.3, 138.6, 137.9,
138.4, 132.8, 129.2, 128.5, 126.7, 125.1, 122.8, 121.6, 103.2, 132.7, 130.1, 129.3, 129.2, 128.6, 126.4, 122.7, 121.7, 103.4,
62.1, 55.6, 14.4; IR (CHCl3): νmax 3415, 2960, 1732, 1714, 1620, 62.1, 55.5, 21.5, 14.4; IR (CHCl3): νmax 2978, 2932, 1738, 1713,
1555, 1475, 1268, 1226 cm−1; ESI-MS: m/z 314.00; [M + H]+; 1620, 1474, 1406, 1367, 1257, 1224, 1106 cm−1; ESI-MS: m/z
HRMS: m/z 314.0844 (ESI) calcd for C17H15NO3S
(314.0845).
+ +
H+ 322.10 [M H]+; HRMS: m/z 322.1410 (ESI) calcd for
C20H19NO3 + H+ (322.1438).
Ethyl
4-(4-(trifluoromethyl)phenyl)-6-methoxyquinoline-2-
Ethyl 8-phenyl-[1,3]dioxolo[4,5-g]quinoline-6-carboxylate (1i).
carboxylate (1d). Brown solid; m.p. 161–162 °C; 1H NMR Brown solid; m.p. 237–238 °C; 1H NMR (CDCl3, 400 MHz):
(CDCl3, 400 MHz): δ 8.31 (d, J = 8.0 Hz, 1H), 8.08 (s, 1H), 7.84 δ 8.00 (s, 1H), 7.64 (s, 1H), 7.56–7.47 (m, 5H), 7.19 (s, 1H), 6.13
(d, J = 8.0 Hz, 2H), 7.69 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.0 Hz, (s, 2H), 4.56–4.51 (m, 2H), 1.47 (t, J = 4.0 Hz, 3H); 13C NMR
1H), 7.10 (s, 1H), 4.59–4.54 (q, J = 8.0, 16.0 Hz, 2H), 3.83 (s, (CDCl3, 100 MHz): δ 165.6, 151.1, 149.9, 148.2, 146.8, 145.6,
3H), 1.49 (t, J = 4.0 Hz, 3H); 13C NMR (CDCl3, 100 MHz): 138.1, 129.4, 128.8, 128.6, 125.6, 120.4, 107.0, 102.2, 100.9,
δ 165.4, 159.8, 146.4, 145.4, 144.3, 141.6, 133.0, 129.8, 128.8, 62.1, 14.4; IR (CHCl3): νmax 3435, 2918, 1696, 1462, 1276, 1239,
1
125.8, (t, JCF = 3.77 Hz), 123.1, 121.8, 102.8, 62.3, 55.7, 14.4; 1111, 1036 cm−1; ESI-MS: m/z 322.00 [M + H]+; HRMS: m/z
19F NMR (376.50 MHz, CDCl3): δ −62.81 (s, 3F); IR (CHCl3): 322.1077 (ESI) calcd for C19H15NO4 + H+ (322.1074).
νmax 3434, 2927, 2851, 1620, 1512, 1476, 1324, 1228,
1066 cm−1; ESI-MS: m/z 376.00 [M + H]+; HRMS: m/z 376.1162 Yellow solid; m.p. 220–221 °C; 1H NMR (CDCl3, 400 MHz):
(ESI) calcd for C20H16F3NO3 + H+ (376.1155).
δ 7.98 (s, 1H), 7.63 (s, 1H), 7.39–7.33 (m, 4H), 7.22 (s, 1H),
Ethyl 8-p-tolyl-[1,3]dioxolo[4,5-g]quinoline-6-carboxylate (1j).
Ethyl 4-(4-tert-butylphenyl)-6-methoxyquinoline-2-carboxy- 6.12 (s, 2H), 4.57–4.51 (m, 2H), 2.47 (s, 3H), 1.47 (t, J = 8.0 Hz,
late (1e).28 White solid; m.p. 174–175 °C; 1H NMR (CDCl3, 3H); 13C NMR (CDCl3, 100 MHz): δ 165.7, 151.1, 149.8, 148.4,
400 MHz): δ 8.28 (d, J = 8.0 Hz, 1H), 8.10 (s, 1H), 7.58 (d, J = 146.8, 145.6, 138.6, 135.1, 129.4, 129.3, 125.7, 120.4, 106.1,
8.0 Hz, 2H), 7.52 (d, J = 12.0 Hz, 2H), 7.45–7.43 (dd, J = 4.0, 102.1, 101.0, 62.1, 21.3, 14.4; IR (CHCl3): νmax 3401, 2921,
4.0 Hz, 1H), 7.31 (s, 1H), 4.57–4.52 (m, 2H), 3.84 (s, 3H), 1.48 1703, 1617, 1504, 1463, 1376, 1237, 1110 cm−1; ESI-MS: m/z
(t, J = 8.0 Hz, 3H), 1.42 (s, 9H); 13C NMR (CDCl3, 100 MHz): 336.00 [M
+
H]+; HRMS: m/z 336.1236 (ESI) calcd for
δ 165.7, 159.4, 151.8, 148.1, 145.4, 144.4, 134.9, 132.7, 129.2, C20H17NO4 + H+ (336.1230).
129.1, 125.8, 122.6, 121.9, 103.6, 62.1, 55.6, 34.8, 31.4, 14.4; IR
Ethyl 8-(4-(trifluoromethyl)phenyl)-[1,3]dioxolo[4,5-g]quino-
(CHCl3): νmax 3401, 2961, 2866, 1739, 1715, 1620, 1498, 1474, line-6-carboxylate (1k). Brown solid; m.p. 161–162 °C; 1H NMR
1251, 1224 cm−1; ESI-MS: m/z 364.10 [M + H]+; HRMS: m/z (CDCl3, 400 MHz): δ 8.02 (s, 1H), 7.84 (d, J = 8.0 Hz, 2H), 7.74
364.1903 (ESI) calcd for C23H25NO3 + H+ (364.1907).
(s, 1H), 7.63 (d, J = 8.0 Hz, 2H), 7.09 (s, 1H), 6.18 (s, 2H),
Ethyl 4-(4-bromophenyl)-6-methoxyquinoline-2-carboxylate 4.59–4.54 (m, 2H), 1.49 (t, J = 4.0 Hz, 3H); 13C NMR (CDCl3,
(1f). Pale yellow solid; m.p. 171–172 °C; 1H NMR (CDCl3, 100 MHz): δ 165.0, 152.2, 150.7, 147.9, 145.7, 144.4, 141.2,
1
400 MHz): δ 8.28 (d, J = 8.0 Hz, 1H), 8.06 (s, 1H), 7.70 (d, J = 129.8, 125.9 (t, JCF = 3.77 Hz), 125.6, 131.3, 131.0, 120.3,
8.0 Hz, 2H), 7.44 (d, J = 8.0 Hz, 3H), 7.13 (s, 1H), 4.58–4.53 (m, 106.1, 102.7, 100.5, 62.7, 14.4; 19F NMR (376.50 MHz, CDCl3)
2H), 3.82 (s, 3H), 1.49 (t, J = 8.0 Hz, 3H); 13C NMR (CDCl3, δ −62.95 (s, 3F); IR (CHCl3): νmax 3400, 2919, 2850, 1617, 1419,
100 MHz): δ 165.5, 159.7, 146.7, 145.4, 144.3, 136.8, 132.9, 1090 cm−1; ESI-MS: m/z 390.00 [M + H]+; HRMS: m/z 390.0953
132.1, 131.0, 130.9, 128.9, 123.1, 123.0, 121.7, 102.9, 102.8, (ESI) calcd for C20H14F3NO4 + H+ (390.0948).
62.2, 55.6, 14.4; IR (CHCl3): νmax 3400, 2923, 2850, 1730, 1715,
1619, 1488, 1473, 1434, 1367, 1274, 1226 cm−1; ESI-MS: m/z Pale yellow solid; m.p. 126–127 °C; 1H NMR (CDCl3, 400 MHz):
387.90 [M
H]+; HRMS: m/z 388.0374 (ESI) calcd for δ 7.98 (s, 1H), 7.63 (s, 1H), 7.42 (t, J = 8.0 Hz, 1H), 7.32–7.28
C19H16BrNO3 + H+ (386.0386).
(m, 3H), 7.20 (s, 1H), 6.13 (s, 2H), 4.56–4.51 (m, 2H), 2.46 (s,
Ethyl 8-m-tolyl-[1,3]dioxolo[4,5-g]quinoline-6-carboxylate (1l).
+
Ethyl 6-methoxy-4-(4-methoxyphenyl)quinoline-2-carboxylate 3H), 1.47 (t, J = 8.0 Hz, 3H); 13C NMR (CDCl3, 100 MHz):
(1g).28 Pale yellow solid; m.p. 119–120 °C; 1H NMR (CDCl3, δ 165.7, 151.1, 149.8, 148.5, 146.8, 145.6, 138.5, 138.1, 130.0,
400 MHz): 8.27 (d, J = 8.0 Hz, 1H), 8.07 (s, 1H), 7.51 (d, J = 129.3, 128.4, 126.4, 125.8, 120.4, 107.0, 102.1, 101.0, 62.1, 21.5,
8.0 Hz, 2H), 7.44 (d, J = 8.0 Hz, 1H), 7.27 (s, 1H), 7.10 (s, 2H), 14.4; IR (CHCl3): νmax 3400, 2922, 1617, 1462, 1384, 1237,
4.58–4.53 (m, 2H), 3.92 (s, 3H), 3.83 (s, 3H), 1.49 (t, J = 8.0 Hz, 1037 cm−1; ESI-MS: m/z 336.3602 [M + H]+; HRMS: m/z
3H); 13C NMR (CDCl3, 100 MHz): δ 165.8, 160.0, 159.4, 147.8, 336.3600 (ESI) calcd for C20H17NO4 + H+ (336.3607).
145.4, 144.4, 132.7, 130.6, 130.2, 129.4, 122.8, 121.8, 114.2,
Ethyl 8-(3-chlorophenyl)-[1,3]dioxolo[4,5-g]quinoline-6-car-
103.3, 62.1, 55.6, 55.4, 14.4; IR (CHCl3): νmax 3400, 2019, 2850, boxylate (1m). Yellow solid; m.p. 133–134 °C; 1H NMR (CDCl3,
This journal is © The Royal Society of Chemistry 2014
Org. Biomol. Chem., 2014, 12, 6267–6277 | 6273