The Journal of Organic Chemistry
Page 12 of 22
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8.10 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.1 Hz, 2H), 7.82-7.77 (m, 4H), 7.58 (td, J = 7.3, 1.0 Hz, 1H), 2.78 (s, 3H); 13C{1H} NMR
(101 MHz, CDCl3) δ 195.7, 156.7, 148.3, 140.2, 137.5, 134.9 (q, JF-C = 32.7 Hz), 131.6, 131.2, 130.4, 128.8, 128.2, 127.0, 125.8
(q, JF-C = 3.7 Hz), 125.1, 123.5 (q, JF-C = 272.8 Hz), 24.4; 19F NMR (376 MHz, CDCl3) δ -63.09; ATR-FTIR (cm-1): 2923, 1665,
1617, 1488, 1411, 1325, 1019, 913, 863, 753; HRMS (ESI-TOF) m/z: [M+H]+ calcd for C18H13F3NO 316.0943; found 316.0946.
2-(Methyl)-3-(naphthalen)formylquinoline (3k)
Compound 3k was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
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(PE:EA = 20:1) afforded 3k (46.8 mg, 52%) as a yellow oil; H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.2, 1.0 Hz, 1H), 8.16
(s, 1H), 8.08 (t, J = 9.0 Hz, 2H), 7.97-7.95 (m, 1H), 7.81-7.77 (m, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.65-7.58 (m, 3H), 7.54-7.45 (m,
2H), 2.87 (s, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 198.6, 157.6, 148.3, 138.8, 135.6, 134.0, 133.5, 133.4, 131.5, 131.1,
130.8, 128.7, 128.6, 128.4, 128.3, 126.9, 126.7, 125.7, 125.5, 124.4, 24.8; ATR-FTIR (cm-1): 2922, 1655, 1616, 1591, 1562,
1417, 1281, 1237, 1187, 1116, 909, 887, 768, 755, 597; HRMS (ESI-TOF) m/z: [M+H]+ calcd for C21H16NO 298.1226; found
298.1228.
2-(Methyl)-3-(thiophen)formylquinoline (3l)
Compound 3l was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
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(PE:EA = 10:1) afforded 3l (45.6 mg, 60%) as a yellow solid; m.p. 56.3-57.9 C; H NMR (400 MHz, CDCl3) δ 8.25 (s, 1H),
8.09 (d, J = 8.4 Hz, 1H), 7.84-7.77 (m, 3H), 7.59-7.55 (m, 1H), 7.48 (dd, J = 3.8, 1.2 Hz, 1H), 7.17 (dd, J = 4.9, 3.8 Hz, 1H),
2.80 (s, 3H); 13C{1H} NMR (101 MHz, CDCl3) δ 188.6, 156.5, 148.1, 144.5, 136.2, 135.8, 135.8, 132.0, 131.2, 128.7, 128.5,
128.1, 126.8, 125.2, 24.0; ATR-FTIR (cm-1): 3082, 1637, 156, 1514, 1419, 1407, 1352, 1258, 1052, 868, 831, 740; HRMS
(ESI-TOF) m/z: [M+H]+ calcd for C15H12NOS 254.0634; found 254.0635.
2-(Methyl)-3-(ethanone)quinoline (3m)
Compound 3m was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
(PE:EA = 10:1) afforded 3m (46.5 mg, 84%) as a white solid; m.p. 55.4-56.1 oC (74.0-75.0 oC)17; 1H NMR (400 MHz, CDCl3) δ
8.48 (s, 1H), 8.04 (d, J = 8.5 Hz, 1H), 7.86 (d, J = 8.1 Hz, 1H), 7.81-7.77 (m, 1H), 7.58-7.54 (m, 1H), 2.92 (s, 3H), 2.72 (s, 3H);
13C{1H} NMR (101 MHz, CDCl3) δ 200.0, 157.6, 148.3, 138.3, 131.8, 131.1, 128.6, 128.4, 126.7, 125.6, 29.3,25.7; ATR-FTIR
(cm-1): 2920, 1677, 1619, 1562, 1487, 1418, 1352, 1197, 1031, 946, 926, 862, 780, 655, 584; The 1H NMR and 13C NMR spectra
data are consistent with the reported literature.43
Methyl-2-methylquinoline-3-carboxylate (3n)
Compound 3n was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
(PE:EA = 20:1) afforded 3n (31.4 mg, 52%) as a white solid; m.p. 65.6-66.9 oC (61.0-63.0 oC)16; 1H NMR (400 MHz, CDCl3) δ
8.75 (s, 1H), 8.04 (d, J = 8.5 Hz, 1H), 7.86 (d, J = 8.1 Hz, 1H), 7.81-7.77 (m, 1H), 7.57-7.53 (m, 1H), 3.98 (s, 3H), 3.00 (s, 3H);
13C{1H} NMR (101 MHz, CDCl3) δ 167.0, 158.5, 148.7, 140.1, 131.8, 128.5, 128.5, 126.6, 125.7, 123.5, 52.4, 25.7; ATR-FTIR
(cm-1): 3257, 1620, 1568, 1492, 1439, 1421, 1282, 1253, 1204, 1133, 1066, 788, 751; The H NMR and 13C NMR spectra data
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are consistent with the reported literature.7a
3,4-Dihydroacridin-1(2H)-one (3o)
Compound 3o was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
(PE:EA = 5:1) afforded 3o (51.5 mg, 87%) as a light yellow solid; m.p. 95.5-96.8 C (109.0-111.0 C)44; H NMR (400 MHz,
CDCl3) δ 8.86 (s, 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.94 (d, J = 8.2 Hz, 1H), 7.82 (dd, J = 8.4, 7.0 Hz, 1H), 7.56 (t, J = 7.5 Hz, 1H),
3.33 (t, J = 6.1 Hz, 2H), 2.81 (t, J = 6.5 Hz, 2H), 2.30 (dd, J = 12.7, 5.8 Hz, 2H); 13C{1H} NMR (101 MHz, CDCl3) δ 198.0,
162.0, 150.0, 137.2, 132.4, 129.8, 128.6, 126.8, 126.7, 126.3, 39.1, 33.5, 21.8; ATR-FTIR (cm-1): 2921, 1678, 1616, 1592, 1493,
1463, 1411, 1205, 1171, 1128, 791, 766; The 1H NMR and 13C NMR spectra data are consistent with the reported literature.7a
11H-Indeno[1,2-b]quinolin-11-one (3p)
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Compound 3p was synthesized in accordance with the typical procedure. Purification by column chromatography on silica gel
(PE:EA = 20:1) afforded 3p (52.0 mg, 75%) as a light yellow solid; m.p. 172.9-173.5 oC (172.0-174.0 oC)45; 1H NMR (400 MHz,
CDCl3) δ 8.36 (s, 1H), 8.09 (t, J = 8.5 Hz, 2H), 7.84 (dd, J = 16.0, 7.8 Hz, 2H), 7.78-7.74 (m, 1H), 7.68 (td, J = 7.5, 1.0 Hz, 1H),
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