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248.1070, found 248.1073. Anal. Calcd for C17H13NO: C, 82.57; H,
5.30; N, 5.66. Found: C, 82.65; H, 5.33; N, 5.67.
1H); 13C NMR (100 MHz, CDCl3) δ 196.3, 163.7, 150.8, 146.1, 139.7,
135.9, 132.5, 131.0, 129.3, 128.2, 127.9, 125.8, 121.5, 113.6, 55.4; IR
(KBr) ν 3073, 1659, 1595, 1495, 1260, 1170, 1025, 929, 797 cm−1;
HRMS (ESI-TOF) m/z [M + Na]+ calcd for C17H13NO2 286.0838,
found 286.0842. Anal. Calcd for C17H13NO2: C, 77.55; H, 4.98; N, 5.32.
Found: C, 77.59; H, 4.98; N, 5.41;
(3-Methoxyphenyl)(quinolin-8-yl)methanone (4h). Methyl
quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (3-methoxyphenyl)-
boronic acid (30.4 mg, 0.20 mmol) were used for the preparation of the
title compound and purified by silica gel column chromatography
(EtOAc/hexane = 1/8) as a yellow viscous liquid (22.4 mg, 85%): 1H
NMR (400 MHz, CDCl3) δ 3.82 (s, 3H), 7.09−7.10 (m, 1H), 7.25 (s,
2H), 7.40 (dd, J = 8.0, 4.0 Hz, 1H), 7.53 (s, 1H), 7.61 (t, J = 7.2 Hz, 1H),
7.72 (d, J = 6.8 Hz, 1H), 7.94 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 8.0 Hz,
1H), 8.84 (d, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 197.6,
159.7, 150.8, 146.1, 139.4, 139.2, 135.9, 129.6, 129.2, 128.2, 128.1, 125.8,
123.6, 121.6, 119.9, 113.7, 55.4; IR (KBr) ν 1670, 1579, 1436, 1318,
1280, 1040, 800, 739, 721 cm−1; HRMS (ESI-TOF) m/z [M + Na]+
calcd for C17H13NO2 286.0838, found 286.0845. Anal. Calcd for
C17H13NO2: C, 77.55; H, 4.98; N, 5.32. Found: C, 77.67; H, 5.01; N,
5.32;
(3,4-Dimethoxyphenyl)(quinolin-8-yl)methanone (4i). Methyl
quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (3,4-
dimethoxyphenyl)boronic acid (36.4 mg, 0.20 mmol) were used for
the preparation of the title compound and purified by silica gel column
chromatography (EtOAc/hexane = 1/2) as a yellow solid (15.5 mg,
53%): mp 130−132 °C; 1H NMR (400 MHz, CDCl3) δ 3.88 (s, 3H),
3.92 (s, 3H), 6.73 (d, J = 8.4 Hz, 1H), 7.14 (dd, J = 8.4 Hz, 1.6 Hz, 1H),
7.40 (dd, J = 8.4 Hz, 4.4 Hz, 1H), 7.60 (t, J = 8.4 Hz, 1H), 7.69−7.72 (m,
2H), 7.92 (dd, J = 8.4 Hz, 1.2 Hz, 1H), 8.19 (dd, J = 8.4 Hz, 1.6 Hz, 1H),
8.85 (dd, J = 4.0 Hz, 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 196.3,
153.6, 150.8, 149.1, 146.2, 139.6, 135.9, 131.1, 129.3, 128.1, 127.9, 126.4,
125.7, 121.5, 111.2, 109.8, 56.0, 55.9; IR (KBr) ν 1660, 1592, 1515,
1463, 1417, 1271, 1138, 1022, 802 cm−1; HRMS (ESI-TOF) m/z [M +
Na]+ calcd for C18H15NO3 316.0944, found 316.0947. Anal. Calcd for
C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.87; H, 5.26; N,
4.79.
Quinolin-8-yl(3,4,5-trimethoxyphenyl)methanone (4j). Meth-
yl quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (3,4,5-
trimethoxyphenyl)boronic acid (42.4 mg, 0.20 mmol) was used for
the preparation of the title compound and purified by silica gel column
chromatography (EtOAc/hexane = 1/2) as a yellow solid (12.9 mg,
40%): mp 158−160 °C; 1H NMR (400 MHz, CDCl3) δ 3.77 (s, 6H),
3.93 (s, 3H), 7.14 (s, 2H), 7.46 (dd, J = 8.4, 4.4 Hz, 1H), 7.65 (t, J = 7.2
Hz, 1H), 7.75 (d, J = 7.2 Hz, 1H), 7.98 (d, J = 8.0 Hz, 1H), 8.25 (dd, J =
8.4, 1.2 Hz, 1H), 8.91 (dd, J = 4.0, 1.2 Hz, 1H); 13C NMR (100 MHz,
CDCl3) δ 196.4, 152.8, 150.8, 146.0, 143.0, 139.1, 136.0, 132.7, 129.6,
128.1, 128.0, 125.7, 121.6, 108.0, 60.8, 56.1; IR (KBr) ν 3063, 2938,
2836, 1655, 1583, 1502, 1461, 1413, 1335, 1232, 1129, 1001, 803, 733
cm−1; HRMS (ESI-TOF) m/z [M + H]+ calcd for C19H17NO4
324.1230, found 324.1235. Anal. Calcd for C19H17NO4: C, 70.58; H,
5.30; N, 4.33. Found: C, 70.68; H, 5.37; N, 4.35;
(Quinolin-8-yl)(m-tolyl)methanone (4c). Methyl quinoline-8-
carboxylate (18.7 mg, 0.10 mmol) and m-tolylboronic acid (27.2 mg,
0.20 mmol) were used for the preparation of the title compound and
purified by silica gel column chromatography (EtOAc/hexane = 1/10)
as a white solid (21.7 mg, 88%): mp 96−98 °C; 1H NMR (400 MHz,
CDCl3) δ 2.35 (s, 3H), 7.27 (t, J = 7.6 Hz, 1H), 7.36 (d, J = 7.2 Hz, 1H),
7.41 (dd, J = 8.0, 4.0 Hz, 1H), 7.55 (d, J = 7.6 Hz, 1H), 7.62 (t, J = 7.6 Hz,
1H), 7.72 (d, J = 8.4 Hz, 2H), 7.95 (d, J = 8.0 Hz, 1H), 8.21 (d, J = 8.4
Hz, 1H), 8.84 (d, J = 2.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 197.9,
150.7, 146.1, 139.5, 138.0, 137.8, 135.9, 134.0, 130.2, 129.5, 128.2, 128.1,
128.0, 127.7, 125.7, 121.5, 21.2; Anal. Calcd for C17H13NO: C, 82.57; H,
5.30; N, 5.66. Found: C, 82.69; H, 5.38; N, 5.69; IR (KBr) ν 3047, 2923,
1669, 1599, 1494, 1318, 1280, 1183, 1146, 947, 801, 731, 629 cm−1;
HRMS (ESI-TOF) m/z [M + Na]+ calcd for C17H13NO 270.0889,
found 270.0893.
(Quinolin-8-yl)(p-tolyl)methanone (4d). Methyl quinoline-8-
carboxylate (18.7 mg, 0.10 mmol) and p-tolylboronic acid (27.2 mg,
0.20 mmol) were used for the preparation of the title compound and
purified by silica gel column chromatography (EtOAc/hexane = 1/10)
as a white solid (22.7 mg, 92%): mp 112−114 °C ; 1H NMR (400 MHz,
CDCl3) δ 2.40 (s, 3H), 7.20 (d, J = 7.6 Hz, 2H), 7.41 (dd, J = 8.0 Hz, 4.0
Hz, 1H), 7.62 (t, J = 7.6 Hz, 1H), 7.72 (m, 3H), 7.95 (d, J = 8.0 Hz, 1H),
8.21 (d, J = 8.0 Hz, 1H), 8.85 (dd, J = 4.0 Hz, 2.8 Hz, 1H); 13C NMR
(100 MHz, CDCl3) δ 197.4, 150.7, 146.1, 144.0, 139.7, 135.9, 135.4,
130.3, 129.4, 129.0, 128.2, 128.0, 125.8, 121.5, 21.6; IR (KBr) ν 3050,
2923, 1665, 1595, 1494, 1407, 1320, 1278, 1216, 1178, 929, 796, 739,
604 cm−1; HRMS (ESI-TOF) m/z [M + Na]+ calcd for C17H13NO
270.0889, found 270.0890. Anal. Calcd for C17H13NO: C, 82.57; H,
5.30; N, 5.66. Found: C, 82.61; H, 5.33; N, 5.65.
(4-tert-Butylphenyl)(quinolin-8-yl)methanone (4e). Methyl
quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (4-tert-butylphenyl)-
boronic acid (35.6 mg, 0.20 mmol) was used for the preparation of the
title compound and purified by silica gel column chromatography
(EtOAc/hexane = 1/10) as a white solid (26.0 mg, 90%): mp 98−100
°C; 1H NMR (400 MHz, CDCl3) δ 1.34 (s, 9H), 7.41−7.45 (m, 3H),
7.63 (t, J = 8.0 Hz, 1H), 7.72 (dd, J = 7.2 Hz, 1.2 Hz, 1H), 7.80 (d, J = 8.4
Hz, 2H), 7.96 (dd, J = 8.0 Hz, 0.8 Hz, 1H), 8.22 (dd, J = 8.0 Hz, 1.2 Hz,
1H), 8.87 (dd, J = 4.0 Hz, 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ
197.4, 157.0, 150.8, 146.1, 139.7, 135.9, 135.2, 130.2, 129.4, 128.2, 127.9,
125.8, 125.3, 121.5, 35.1, 31.0; IR (KBr) ν 3053, 2962, 2868, 1670, 1600,
1573, 1494, 1319, 1278, 1183, 1109, 930, 795 cm−1; HRMS (ESI-TOF)
m/z [M + Na]+ calcd for C20H19NO 312.1359, found 312.1367. Anal.
Calcd for C20H19NO: C, 83.01; H, 6.62; N, 4.84. Found: C, 83.10; H,
6.71; N, 4.88.
(3,5-Dimethylphenyl)(quinolin-8-yl)methanone (4f). Methyl
quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (3,5-
dimethylphenyl)boronic acid (30 mg, 0.20 mmol) were used for the
preparation of the title compound and purified by silica gel column
chromatography (EtOAc/hexane = 1/10) as a yellow solid (22.7 mg,
87%): mp 95−97 °C; 1H NMR (400 MHz, CDCl3) δ 2.29 (s, 6H), 7.19
(s, 1H), 7.42 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.45 (s, 2H), 7.62 (t, J = 8.0
Hz, 1H), 7.70 (dd, J = 6.8 Hz, 1.2 Hz, 1H), 7.95 (dd, J = 8.0 Hz, 1.6 Hz,
1H), 8.21 (dd, J = 8.0 Hz, 1.6 Hz, 1H), 8.86 (dd, J = 4.4 Hz, 1.6 Hz, 1H);
13C NMR (100 MHz, CDCl3) δ 198.1, 150.8, 146.2, 139.8, 137.96,
137.90, 135.9, 135.0, 129.4, 128.2, 127.9, 125.7, 121.5, 21.1; IR (KBr) ν
1714, 1485, 1416, 1269, 1209, 1154, 1017, 910, 867, 732 cm−1; HRMS
(ESI-TOF) m/z [M + Na]+ calcd for C18H15NO 284.1046, found
284.1050. Anal. Calcd for C18H15NO: C, 82.73; H, 5.79; N, 5.36. Found:
C, 82.76; H, 5.88; N, 5.39.
Naphthalen-1-yl(quinolin-8-yl)methanone (4k). Methyl quino-
line-8-carboxylate (18.7 mg, 0.10 mmol) and naphthalen-1-ylboronic
acid (34.4 mg, 0.20 mmol) was used for the preparation of the title
compound and purified by silica gel column chromatography (EtOAc/
hexane = 1/10) as a white solid (24.6 mg, 87%): mp 136−138 °C; 1H
NMR (600 MHz, CDCl3) δ 7.32 (t, J = 7.8 Hz, 1H), 7.39 (dd, J = 8.4 Hz,
4.2 Hz, 1H), 7.55−7.63 (m, 3H), 7.67 (t, J = 7.8 Hz, 1H), 7.82 (d, J = 7.2
Hz, 1H), 7.91 (d, J = 7.8 Hz, 1H), 7.96−8.00 (m, 2H), 8.21 (d, J = 7.8
Hz, 1H), 8.80 (d, J = 2.4 Hz, 1H), 9.14 (d, J = 9.0 Hz, 1H); 13C NMR
(150 MHz, CDCl3) δ199.7, 150.9, 146.2, 140.7, 135.9, 135.5, 133.9,
133.3, 132.5, 131.1, 130.1, 129.0, 128.3, 128.2, 126.5, 126.4, 125.7, 124.1,
121.5; IR (KBr) v1658, 1572, 1508, 1494, 1255, 1221, 1103, 911, 742
cm−1; HRMS (ESI-TOF) m/z [M + H]+ calcd for C20H13NO 284.1070,
found 284.1073. Anal. Calcd for C20H13NO: C, 84.78; H, 4.62; N, 4.94.
Found: C, 84.78; H, 4.66; N, 4.94.
(4-Methoxyphenyl)(quinolin-8-yl)methanone (4g). Methyl
quinoline-8-carboxylate (18.7 mg, 0.10 mmol) and (4-methoxyphenyl)-
boronic acid (30.4 mg, 0.20 mmol) were used for the preparation of the
title compound and purified by silica gel column chromatography
(EtOAc/hexane = 1/8) as a white solid (23.9 mg, 91%): mp 113−114
°C; 1H NMR (400 MHz, CDCl3) δ 3.83 (s, 3H), 6.87 (d, J = 8.8 Hz,
2H), 7.40 (dd, J = 8.4 Hz, 4.4 Hz, 1H), 7.60 (t, J = 8.0 Hz, 1H), 7.70 (dd,
J = 6.8 Hz, 1.2 Hz, 1H), 7.81 (d, J = 8.8 Hz, 2H), 7.94 (dd, J = 8.4 Hz, 1.2
Hz, 1H), 8.20 (dd, J = 8.4 Hz, 1.6 Hz, 1H), 8.85 (dd, J = 4.0 Hz, 1.6 Hz,
(Naphthalen-2-yl)(quinolin-8-yl)methanone (4l). Methyl qui-
noline-8-carboxylate (18.7 mg, 0.10 mmol) and naphthalen-2-ylboronic
acid (34.4 mg, 0.20 mmol) were used for the preparation of the title
F
dx.doi.org/10.1021/jo400949p | J. Org. Chem. XXXX, XXX, XXX−XXX