A Facile Synthesis of Benzo[h]quinolines
3.19 (m, 1H), 2.78 (s, 3H), 1.47 (d, J=6.9 Hz, 6H),
1.42 (d, J=6.9 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ:
165.0, 153.3, 145.2, 133.0, 132.3, 131.9, 127.6, 126.2,
125.5, 123.7, 122.5, 120.4, 115.7, 37.2, 28.4, 23.2, 22.9,
20.4; IR (KBr) ν: 3064, 2925, 1590, 768 cm1. HRMS
(EI) calcd for C20H23N [M+] 277.1830, found 277.1828.
128.7, 128.6, 127.9, 127.3, 126.8, 124.9, 122.5, 122.4,
122.0, 121.8, 119.4, 23.4; IR (KBr) ν: 3216, 3048, 2919,
1645, 1604, 780 cm1. HRMS (EI) calcd for C27H20N2O
[M+] 388.1576, found 388.1574.
6-Methoxy-2,4-dimethylbenzo[h]quinolone (3da)
White solid; 1H NMR (400 MHz, CDCl3) δ: 9.33 (d, J=
8.0 Hz, 1H), 8.32 (d, J=7.8 Hz, 1H), 7.92-7.49 (m,
2H), 7.15 (s, 1H), 6.90 (s, 1H), 4.05 (s, 3H), 2.75 (s, 3H),
2.59 (s, 3H); 13C NMR (101 MHz, CDCl3) δ: 153.3,
152.0, 141.3, 140.9, 131.2, 126.3, 126.2, 123.5, 123.3,
122.3, 120.4, 94.9, 53.8, 23.9, 18.2; IR (KBr) ν: 3031,
2963, 1627, 1107, 778 cm1. HRMS (EI) calcd for
C16H15NO [M+] 227.1154, found 237.1153.
6-Methyl-2,4-diphenylbenzo[h]quinolone
(3bd)
1
Yellow solid; H NMR (400 MHz, CDCl3) δ: 9.71 (d,
J=7.9 Hz, 1H), 8.42 (d, J=7.6 Hz, 2H), 8.06 (d, J=
7.8 Hz, 1H), 7.96 (s, 1H), 7.86-7.72 (m, 2H), 7.66 (s,
1H), 7.64-7.54 (m, 7H), 7.55-7.45 (m, 1H), 2.71 (s,
3H); 13C NMR (101 MHz, CDCl3) δ: 152.9, 147.1,
145.1, 138.7, 137.9, 132.4, 132.4, 130.9, 128.6, 127.7,
127.5, 127.1, 126.3, 125.5, 124.5, 122.9, 122.1, 121.3,
118.5, 19.0; IR (KBr) ν: 3061, 3025, 2938, 2857, 1633,
1586, 1544, 1508, 1475, 1447, 1424, 1387, 735, 727
cm1. HRMS (EI) calcd for C26H19N [M+] 345.1517,
found 345.1519.
2,4-Diethyl-6-methoxybenzo[h]quinolone
(3db)
White solid; 1H NMR (400 MHz, CDCl3) δ: 9.40 (d, J=
8.1 Hz, 1H), 8.33 (d, J=8.0 Hz, 1H), 7.88-7.55 (m,
2H), 7.21 (s, 1H), 7.01 (s, 1H), 3.52-2.73 (m, 1H),
1.50 (t, J=7.6 Hz, 3H), 1.42 (t, J=7.5 Hz, 3H); 13C
NMR (101 MHz, CDCl3) δ: 158.5, 152.0, 146.8, 141.1,
131.7, 126.4, 126.4, 126.1, 123.8, 122.6, 120.6, 119.0,
94.9, 54.3, 30.8, 24.5, 12.8; IR (KBr) ν: 3069, 2961,
1627, 1109, 763 cm1. HRMS (EI) calcd for C18H19NO
[M+] 265.1467, found 265.1468.
N-(2,4-Dimethylbenzo[h]quinolin-7-yl)acetamide
1
(3ca) Gray solid; H NMR (400 MHz, DMSO-d6) δ:
10.07 (s, 1H), 9.10 (s, 1H), 8.24-7.55 (m, 4H), 7.39 (s,
1H), 2.69 (s, 6H), 2.22 (s, 3H); 13C NMR (101 MHz,
DMSO-d6) δ: 169.0, 157.1, 144.6, 144.2, 133.9, 131.6,
127.6, 126.2, 124.2, 123.5, 123.0, 121.5, 121.3, 120.9,
24.9, 23.4, 18.3; IR (KBr) ν: 3275, 3028, 2922, 1653,
1597, 773 cm1. HRMS (EI) calcd for C17H16N2O [M+]
264.1263, found 264.1262.
2,4-Diisopropyl-6-methoxybenzo[h]quinolone
1
(3dc) White solid; H NMR (400 MHz, CDCl3) δ:
9.43 (d, J=8.2 Hz, 1H), 8.31 (d, J=7.8 Hz, 1H), 7.83
-7.56 (m, 2H), 7.29 (s, 1H), 7.12 (s, 1H), 4.11 (s, 3H),
3.80-3.49 (m, 1H), 3.49-2.81 (m, 1H), 1.55-1.38
(m, 12H), 0.73-0.71 (m, 1H); 13C NMR (101 MHz,
CDCl3) δ: 162.3, 152.1, 152.0, 151.3, 141.1, 132.0,
126.4, 126.4, 126.1, 124.0, 122.2, 120.5, 114.7, 94.5,
54.4, 35.9, 27.7, 21.7; IR (KBr) ν: 3072, 2962, 1624,
1107, 774 cm1. HRMS (EI) calcd for C20H23NO [M+]
293.1780, found 293.1779.
N-(2,4-Diethylbenzo[h]quinolin-7-yl)acetamide
1
(3cb) Gray solid; H NMR (400 MHz, DMSO-d6) δ:
10.07 (s, 1H), 9.14 (d, J=8.2 Hz, 1H), 8.04 (s, 2H),
7.82 (d, J=7.5 Hz, 1H), 7.69 (t, J=7.9 Hz, 1H), 7.44 (s,
1H), 3.30-3.05 (m, 2H), 3.07-2.93 (m, 2H), 2.22 (s,
3H), 1.41 (t, J=7.6 Hz, 3H), 1.37-1.27 (m, 3H); 13C
NMR (101 MHz, DMSO-d6) δ: 169.0, 161.9, 149.8,
144.8, 133.9, 132.0, 127.5, 126.2, 124.2, 122.4, 121.6,
121.0, 120.9, 120.6, 24.6, 23.4, 14.5, 13.5; IR (KBr) ν:
3266, 3059, 2968, 1655, 1595, 775 cm1. HRMS (EI)
calcd for C19H20N2O [M+] 292.1576, found 292.1578.
N-(2,4-Diisopropylbenzo[h]quinolin-7-yl)acet-
6-Methoxy-2,4-diphenylbenzo[h]quinolone (3dd)
White solid; 1H NMR (400 MHz, CDCl3) δ: 9.59 (d, J=
8.0 Hz, 1H), 8.54-8.17 (m, 3H), 7.92 (s, 1H), 7.82 (t,
J=4.0 Hz, 1H), 7.75 (t, J=4.0 Hz, 1H), 7.67-7.51 (m,
7H), 7.48 (t, J=7.3 Hz, 1H), 7.04 (s, 1H), 3.93 (s, 3H);
13C NMR (101 MHz, CDCl3) δ: 154.1, 152.6, 147.5,
143.4, 139.9, 139.3, 132.8, 129.5, 128.9, 128.8, 128.7,
128.2, 128.1, 128.0, 127.5, 127.2, 125.2, 124.2, 121.9,
119.7, 97.9, 55.4; IR (KBr) ν: 3057, 2934, 1623, 1118,
1103, 770 cm1. HRMS (EI) calcd for C26H19NO [M+]
361.1467, found 361.1471.
amide (3cc)
Gray solid; 1H NMR (400 MHz,
DMSO-d6) δ: 10.09 (s, 1H), 9.19 (d, J=8.1 Hz, 1H),
8.50-7.95 (m, 2H), 7.84 (d, J=7.4 Hz, 1H), 7.70 (t,
J=7.9 Hz, 1H), 7.49 (s, 1H), 4.02-3.65 (m, 1H), 3.53
(s, 1H), 3.35 (s, 1H), 3.36-3.12 (m, 1H), 2.23 (s, 3H),
1.49-1.29 (m, 12H); 13C NMR (101 MHz, DMSO-d6)
δ: 169.0, 165.6, 154.2, 144.7, 133.8, 132.2, 127.3, 126.2,
124.1, 121.9, 121.6, 121.1, 120.6, 116.4, 40.1, 39.9,
39.7, 39.4, 39.2, 39.0, 38.8, 36.3, 27.9, 22.5; IR (KBr) ν:
3282, 3060, 2963, 1662, 1591, 774 cm1. HRMS (EI)
calcd for C21H24N2O [M+] 320.1889, found 320.1888.
N-(2,4-Diphenylbenzo[h]quinolin-7-yl)acetamide
2-Methyl-4-phenylbenzo[h]quinolone (3ae-1)[10]
1
Yellow oil; H NMR (400 MHz, CDCl3) δ: 9.32 (d, J=
8.0 Hz, 1H), 7.76 (d, J=7.6 Hz 1H), 7.69-7.52 (m,
4H), 7.48-7.33 (m, 5H), 7.23 (s, 1H), 2.76 (s, 3H).
4-Methyl-2-phenylbenzo[h]quinoline
(3ae-2)
White solid; 1H NMR (400 MHz, CDCl3) δ: 9.53 (d, J=
8.0 Hz, 1H), 8.35 (d, J=7.4 Hz, 2H), 7.92 (d, J=8.8 Hz,
2H), 7.88-7.78 (m, 2H), 7.78-7.62 (m, 2H), 7.57 (t,
J=7.5 Hz, 2H), 7.48 (t, J=7.3 Hz, 1H), 2.82 (s, 3H);
13C NMR (101 MHz, CDCl3) δ: 155.0, 146.0, 144.6,
139. 9, 133.6, 132.2, 129.1, 128.8, 128.0, 127.7, 127.4,
127.1, 126.8, 125.2, 124.8, 121.3, 120.0, 19.5; IR (KBr)
ν: 3060, 2970, 1590, 1550, 751 cm1. HRMS (EI) calcd
1
(3cd) Gray solid; H NMR (400 MHz, DMSO-d6) δ:
10.10 (s, 1H), 9.35 (d, J=8.8 Hz, 1H), 8.49 (d, J=7.4
Hz, 2H), 8.19 (s, 1H), 8.04 (d, J=9.5 Hz, 1H), 7.88 (d,
J=7.4 Hz, 2H), 7.80 (t, J=8.0 Hz, 2H), 7.74-7.55 (m,
7H), 7.54 (d, J=7.1 Hz, 2H), 3.38 (s, 12H), 2.20 (s, 3H);
13C NMR (101 MHz, DMSO-d6) δ: 169.1, 154.3, 148.7,
145.8, 138.6, 137.7, 134.2, 132.0, 129.7, 129.6, 128.9,
Chin. J. Chem. 2017, XX, 1—7
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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