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MedChemComm
Page 10 of 12
DOI: 10.1039/C7MD00162B
ARTICLE
Journal Name
6.65 (m, 2H), 4.48 (s, br, NH, 1H), 2.78-2.60 (m, 3H), 1.09-1.03 (m, 135.45, 134.44, 128.54, 127.62, 119.16, 118.80, 117.30, 115.96,
1H), 0.62-0.56 (m, 2H), 0.30-0.21 (m, 2H); 13C NMR (100 MHz, 111.89 (d), 111.68, 104.30 (t), 50.64, 44.34; LC-MS (ESI): m/z Calcd.
CDCl3): δ 194.03, 151.44, 135.19, 127.53, 119.15, 117.95, 115.68, for C15H11F2NO: 259.08, Found 260.54 [M+H]+
59.32, 44.26, 15.96, 3.18, 3.12; LC-MS (ESI): m/z Calcd. for
C12H13NO: 187.10, Found 188.16 [M+H]+
4.1.3.9. 2-(4-Methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (5i):
IR (KBr, cm-1): 3436 (NH), 1660 (CO); 1H NMR (400 MHz, CDCl3): δ
7.87 (d, J = 10.4Hz, 1H), 7.40-7.30 (m, 3H), 6.93 (d, J = 11.6Hz, 2H),
4.1.3.3. 2-Ethyl-2,3-dihydroquinolin-4(1H)-one (5c):
IR (KBr, cm-1): 3445 (NH), 1651 (CO); 1H NMR (400 MHz, CDCl3): δ 6.78 (t, J = 10.0Hz, 1H), 6.69 (d, J = 11.2Hz, 1H), 4.70 (dd, J = 4.8,
7.81 (dd, J = 1.6, 8.0Hz, 1H), 7.30-7.26 (m, 1H), 6.72 (t, J = 7.6Hz, 18.0Hz, 1H), 4.43 (s, NH, 1H), 3.83 (s, 3H), 2.93-2.76 (m, 2H); LC-MS
1H), 6.66 (d, J = 8.4Hz, 1H), 4.32 (s, br, NH, 1H), 3.58-3.53 (m, 1H), (ESI): m/z Calcd. for C16H15NO2: 253.11, Found 254.31 [M+H]+
2.67 (dd, J = 3.6, 16.0Hz, 1H), 2.51-2.43 (m, 1H), 1.70-1.63 (m, 2H),
1.01 (t, J = 7.8Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 194.05, 151.44, 4.1.3.10. 2-(3-Methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (5j):
135.13, 127.47, 119.12, 117.91, 115.71, 54.66, 43.48, 28.05, 9.63; MR: 109-112 °C; IR (KBr, cm-1): 3467 (NH), 1655 (CO); H NMR (400
1
LC-MS (ESI): m/z Calcd. for C11H13NO: 175.10, Found 176.13 [M+H]+
MHz, CDCl3): δ 7.87 (dd, J = 1.6, 10.8Hz, 1H), 7.36-7.25 (m, 2H),
7.04-7.01 (m, 2H), 6.88 (dd, J = 2.0, 9.6Hz, 1H), 6.79 (t, J = 9.2Hz,
1H), 6.71 (t, J = 11.2Hz, 1H), 4.72 (dd, J = 6.0, 17.6Hz, 1H), 4.51 (s,
4.1.3.4. 2-Cyclohexyl-2,3-dihydroquinolin-4(1H)-one (5d):
MR: 121-125 °C; IR (KBr, cm-1): 3444 (NH), 1650 (CO); H NMR (400 NH, 1H), 3.82 (s, 3H), 2.92-2.73 (m, 2H); 13C NMR (100 MHz, CDCl3):
MHz, CDCl3): δ 7.80 (dd, J = 1.2, 8.0Hz, 1H), 7.28 (t, J = 8.4Hz, 1H), δ 193.20, 160.01, 151.47, 142.65, 135.38, 130.06, 127.61, 119.02,
6.71 (t, J = 6.8Hz, 1H), 6.66 (d, J = 8.0Hz, 1H), 4.34 (s, NH, 1H), 3.44- 118.82, 118.46, 115.89, 113.71, 112.23, 58.46, 55.29, 46.44; LC-MS
3.39 (m, 1H), 2.66-2.51 (m, 2H), 1.83-1.69 (m, 5H), 1.57-1.49 (m, (ESI): m/z Calcd. for C16H15NO2: 253.11, Found 254.22 [M+H]+
6H); 13C NMR (100 MHz, CDCl3): δ 194.53, 151.62, 135.13, 127.38,
1
119.01, 117.73, 115.74, 58.12, 41.53, 40.98, 28.87, 28.56, 26.29, 4.1.3.11.
26.07; LC-MS (ESI): m/z Calcd. for C15H19NO: 229.14, Found 230.67 (5k):
2-(2-Methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one
[M+H]+
IR (KBr, cm-1): 3436 (NH), 1660 (CO); 1H NMR (400 MHz, CDCl3): δ
7.85 (dd, J = 1.6, 8.0Hz, 1H), 7.48 (dd, J = 1.2, 7.6Hz, 1H), 7.33-7.25
(m, 2H), 6.98 (t, J = 8.0Hz, 1H), 6.90 (d, J = 8.0Hz, 1H), 6.76-6.69 (m,
4.1.3.5. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (5e):
1
MR: 133-136 °C;IR (KBr, cm-1): 3436 (NH), 1650 (OH); H NMR (400 2H), 5.16 (dd, J = 4.4, 7.6Hz, 1H), 3.84 (s, 3H), 2.93-2.78 (m, 2H); 13C
MHz, CDCl3): δ 7.87 (dd, J = 1.2, 8.4Hz, 1H), 7.46 (dd, J = 1.6, 8.0Hz, NMR (100 MHz, CDCl3): δ 193.88, 156.57, 151.93, 135.18, 131.91,
2H), 7.42-7.32 (m, 4H), 6.79 (t, J = 8.0Hz, 1H), 6.71 (d, J = 8.0Hz, 1H), 129.01, 127.46, 126.41, 120.83, 118.96, 118.02, 116.05, 110.52,
4.75 (dd, J = 4.0, 13.6Hz, 1H), 4.50 (m, br, NH, 1H), 2.89-2.79 (m, 55.32, 51.24, 43.67; LC-MS (ESI): m/z Calcd. for C16H15NO2: 253.11,
2H); 13C NMR (100 MHz, CDCl3): δ 193.24, 151.53, 141.00, 135.38, Found 254.28 [M+H]+
128.99, 128.47, 127.62, 126.61, 119.05, 118.45, 115.88, 58.50,
46.44; LC-MS (ESI): m/z Calcd. for C15H13NO: 223.10, Found: 224.62 4.1.3.12. 2-(3,4-Dimethylphenyl)-2,3-dihydroquinolin-4(1H)-one
[M+H]+
(5l):
IR (KBr, cm-1): 3327 (NH), 1663 (CO); 1H NMR (400 MHz, CDCl3): δ
7.87 (d, J = 8.0Hz, 1H), 7.32 (t, J = 8.8Hz, 1H), 7.22 (s, 1H), 7.17-7.14
4.1.3.6. 2-(4-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (5f):
MR: 165-169 °C;IR (KBr, cm-1): 3467 (NH), 1644 (CO); H NMR (400 (m, 2H), 6.77 (t, J = 7.6Hz, 1H), 6.69 (d, J = 8.4Hz, 1H), 4.68 (dd, J =
MHz, CDCl3): δ 7.87 (d, J = 8.0Hz, 1H), 7.52 (d, J = 8.4Hz, 2H), 7.40- 3.6, 13.6Hz, 1H), 4.45 (s, br, NH, 1H), 2.92-2.71 (m, 2H), 2.28 (d, J =
7.33 (m, 3H), 6.81 (t, J = 8.0Hz, 1H), 6.72 (d, J = 7.6Hz, 1H), 4.72 (dd, 4.4Hz, 6H); 13C NMR (100 MHz, CDCl3): δ 193.50, 151.60, 138.46,
J = 4.0, 12.8Hz, 1H), 4.47 (s, NH, 1H), 2.84-2.76 (m, 2H); 13C NMR 137.27, 136.91, 135.31, 130.12, 127.83, 127.61, 123.98, 119.00,
(100 MHz, CDCl3): δ 192.77, 151.28, 140.05, 135.49, 132.13, 128.30, 118.32, 115.85, 58.23, 46.248, 19.83, 19.46; LC-MS (ESI): m/z Calcd.
127.62, 122.25, 119.07, 118.74, 115.94, 57.96, 46.36; LC-MS (ESI): for C17H17NO: 251.13, Found 252.30 [M+H]+
1
m/z Calcd. for C15H12BrNO: 302.01, Found 304.12 [M+2]+2 (Note:
During the reduction of 3-(4-Bromophenyl)-3-hydroxy-1-(2- 4.1.3.13. 2-(Pyridin-2-yl)-2,3-dihydroquinolin-4(1H)-one (5m):
nitrophenyl)propan-1-one (2f) using Iron (1.0 eq) and acetic acid IR (KBr, cm-1): 3435 (NH), 1611 (CO); 1H NMR (400 MHz, CDCl3): δ
(3.0) in toluene at reflux for 6 h, directly isolated cyclized 2-(4- 8.60 (d, J = 4.8Hz, 1H), 7.84 (dd, J = 1.6, 8.0Hz, 1H), 7.73-7.69 (m,
Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (5f) in 56% yield).
1H), 7.36-7.30 (m, 2H), 7.24-7.18 (m, 1H), 6.78-6.73 (m, 2H), 5.37-
5.34 (s, NH, 1H), 4.86 (dd, J = 4.4, 12.4Hz, 1H), 3.04-2.89 (m, 2H); 13C
4.1.3.7. 2-(4-(Trifluoromethyl)phenyl)-2,3-dihydroquinolin-4(1H)- NMR (100 MHz, CDCl3): δ 193.06, 158.80, 151.06, 149.44, 137.19,
one (5g):
135.46, 131.34, 127.47, 122.99, 120.44, 118.17, 116.14, 57.35,
IR (KBr, cm-1): 3337 (NH), 1610 (CO); 1H NMR (300 MHz, CDCl3): δ 43.46; LC-MS (ESI): m/z Calcd. for C14H12N2O: 224.09, Found 225.11
7.88 (d, J = 8.1Hz, 1H), 7.68-7.51 (m, 4H), 7.37 (t, J = 6.9Hz, 1H), 6.83 [M+H]+
(t, J = 7.5Hz, 1H), 6.74 (d, J = 8.1Hz, 1H), 4.84 (dd, J = 5.1, 12.6Hz,
1H), 4.49 (s, NH, 1H), 2.87-2.76 (m, 2H); LC-MS (ESI): m/z Calcd. for 4.1.3.14. 2-(Pyridin-3-yl)-2,3-dihydroquinolin-4(1H)-one (5n):
1
C16H12F3NO: 291.09, Found 292.08 [M+H]+
MR: 152-155 °C; IR (KBr, cm-1): 3344 (NH), 1607 (CO); H NMR (400
MHz, CDCl3): δ 8.69 (s, 1H), 8.60 (d, J = 3.6Hz, 1H), 7.88 (d, J = 8.0Hz,
4.1.3.8.
(5h):
2-(2,4-Difluorophenyl)-2,3-dihydroquinolin-4(1H)-one 1H), 7.82 (d, J = 7.6Hz, 1H), 7.38-7.32 (m, 2H), 6.82 (t, J = 7.6Hz, 1H),
6.74 (d, J = 8.0Hz, 1H), 4.80 (dd, J = 3.2, 12.8Hz, 1H), 4.57 (s NH, 1H),
IR (KBr, cm-1): 3287 (NH), 1647 (CO); 1H NMR (400 MHz, CDCl3): δ 2.92-2.77 (m, 2H); 13C NMR (100 MHz, CDCl3): δ 192.30, 151.19,
7.87 (dd, J = 8.4, 1.2Hz, 1H), 7.57-7.50 (m, 1H), 7.35 (t, J = 8.4Hz, 150.00, 148.52, 136.52, 135.54, 134.21, 127.64, 123.80, 119.19,
1H), 6.95-6.79 (m, 3H), 6.72 (d, J = 8.4Hz, 1H), 5.09 (t, J = 8.4Hz, 1H), 118.95, 116.01, 56.17, 46.02; LC-MS (ESI): m/z Calcd. for C14H12N2O:
2.87 (d, J = 8.1Hz, 2H); 13C NMR (100 MHz, CDCl3): δ 192.49, 151.17, 224.09, Found 225.27 [M+H]+
10 | J. Name., 2012, 00, 1-3
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