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(1H, m), 7.10 (1H, d, J ¼ 9.0 Hz), 3.63 (3H, s), 3.340 (3H, s). 13
C
2-Chloro-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
dione (3o). Yield: 79% (122 mg); white solid; mp: 268–270 C. IR
ꢀ
NMR (150 MHz, CDCl3): 160.1, 160.0, 154.1, 136.7, 135.3, 134.6,
133.7, 132.4, 129.6, 128.5, 127.0, 123.2, 120.3, 113.9, 113.0,
104.5, 29.6, 20.7. HRMS m/z (M+): calcd for C18H13NO3:
291.0895; found: 291.0893.
(ATR): 2878, 2120, 1702, 1652, 1510, 1434, 1348, 1321, 1212, 1121,
1037, 966, 827 cmꢁ1. 1H NMR (600 MHz, CDCl3): d 9.52 (1H, dd, J ¼
8.4, 1.2 Hz), 8.38 (1H, dd, J ¼ 7.8, 1.2 Hz), 8.23 (1H, d, J ¼ 8.4 Hz),
7.87–7.84 (1H, m), 7.61–7.58 (1H, m), 7.39 (1H, d, J ¼ 1.2 Hz), 7.30
(1H, dd, J ¼ 8.4, 1.2 Hz), 3.76 (3H, s).13C NMR (150 MHz, CDCl3):
d 160.5, 159.8, 154.2, 139.6, 138.9, 135.7, 134.4, 130.0, 129.0, 127.1,
125.4, 123.3, 120.5, 114.3, 112.1, 105.0, 29.9. HRMS m/z (M+): calcd
for C17H10ClNO3: 311.0349; found: 311.0349.
3-Isopropyl-12-methyl-6H-isochromeno[4,3-c]quinoline-
6,11(12H)-dione (3j). Yield: 81% (129 mg); white solid; mp:
228–230 ꢀC. IR (ATR): 2978, 1902, 1772, 1692, 1539, 1405,
1379, 1292, 1154, 1024, 978, 817 cmꢁ1 1H NMR (600 MHz,
.
CDCl3): d 9.57 (1H, dd, J ¼ 8.4, 1.2 Hz), 8.37 (1H, dd, J ¼ 7.8,
1.2 Hz), 8.12 (1H, d, J ¼ 1.8 Hz), 7.84–7.81 (1H, m), 7.57–7.55
(1H, m), 7.53 (1H, dd, J ¼ 8.4, 2.4 Hz), 7.31 (1H, d, J ¼ 9.0 Hz),
3.75 (3H, s), 3.07–3.01 (1H, m), 1.31 (6H, d, J ¼ 6.6 Hz). 13C
NMR (150 MHz, CDCl3): d 160.5, 160.3, 154.6, 143.5, 137.3,
135.5, 134.8, 131.4, 129.8, 128.6, 127.1, 121.1, 120.4, 114.3,
113.4, 104.7, 33.6, 29.7, 24.0. HRMS m/z (M+): calcd for
9,12-Dimethyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
dione (4a). Yield: 75% (109 mg); white solid; mp: 271–273 ꢀC. IR
(ATR): 2921, 2855, 1800, 1724, 1640, 1372, 1238, 1191, 1029, 907,
1
836 cmꢁ1. H NMR (600 MHz, CDCl3): d 9.37 (1H, s), 8.29 (1H,
dd, J ¼ 7.8, 1.2 Hz), 8.26 (1H, d, J ¼ 7.8 Hz), 7.65–7.62 (1H, m),
7.38 (2H, d, J ¼ 9.0 Hz), 7.33–7.30 (1H, m), 3.77 (3H, s), 2.53 (3H,
s). 13C NMR (150 MHz, CDCl3): d 160.7, 160.1, 154.7, 146.9,
138.8, 134.6, 132.4, 130.0, 129.9, 127.2, 124.1, 122.7, 118.1,
114.1, 113.6, 104.9, 29.7, 22.6. HRMS m/z (M+): calcd for
C
20H17NO3: 319.1208; found: 319.1201.
2-Methoxy-12-methyl-6H-isochromeno[4,3-c]quinoline-
6,11(12H)-dione (3k). Yield: 68% (100 mg); white solid; mp:
252–254 ꢀC. IR (ATR): 2880, 1839, 1657, 1600, 1493, 1393,
C
18H13NO3: 291.0895; found: 291.0898.
9-Methoxy-12-methyl-6H-isochromeno[4,3-c]quinoline-
1352, 1256, 1180, 1127, 1034, 911, 814 cmꢁ1 1H NMR (600
.
MHz, CDCl3): d 9.48 (1H, d, J ¼ 8.4 Hz), 8.34 (1H, dd, J ¼ 7.8,
1.2 Hz), 8.17 (1H, d, J ¼ 9.0 Hz), 7.83–7.80 (1H, m), 7.54–7.52
(1H, m), 6.87 (1H, dd, J ¼ 9.0, 2.4 Hz), 6.74 (1H, d, J ¼ 2.4 Hz),
3.90 (3H, s), 3.71 (3H, s). 13C NMR (150 MHz, CDCl3): d 163.3,
161.0, 160.3, 154.8, 140.8, 135.5, 135.0, 129.7, 128.1, 126.7,
125.7, 120.0, 110.3, 107.3, 102.5, 98.5, 55.67, 29.72. HRMS m/
z (M+): calcd for C18H13NO4: 307.0845; found: 307.0843.
4-Chloro-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
6,11(12H)-dione (4b). Yield: 72% (110 mg); white solid; mp:
273–275 ꢀC. IR (ATR): 2922, 2853, 1925, 1799, 1729, 1640,
1562, 1466, 1382, 1245, 1044, 975, 880 cmꢁ1 1H NMR (600
.
MHz, CDCl3): d 9.14 (1H, d, J ¼ 2.4 Hz), 8.32 (1H, dd, J ¼ 8.4,
1.8 Hz), 8.27 (1H, d, J ¼ 9.0 Hz), 7.67–7.64 (1H, m), 7.40 (1H,
d, J ¼ 7.8 Hz), 7.33 (1H, t, J ¼ 7.8 Hz), 7.09 (1H, dd, J ¼ 9.0
Hz), 3.99 (3H, s), 3.78 (3H, s). 13C NMR (150 MHz, CDCl3):
d 165.4, 160.8, 159.8, 155.3, 138.9, 137.1, 132.6, 131.8, 124.2,
122.8, 117.7, 114.2, 113.7, 113.4, 109.0, 104.8, 55.8, 29.7.
HRMS m/z (M+): calcd for C18H13NO4: 307.0845; found:
307.0842.
ꢀ
dione (3l). Yield: 84% (130 mg); white solid; mp: 260–262 C. IR
(ATR): 2881, 2025, 1656, 1529, 1445, 1400, 1312, 1235, 1140, 1032,
911 cmꢁ1. 1H NMR (600 MHz, CDCl3): d 9.55 (1H, d, J ¼ 8.4 Hz), 8.37
(1H, dd, J ¼ 7.8, 1.2 Hz), 7.85–7.82 (1H, m), 7.61–7.59 (1H, m), 7.46
(1H, t, J ¼ 8.4 Hz), 7.34–7.31 (2H, m), 3.77 (3H, s). 13C NMR (150
MHz, CDCl3): d 160.0, 159.3, 154.4, 141.0, 135.0, 134.3, 132.5, 131.5,
129.5, 129.1, 127.4, 126.8, 120.4, 113.2, 111.4, 105.8, 30.8. HRMS m/z
(M+): calcd for C17H10ClNO3: 311.0349; found: 311.0398.
2-Methyl-9-phenyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
ꢀ
dione (4c). Yield: 78% (137 mg); white solid; mp: 263–265 C. IR
(ATR): 3062, 1757, 1656, 1599, 1386, 1253, 1180, 1030, 1018,
846 cmꢁ1. 1H NMR (600 MHz, CDCl3): d 9.89 (1H, d, J ¼ 1.8 Hz),
8.42 (1H, d, J ¼ 8.4 Hz), 8.33 (1H, dd, J ¼ 8.4, 1.2 Hz), 7.82 (1H, dd, J
¼ 8.4, 1.2 Hz), 7.77–7.75 (2H, m), 7.67–7.64 (1H, m), 7.50–7.47 (2H,
m), 7.43–7.40 (2H, m), 7.34 (1H, t, J ¼ 7.2 Hz), 3.80 (3H, s). 13C NMR
(150 MHz, CDCl3): d 160.7, 160.1, 154.9, 148.1, 139.6, 139.0, 135.1,
132.6, 130.4, 129.0, 128.7, 127.7, 127.5, 125.5, 124.1, 122.8, 119.1,
114.2, 113.6, 104.0, 29.8. HRMS m/z (M+): calcd for C23H15NO3:
353.1052; found: 353.1055.
3-Chloro-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
ꢀ
dione (3m). Yield: 85% (132 mg); white solid; mp: 250–252 C. IR
(ATR): 2881, 2025, 1656, 1529, 1445, 1400, 1312, 1235, 1140, 1032,
911 cmꢁ1. 1H NMR (600 MHz, CDCl3): d 9.40 (1H, dd, J ¼ 8.4, 1.2
Hz), 8.36 (1H, dd, J ¼ 7.8, 1.2 Hz), 8.21 (1H, d, J ¼ 2.4 Hz), 7.84–7.81
(1H, m), 7.60–7.57 (1H, m), 7.55 (1H, dd, J ¼ 9.4, 2.4 Hz), 7.30 (1H, d,
J ¼ 8.4 Hz), 3.73 (3H, s).13C NMR (150 MHz, CDCl3): d 160.1, 159.6,
153.3, 137.3, 135.6, 134.6, 132.5, 129.9, 129.2, 128.6, 127.2, 123.3,
120.6, 115.7, 114.5, 105.6, 29.9. HRMS m/z (M+): calcd for
C17H10ClNO3: 311.0349; found: 311.0347.
9-Chloro-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
ꢀ
dione (4d). Yield: 84% (130 mg); white solid; mp: 284–286 C. IR
(ATR): 3106, 2881, 2017, 1658, 1539, 1459, 1352, 1226, 1165, 1073,
1037, 909, 878 cmꢁ1. 1H NMR (600 MHz, CDCl3): d 9.67 (1H, d, J ¼
1.8 Hz), 8.34–8.31 (2H, m), 7.72–7.69 (1H, m), 7.55 (1H, dd, J ¼ 8.4,
3-Bromo-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
2.4 Hz), 7.44 (1H, d, J ¼ 8.4 Hz), 7.38–7.35 (1H, m), 3.81 (3H, s). 13
C
ꢀ
dione (3n). Yield: 83% (146 mg); white solid; mp: 278–280 C. IR
(ATR): 2933, 1739, 1543, 1470, 1329, 1238, 1151, 1105, 1024,
NMR (150 MHz, CDCl3): d 160.4, 159.5, 155.4, 142.8, 139.2, 136.0,
133.1, 131.3, 129.3, 127.0, 124.2, 122.9, 118.8, 114.3, 113.3, 104.0,
29.8. HRMS m/z (M+): calcd for C17H10ClNO3: 311.0349; found:
311.0347.
1
970 cmꢁ1. H NMR (600 MHz, CDCl3): d 9.51 (1H, d, J ¼ 4.2 Hz),
8.39–8.36 (2H, m), 7.85 (1H, t, J ¼ 3.6 Hz), 7.71–7.69 (1H, m), 7.60
(1H, t, J ¼ 4.2 Hz), 7.25 (1H, t, J ¼ 4.2 Hz), 3.74 (3H, s). 13C NMR (150
MHz, CDCl3): d 160.2, 159.6, 153.3, 137.7, 135.7, 135.3, 134.2, 130.0,
129.2, 127.2, 126.3, 120.6, 115.9, 114.9, 105.6, 29.9. HRMS m/z (M+):
calcd for C17H10BrNO3: 354.9844; found: 354.9846.
9-Bromo-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-
ꢀ
dione (4e). Yield: 86% (152 mg); white solid; mp: 276–278 C. IR
(ATR): 2926, 1737, 1638, 1577, 1553, 1379, 1309, 1466, 1238, 1115,
17354 | RSC Adv., 2019, 9, 17347–17357
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