5394
L. Liu et al. / Tetrahedron 68 (2012) 5391e5395
extracted with CH2Cl2. The combined organic extracts were washed
with water and saturated brine. The organic layers were dried over
Na2SO4, filtered. Solvents were evaporated under reduced pressure.
The residue was purified by chromatography on silica gel to afford
isocoumarins derivatives and isoquinolone derivatives.
7.71e7.67 (m, 1H), 7.48e7.42 (m, 5H), 6.93 (s, 1H); 13C NMR
(100 MHz, CDCl3):
d 162.2, 153.5, 137.4, 134.7, 131.8, 129.8, 129.5,
128.7, 128.0, 125.9, 125.1, 120.4, 101.7 IR (neat, cmꢁ1): 3447, 3062,
1728, 1234, 1067, 766, 689, 527. HRMS (ESI) Calcd for C15H10O2:
MþH¼223.0752, Found: 223.0755.
4.3. Characterization data of compounds
4.3.9. 3,4-Dimethyl-isochromen-1-one (4b). 1H NMR (400 MHz,
CDCl3):
d
8.31e8.29 (dd, J¼0.8 Hz, 8.0 Hz, 1H), 7.76e7.72 (m, 1H),
4.3.1. 3-Methyl-isochromen-1-one (3a, 3b). 1H NMR (400 MHz,
7.51e7.45 (m, 2H), 2.32 (s, 3H), 2.18 (s, 3H); 13C NMR (100 MHz,
CDCl3):
d
8.24e8.22 (d, J¼8.0 Hz, 1H), 7.68e7.64 (t, J¼7.6 Hz, 1H),
CDCl3): d 162.8, 150.1, 138.6, 134.6, 129.6, 127.1, 122.3, 120.4, 107.6,
7.45e7.42 (t, J¼7.6 Hz, 1H), 7.34e7.32 (d, J¼7.6 Hz, 1H), 6.25 (s, 1H),
17.3, 12.2IR (neat, cmꢁ1): 3403, 2923, 1719, 1650, 1085, 745, 692.
2.28 (s, 3H); 13C NMR (100 MHz, CDCl3):
d
162.9, 154.5, 137.6, 134.6,
HRMS (ESI) Calcd for C11H10O2: MþH¼175.0754, Found: 175.0759.
129.4, 127.5, 124.8, 119.8, 103.5, 19.6 IR (neat, cmꢁ1): 3423, 2920,
2358, 1719, 1437, 1065, 763, 687. HRMS (ESI) Calcd for C10H8O:
MþH¼161.0597, Found: 161.0600.
4.3.10. 1-Oxo-3-phenyl-1H-isochromene-4-carboxylic acid ethyl es-
ter (4c). 1H NMR (400 MHz, CDCl3):
d
8.37e8.35 (d, J¼7.6 Hz, 1H),
7.81e7.77 (m, 2H), 7.75e7.73 (d, J¼7.6 Hz, 2H), 7.65e7.63 (m, 1H),
4.3.2. 6-Chloro-3-methyl-isochromen-1-one (3c). 1H NMR (400
7.59e7.45 (m, 3H), 4.23e4.17 (dd, J¼7.2 Hz, 14.0 Hz, 2H), 1.06e1.02
MHz, CDCl3):
d
8.18e8.16 (d, J¼8.4 Hz, 1H), 7.41e7.38 (dd, J¼2.0 Hz,
(t, J¼7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3):
d 166.2, 161.0, 155.3,
8.4 Hz, 1H), 7.32 (d, J¼1.6 Hz, 1H), 6.20 (s, 1H), 2.29 (s, 3H); 13C NMR
135.2,134.6, 132.5, 130.5, 129.8, 128.7, 128.4, 128.1, 124.1, 119.7, 110.9,
61.8, 13.5 IR (neat, cmꢁ1): 3400, 2984, 2361, 1723, 1241, 1091, 1019,
768, 693. HRMS (ESI) Calcd for C18H14O4: MþH¼295.0965, Found:
295.0970.
(100 MHz, CDCl3):
d 162.1, 156.1, 141.4, 138.9, 131.2, 128.0, 124.4,
118.2, 102.6, 19.7 IR (neat, cmꢁ1): 3402, 2921, 2361, 1744, 1331, 1052,
772, 678. HRMS (ESI) Calcd for C10H7ClO2: MþH¼195.0207, Found:
195.0212.
4.3.11. 3,3-Dimethyl-3,4-dihydro-2H-benzo[c]chromene-1,6-dione
4.3.3. 3,5-Dimethyl-isochromen-1-one (3d, 3e). 1H NMR (400 MHz,
(4d). 1H NMR (400 MHz, CDCl3):
d
9.05e9.03 (d, J¼8.4 Hz, 1H),
CDCl3):
d
8.11e8.09 (d, J¼8.0 Hz, 1H), 7.50e7.48 (d, J¼7.6 Hz, 1H),
8.29e8.27 (dd, J¼0.8 Hz, 8.0 Hz,1H), 7.81e7.77 (m,1H), 7.55e7.51 (t,
7.34e7.30 (t, J¼7.6 Hz, 1H), 6.36 (s, 1H), 2.43 (s, 3H), 2.30 (s, 3H); 13C
J¼7.6 Hz, 1H), 2.80 (s, 2H), 2.52 (s, 2H), 1.18 (s, 6H); 13C NMR
NMR (100 MHz, CDCl3):
d
163.2, 154.0, 136.2, 135.5, 132.4, 127.2,
(100 MHz, CDCl3): d 196.8, 167.9, 160.6, 135.5, 133.8, 129.5, 128.3,
126.9, 119.8, 100.3, 19.8, 19.6 IR (neat, cmꢁ1): 3418, 2943, 2330, 1717,
1426, 1035, 767, 594. HRMS (ESI) Calcd for C11H10O2:
MþH¼175.0754, Found: 175.0759.
125.7, 119.7, 110.5, 52.8, 42.5, 31.9, 28.1 IR (neat, cmꢁ1): 3399, 2958,
2361, 1743, 1672, 1370, 1028, 768, 689. HRMS (ESI) Calcd for
C15H14O3: MþH¼243.1016, Found: 243.1010.
1
4.3.4. 7-Chloro-3,5-dimethyl-isochromen-1-one (3g).
(400 MHz, CDCl3):
2.42 (s, 3H), 2.30 (s, 3H); 13C NMR (100 MHz, CDCl3):
H
NMR
4.3.12. N-Phenylacetamide (6a). 1H NMR (400 MHz, CDCl3):
d 7.86
d
8.07 (d, J¼2.0 Hz, 1H), 7.46 (m, 1H), 6.32 (s, 1H),
(s, 1H), 7.51e7.49 (d, J¼7.2 Hz, 2H), 7.30e7.27 (t, J¼6.8 Hz, 2H),
d
162.1, 154.5,
7.10e7.07 (t, J¼6.8 Hz, 1H), 2.14 (s, 3H); 13C NMR (100 MHz, CDCl3):
135.6, 134.8, 134.6, 132.5, 126.6, 121.1, 99.8, 19.9, 18.5 IR (neat,
cmꢁ1): 3399, 2924, 1730, 1655, 1381, 1066, 913, 744. HRMS (ESI)
Calcd for C11H9ClO2: MþH¼209.0364, Found: 209.0359.
d
168.7, 137.9, 128.8, 124.2, 119.9, 24.4 IR (neat, cmꢁ1): 3552, 2930,
1550, 1321, 758, 535.
4.3.13. N-Pyridin-2-yl-acetamide (6d). 1H NMR (400 MHz, CDCl3):
4.3.5. 7-Fluoro-3-methyl-isochromen-1-one (3i). 1H NMR (400
d
8.45 (s, 1H), 8.26e8.25 (d, J¼4.0 Hz, 1H), 8.22e8.19 (d, J¼4.4 Hz,
MHz, CDCl3):
d
7.91e7.88 (dd, J¼2.4 Hz, 8.8 Hz, 1H), 7.40e7.33 (m,
1H), 7.73e7.68 (m, 1H), 7.05e7.02 (m, 1H), 2.20 (s, 3H)13C NMR
2H), 6.25 (s, 1H), 2.28 (s, 3H); 13C NMR (100 MHz, CDCl3):
(100 MHz, CDCl3):
d 168.6, 151.4, 147.6, 138.4, 119.7, 114.0, 24.7 IR
d
162.6e160.2 (d, JCeF¼247.0 Hz), 162.0 (d, JCeF¼3.0 Hz), 153.9 (d,
(neat, cmꢁ1): 3388, 2923, 1685, 1434, 1303, 744.
JCeF¼2.0 Hz), 134.0 (d, JCeF¼3.0 Hz), 127.0 (d, JCeF¼8.0 Hz),
123.2e122.9 (d, JCeF¼23.0 Hz), 121.4 (d, JCeF¼8.0 Hz), 115.0e114.8
(d, JCeF¼23.0 Hz), 102.7, 19.4 IR (neat, cmꢁ1): 3421, 2922, 1727, 1495,
912, 744. HRMS (ESI) Calcd for C10H7FO2: MþH¼175.0503, Found:
175.0746.
4.3.14. 3,3-Dimethyl-5-phenyl-3,4-dihydro-2H,5H-phenanthridine-
1,6-dione (7a). \1H NMR (400 MHz, CDCl3):
d
9.34e9.31 (d, J¼8.8 Hz,
1H), 8.42e8.39 (dd, J¼1.2 Hz, 8.0 Hz, 1H), 7.79e7.75 (m, 1H),
7.60e7.51 (m, 4H), 7.23e7.21 (m, 2H), 2.49 (s, 2H), 2.38 (s, 2H), 1.04
(s, 6H); 13C NMR (100 MHz, CDCl3):
d 197.0,163.0,152.4,138.2,134.0,
4.3.6. 7-Methoxy-3-methyl-isochromen-1-one
(400 MHz, CDCl3):
7.65 (s, 1H), 7.26 (d, J¼1.2 Hz, 2H), 6.21 (s, 1H),
3.88 (s, 3H), 2.26 (s, 3H); 13C NMR (100 MHz, CDCl3):
163.1, 158.9,
(3k). 1H
NMR
133.8, 130.0, 129.1, 128.2, 127.8, 127.1, 126.1, 124.5, 110.4, 52.5, 43.8,
32.1, 28.0 IR (neat, cmꢁ1): 3397, 2361, 1736, 1654, 913, 744, 662.
HRMS (ESI) Calcd for C21H19NO2: MþH¼318.1489, Found: 318.1482.
d
d
152.3, 131.3, 126.3, 124.4, 120.8, 109.7, 103.1, 55.6, 19.3 IR (neat,
cmꢁ1): 3420, 2957, 2920,1721,1501,1025, 824, 775, 587. HRMS (ESI)
Calcd for C11H10O3: MþH¼191.0703, Found: 191.0706.
4.3.15. 3,3-Dimethyl-5-(3-nitro-phenyl)-3,4-dihydro-2H,5H-phenan-
thridine-1,6-dione (7c). 1H NMR (400 MHz, CDCl3):
d 9.32e9.30 (d,
J¼8.0 Hz, 1H), 8.42e8.36 (m, 2H), 8.16e8.15 (t, J¼2.0 Hz, 1H),
7.81e7.77 (m, 2H), 7.63e7.60 (m, 1H), 7.55e7.51 (m, 1H), 2.55e2.46
(dd, J¼16.0 Hz, 19.6 Hz, 2H), 2.42e2.28 (dd, J¼17.6 Hz, 39.6 Hz, 2H),
4.3.7. 7-Methyl-pyrano[4,3-b]pyridin-5-one
(400 MHz, CDCl3):
8.89e8.87 (dd, J¼2.0 Hz, 4.8 Hz, 1H), 8.50e8.48
(dd, J¼1.2 Hz, 8.0 Hz, 1H), 7.40e7.37 (dd, J¼4.8 Hz, 8.0 Hz, 1H), 6.54
(3l). 1H
NMR
d
1.07 (s, 3H), 1.05 (s, 3H); 13C NMR (100 MHz, CDCl3):
d 196.6, 162.8,
(s, 1H), 2.35 (s, 3H); 13C NMR (100 MHz, CDCl3):
d
162.6, 158.8, 156.1,
150.8, 149.2, 139.2, 134.9, 134.2, 133.9, 130.9, 127.8, 127.5, 126.3,
124.2, 124.2, 124.0, 111.0, 52.4, 44.0, 32.3, 28.2, 27.8 IR (neat, cmꢁ1):
3400, 1655, 1532, 1381, 913, 745. HRMS (ESI) Calcd for C21H18N2O4:
MþH¼363.1339, Found: 363.1329.
154.9, 137.5, 122.5, 116.2, 105.8, 19.9 IR (neat, cmꢁ1): 3399, 1737,
1655, 1217, 1068, 913, 772, 745. HRMS (ESI) Calcd for C9H7NO2:
MþH¼162.0550, Found: 162.0554.
4.3.8. 3-Phenyl-isochromen-1-one (4a). 1H NMR (400 MHz, CDCl3):
4.3.16. 2-(1-Acetyl-2-hydroxy-propenyl)ebenzoic acid (A00). 1H NMR
d
8.29e8.27 (d, J¼8.0 Hz, 1H), 7.87e7.85 (dd, J¼1.6 Hz, 8.0 Hz, 2H),
(400 MHz, CDCl3):
d
8.11e8.09 (d, J¼7.6 Hz, 1H), 7.62e7.58 (t,