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5.84–5.73 (m, 1H), 5.04 (dd, J = 1.3, 10.3 Hz, 1H), 4.83–4.69 (m, 2H),
4.59 (d, J = 2.1 Hz, 2H), 4.39 (s, 2H), 4.15 (dd, J = 5.4, 15.3 Hz, 1H),
3.88 (s, 3H), 3.26 (s, 3H). EIMS: m/z 365 (M+, 78). HRMS-EI (calcd
for C22H23NO4): 365.1627, found 365.1629.
5.2.13. 2-Allyl-3-(2-hydroxymethyl-4,5-dimethoxyphenyl)-2H-
isoquinolin-1-one (12b)
The procedure described for compound 12a was used with
compound 11b (1 g, 2.5 mmol) in THF (15 mL) and 10% HCl
(10 mL) to afford the alcohol 12b as white solid (615 mg, 70%).
mp: 151–153 °C. IR (cmÀ1): 3300 (OH), 1641 (C@O). 1H NMR
(300 MHz, CDCl3) d: 8.45 (d, J = 7.9 Hz, 1H), 7.69–7.63 (m, 1H),
7.53–7.47 (m, 2H), 7.12 (s, 1H), 6.77 (s, 1H), 6.43 (s, 1H), 5.89–
5.79 (m, 1H), 5.06 (dd, J = 1.3, 11.6 Hz, 1H), 4.80 (dd, J = 1.4,
17.2 Hz, 1H), 4.63 (dd, J = 5.3, 15.4 Hz, 1H), 4.49 (s, 2H), 4.25 (dd,
J = 5.2, 15.3 Hz, 1H), 3.98 (s, 3H), 3.86 (s, 3H), 1.83 (bs, 1H). EIMS:
m/z 351 (M+, 98). HRMS-EI (calcd for C21H21NO4): 351.1470, found
351.1481.
5.2.9. 2-Allyl-3-(4,5-dimethoxy-2-methoxymethoxymethyl-
phenyl)-2H-isoquinolin-1-one (11b)
The procedure described for compound 11a was used with
3-arylisoquinoline 8b (1.2 g, 3.4 mmol), K2CO3 (970 mg, 7 mmol)
in DMF (20 mL) and allyl bromide (847 mg, 7 mmol) to give com-
pound 11b as yellow oil (1.05 g, 78%). IR (cmÀ1): 1650 (C@O). 1H
NMR (300 MHz, CDCl3) d: 8.47 (d, J = 7.9 Hz, 1H), 7.68–7.63 (m,
1H), 7.53–7.46 (m, 2H), 7.05 (s, 1H), 6.79 (s, 1H), 6.43 (s, 1H),
5.89–5.80 (m, 1H), 5.06 (dd, J = 1.3, 10.3 Hz, 1H), 4.83 (dd, J = 1.4,
17.1 Hz, 1H), 4.74 (dd, J = 5.0, 15.4 Hz, 1H), 4.58 (d, J = 2.1 Hz,
2H), 4.37 (s, 2H), 4.21–4.13 (m, 1H), 3.97 (s, 3H), 3.85 (s, 3H),
3.25 (s, 3H). EIMS: m/z 395 (M+, 100). HRMS-EI (calcd for
5.2.14. 2-Allyl-3-(6-hydroxymethylbenzo[1,3]dioxol-5-yl)-7,8-
dimethoxyisoquinolin-1(2H)-one (12c)
The procedure described for compound 12a was used with
compound 11c (200 mg, 0.455 mmol) in THF (15 mL) and 10%
HCl (10 mL) to give the alcohol 12c as yellow oil (110 mg, 61%).
IR (cmÀ1): 3300 (OH), 1641 (C@O). 1H NMR (300 MHz, CDCl3) d:
7.32 (d, J = 8.6 Hz, 1H), 7.18 (d, J = 8.7 Hz, 1H), 7.06 (s, 1H), 6.71
(s, 1H), 6.25 (s, 1H), 6.03 (dd, J = 1.3, 6.2 Hz, 2H), 5.89–5.80 (m,
1H), 5.04 (dd, J = 1.4, 10.2 Hz, 1H), 4.79 (dd, J = 1.4, 17.1 Hz, 1H),
4.54 (dd, J = 5.7, 15.3 Hz, 1H), 4.41 (s, 2H), 4.27 (dd, J = 4.9,
16.9 Hz, 1H), 4.00 (s, 3H), 3.94 (s, 3H) 1.88 (bs, 1H). EIMS: m/z
395 (M+, 87). HRMS-EI (calcd for C22H21NO6): 395.1369, found
395.1361.
C23H25NO5): 395.1733, found 395.1743.
5.2.10. 2-Allyl-7,8-dimethoxy-3-(6-methoxymethoxymethyl-
benzo[1,3]dioxol-5-yl)-2H-isoquinolin-1-one (11c)
The procedure described for compound 11a was used with 3-
arylisoquinoline 8c (330 mg, 0.83 mmol) and K2CO3 (350 mg,
2.5 mmol) in DMF (20 mL) and allyl bromide (200 mg, 1.7 mmol)
to give compound 11c as yellow oil (221 mg, 61%). IR (cmÀ1):
1650 (C@O). 1H NMR (300 MHz, CDCl3) d: 7.33 (d, J = 8.7 Hz, 1H),
7.18 (d, J = 8.6 Hz, 1H), 7.02 (s, 1H), 6.73 (s, 1H), 6.26 (s, 1H), 6.03
(dd, J = 1.3, 6.4 Hz, 2H), 5.88–5.79 (m, 1H), 5.04 (dd, J = 1.3,
10.2 Hz, 1H), 4.81 (dd, J = 1.4, 17.2 Hz, 1H), 4.65 (dd, J = 5.4,
15.3 Hz, 1H), 4.57 (s, 2H), 4.30 (s, 2H), 4.18 (dd, J = 5.3, 15.4 Hz,
1H), 4.01 (s, 3H), 3.95 (s, 3H), 3.27 (s, 3H). EIMS: m/z 439 (M+,
45). HRMS-EI (calcd for C24H25NO7): 439.1631, found 439.1635.
5.2.15. 2-Allyl-3-(6-hydroxymethylbenzo[1,3]dioxol-5-yl)-2H-
isoquinolin-1-one (12d)
The procedure described for compound 12a was used with
compound 11d (480 mg, 1.26 mmol) in THF (15 mL) and 10% HCl
(10 mL) to give compound 12d as pale yellow oil (370 mg, 87%).
IR (cmÀ1): 3300 (OH), 1641 (C@O). 1H NMR (300 MHz, CDCl3) d:
8.37 (d, J = 8.3 Hz, 1H), 7.64–7.59 (m, 1H), 7.47–7.42 (m, 2H),
7.10 (s, 1H), 6.69 (s, 1H), 6.40 (s, 1H), 6.02 (dd, J = 1.3, 6.6 Hz,
2H), 5.80–5.69 (m, 1H), 5.02 (dd, J = 1.3, 10.3 Hz, 1H), 4.77 (dd,
J = 1.3, 17.1 Hz, 1H), 4.60 (dd, J = 5.5, 15.4 Hz, 1H), 4.38 (d,
J = 1.7 Hz, 2H), 4.22 (dd, J = 5.0, 15.4 Hz, 1H). EIMS: m/z 335 (M+,
78). HRMS-EI (calcd for C20H17NO4): 335.1157, found 335.1152.
5.2.11. 2-Allyl-3-(6-((methoxymethoxy)methyl)benzo[d][1,3]-
dioxol-5-yl)isoquinolin-1(2H)-one (11d)
The procedure described for compound 11a was used with 3-
arylisoquinoline 8d (800 mg, 2.36 mmol), K2CO3 (1.24 g, 9 mmol)
in DMF (20 mL) and allyl bromide (570 mg, 4.7 mmol) to afford
compound 11d as oil (537 mg, 60%). IR (cmÀ1): 1650 (C@O). 1H
NMR (300 MHz, CDCl3) d: 8.46 (d, J = 7.9 Hz, 1H), 7.67–7.62 (m,
1H), 7.52–7.46 (m, 2H), 7.03 (s, 1H), 6.75 (s, 1H), 6.41 (s, 1H),
6.04 (dd, J = 1.3, 6.0 Hz, 2H), 5.86–5.77 (m, 1H), 5.07 (dd, J = 1.3,
10.2 Hz, 1H), 4.84 (dd, J = 1.4, 17.1 Hz, 1H), 4.70 (dd, J = 5.4,
16.9 Hz, 1H), 4.56 (s, 2H), 4.30 (s, 2H), 4.23 (dd, J = 5.2, 15.4 Hz,
1H), 3.25 (s, 3H). EIMS: m/z 379 (M+, 81). HRMS-EI (calcd for
5.2.16. 2-(2-Allyl-1-oxo-1,2-dihydroisoquinolin-3-yl)-5-meth-
oxybenzaldehyde (13a)
To a solution of alcohol 12a (600 mg, 1.87 mmol) in methy-
lene chloride (30 mL) was added PDC (1.5 g, 4 mmol), and the
mixture was stirred for 2 h at room temperature. The reaction
mixture was filtered and the filtrate was washed with CH2Cl2.
The solvent was evaporated and the residue was purified by col-
umn chromatography on silica gel with n-hexane–ethyl acetate
(2:1) to afford the aldehyde 13a as yellow oil (510 mg, 85%) IR
(cmÀ1): 1700, 1640 (C@O). 1H NMR (300 MHz, CDCl3) d: 9.90
(s, 1H), 8.48 (d, J = 8.0 Hz, 1H), 7.70–7.66 (m, 1H), 7.55–7.47
(m, 3H), 7.38 (d, J = 8.3 Hz, 1H), 7.22 (dd, J = 2.7, 8.4 Hz, 1H),
6.43 (s, 1H), 5.85–5.72 (m, 1H), 5.04 (d, J = 10.2 Hz, 1H), 4.75
(d, J = 17.1 Hz, 1H), 4.50 (d, J = 5.4 Hz, 2H), 3.93 (s, 3H). EIMS:
m/z 319 (M+, 100). HRMS-EI (calcd for C20H17NO3): 319.1208,
found 319.1212.
C22H21NO5): 379.1420, found 379.1427.
5.2.12. 2-Allyl-3-(2-hydroxymethyl-4-methoxyphenyl)-2H-
isoquinolin-1-one (12a)
To a solution of compound 11a (800 mg, 2.2 mmol) in THF
(15 mL) was added 10% HCl (10 mL) and the reaction was refluxed
for 2 h. After cooling to room temperature, the reaction mixture
was poured into water and extracted with ethyl acetate. The ethyl
acetate extracts were washed with water and brine and dried over
anhydrous sodium sulfate. After removal of the solvent in vacuo,
the residue was purified by column chromatography on silica gel
with n-hexane–ethyl acetate (1:2) to produce the alcohol 12a as
white solid (650 mg, 92%). mp: 109–110 °C. IR (cmÀ1): 3300
(OH), 1641 (C@O). 1H NMR (300 MHz, CDCl3) d: 8.39 (d,
J = 6.6 Hz, 1H), 7.65–7.59 (m, 1H), 7.47–7.42 (m, 2H), 7.19–7.15
(m, 2H), 6.86 (dd, J = 2.7, 8.4 Hz, 1H), 6.38 (s, 1H), 5.79–5.68 (m,
1H), 5.00 (d, J = 10.2 Hz, 1H), 4.73 (d, J = 17.8 Hz, 1H), 4.61 (dd,
J = 5.5, 15.3 Hz, 1H), 4.48 (d, J = 5.5 Hz, 2H), 4.15 (dd, J = 5.2,
15.3 Hz, 1H), 3.87 (s, 3H), 2.74 (bs, 1H). EIMS: m/z 321 (M+, 66).
HRMS-EI (calcd for C20H19NO3): 321.1365, found 321.1368.
5.2.17. 2-(2-Allyl-1-oxo-1,2-dihydroisoquinolin-3-yl)-4,5-
dimethoxybenzaldehyde (13b)
The procedure described for compound 13a was used with
alcohol 12b (660 mg, 1.9 mmol) and PDC (1.5 g, 4 mmol) in CH2Cl2
(30 mL) to afford the aldehyde 13b as yellow solid (597 mg, 91%).
mp: 135–137 °C. IR (cmÀ1): 1700, 1640 (C@O). 1H NMR
(300 MHz, CDCl3) d: 9.81 (s, 1H), 8.48 (d, J = 8.0 Hz, 1H),
7.72–7.66 (m, 1H), 7.57–7.49 (m, 3H), 6.89 (s, 1H), 6.48 (s, 1H),