Med Chem Res
600), 7.01–7.02 (m, 2H, H-300, 500), 6.0 (s, 1H, H-4), 3.80 (s,
2H, H-10); 13C NMR (75 MHz, DMSO): d = 162.9 (C-1),
162.3 (J = 245.5 Hz, C-400), 156.8 (C-3), 137.1 (C-4a),
134.4 (C-6), 131.1 (J = 3.2 Hz, C-100), 130.2 (J = 8.5 Hz,
C-200, 600), 129.8 (C-8a), 127.2 (C-7), 125.8 (C-8), 120.2 (C-
5), 115.3 (J = 21.5 Hz, C-300, 500), 103.6 (C-4), 39.2 (C-10);
EIMS: m/z 253 (21.0) [M]?, 225 (14.9), 119 (22.1), 115
(29.0), 102 (7.2), 89 (100), 63 (29.0); Anal. Calcd. for
C16H12ONF: C, 75.88; H, 4.78; N, 5.53. Found: C, 76.28;
H, 4.84; N, 5.68.
Fig. 2 Labeling scheme of
protons and carbons for
compounds (2a–2i)
O
4
8
5"
2"
4"
6"
1"
7
6
NH
3
R
3"
5
1'
3-(2-Fluorobenzyl)isoquinolin-1(2H)-one (2a)
Yellow solid; yield, 59 %; mp = 170–172 ꢁC; IR (KBr)
tmax 2760–3245, 1668, 1645 cm-1; H NMR (300 MHz,
1
DMSO): d = 11.42 (s (br), 1H, NH), 8.60 (1H, d,
J = 7.8 Hz, H-8), 7.57 (1H, dt, J = 7.2, 1.2 Hz, H-6), 7.45
(1H, dt, J = 8.1, 1.2 Hz, H-7), 7.32–7.36 (m, 2H, H-5, 600),
7.22–7.30 (m, 3H, H-300, 400, 500), 6.12 (s, 1H), 3.81 (s, 2H,
C-10); 13C NMR (75 MHz, DMSO): d = 162.8 (C-1),
162.1 (J = 245.1 Hz, C-200), 155.6 (C-4a), 137.4 (C-5),
134.9 (C-6), 131.9 (J = 8.1 Hz, C-400), 130.8 (C-3), 129.7
(C-7), 129.1 (J = 8.1 Hz, C-600), 128.6 (C-8), 125.2 (C-8a),
123.4 (J = 3.7 Hz, C-500), 122.3 (J = 15.0 Hz, C-300),
115.6 (J = 21.2 Hz, C-100), 103.8 (C-4), 39.3 (C-10); EIMS
m/z 253 (24.0) [M]?, 225 (12.2), 119 (33.8), 115 (26.2),
102 (6.8), 89 (100), 63 (34.2). Anal. Calcd. for
C16H12ONF: C, 75.88; H, 4.78; N, 5.53. Found: C, 76.10;
H, 4.94; N, 5.63.
3-(2-Chlorobenzyl)isoquinolin-1(2H)-one (2d)
Yellow solid; yield, 52 %; mp = 219–221 ꢁC; IR (KBr)
tmax 2730–3148, 1674, 1643, 1049 cm-1
;
1H-NMR
(300 MHz, DMSO): d = 11.31 (1H, s, NH), 8.14 (1H, d,
J = 8.1 Hz), 7.48–7.51 (2H, m), 7.40–7.45 (2H, m),
7.31–7.37 (3H, dt, J = 7.5, 1.2, Hz), 6.01 (1H, s), 3.99
(2H, s); 13C NMR (75 MHz, DMSO): d = 163.4 (C-1),
142.6 (C-100), 139.9 (C-4a), 137.5 (C-6), 132.5 (C-300),
131.4 (C-600), 131.1 (C-3), 130.6 (C-7), 128.7 (C-400), 128.3
(C-500), 128.0 (C-8), 127.4 (C-8a), 126.3 (C-5), 124.9 (C-
200), 104.9 (C-4), 38.5 (C-10); EIMS: m/z 269 (43.0) [M]?,
234 (100), 233 (15.2), 204 (8.7), 178 (5.9), 125 (9.3), 115
(11.0), 90 (13.1), 89 (87.5), 63 (25.2); Anal. Calcd. for
C16H12ONCl: C, 71.37; H, 4.46; N, 5.20. Found: C, 71.26;
H, 4.55; N, 5.06.
3-(3-Fluorobenzyl)isoquinolin-1(2H)-one (2b)
Yellow solid; yield, 51 %; mp = 188–190 ꢁC; IR (KBr)
3-(3-Chlorobenzyl)isoquinolin-1(2H)-one (2e)
1
tmax 2675–3190, 1670, 1643 cm-1; H NMR (300 MHz,
DMSO): d = 11.32 (s (br), 1H, NH), 8.46 (d, 1 H,
J = 7.8 Hz, H-8), 7.51 (dt, 1H, J = 7.8, J = 1.2 Hz, H-6),
7.43 (dt, 1H, J = 7.2, 0.9 Hz, H-7), 7.31–7.38 (m, 2H,
H-5,500), 7.10–7.21 (m, 3H, H-200, 400, 600), 6.13 (s, 1H, H-4),
3.75 (s, 2H, H-10); 13C NMR (75 MHz, DMSO): d = 162.8
(C-1), 162.6 (J = 244.5 Hz, C-300), 156.3 (C-4a), 138.4
(J = 7.8 Hz, C-100), 137.5 (C-3), 134.4 (C-7), 130.7
(J = 8.7 Hz, C-500), 129.8 (C-6), 128.4 (C-8), 125.8 (C-8a),
124.6 (J = 3.2 Hz, C-600), 120.1 (C-5), 116.8
(J = 21.0 Hz, C-400), 114.1 (J = 21.0 Hz, C-200), 104.6 (C-
4), 39.8 (C-10); EIMS m/z 253 (31.0) [M]?, 225 (19.0), 119
(30.8), 115 (21.9), 102 (8.8), 89 (100), 63 (31.0). Anal.
Calcd. for C16H12ONF: C, 75.88; H, 4.78; N, 5.53. Found:
C, 76.22; H, 4.88; N, 5.69.
Yellow solid; yield, 45 %; mp = 200–201 ꢁC; IR (KBr)
tmax 2810–3216, 1663, 1641, 1083 cm-1
;
1H NMR
(300 MHz, DMSO): d = 11.41 (1H, s, NH), 8.12 (1H, d,
J = 8.4 Hz, H-8), 7.65 (1H, dt, J = 7.5, 1.5 Hz, H-6), 7.55
(1H, d, J = 7.5 Hz, H-7), 7.46 (1H, d, J = 7.5 Hz, H-5),
7.42 (1H, dt, J = 8.1, 1.5 Hz, H-500), 7.29–7.36 (3H, m,
H-200, 400, 600), 6.38 (1H, s, H-4), 3.84 (2H, s, H-10); 13C
NMR (75 MHz, DMSO): d = 162.9, 141.4, 141.0, 138.4,
133.5, 132.9, 130.8, 129.2, 128.1, 127.1, 127.0, 126.4,
126.3, 124.9, 103.8, 38.1; EIMS: m/z 269 (96.4) [M]?, 234
(14.2), 233(12.8), 204 (9.5), 178 (4.9), 125 (8.6), 115
(14.2), 90 (22.2), 89(100), 63 (35.0); Anal. Calcd. for
C16H12ONCl: C, 71.37; H, 4.46; N, 5.20. Found: C, 71.49;
H, 4.61; N, 5.33.
3-(4-Fluorobenzyl)isoquinolin-1(2H)-one (2c)
3-(4-Chlorobenzyl)isoquinolin-1(2H)-one (2f)
Yellow solid; yield, 61 %; mp = 216–218C; IR (KBr) tmax
Yellow solid; yield, 43 %; mp = 231–233 ꢁC; IR (KBr)
2800–3200, 1667, 1644 cm-1
;
1H NMR (300 MHz,
tmax 2680–3210, 1672, 1644, 1093 cm-1
;
1H NMR
DMSO): d = 11.35 (s (br), 1H, NH), 8.29 (d, 1 H,
J = 7.5 Hz, H-8), 7.58 (dt, 1H, J = 7.5, 1.2 Hz, H-6), 7.42
(dt, 1H, J = 8.1, 1.2 Hz, H-7), 7.22–7.30 (m, 3H, H-5, 200,
(300 MHz, DMSO): d = 11.40 (1H, s, NH), 8.12 (1H, d,
J = 7.8 Hz, H-8), 7.64 (1H, t, J = 7.5, Hz, H-6), 7.54 (1H,
d, J = 7.8 Hz, H-7), 7.38–7.44 (5H, m, H-5,200, 400, 500, 600),
123