UPDATES
1
127.5, 127.3, 126.8, 126.5, 125.8, 118.2, 72.0, 13.0; FTIR (KBr)
3099, 3062, 2985, 2865, 1662, 1608, 1552, 1477, 1386, 1322,
1180, 1020 cmÀ1.
1548C];[9k] Rf 0.53 (20% ethyl acetate in hexanes); H NMR
1
2
3
4
5
6
7
8
9
(CDCl3, 400 MHz, ppm) d 8.73 (d, J=8.0 Hz, 1H), 7.74–7.62
(m, 2H), 7.41 (d, J=8.8 Hz, 1H), 7.29 (d, J=7.6 Hz, 2H),
7.23–7.17 (m, 4H), 7.14 (d, J=8.0 Hz, 2H), 3.88 (s, 3H), 2.48–
2.44 (m, 6H); 13C NMR (CDCl3, 100 MHz, ppm) d 158.3,
140.1, 138.1, 136.9, 136.8, 132.6, 132.3, 131.5, 130.6, 128.94,
128.85, 128.3, 127.8, 126.7, 126.4, 125.9, 118.4, 63.5, 21.4, 21.3;
FTIR (KBr) 3047, 3020, 2972, 1657, 1605, 1542, 1509, 1476,
1323, 1261, 1175, 1101, 817 cmÀ1; HRMS (m/z): [M+H]+
calcd. for C24H22NO2 356.1652; found: 356.1642.
2-(Benzyloxy)-3,4-diphenylisoquinolin-1(2H)-one (3p): Yield
76%; 153.3 mg; white solid; mp. 208–2108C; Rf 0.46 (15%
1
ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz, ppm)
d 8.64–8.60 (m, 1H), 7.62–7.51 (m, 2H), 7.32–7.16 (m, 13H),
7.15–7.10 (m, 2H), 6.89–6.82 (m, 2H), 4.95 (s, 2H); 13C NMR
(CDCl3, 100 MHz, ppm) d 158.5, 140.5, 136.7, 135.6, 133.6,
132.4, 132.0, 131.8, 131.2, 130.0, 129.0, 128.4, 128.3, 127.9,
127.7, 127.3, 127.0, 126.6, 126.0, 118.4, 77.7; FTIR (KBr)
3117, 3057, 2957, 2865, 1663, 1604, 1560, 1508, 1477, 1457,
1375, 1170, 1105 cmÀ1; HRMS (m/z): [M+Na]+ calcd. for C28
H21NO2Na 426.1470; found: 426..1467.
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11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
2-Methoxy-3,4-bis(4-methoxyphenyl)isoquinolin-1(2H)-one
(3v):[12a] Yield 51%; 98.8 mg; white solid; mp. 196–1988C [lit.
193–1958C];[9k] Rf 0. 30 (40% ethyl acetate in hexanes); H
1
NMR (CDCl3, 400 MHz, ppm) d 8.55 (dd, J=7.6 Hz, 1.2 Hz,
1H), 7.58–7.46 (m, 2H), 7.30–7.25 (m, 1H), 7.15 (d, J=
8.8 Hz, 2H), 7.00 (d, J=8.8 Hz, 2H), 6.83–6.72 (m, 4H), 3.81–
3.75 (m, 6H), 3.70 (s, 3H); 13C NMR (CDCl3, 100 MHz, ppm)
d 159.3, 158.6, 158.4, 140.0, 137.0, 132.8, 132.3, 132.2, 127.94,
127.86, 127.2, 126.7, 125.9, 124.1, 118.2, 113.1, 63.5, 55.28,
55.25; FTIR (KBr) 3078, 3046, 2972, 2924, 1642, 1602, 1575,
1559, 1522, 1485, 1383, 1260, 1209, 1135, 1096, 853, 803 cmÀ1;
HRMS (m/z): [M+Na]+ calcd. for C24H21NO4Na 410.1395;
found: 410.1396.
2-(Benzyloxy)-6-methyl-3,4-diphenylisoquinolin-1(2H)-one
(3q): Yield 66%; 137.6 mg; white solid; mp. 208–2108C; Rf
0.46 (15% ethyl acetate in hexanes); 1H NMR (CDCl3,
400 MHz, ppm) d 8.51 (d, J=6.8 Hz, 1H), 7.37 (dd, J=
6.4 Hz, 1.2 Hz, 1H), 7.29–7.21 (m, 9H), 7.20–7.17 (m, 2H),
7.15–7.11 (m. 2H), 6.87–6.82 (m, 2H), 4.93 (s, 2H), 2.38 (s,
3H); 13C NMR (CDCl3, 100 MHz, ppm) d 158.5, 143.1, 140.4,
136.8, 135.7, 133.6, 132.1, 131.8, 129.4, 128.9, 128.6, 128.4,
128.3, 128.2, 127.9, 127.6, 127.2, 125.6, 124.3, 118.2, 77.2, 22.2;
FTIR (KBr) 3073, 3060, 2982, 2853, 1662, 1614, 1554, 1481,
1441, 1330, 1170, 1076 cmÀ1.
2-Methoxy-3,4-di–m-tolylisoquinolin-1(2H)-one (3w): Yield
61%; 108.4 mg; white solid; mp. 186–1888C; Rf 0.30 (20%
ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz, ppm)
d 8.50 (d, J=7.6 Hz, 1H), 7.25–7.14 (m, 2H), 7.10–6.90 (m,
7H), 6.87–6.76 (m, 2H), 3.67 (s, 3H), 2.30–2.15 (m, 6H); 13C
NMR (CDCl3, 100 MHz, ppm) d 158.3, 137.7, 137.1, 135.5,
132.4, 132.3, 131.7, 131.5, 129.1, 128.8, 127.99, 127.95, 127.9,
127.8, 127.4, 126.8, 126.4, 118.5, 63.6, 21.4; FTIR (KBr) 3020,
2925, 1657, 1600, 1519, 1481, 1164, 766, 705 cmÀ1; HRMS (m/
z): [M+H]+ calcd. for C24H22NO2 356.1640; found: 356.1651.
1
2-(Benzyloxy)-6,7-dimethoxy-3,4-diphenylisoquinolin-1(2H)-
one (3r): Yield 63%; 146 mg; white solid; mp. 200–2028C; Rf
0.36 (30% ethyl acetate in hexanes); 1H NMR (CDCl3,
400 MHz, ppm) d 7.98 (s, 1H), 7.30–7.11 (m, 13H), 6.90–6.83
(m, 2H), 6.86 (s, 1H), 4.93 (s, 2H), 4.06 (s, 3H), 3.32 (s, 3H);
13C NMR (CDCl3, 100 MHz, ppm) d 157.8, 153.4, 149.4,
139.0, 135.9, 133.7, 132.12, 132.08, 131.7, 131.3, 130.0, 129.0,
128.4, 128.3, 127.6, 127.3, 120.5, 117.8, 107.7, 106.2, 77.7, 56.4,
56.0; FTIR (KBr) 3106, 3072, 3025, 2990, 2843, 1668, 1608,
1583, 1481, 1332, 1170, 1118 cmÀ1.
3,4-Bis(4-fluorophenyl)-2-methoxyisoquinolin-1(2H)-one
(3x): Yield 83%; 150.8 mg; white solid; mp. 206–2088C [lit.
205–2078C];[9i] Rf 0. 30 (20% ethyl acetate in hexanes); H
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6-Methoxy-4,5-diphenylthieno[2,3-c]pyridin-7(6H)-one
NMR (CDCl3, 400 MHz, ppm) d 8.57 (dd, J=8.0 Hz, 1.2 Hz,
1H), 7.62–7.50 (m, 2H), 7.25–7.17 (m, 3H), 7.10–7.02 (m,
2H), 7.00–6.91 (m, 4H), 3.72 (s, 3H); 13C NMR (CDCl3,
100 MHz, ppm) d 162.5 (d, Jc-f =248.0 Hz), 162.0 (d, Jc-f
245.0 Hz), 158.2, 139.9, 136.4, 133.2 (d, Jc-f =8.0 Hz), 132.61
(d, Jc-f =8.0 Hz), 132.62, 131.3 (d, Jc-f =3.0 Hz), 128.0, 127.5
(3s):[9i] Yield 78%; 130 mg; white solid; mp. 202–2048C [lit.
1
205–2078C];[9i] Rf 0.47 (30% ethyl acetate in hexanes); H
NMR (CDCl3, 400 MHz, ppm) d 7.65 (d, J=5.6 Hz, 1H),
7.30–7.17 (m, 8H), 7.13–7.06 (m, 2H), 6.97 (d, J=5.2 Hz,
2H), 3.73 (s, 3H); 13C NMR (CDCl3, 100 MHz, ppm) d 154.6,
145.1, 141.1, 136.1, 133.3, 131.3, 131.1, 130.9, 129.8, 128.6,
128.3, 127.8, 127.3, 125.0, 116.8, 63.9; FTIR (KBr) 3057, 3026,
2733, 1662, 1600, 1578, 1518, 1166 cmÀ1; HRMS (m/z): [M+
H]+ calcd. for C20H15NSO2 334.0902; found: 334.0899.
=
(d, Jc-f =4.0 Hz), 127.2, 126.5, 125.7, 117.7, 115.5 (d, Jc-f
=
21.0 Hz), 115.0 (d, Jc-f =22.0 Hz), 63.6; FTIR (KBr) 3069,
3052, 2983, 1657, 1609, 1544, 1507, 1485, 1223, 1154, 1101,
833, 780 cmÀ1; HRMS (m/z): [M+Na]+ calcd. for C22H15NO2
F2Na 386.0969; found: 386.0966.
6-(Benzyloxy)-4,5-diphenylthieno[2,3-c]pyridin-7(6H)-one
(3t): Yield 73%; 149.5 mg; white solid; mp. 176–178; Rf 0.48
3,4-Bis(3-fluorophenyl)-2-methoxyisoquinolin-1(2H)-one
(3y): Yield 61%; 110.8 mg; white solid; mp. 198–2008C; Rf 0.
48 (30% ethyl acetate in hexanes); 1H NMR (CDCl3,
400 MHz, ppm) d 8.57 (dd, J=8.0 Hz, 1.2 Hz, 1H), 7.66–7.50
(m, 2H), 7.28–7.17 (m, 3H), 7.08–6.78 (m, 6H), 3.76 (s, 3H);
13C NMR (CDCl3, 100 MHz, ppm) d 162.6 (d, Jc-f =246.0 Hz),
162.0 (d, Jc-f =246.0 Hz), 158.1, 138.9, 137.4 (d, Jc-f =8.0 Hz),
136.0, 133.4 (d, Jc-f =8.0 Hz), 132.7, 130.0, 129.5 (d, Jc-f
9.0 Hz), 128.1, 127.5 (d, Jc-f =3.0 Hz), 126.3, 126.62, 126.56 (d,
c-f =4.0 Hz)„ 125.6, 118.6 (d, Jc-f =21.0 Hz), 117.8 (d, Jc-f
1
47 (20% ethyl acetate in hexanes); H NMR (CDCl3, 400 MHz,
ppm) d 7.76 (d, J=5.2 Hz, 1H), 7.39–7.15 (m, 13H), 7.09 (d,
J=5.2 Hz, 1H), 6.96 (d, J=7.2 Hz, 2H), 5.02 (s, 2H); 13C
NMR (CDCl3, 100 MHz, ppm) d 154.8, ‘45.1, 141.4, ‘36.1,
133.4, 133.3, 131.6, 131.4, 130.9, 130.1, 129.9, 129.0, 128.6,
128.4, 128.3, 127.8, 127.3, 125.1, 116.6, 78.1; FTIR (KBr)
3059, 3036, 2831, 1664, 1598, 1573, 1522, 1176, 1126 cmÀ1;
HRMS (m/z): [M+H]+ calcd. for C26H20NSO2 410.1215;
found: 410.1219.
48
49
50
51
52
53
54
55
56
57
=
J
=
23.0 Hz), 117.4, 115.9 (d, Jc-f =21.0 Hz), 114.7 (d, Jc-f
=
2-Methoxy-3,4-di-p-tolylisoquinolin-1(2H)-one (3u): Yield
70%; 124.4 mg; white solid; mp. 150–1528C [lit. 152–
Adv. Synth. Catal. 2017, 359, 1–13
8
ꢀ 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
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