Page 7 of 12
The Journal of Organic Chemistry
7.24 (s, 1H), 5.33 (s, 2H), 4.06 (s, 3H); 13C{1H} NMR (100 21%); mp 235 - 237 °C; 1H NMR (300 MHz, Chloroform-d) δ
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MHz, Chloroform-d) δ 194.5, 153.8, 151.2, 148.9, 147.9,
137.3, 135.8, 132.4, 132.4, 130.8, 128.8, 128.3, 128.0, 127.4,
125.9, 122.2, 107.1, 106.2, 70.9, 56.2; MS (ESI): HRMS (ESI)
m/z: [M + H]+ calcd for C24H20NO3 370.1438; Found
370.1462.
10.91 (bs, 1H), 9.19 (d, J = 0.5 Hz, 1H), 8.91 (s, 1H), 8.20 (d,
J = 7.9 Hz, 1H), 7.77 (d, J = 8.3 Hz, 1H), 7.60 (ddd, J = 8.3,
7.2, 1.1 Hz, 1H), 7.37 – 7.31 (m, 1H), 4.56 (q, J = 7.1 Hz, 2H),
1.47 (t, J = 7.1 Hz, 3H); 13C{1H} NMR (100 MHz,
Chloroform-d) δ 166.3, 141.2, 137.7, 137.4, 133.6, 129.0,
121.8, 121.6, 120.8, 120.7, 117.9, 112.5, 61.6, 14.5; HRMS
(ESI) m/z: [M + H]+ calcd for C14H13N2O2 241.0977; Found
241.0975.
Phenyl(6,7,8-trimethoxyisoquinolin-3-yl)methanone (3ea).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 60/40) to afford 3ea as white solid (129
mg, 80%); mp 153 – 155 °C; 1H NMR (400 MHz,
Chloroform-d) δ 9.45 (s, 1H), 8.30 (s, 1H), 8.07 (dd, J = 5.2,
3.3 Hz, 2H), 7.60 (t, J = 7.4 Hz, 1H), 7.50 (t, J = 7.6 Hz, 2H),
7.04 (s, 1H), 4.14 (s, 3H), 4.04 (s, 3H), 4.02 (s, 3H); 13C{1H}
NMR (100 MHz, Chloroform-d) δ 194.5, 157.4, 149.0, 148.7,
145.9, 142.9, 137.1, 133.6, 132.5, 130.9, 128.1, 122.0, 120.9,
102.1, 61.9, 61.3, 56.2; HRMS (ESI) m/z: [M + H]+ calcd for
C19H18NO4 324.1230; Found 324.1250.
(7-(Benzyloxy)-6-methoxyisoquinolin-3-yl)(naphthalen-2-
yl)methanone (3jj).
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Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 50/50) to afford 3jj as white solid (172
mg, 82%); mp 152 - 154 °C; 1H NMR (500 MHz, Chloroform-
d) δ 9.01 (s, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 8.05 (dd, J = 8.6,
1.6 Hz, 1H), 7.86 (dd, J = 8.2, 4.3 Hz, 2H), 7.81 (d, J = 8.1
Hz, 1H), 7.55 – 7.48 (m, 1H), 7.45 (dd, J = 10.8, 4.0 Hz, 3H),
7.35 (t, J = 7.4 Hz, 2H), 7.31 – 7.25 (m, 2H), 7.18 (s, 1H),
5.26 (s, 2H), 3.98 (s, 3H); 13C{1H} NMR (100 MHz,
Chloroform-d) δ 194.4, 153.9, 151.2, 149.0, 148.1, 135.8,
135.3, 134.6, 132.9, 132.4, 129.8, 129.7, 128.8, 128.5, 128.3,
128.2, 127.8, 127.7, 127.4, 126.4, 126.0, 122.3, 107.1, 106.2,
70.9, 56.3; HRMS (ESI) m/z: [M + H]+ calcd for C28H22NO3
420.1594; Found: 420.1600.
(7-Fluoroisoquinolin-3-yl)(phenyl)methanone (3fa).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 65/35) to afford 3fa as white solid (92
mg, 73%); mp 128 – 130 °C; 1H NMR (400 MHz,
Chloroform-d) δ 9.30 (s, 1H), 8.50 (s, 1H), 8.07 (dd, J = 8.0,
7.0 Hz, 2H), 8.06 – 7.98 (m, 1H), 7.70 (d, J = 8.5 Hz, 1H),
7.66 – 7.55 (m, 2H), 7.51 (dd, J = 11.5, 4.2 Hz, 2H); 13C{1H}
NMR (125 MHz, Chloroform-d) δ 194.0, 162.3 (d, J = 253.2
Hz), 150.7, 150.7, 148.6, 136.9, 132.7, 131.1 (d, J = 8.8 Hz),
130.9, 130.5 (d, J = 8.9 Hz), 128.1, 123.2, 121.8 (d, J = 25.5
Hz), 111.0 (d, J = 21.0 Hz); 19F NMR (375 MHz, Chloroform-
d) δ 107.0; HRMS (ESI) m/z: [M + H]+ calcd for C16H11FNO
252.0819; Found 252.0823.
(7-(Benzyloxy)-6-methoxyisoquinolin-3-yl)(p-tolyl)methanone
(3jb).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 60/40) to afford 3jb as white solid (163
mg, 85%); mp 155 - 157 °C; 1H NMR (500 MHz, Chloroform-
d) δ 9.05 (s, 1H), 8.31 (s, 1H), 7.98 (d, J = 8.2 Hz, 2H), 7.54 –
7.48 (m, 2H), 7.45 – 7.39 (m, 2H), 7.39 – 7.34 (m, 1H), 7.33
(s, 1H), 7.30 (s, 1H), 7.28 (s, 1H), 7.24 (s, 1H), 5.33 (s, 2H),
4.05 (s, 3H), 2.44 (s, 3H); 13C{1H} NMR (125 MHz,
Chloroform-d) δ 194.2, 153.8, 151.1, 148.9, 148.2, 143.2,
135.8, 134.6, 132.4, 131.0, 130.8, 128.8, 128.3, 127.4, 125.9,
122.10, 107.1, 106.1, 70.9, 56.2, 21.7; HRMS (ESI) m/z: [M +
H]+ calcd for C25H22NO3 384.1594; Found 384.1599.
(6-Nitroisoquinolin-3-yl)(phenyl)methanone (3ga).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 65/35) to afford 3ga as white solid (104
mg, 75%); mp 153 – 155 °C; 1H NMR (300 MHz,
Chloroform-d) δ 9.34 (s, 1H), 9.03 (s, 1H), 8.64 (s, 1H), 8.54 –
8.41 (m, 2H), 8.12 (d, J = 7.0 Hz, 1H), 8.07 (d, J = 7.2 Hz,
1H), 7.90 – 7.78 (m, 2H), 7.72 (t, J = 8.0 Hz, 1H); 13C{1H}
NMR (100 MHz Chloroform-d) δ 191.6, 151.7, 147.9, 138.4,
136.5, 135.7, 131.4, 130.1, 129.2, 128.4, 127.8, 126.8, 126.2,
124.0; HRMS (ESI) m/z: [M + H]+ calcd for C16H11N2O3
279.0764; Found 279.0778.
(7-(Benzyloxy)-6-methoxyisoquinolin-3-yl)(4-methoxyphenyl)
methanone (3jc).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 60/40) to afford 3jc as white solid (176
mg, 88%); mp 161 - 163 °C; 1H NMR (300 MHz, Chloroform-
d) δ 9.04 (s, 1H), 8.30 (s, 1H), 8.13 (d, J = 8.8 Hz, 2H), 7.52
(d, J = 7.1 Hz, 2H), 7.46 – 7.35 (m, 3H), 7.33 (s, 1H), 7.23 (s,
1H), 6.98 (d, J = 8.8 Hz, 2H), 5.33 (s, 2H), 4.05 (s, 3H), 3.89
(s, 3H); 13C{1H} NMR (125 MHz, Chloroform-d) δ 192.8,
163.2, 153.8, 151.1, 148.6, 148.4, 135.8, 133.4, 132.5, 129.95,
128.8, 128.3, 127.4, 125.8, 121.9, 113.4, 107.1, 106.1, 70.9,
56.2, 55.5; HRMS (ESI) m/z: [M + H]+ calcd for C25H22NO4
400.1543; Found: 400.1555.
(5,6-Dihydrobenzo[f]isoquinolin-2-yl)(phenyl)methanone
(3ha).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 65/35) to afford 3ha as thick oil (97 mg,
68%); 1H NMR (400 MHz, Chloroform-d) δ 9.05 (s, 1H), 8.13
– 8.08 (m, 2H), 7.95 (s, 1H), 7.87 (d, J = 7.2 Hz, 1H), 7.63 –
7.57 (m, 1H), 7.52 – 7.47 (m, 2H), 7.36 (tdd, J = 8.8, 7.3, 1.6
Hz, 2H), 7.30 (dd, J = 7.2, 1.4 Hz, 1H), 3.02 – 2.92 (m, 4H);
13C{1H} NMR (100 MHz, Chloroform-d) δ 193.8, 153.3,
146.6, 143.7, 137.8, 136.6, 132.9, 132.8, 130.9, 130.0, 129.3,
128.6, 128.1, 127.5, 124.0, 124.0, 28.2, 27.9; HRMS (ESI)
m/z: [M + H]+ calcd for C20H16NO 286.1226; Found 286.1243.
Isoquinolin-3-yl(p-tolyl)methanone (3ab).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 60/40) to afford 3ab as white solid (93
mg, 75%); mp 116 - 118 °C; 1H NMR (300 MHz, Chloroform-
d) δ 9.39 (s, 1H), 8.45 (s, 1H), 8.11 (d, J = 8.0 Hz, 1H), 8.00
(dd, J = 13.9, 8.1 Hz, 3H), 7.88 – 7.73 (m, 2H), 7.32 (d, J =
8.0 Hz, 2H), 2.45 (s, 3H); 13C{1H} NMR (100 MHz,
Chloroform-d) δ 193.5, 151.4, 148.4, 143.7, 135.8, 134.2,
Ethyl 9H-pyrido[3,4-b]indole-3-carboxylate (3il).
Purified by column chromatography on silica gel (petroleum
ether/ethyl acetate = 55/45) to afford 3il as white solid (25 mg,
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