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4-(1-Oxoisoquinolin-2(1H)-yl) benzonitrile (3g): Yield:
δ: 161.7, 139.3, 136.8, 132.6, 131.9, 128.3, 127.2, 126.5, 125.9,
125.3, 125.2, 119.3, 106.5; HRMS (ESI) m/z: [M+H]+ calcd.
for C13H10ONS: 228.0478, found: 228.0484.
1
°
78 mg, 73%; white solid; mp: 209–211 C; H NMR (200 MHz,
CDCl3) δ: 8.40–8.52 (m, 1H), 7.80–7.86 (m, 2H), 7.68–7.76 (m,
1H), 7.61–7.65 (m, 2H), 7.54–7.61 (m, 2H), 7.16 (d, J=7.5 Hz,
1H), 6.64 (d, J=7.4 Hz, 1H); 13C{1H} NMR (101 MHz, CDCl3)
δ: 161.6, 145.0, 136.8, 133.2, 133.1, 130.7, 128.3, 127.7, 127.7,
126.3, 126.2, 118.1, 111.8, 107.3; HRMS (ESI) m/z: [M+H]+
calcd. for C16H11ON2: 247.0866, found: 247.0866.
5-Bromo-2-phenylisoquinolin-1(2H)-one (3o): Yield: 132 mg,
78%; yellow solid; mp: 106–108 C; 1H NMR (200 MHz,
°
CDCl3) δ: 8.46 (d, J=8.1 Hz, 1H), 7.93 (dd, J=7.8, 1.1 Hz,
1H), 7.49–7.56 (m, 2H), 7.41–7.48 (m, 3H), 7.38 (t, J=7.9 Hz,
1H), 7.29 (d, J=7.6 Hz, 1H), 6.94 (d, J=7.8 Hz, 1H); 13C{1H}
NMR (101 MHz, CDCl3) δ: 161.3, 141.0, 136.4, 136.3, 133.3,
129.4, 128.4, 128.1, 127.9, 127.7, 126.7, 120.6, 104.9; HRMS
(ESI) m/z: [M+H]+ calcd. for C15H11ONBr: 300.0019, found:
300.0023.
2-(4-Acetylphenyl) isoquinolin-1(2H)-one (3i): Yield: 73 mg,
1
°
67%; white solid; mp: 203–204 C; H NMR (200 MHz, CDCl3)
δ: 8.48 (dt, J=8.1, 0.7 Hz, 1H), 8.11–8.13 (m, 1H), 8.09–8.11
(m, 1H), 7.68–7.74 (m, 1H), 7.53–7.61 (m, 4H), 7.19 (d, J=
7.5 Hz, 1H), 6.63 (d, J=7.4 Hz, 1H), 2.67 (s, 3H); 13C{1H}
NMR (101 MHz, CDCl3) δ: 197.1, 161.8, 145.2, 136.9, 136.4,
132.9, 131.2, 129.4, 128.3, 127.5, 127.0, 126.5, 126.1, 106.9,
26.7; HRMS (ESI) m/z: [M+H]+ calcd. for C17H14O2N:
264.1019, found: 264.1020.
5-Bromo-2-(3,5-dimethoxyphenyl)
isoquinolin-1(2H)-one
(3p): Yield: 61 mg, 87%; White solid; mp: 132–134 C; 1H
NMR (500 MHz, CDCl3) δ: 8.46 (dt, J=7.9, 1.0 Hz, 1H), 7.93
(dd, J=7.8, 1.3 Hz, 1H), 7.38 (t, J=7.9 Hz, 1H), 7.27 (d, J=
7.5 Hz, 1H), 6.92 (dd, J=7.6, 0.6 Hz, 1H), 6.57–6.59 (m, 2H),
6.53–6.55 (m, 1H), 3.83 (s, 6H); 13C{1H} NMR (101 MHz,
CDCl3) δ: 161.2, 161.1, 142.6, 136.4, 136.3, 133.3, 128.1,
127.9, 127.7, 120.6, 105.2, 104.7, 100.8, 55.6. HRMS (ESI)
m/z: [M+H]+ calcd. for C17H15O3NBr: 360.0230, found:
360.0231.
°
2-(p-Tolyl) isoquinolin-1(2H)-one (3j): Yield: 89 mg, 82%;
1
yellow viscous liquid; H NMR (500 MHz, CDCl3) δ: 8.48 (dd,
J=7.6, 1.1 Hz, 1H), 7.64–7.70 (m, 1H), 7.56 (d, J=7.8 Hz,
1H), 7.49–7.55 (m, 1H), 7.32 (s, 4H), 7.18 (d, J=7.3 Hz, 1H),
6.56 (d, J=7.3 Hz, 1H), 2.43 (s, 3H) ; 13C{1H} NMR
(101 MHz, CDCl3) δ: 161.8, 138.5, 137.7, 136.8, 132.1, 132.0,
129.5, 128.0, 126.8, 126.2, 125.6, 105.7, 20.8; HRMS (ESI)
m/z: [M+H]+ calcd. for C16H14ON: 236.1070, found:
236.1066.
4-Bromo-2-(4-iodophenyl) isoquinolin-1(2H)-one (3q): Yield:
98 mg, 77%; light yellow solid; mp: 175–177 C; 1H NMR
°
(400 MHz, CDCl3) δ: 8.46–8.53 (m, 1H), 7.77–7.97 (m, 4H),
7.57–7.66 (m, 1H), 7.46 (s, 1H), 7.18–7.24 (m, 2H); 13C{1H}
NMR (101 MHz, CDCl3) δ: 160.9, 140.1, 138.6, 135.5, 133.5,
131.9, 128.8, 128.7, 128.6, 128.3, 126.09, 100.7, 93.8; HRMS
(ESI) m/z: [M+H]+ calcd. for C15H10ONBrI: 425.8985, found:
425.8994.
2-(4-Methoxyphenyl) isoquinolin-1(2H)-one (3k): Yield:
189 mg, 83%; yellow solid; mp: 138–139 C; 1H NMR
°
(500 MHz, CDCl3) δ: 8.45–8.50 (m, 1H), 7.64–7.72 (m, 1H),
7.49–7.58 (m, 2H), 7.33–7.38 (m, 2H), 7.18 (d, J=7.4 Hz, 1H),
6.99–7.05 (m, 2H), 6.56 (d, J=7.4 Hz, 1H), 3.87 (s, 3 H); 13C
{1H} NMR (101 MHz, CDCl3) δ: 162.3, 159.1, 137.1, 134.3,
132.5, 132.5, 128.3, 127.9, 127.1, 126.5, 125.9, 114.5, 106.0,
55.5; HRMS (ESI) m/z: [M+H]+ calcd. for C16H14O2N:
252.1019, found: 252.1021.
2-Benzylisoquinolin-1(2H)-one (3r): Yield: 78 mg, 79%; light
1
°
yellow solid; mp: 67–68 C; H NMR (400 MHz, CDCl3) δ:
8.45–8.51 (m, 1H), 7.60–7.68 (m, 1H), 7.47–7.56 (m, 2H),
7.32–7.41 (m, 4H), 7.27–7.32 (m, 1H), 7.10 (d, J=7.4 Hz, 1H),
6.50 (d, J=7.4 Hz, 1H), 5.24 (s, 2H); 13C{1H} NMR (101 MHz,
CDCl3) δ: 162.3, 137.0, 136.9, 132.2, 131.3, 128.8, 128.1,
127.9, 127.8, 126.9, 126.3, 125.9, 106.5, 51.7; HRMS (ESI)
m/z: [M+H]+ calcd. for C16H14ON: 236.1070, found:
236.1072.
2-(3,5-Dimethylphenyl) isoquinolin-1(2H)-one (3l): Yield:
65 mg, 87%; yellow viscous liquid; 1H NMR (400 MHz,
CDCl3) δ: 8.46–8.51 (m, 1H), 7.64–7.71 (m, 1H), 7.49–7.58 (m,
2H), 7.17 (d, J=7.8 Hz, 1H), 7.03–7.07 (m, 3H), 6.55 (d, J=
7.3 Hz, 1 H), 2.38 (s, 6 H); 13C{1H} NMR (101 MHz, CDCl3) δ:
162.1, 141.2, 139.1, 137.1, 132.4, 132.4, 129.8, 128.2, 127.0,
126.6, 125.9, 124.5, 105.9, 21.2; HRMS (ESI) m/z: [M+H]+
calcd. for C17H16ON: 250.1226, found: 250.1227.
4-((1-Oxoisoquinolin-2(1H)-yl) methyl) benzonitrile (3s):
Yield: 78 mg, 74%; white solid; mp: 167–168 C; 1H NMR
°
(500 MHz, CDCl3) δ: 8.43 (d, J=8.0 Hz, 1H), 7.64–7.70 (m,
1H), 7.61 (m, J=8.3 Hz, 2H), 7.48–7.57 (m, 2H), 7.41 (m, J=
8.4 Hz, 2H), 7.08 (d, J=7.3 Hz, 1H), 6.55 (d, J=7.4 Hz, 1H),
5.25 (s, 2H); 13C{1H} NMR (101 MHz, CDCl3) δ: 162.1, 142.2,
136.9, 132.5, 131.0, 128.2, 127.9, 127.2, 126.1, 126.1, 118.5,
111.6, 107.0, 51.7; HRMS (ESI) m/z: [M+H]+ calcd. for
C17H13ON2: 261.1022, found: 261.1030.
2-(3,5-Dimethoxyphenyl) isoquinolin-1(2H)-one (3m): Yield:
76 mg, 89%; yellow solid; mp: 153–154 C; 1H NMR
°
(200 MHz, CDCl3) δ: 8.48 (dd, J=8.1, 0.6 Hz, 1H), 7.65–7.72
(m, 1H), 7.50–7.59 (m, 2 H), 7.17 (d, J=7.4 Hz, 1H), 6.58 (d,
J=2.3 Hz, 2H), 6.56 (d, J=7.4 Hz, 1H), 6.52–6.54 (m, 1H),
3.82 (s, 6H); 13C{1H} NMR (101 MHz, CDCl3) δ: 161.9, 161.1,
143.0, 137.0, 132.6, 132.1, 128.2, 127.1, 126.5, 125.9, 106.1,
105.3, 100.6, 55.6; HRMS (ESI) m/z: [M+H]+ calcd. for
C17H16O3N: 282.1125, found: 282.1123.
2-(4-Nitrobenzyl) isoquinolin-1(2H)-one (3t): Yield: 89 mg,
1
°
69%; white solid; mp: 153–154 C; H NMR (200 MHz, CDCl3)
δ: 8.39–8.49 (m, 1H), 8.13–8.28 (m, 2H), 7.69 (ddd, J=8.1,
7.0, 1.3 Hz, 1H), 7.54 (td, J=8.4, 1.8 Hz, 2H), 7.48 (m, J=
8.9 Hz, 2H), 7.10 (d, J=7.4 Hz, 1H), 6.57 (d, J=7.4 Hz, 1H),
5.31 (s, 2H); 13C{1H} NMR (101 MHz, CDCl3) δ: 162.2, 147.5,
144.2, 137.0, 132.6, 131.0, 128.4, 128.0, 127.3, 126.2, 126.1,
124.0, 107.1, 51.6; HRMS (ESI) m/z: [M+H]+ calcd. for
C16H13O3N2: 281.0921, found: 281.0926.
2-(Thiophen-3-yl) isoquinolin-1(2H)-one (3n): Yield: 74 mg,
76%; yellow solid; mp: 109–112 C; 1H NMR (200 MHz,
°
CDCl3) δ: 8.48 (dt, J=8.0, 0.6 Hz, 1H), 7.62–7.72 (m, 1 H),
7.51–7.58 (m, 2H), 7.44–7.51 (m, 1H), 7.41 (dd, J=5.2,
3.2 Hz, 1H), 7.32 (dd, J=5.2, 1.4 Hz, 1H), 7.26 (d, J=4.5 Hz,
1H), 6.57 (d, J=7.4 Hz, 1H); 13C{1H} NMR (101 MHz, CDCl3)
Adv. Synth. Catal. 2021, 363, 1390–1400
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