Copper-catalyzed intramolecular C–N coupling reaction of…
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3
J = 7.8 Hz, 1H); C NMR (150 MHz, DMSO-d ): d 160.9, 136.7, 134.4, 132.9,
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29.7, 128.0, 127.6, 125.8, 123.4, 122.7, 122.4, 117.7, 116.3.
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(
-Fluorophenanthridin-6(5H)-one (2b) White solid, mp: 266–268 °C; H NMR
600 MHz, DMSO-d ): d 11.76 (br, 1H), 8.46–8.42 (m, 2H), 8.29 (dd, J = 7.8,
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.2 Hz, 1H), 7.84 (td, J = 7.8, 1.2 Hz, 1H), 7.62 (t, J = 7.8 Hz, 1H), 7.12–7.09 (m,
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J = 12.0 Hz), 133.9, 133.1, 127.9, 127.6, 125.9 (d, J = 9.0 Hz), 125.2, 122.7,
H); C NMR (150 MHz, DMSO-d ): d 162.6 (d, J = 243 Hz), 161.1, 138.3 (d,
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14.6, 109.9 (d, J = 22.5 Hz), 102.2 (d, J = 24.0 Hz).
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-Methylphenanthridin-6(5H)-one (2c) White solid, mp: 222–224 °C; H NMR
(
J = 7.8, 0.6 Hz, 1H), 8.24 (d, J = 7.8 Hz, 1H), 7.81 (td, J = 7.8, 1.2 Hz, 1H), 7.59
600 MHz, DMSO-d ): d 11.59 (br, 1H), 8.43 (d, J = 7.8 Hz, 1H), 8.28 (dd,
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t, J = 7.8 Hz, 1H), 7.15 (s, 1H), 7.08 (d, J = 8.4 Hz, 1H), 2.37 (s, 3H); C NMR
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(
(
150 MHz, DMSO-d ): d 161.2, 139.6, 136.8, 134.6, 133.0, 127.7 (2C), 125.5,
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23.8, 123.4, 122.6, 116.2, 115.5, 21.3.
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-Methoxyphenanthridin-6(5H)-one (2d) White solid, mp: 249–250 °C;
H
NMR (600 MHz, DMSO-d ): d 11.55 (br, 1H), 8.33 (d, J = 8.4 Hz, 1H), 8.25 (td,
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J = 7.5, 0.6 Hz, 2H), 7.77 (td, J = 7.8, 1.2 Hz, 1H), 7.53 (t, J = 7.2 Hz, 1H), 6.88
(
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d, J = 2.4 Hz, 1H), 6.84 (dd, J = 9.0, 2.4 Hz, 1H), 3.81 (s, 3H); C NMR
3
(
150 MHz, DMSO-d ): d 161.4, 160.5, 138.3, 134.7, 132.9, 127.6, 126.9, 124.9,
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24.6, 122.2, 111.3, 110.3, 99.7, 55.5.
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,3-Dimethoxyphenanthridin-6(5H)-one (2e) Yellow solid, mp: 253–255 °C; H
NMR (600 MHz, DMSO-d ): d 11.48 (br, 1H), 8.42 (d, J = 8.4 Hz, 1H), 8.27 (dd,
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J = 8.4, 1.2 Hz, 1H), 7.79–7.76 (m, 2H), 7.52 (td, J = 7.8, 0.6 Hz, 1H), 6.95 (s,
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H), 3.88 (s, 3H), 3.81 (s, 3H); C NMR (150 MHz, DMSO-d ): d 160.9, 151.0,
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45.3, 134.7, 132.6, 131.6, 127.6, 126.7, 124.9, 122.6, 110.2, 105.7, 99.3, 56.3,
5.7.
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-Chloro-2,3-dimethoxyphenanthridin-6(5H)-one (2f) Yellow solid, mp:
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J = 1.8 Hz, 1H), 8.24 (d, J = 8.4 Hz, 1H), 7.83 (s, 1H), 7.55 (dd, J = 8.4,
28–330 °C; H NMR (600 MHz, DMSO-d ): d 11.55 (br, 1H), 8.59 (d,
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.8 Hz, 1H), 6.92 (s, 1H), 3.89 (s, 3H), 3.81 (s, 3H); C NMR (150 MHz, DMSO-
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d6): d 160.3, 151.7, 145.5, 138.3, 136.6, 132.2, 129.9, 126.9, 123.5, 122.3, 109.3,
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06.0, 99.2, 56.5, 55.8.
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-Fluoro-2,3-dimethoxyphenanthridin-6(5H)-one (2g) White solid, mp:
1
07–308 °C; H NMR (600 MHz, DMSO-d ): d 11.46 (br, 1H), 8.31–8.28 (m,
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H), 7.76 (s, 1H), 7.34 (t, J = 8.4 Hz, 1H), 6.91 (s, 1H), 3.88 (s, 3H), 3.81 (s, 3H);
C NMR (150 MHz, DMSO-d ): d 165.3 (d, J = 246.0 Hz), 160.3, 151.6, 145.4,
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137.6 (d, J = 10.5 Hz), 132.2, 131.0 (d, J = 10.5 Hz), 121.6, 114.8 (d,
J = 22.5 Hz), 109.7, 108.5 (d, J = 24.0 Hz), 106.2, 99.1, 56.4, 55.7.
2
,3-Dimethoxy-9-(trifluoromethyl)phenanthridin-6(5H)-one (2h) Yellow solid,
1
mp: 328–330 °C; H NMR (600 MHz, DMSO-d ): d 11.72 (br, 1H), 8.83 (s, 1H),
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.45 (d, J = 7.8 Hz, 1H), 7.94 (s, 1H), 7.82 (dd, J = 8.4, 1.2 Hz, 1H), 6.96 (s, 1H),
123