F
P. Gandeepan et al.
Special Topic
Synthesis
13C NMR (100 MHz, CDCl3): δ = 176.5 (C=O), 140.4 (C), 133.5 (C), 130.1
(C), 127.8 (CH), 126.9 (CH), 126.3 (CH), 126.0 (C), 124.2 (CH), 123.9
(CH), 104.9 (CH), 35.4 (CH2).
13C NMR (100 MHz, DMSO-d6): δ = 161.3 (C=O), 136.3 (C), 133.7 (C),
133.6 (CH), 132.8 (CH), 129.3 (CH), 128.1 (CH), 126.4 (C), 126.4 (CH),
123.7 (CH), 120.2 (C), 118.8 (CH), 115.1 (C).
HRMS (EI): m/z [M]+ calcd for C12H9NO: 183.0684; found: 183.0679.
HRMS (EI): m/z [M]+ calcd for C13H8BrNO: 272.9789; found: 272.9784.
3,4-Dihydroquinolin-2(1H)-one (4a)
2-Fluorophenanthridin-6(5H)-one (6e)
Yield: 15 mg (20%); pale yellow solid; mp 165–167 °C.
Yield: 88 mg (83%); pale yellow solid; mp 309–311 °C.
IR (KBr): 2923, 2854, 1681, 1388, 748 cm–1
.
IR (KBr): 2861, 1689, 1504, 1265, 1149, 879, 763 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.52 (s, NH), 7.19-7.15 (m, 2 H), 6.99 (t,
J = 7.2 Hz, 1 H), 6.78 (d, J = 7.6 Hz, 1 H), 2.97 (t, J = 7.2 Hz, 2 H), 2.64 (t,
J = 7.2 Hz, 2 H).
1H NMR (400 MHz, DMSO-d6): δ = 11.71 (s, NH), 8.48 (d, J = 8.4 Hz, 1
H), 8.30 (d, J = 8.0 Hz, 1 H), 8.23 (d, J = 7.6 Hz, 1 H), 7.83 (t, J = 8.0 Hz, 1
H), 7.65 (t, J = 7.6 Hz, 1 H), 7.35 (d, J = 6.0 Hz, 2 H).
13C NMR (100 MHz, CDCl3): δ = 172.2 (C=O), 137.3 (C), 128.2 (CH),
127.7 (CH), 123.9 (C), 123.4 (CH), 115.6 (CH), 29.9 (CH2), 25.5 (CH2).
HRMS (EI): m/z [M]+ calcd for C9H9NO: 147.0684; found: 147.0679
13C NMR (100 MHz, DMSO-d6): δ = 160.4 (C=O), 157.8 (d, JC,F = 235.8
Hz, C), 133.5 (d, JC,F = 3.0 Hz, C), 133.1 (d, JC,F = 1.4 Hz, C), 132.8 (CH),
128.5 (CH), 127.4 (CH), 125.8 (C), 123.1 (CH), 118.8 (d, JC,F = 8.3 Hz, C),
117.7 (d, JC,F = 8.4 Hz, CH), 117.1 (d, JC,F = 23.8 Hz, CH), 109.1 (d,
JC,F = 23.9 Hz, CH).
2-Methylphenanthridin-6(5H)-one (6a)
HRMS (EI): m/z [M]+ calcd for C13H8FNO: 213.0590; found: 213.0584.
Yield: 90 mg (86%); pale yellow solid; mp 263–266 °C.
IR (KBr): 1658, 1612, 1558, 1504, 1465, 1365, 771 cm–1
.
2-Phenylphenanthridin-6(5H)-one (6f)
1H NMR (400 MHz, CDCl3): δ = 10.89 (s, NH), 8.57 (d, J = 7.0 Hz, 1 H),
8.27 (d, J = 8.0 Hz, 1 H), 7.99 (s, 1 H), 7.77 (t, J = 8.0 Hz, 1 H), 7.59 (t,
J = 7.2 Hz, 1 H), 7.30–7.26 (m, 2 H), 2.46 (s, 3 H).
Yield: 93 mg (86%); pale yellow solid; mp 321–323 °C.
IR (KBr): 1673, 1604, 1349, 1249, 871, 748 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.75 (s, NH), 8.71 (d, J = 8.0 Hz, 1
H), 8.63 (s, 1 H), 8.32 (d, J = 7.6 Hz, 1 H), 7.88–7.80 (m, 4 H), 7.68 (t,
J = 7.6 Hz, 1 H), 7.49–7.36 (m, 4 H).
13C NMR (100 MHz, CDCl3): δ = 162.8 (C=O), 134.7 (C), 133.8 (C), 132.6
(CH), 132.3 (C), 130.6 (CH), 128.2 (CH), 127.6 (CH), 125.7 (C), 122.7
(CH), 121.9 (CH), 118.4 (C), 116.5 (CH), 21.2 (CH3).
13C NMR (100 MHz, DMSO-d6): δ = 161.4 (C=O), 140.3 (C), 136.6 (C),
134.9 (2 × C), 133.4 (CH), 129.5 (2 × CH), 128.8 (CH), 128.7 (CH), 128.1
(CH), 127.8 (CH), 127.4 (2 × CH), 126.4 (C), 123.7 (CH), 121.8 (CH),
118.6 (C), 117.4 (CH).
HRMS (EI): m/z [M]+ calcd for C14H11NO: 209.0841; found: 209.0835.
2-Methoxyphenanthridin-6(5H)-one (6b)
Yield: 92 mg (82%); pale yellow solid; mp 227–230 °C.
HRMS (EI): m/z [M]+ calcd for C19H13NO: 271.0997; found: 271.0992.
IR (KBr): 1666, 1604, 1504, 1465, 1365, 1272, 1218, 1303, 763 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.55 (s, NH), 8.51 (d, J = 8.0 Hz, 1
H), 8.30 (d, J = 8.0 Hz,1 H), 7.84–7.79 (m, 2 H), 7.61 (t, J = 7.2 Hz, 1 H),
7.28 (d, J = 9.2 Hz, 1 H), 7.11 (dd, J = 9.2, 2.4 Hz, 1 H), 3.85 (s, 3 H).
13C NMR (100 MHz, DMSO-d6): δ = 161.0 (C=O), 155.4 (C), 134.7 (C),
133.2 (CH), 131.3 (C), 128.6 (CH), 128.1 (CH), 126.5 (C), 123.6 (CH),
118.9 (C), 118.4 (CH), 117.9 (CH), 106.8 (CH), 56.3 (CH3).
Ethyl 6-Oxo-5,6-dihydrophenanthridine-2-carboxylate (6g)
Yield: 104 mg (78%); pale yellow solid; mp 262–265 °C.
IR (KBr): 1673, 1612, 1558, 1357, 1249, 1110, 863 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.98 (s, NH), 8.84 (s, 1 H), 8.50 (d,
J = 8.0 Hz, 1 H), 8.30 (d, J = 8.0 Hz, 1 H), 8.01 (dd, J = 8.4 Hz, J = 0.8 Hz,
1 H), 7.87 (t, J = 8.4 Hz, 1 H), 7.67 (t, J = 7.6 Hz, 1 H), 7.41 (d, J = 8.4 Hz,
1 H), 4.33 (q, J = 7.2 Hz, 2 H), 1.34 (t, J = 7.2 Hz, 3 H).
HRMS (EI): m/z [M]+ calcd for C14H11NO2: 225.0790; found: 225.0784.
13C NMR (100 MHz, DMSO-d6): δ = 166.0 (C=O), 161 (C=O), 140.7 (C),
134.1 (C), 133.9 (CH), 130.7 (CH), 129.2 (CH), 128.2 (CH), 126.3 (C),
125.3 (CH), 124.3 (C), 123.4 (CH), 117.9 (C), 117.0 (CH), 61.4 (CH2),
14.9 (CH3).
2-Chlorophenanthridin-6(5H)-one (6c)
Yield: 90 mg (79%); pale yellow solid; mp 340–342 °C.
IR (KBr): 2861, 1689, 1612, 1473, 1365, 879, 809, 771 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.78 (s, NH), 8.53 (d, J = 8.0 Hz, 1
H), 8.44 (s, 1 H), 8.29 (d, J = 7.6 Hz, 1 H), 7.84 (t, J = 7.2 Hz, 1 H), 7.66 (t,
J = 7.6 Hz, 1 H), 7.51 (dd, J = 8.4, 2.0 Hz, 1 H), 7.34 (d, J = 8.8 Hz, 1 H).
HRMS (EI): m/z [M]+ calcd for C16H13NO3: 267.0895; found: 267.0890.
Phenanthridin-6(5H)-one (6h)
13C NMR (100 MHz, DMSO-d6): δ = 161.3 (C=O), 136.0 (C), 133.8 (C),
133.6 (CH), 130.1 (CH), 129.3 (CH), 128.1 (CH), 127.2 (C), 126.4 (C),
123.8 (CH), 123.5 (CH), 119.8 (C), 118.5 (CH).
Yield: 77 mg (79%); pale yellow solid; mp 290–291 °C.
IR (KBr): 1666, 1544, 1457, 1349, 717 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.47 (s, NH), 8.29 (t, J = 8.0 Hz, 2
H), 8.17 (d, J = 8.0 Hz, 1 H), 7.73 (t, J = 8.0 Hz, 1 H), 7.51 (t, J = 8.0 Hz, 1
H), 7.37–730 (m, 2 H), 7.17 (t, J = 7.6 Hz, 1 H).
13C NMR (100 MHz, DMSO-d6): δ = 161.3 (C=O), 136.3 (C), 134.3 (C),
132.5 (CH), 129.2 (CH), 127.5 (2 CH), 125.6 (C), 122.6 (CH), 122.2
(CH), 122.0 (CH), 117.7 (C), 116.3 (CH).
HRMS (EI): m/z [M]+ calcd for C13H8ClNO: 229.0294; found: 229.0289.
2-Bromophenanthridin-6(5H)-one (6d)
Yield: 98 mg (72%); pale yellow solid; mp 329–331 °C.
IR (KBr): 1673, 1349, 871, 763 cm–1
.
1H NMR (400 MHz, DMSO-d6): δ = 11.77 (s, NH), 8.56 (s, 1 H), 8.53 (d,
J = 8.0 Hz, 1 H), 8.29 (d, J = 8.0 Hz, 1 H), 7.83 (t, J = 7.6 Hz, 1 H), 7.67–
7.61 (m, 2 H), 7.28 (d, J = 8.4 Hz, 1 H).
HRMS (EI): m/z [M]+ calcd for C13H9NO: 195.0684; found: 195.0679.
3-Methylphenanthridin-6(5H)-one (6i)
Yield: 91 mg (87%); pale yellow solid; mp 248–250 °C.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–H