The Journal of Organic Chemistry
Page 12 of 22
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Hz, 1H), 8.56 (d, J = 7.6 Hz, 1H), 8.07 (d, J = 8.4 Hz, 1H), 7.96 (d, J = 8.8 Hz, 1H), 7.74–7.64 (m,
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C
H), 7.24 (t, J = 6.6 Hz, 1H), 4.85 (s, 1H), 3.68 (t, J = 5.0 Hz, 2H), 3.52 (t, J = 7.6 Hz, 2H), 2.09–
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.02 (m, 2H). C{ H} NMR (100 MHz, DMSO-d ) δ (ppm) 150.8, 149.1, 146.3, 144.6, 130.7,
29.4, 129.0, 128.7, 126.1, 122.6, 121.3, 117.8, 113.4, 60.7, 33.0, 30.8. HRMS (ESI) m/z calcd for
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17
H
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N
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O [M+H] 278.1288, found 278.1290.
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-(9-Methylpyrido[2',1':2,3]imidazo[4,5-c]quinolin-6-yl)propan-1-ol (3b). White solid (41.3 mg,
o
1
1% yield). mp 198−200 C. H NMR (400 MHz, DMSO-d
.0 Hz, 1H), 8.05 (d, J = 8.4 Hz, 1H), 7.84 (d, J = 9.2 Hz, 1H), 7.73 (t, J = 7.4 Hz, 1H), 7.64 (t, J
7.4 Hz, 1H), 7.57 (d, J = 9.2 Hz, 1H), 5.01 (s, 1H), 3.69 (t, J = 5.8 Hz, 2H), 3.51 (t, J = 7.8 Hz,
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) δ (ppm) 8.93 (s, 1H), 8.53 (d, J =
=
13
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2
1
1
3
H), 2.43 (s, 3H), 2.07–2.00 (m, 2H). C{ H} NMR (100 MHz, DMSO-d
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) δ (ppm) 150.8, 148.2,
46.3, 144.3, 133.5, 128.8, 128.6, 126.7, 126.0, 122.8, 122.6, 121.4, 121.1, 117.1, 60.6, 32.9, 30.9,
+
+
8.2. HRMS (ESI) m/z calcd for C18
18 3
H N O [M+H] 292.1444, found 292.1448.
-(10-Methylpyrido[2',1':2,3]imidazo[4,5-c]quinolin-6-yl)propan-1-ol (3c). White solid (44.3 mg,
o
1
76% yield). mp 225−227 C. H NMR (400 MHz, CDCl
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) δ (ppm) 8.92 (d, J = 5.2 Hz, 1H), 8.71
(d, J = 7.6 Hz, 1H), 8.48 (d, J = 7.2 Hz, 1H), 7.85–7.73 (m, 3H), 7.09 (d, J = 4.8 Hz, 1H), 5.32 (s,
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1H), 3.91–3.89 (m, 4H), 2.61 (s, 3H), 2.33–2.27 (m, 2H). C{ H} NMR (100 MHz, DMSO-d
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) δ
(ppm) 150.4, 149.8, 146.7, 144.3, 144.3, 142.1, 128.8, 128.7, 128.5, 126.1, 122.7, 121.3, 121.2,
+
+
18 3
116.0, 60.7, 32.7, 30.9, 21.6. HRMS (ESI) m/z calcd for C18H N O [M+H] 292.1444, found
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92.1448.
-(11-Methylpyrido[2',1':2,3]imidazo[4,5-c]quinolin-6-yl)propan-1-ol (3d). White solid (43.1 mg,
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o
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7
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4% yield). mp 179−181 C. H NMR (400 MHz, DMSO-d ) δ (ppm) 8.95 (d, J = 6.8 Hz, 1H),
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.56 (d, J = 7.6 Hz, 1H), 8.06 (d, J = 8.0 Hz, 1H), 7.73 (t, J = 7.2 Hz, 1H), 7.64 (t, J = 7.4 Hz, 1H),
.52 (d, J = 6.8 Hz, 1H), 7.13 (t, J = 6.8 Hz, 1H), 3.67 (t, J = 6.0 Hz, 2H), 3.48 (t, J = 7.8 Hz, 2H),
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.69 (s, 3H), 2.07–2.00 (m, 2H). C{ H} NMR (100 MHz, DMSO-d
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) δ (ppm) 150.7, 149.6,
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45.9, 144.3, 129.0, 128.7, 127.3, 126.9, 126.1, 122.7, 121.8, 121.4, 113.3, 60.7, 32.8, 30.8, 17.7.
+
+
HRMS (ESI) m/z calcd for C18
H
18
N
3
O [M+H] 292.1444, found 292.1448.
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-(10-Methoxypyrido[2',1':2,3]imidazo[4,5-c]quinolin-6-yl)propan-1-ol (3e). White solid (46.1
o
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mg, 75% yield). mp 201−203 C. H NMR (400 MHz, DMSO-d
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) δ (ppm) 8.95 (d, J = 7.2 Hz,
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H), 8.50 (d, J = 7.6 Hz, 1H), 8.05 (d, J = 8.0 Hz, 1H), 7.71 (t, J = 6.8 Hz, 1H), 7.62 (t, J = 6.8 Hz,
H), 7.31 (s, 1H), 6.90 (d, J = 6.0 Hz, 1H), 4.85 (s, 1H), 3.97 (s, 3H), 3.66 (t, J = 5.8 Hz, 2H), 3.46
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