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provide 8-methoxy-10-oxa-5,14b-diazaindeno [1,2,3-g,h]tetra- MHz, DMSO) d 174.9, 150.6, 143.4, 135.8, 134.0, 132.1, 131.5,
phene 9b as a yellow solid (41 mg, 95% yield), mp 173.5– 129.7, 128.9, 128.8, 128.1, 128.0, 123.3, 122.8 ppm.
ꢀ
1
3
1
8
74.4 C. H NMR (400 MHz, CDCl ) d 8.33 (d, J ¼ 8.0 Hz, 1H),
7H-7l -Benzo[4,5]iodolo[2,3-c]quinolin-7-yl
.24 (d, J ¼ 8.6 Hz, 1H), 8.02 (dd, J ¼ 17.2, 8.0 Hz, 2H), 7.75 (d, J uoromethanesulfonate (1g). To a stirred solution of 3-iodo-4-
7.3 Hz, 1H), 7.58 (t, J ¼ 7.8 Hz, 1H), 7.44 (t, J ¼ 7.5 Hz, 1H), phenylquinoline 1g–l (2.0 g, 6.04 mol) in anhydrous DCM (20
.32 (t, J ¼ 7.6 Hz, 1H), 7.27–7.21 (m, 1H), 6.92 (d, J ¼ 10.1 Hz, mL) was added TfOH (1.60 mL, 3.0 equiv.) and followed by the
tri-
3
¼
7
2
1
1
1
3
1
3
H), 3.93 (s, 3H) ppm. C NMR (100 MHz, CDCl
48.0, 139.5, 132.8, 131.2, 130.3, 129.1, 126.3, 125.8, 125.1, was stirred for 2 h at rt before DCM was removed by rotary
24.6, 121.6, 119.2, 118.1, 116.7, 114.8, 114.0, 113.6, 112.4, evaporation. Et O (20 mL) was added to the remained solid. The
02.2, 55.8 ppm. HRMS (ESI) m/z calcd for C H N O [M + H] : mixture was stirred for 30 min, and then ltered. The obtained
3
) d 163.3, 158.1, slow addition of m-CPBA (85%, 1.84 g, 1.5 equiv.). The solution
2
+
2
2
15 2 2
39.1128, found: 339.1122.
solid was washed with Et O three times and dried in high vacuo
to provide 1g (2.43 g, 84% yield) as a yellow solid. H NMR (400
2
1
MHz, DMSO) d 9.53 (s, 1H), 9.14 (d, J ¼ 7.9 Hz, 1H), 9.09 (d, J ¼
The general synthesis of heterocyclic iodoniums 1
8
.8 Hz, 1H), 8.45 (d, J ¼ 7.6 Hz, 1H), 8.30 (d, J ¼ 7.9 Hz, 1H), 8.03
13
All the synthetic heterocyclic idoniums are reported in our (t, J ¼ 7.6 Hz, 2H), 7.97–7.86 (m, 2H) ppm. C NMR (100 MHz,
previous work, and they are prepared conveniently using re- DMSO) d 148.6, 147.9, 144.8, 141.2, 132.4, 132.3, 131.2, 131.1,
10,18
ported procedure.
1-Oxo-11H-benzo[b]chromeno[2,3-d]iodol-10-ium triate
131.1, 131.0, 130.6, 129.1, 126.4, 124.2, 123.9, 117.7 ppm.
3
1
9-Methyl-7H-7l -benzo[4,5]iodolo[2,3-c]quinolin-7-yl
tri-
1
1
(
1a). H NMR (400 MHz, DMSO) d 8.50–8.35 (m, 2H), 8.22 (dd, J uoromethanesulfonate (1h). H NMR (400 MHz, DMSO) d 9.48
¼
7.9, 1.4 Hz, 1H), 8.11–8.02 (m, 2H), 8.01–7.91 (m, 2H), 7.72 (t, J (s, 1H), 9.04 (d, J ¼ 8.4 Hz, 1H), 8.99 (d, J ¼ 8.4 Hz, 1H), 8.28 (dd,
13
¼
7.5 Hz, 1H) ppm. C NMR (100 MHz, DMSO) d 172.3, 164.1, J ¼ 8.4, 1.0 Hz, 1H), 8.20 (s, 1H), 8.02 (dd, J ¼ 11.3, 4.0 Hz, 1H),
1
3
1
1
55.2, 135.9, 135.2, 134.7, 131.4, 131.3, 128.9, 127.0, 125.2, 7.95–7.88 (m, 1H), 7.81 (d, J ¼ 7.5 Hz, 1H), 2.56 (s, 3H) ppm.
22.5, 119.6, 118.8, 108.4 ppm. NMR (100 MHz, DMSO) d 148.4, 147.7, 144.8, 143.2, 138.4,
-Methyl-11-oxo-10l -benzo[b]chromeno[2,3-d]iodol-10(11H)-yl 132.0, 131.9, 131.1, 131.0, 130.5, 129.0, 126.2, 124.2, 124.0,
C
3
8
1
triuoromethanesulfonate (1b). H NMR (400 MHz, DMSO) d 8.31 122.4, 119.1, 117.0, 21.2 ppm.
3
(
(
7
d, J ¼ 8.0 Hz, 1H), 8.23 (s, 1H), 8.21 (dd, J ¼ 8.0, 1.5 Hz, 1H), 8.03
9-Chloro-7H-7l -benzo[4,5]iodolo[2,3-c]quinolin-7-yl
tri-
1
ddd, J ¼ 8.6, 7.1, 1.7 Hz, 1H), 7.95 (d, J ¼ 7.9 Hz, 1H), 7.88 (d, J ¼ uoromethanesulfonate (1i). H NMR (400 MHz, DMSO) d 9.46
13
.7 Hz, 1H), 7.74–7.68 (m, 1H), 2.58 (s, 3H) ppm. C NMR (100 (s, 1H), 9.03 (d, J ¼ 8.9 Hz, 1H), 8.94 (d, J ¼ 8.5 Hz, 1H), 8.38 (d, J
MHz, DMSO) d 172.2, 164.0, 155.1, 146.2, 135.8, 132.5, 132.2, 131.2, ¼ 2.2 Hz, 1H), 8.27 (dd, J ¼ 8.4, 1.1 Hz, 1H), 8.05–7.97 (m, 2H),
1
3
1
28.5, 126.9, 125.2, 122.4, 119.7, 118.7, 107.4, 21.8 ppm.
7.90 (ddd, J ¼ 8.4, 7.0, 1.3 Hz, 1H) ppm. C NMR (100 MHz,
3
8
-Chloro-11-oxo-10l -benzo[b]chromeno[2,3-d]iodol-10(11H)-yl DMSO) d 148.4, 147.9, 143.8, 140.1, 136.2, 133.2, 131.4, 130.7,
1
triuoromethanesulfonate (1c). H NMR (400 MHz, DMSO) d 8.42 130.5, 129.3, 126.2, 124.9, 124.1, 122.4, 119.1, 118.2 ppm.
3
(
1
8
d, J ¼ 1.8 Hz, 1H), 8.39 (d, J ¼ 8.4 Hz, 1H), 8.21 (dd, J ¼ 7.9, 1.2 Hz,
2-Fluoro-7H-7l -benzo[4,5]iodolo[2,3-c]quinolin-7-yl
tri-
1
H), 8.14 (dd, J ¼ 8.4, 1.8 Hz, 1H), 8.07–8.00 (m, 1H), 7.95 (d, J ¼ uoromethanesulfonate (1j). H NMR (400 MHz, DMSO) d 9.54
13
.3 Hz, 1H), 7.71 (t, J ¼ 7.5 Hz, 1H) ppm. C NMR (100 MHz, (d, J ¼ 3.4 Hz, 1H), 9.15 (dd, J ¼ 7.7, 2.7 Hz, 1H), 8.89–8.72 (m,
DMSO) d 172.2, 163.2, 155.1, 138.5, 136.0, 134.3, 131.9, 131.3, 1H), 8.46 (dd, J ¼ 8.1, 2.3 Hz, 1H), 8.40 (ddd, J ¼ 9.3, 6.0, 3.4 Hz,
1
3
1
30.9, 129.8, 128.5, 127.1, 125.3, 122.5, 120.1, 118.8, 109.1 ppm.
1H), 8.08–7.85 (m, 3H) ppm. C NMR (100 MHz, DMSO)
d 162.4, 159.9, 148.0, 145.3, 144.5, 144.4, 140.7, 133.7, 133.6,
3
8
-Fluoro-11-oxo-10l -benzo[b]chromeno[2,3-d]iodol-10(11H)-yl
1
triuoromethanesulfonate (1d). H NMR (400 MHz, DMSO) 132.4, 132.2, 131.2, 131.2, 127.0, 126.9, 123.7, 122.3, 121.2,
d 8.50–8.44 (m, 1H), 8.22 (ddd, J ¼ 8.0, 5.9, 2.3 Hz, 2H), 8.09–8.00 121.0, 119.1, 118.9, 108.8, 108.6 ppm.
13
1
(
m, 1H), 8.01–7.91 (m, 2H), 7.71 (dd, J ¼ 10.6, 4.3 Hz, 1H) ppm.
C
Benzo[4,5]iodolo[3,2-c]isoquinolin-11-ium triate (1k).
H
NMR (100 MHz, DMSO) d 172.1, 165.2, 163.2, 162.7, 155.2, 136.0, NMR (400 MHz, DMSO) d 9.73 (s, 1H), 8.59–8.51 (m, 2H), 8.43
1
32.1, 130.8, 130.7, 127.1, 125.3, 122.5, 120.3, 120.2, 112.0, 119.7, (dd, J ¼ 10.6, 8.3 Hz, 2H), 8.18–8.07 (m, 1H), 7.97 (t, J ¼ 7.5 Hz,
13
119.3, 119.0, 118.8, 108.5 ppm.
2H), 7.90–7.81 (m, 1H) ppm. C NMR (100 MHz, DMSO)
d 155.6, 153.4, 140.6, 134.5, 133.6, 132.6, 131.1, 130.7, 130.1,
3
7
-Fluoro-11-oxo-10l -benzo[b]chromeno[2,3-d]iodol-10(11H)-yl
1
triuoromethanesulfonate (1e). H NMR (400 MHz, DMSO) d 8.50– 129.5, 129.3, 126.7, 122.3, 121.4, 120.5 ppm.
3
8
8
8
.43 (m, 1H), 8.39 (dd, J ¼ 5.6, 2.7 Hz, 1H), 8.23 (d, J ¼ 7.9 Hz, 1H),
9-Methyl-11H-11l -benzo[4,5]iodolo[3,2-c]isoquinolin-11-yl
1
.06 (t, J ¼ 7.5 Hz, 1H), 7.95 (dd, J ¼ 8.2, 2.3 Hz, 1H), 7.87 (ddd, J ¼ triuoromethanesulfonate (1l). H NMR (400 MHz, DMSO)
13
.9, 6.2, 2.7 Hz, 1H), 7.73 (t, J ¼ 6.2 Hz, 1H) ppm. C NMR (100 d 9.58 (s, 1H), 8.40 (d, J ¼ 8.2 Hz, 1H), 8.34 (d, J ¼ 8.1 Hz, 1H),
MHz, DMSO) d 172.3, 164.9, 163.0, 162.4, 155.1, 137.5, 137.4, 136.1, 8.24 (d, J ¼ 7.9 Hz, 1H), 8.07 (s, 1H), 8.06–8.01 (m, 1H), 7.89 (t, J
1
3
1
1
33.7, 133.6, 127.1, 125.3, 122.4, 122.3, 122.0, 118.8, 115.9, 115.7, ¼ 7.3 Hz, 1H), 7.66 (d, J ¼ 7.8 Hz, 1H), 2.51 (s, 3H) ppm.
C
13.6, 109.7 ppm.
1
NMR (100 MHz, DMSO) d 155.4, 153.2, 143.2, 137.8, 134.3,
133.5, 132.0, 130.2, 129.8, 129.4, 129.2, 128.6, 126.4, 121.2,
3
1-Oxo-10l -benzo[b]thiochromeno[2,3-d]iodol-10(11H)-
yl triuoromethanesulfonate (1f). H NMR (400 MHz, DMSO) 119.5, 21.5 ppm.
1
3
d 8.46 (t, J ¼ 9.1 Hz, 2H), 8.34 (d, J ¼ 7.8 Hz, 1H), 8.22 (d, J ¼
6-Oxo-7l -benzo[b]chromeno[4,3-d]iodol-7(6H)-yl
tri-
1
8
.1 Hz, 1H), 8.04 (d, J ¼ 7.6 Hz, 1H), 8.01–7.96 (m, 1H), 7.92 (t, uoromethanesulfonate (1m). H NMR (400 MHz, DMSO)
1
3
J ¼ 7.9 Hz, 1H), 7.87 (t, J ¼ 7.6 Hz, 1H) ppm. C NMR (100 d 9.12–9.02 (m, 1H), 8.81 (d, J ¼ 7.5 Hz, 1H), 8.53 (dd, J ¼ 8.3,
33178 | RSC Adv., 2019, 9, 33170–33179
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