Paper
Organic & Biomolecular Chemistry
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607, 1507, 1408, 1 385 1333, 1289, 1217, 1152, 1109, 1015, mp 390–392 °C; I.R. (A.T.R.) 3014, 2768, 1671, 1634, 1608,
008, 956 cm− . H NMR (400 MHz, DMSO-d ) δ = 12.29 (s, 1H, 1579, 1504, 1493, 1383, 1222, 1191, 1154, 1131, 1103, 1079,
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1
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NH), 11.39 (s, 1H, OH), 8.25 (d, J = 5.0 Hz, 2H, ArH), 7.91 (t, J = 954 cm− . H NMR (400 MHz, DMSO-d
1
1
) δ = 12.41 (s, 1H, OH),
.0 Hz, 3H, ArH), 7.71–7.68 (m, 2H, ArH), 7.56 (d, J = 5.0 Hz, 11.49 (s, 1H, NH), 7.95 (d, J = 8.0 Hz, 1H, ArH), 7.81 (t, J = 8.0
H, ArH), 7.52 (t, J = 10.0 Hz, 2H, ArH), 7.46 (d, J = 10.0 Hz, Hz, 2H, ArH), 7.59–7.52 (m, 6H, ArH), 7.46 (t, J = 8.0 Hz, 1H,
H, ArH), 7.39 (t, J = 5.0 Hz, 1H, ArH), 7.29 (t, J = 5.0 Hz, 1H, ArH), 7.34 (t, J = 8.0 Hz, 1H. ArH), 7.26 (d, J = 8.0 Hz, 2H, ArH),
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ArH); C NMR (100 MHz, DMSO-d ) δ = 193.1, 163.2, 162.1, 6.99 (s, 1H, vCH), 6.87 (t, J = 8.0 Hz, 2H, ArH), 2.30 (s, 3H,
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53.3, 147.0, 145.5, 141.5, 139.1, 138.6, 135.2, 134.0, 133.4, CH3); C NMR (100 MHz, DMSO-d ) δ = 177.5, 162.7, 161.4,
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32.9, 129.3, 129.4, 127.7, 124.5, 124.2, 123.9, 123.8, 120.9, 153.2, 151.6, 140.3, 138.7, 138.2, 133.1, 131.7, 131.6, 129.9,
16.8, 116.6, 116.5, 113.7, 107.4, 98.0 ppm. HRMS (m/z) 129.3, 128.9, 127.4, 125.8, 124.8, 124.4, 118.1, 117.8, 116.9,
+
(ESI-TOF) calcd for C H N O [M + H ] 501.1081, found 116.8, 111.1, 107.6, 102.1, 101.1, 21.3 ppm. HRMS (m/z)
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0
16 2 6
+
5
01.1138.
(ESI-TOF) calcd for C33
5
H21NO [M + H ], 512.1492, found
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-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-phenyl-5a,11a-dihydro- 511.1462.
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9
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H-naphtho[2,3-g]indole-6,11-dione (14). White solid (206 mg =
9-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-8-(4-methoxy-phenyl)-
5%), 295–297 °C. I.R. 3455, 3302, 1698, 1659, 1612, 1574, 2-phenyl-7H-pyrano[2,3-e]indol-4-one (4m). White solid
496, 1488, 1457, 1330, 1291, 1228, 1205, 1109, 1005, (396 mg, 75%), mp 328–330 °C; I.R. (A.T.R.) 3034, 2881, 1669,
59 cm− . H NMR (400 MHz, DMSO-d ) δ = 11.82 (s, 1H, NH), 1607, 1565, 1504, 1494, 1475, 1380, 1246, 1222, 1178, 1152,
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.26 (dd, J = 1.2, 8.0 Hz, 2H, ArH), 7.95 (d, J = 8.0 Hz, 3H, ArH), 1129, 1078, 1030, 986 cm− . H NMR (400 MHz, DMSO-d
1 1
) δ =
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.81 (d, J = 8.0 Hz, 1H, ArH), 7.71 (d, J = 8.0 Hz, 4H, ArH), 7.62 12.37 (s, 1H, OH), 11.48 (s, 1H, NH), 7.96 (d, J = 4.0 Hz, 1H,
(
(
d, J = 8.0 Hz, 1H, ArH), 7.46 (t, J = 8.0 Hz, 3H, ArH), 7.35–7.28 ArH), 7.80 (t, J = 8.0 Hz, 2H, ArH), 7.60–7.53 (m, 6H, ArH), 7.47
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m, 3H, ArH); C NMR (100 MHz, DMSO-d
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) δ = 184.4, 182.7, (t, J = 8.0 Hz, 1H, ArH), 7.34 (t, J = 8.0 Hz, 1H, ArH), 7.04 (d, J =
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62.8, 161.8, 152.8, 144.1, 135.8, 134.4, 134.3, 133.4, 133.3, 8.0 Hz, 2H, ArH), 6.99 (s, 1H, vCH), 6.87 (t, J = 8.0 Hz, 2H,
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32.6, 128.6, 127.8, 126.8, 126.2, 125.6, 124.6, 124.1, 123.8, ArH), 3.76 (s, 3H, OCH3); C NMR (100 MHz, DMSO-d ) δ =
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18.3, 117.2, 116.3, 116.1, 115.9, 115.7, 104.6, 97.5 ppm. 177.5, 162.8, 162.7, 161.4, 159.7, 153.2, 151.5, 140.3, 138.7,
+
HRMS (m/z) (ESI-TOF) calcd for C31
found 484.1221.
H
19NO
5
[M + H ] 484.1179, 133.1, 131.7, 131.6, 128.9, 128.8, 125.8, 124.8, 124.5,
124.4, 118.2, 117.6, 116.9, 116.8, 114.8, 111.1, 107.5, 101.5,
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-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-methyl-8-p-tolylpyrano 100.7, 55.6 ppm; HRMS (m/z) (ESI-TOF) calcd for C33H21NO
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+
[
2,3-e]indol-4(7H)-one (4j). White solid (359 mg, 80%), mp [M + H ], 528.1442, found 528.1505.
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90–392 °C; I.R. (A.T.R.) 3629, 3463, 3238, 2921, 1679, 1642,
9-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-8-(4-nitro-phenyl)-2-
608, 1575, 1544, 1502, 1476, 1412, 1392, 1378, 1229, 1204, phenyl-7H-pyrano[2,3-e]indol-4-one (4n). Grey solid (429 mg,
−1 1
122, 1074, 1027, 968 cm . H NMR (400 MHz, DMSO-d
6
): δ = 79%), mp 392–394 °C; I.R. (A.T.R.) 3362, 3207, 1676, 1594,
2.28 (s, 1H, OH), 11.17 (s, 1H, NH), 7.94 (d, J = 4.0 Hz, 1H, 1563, 1513, 1496, 1473, 1412, 1386, 1339, 1190, 1159, 1128,
ArH), 7.72 (t, J = 8.0 Hz, 2H, ArH), 7.56–7.48 (m, 4H, ArH), 7.40 1105, 1077, 964 cm− . H NMR (400 MHz, DMSO-d
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) δ = 12.76
t, J = 8.0 Hz, 1H, ArH), 7.25 (d, J = 4.0 Hz, 2H, ArH), 6.12 (s, (s, 1H, OH), 11.69 (s, 1H, NH), 8.34 (d, J = 8.0 Hz, 2H, ArH), 7.95
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(
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H, vCH), 2.31 (s, 3H, CH ), 1.92 (s, 3H, CH ); C NMR (d, J = 8.0 Hz, 1H, ArH), 7.90–7.87 (m, 3H, ArH), 7.82 (t, J = 8.0
3 3
(
100 MHz, DMSO-d
6
) δ = 177.3, 164.6, 162.6, 153.1, 151.8, Hz, 1H, ArH), 7.65–7.59 (m, 2H, ArH), 7.53 (d, J = 8.0 Hz, 2H,
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8
C
39.8, 138.4, 138.0, 132.7, 129.8, 129.6, 127.2, 124.8, 124.5, ArH), 7.46 (t, J = 8.0 Hz, 1H, ArH), 7.34 (t, J = 8.0 Hz, 1H, ArH),
24.1, 119.7, 117.7, 117.6, 116.7, 116.2, 110.6, 110.3, 100.4, 7.01 (s, 1H, vCH), 6.88 (t, J = 8.0 Hz, 2H, ArH); C NMR
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8.9, 21.3, 19.6 ppm. HRMS (m/z) (ESI-TOF) calcd for (100 MHz, DMSO-d
6
) δ = 177.3, 162.6, 161.6, 153.3, 151.9, 147.0,
+
28
H
19NO
5
[M + H ], 450.1336, found 450.1398.
140.9, 138.5, 136.1, 133.3, 131.7, 131.6, 129.6, 128.9, 128.3,
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-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2,8-diphenyl-7H-pyrano 126.7, 125.8, 124.8, 124.7, 124.5, 119.2, 118.1, 117.1, 116.8,
[
2,3-e]indol-4-one (4k). White solid (368 mg, 74%), mp 111.5, 107.9, 105.5, 99.8 ppm. HRMS (m/z) (ESI-TOF) calcd for
94–396 °C; I.R. (A.T.R.) 3016, 2206, 1688, 1634, 1601, 1582, [M + H ], C32H N O 543.1187, found 543.1277.
18 2 7
+
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563, 1471, 1406, 1386, 1221, 1193, 1158, 1131, 1079,
9-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-phenyl-2-p-tolyl-
54 cm− . H NMR (400 MHz, DMSO-d
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) δ = 12.48 (s, 1H, OH), 7H-pyrano[2,3-e]indol-4-one (4o). Brown solid (366 mg, 77%),
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1.54 (s, 1H, NH), 7.94 (d, J = 8.0 Hz, 1H, ArH), 7.84–7.78 (m, mp 380–382 °C; I.R. (A.T.R.) 3057, 1633, 1604, 1499, 1378,
H, ArH), 7.64–7.57 (m, 4H, ArH), 7.53 (d, J = 8.0 Hz, 2H, ArH), 1216, 1191, 1151, 1133, 1019, 995 cm− . H NMR (400 MHz,
.45 (t, J = 8.0 Hz, 3H, ArH), 7.37–7.32 (m, 2H, ArH), 6.99 (s, DMSO-d ) δ = 12.26 (s, 1H, OH), 11.38 (s, 1H, NH), 7.80–7.74
H, vCH), 6.87 (t, J = 8.0 Hz, 2H, ArH); C NMR (100 MHz, (m, 3H, ArH), 7.59 (t, J = 8.0 Hz, 2H, ArH), 7.55–7.49 (m, 4H,
1 1
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DMSO-d ) δ = 177.5, 162.9, 162.7, 161.5, 153.2, 151.7, 140.4, ArH), 7.27 (d, J = 8.0 Hz, 2H, ArH), 6.99 (s, 1H, ArH), 6.22 (s,
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38.6, 133.16, 132.1, 131.7, 129.3, 128.9, 127.5, 125.8, 124.86, 1H, vCH), 2.55 (s, 3H, CH
3 3
), 2.33 (s, 3H, CH ); C NMR
24.39, 118.1, 117.9, 116.9, 116.8, 116.7, 111.3, 107.6, (100 MHz, DMSO-d ) δ = 177.6, 167.9, 164.8, 162.2, 161.7,
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02.7, 100.5 ppm. HRMS (m/z) (ESI-TOF) calcd for C H NO
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151.7, 140.1, 137.9, 137.6, 132.1, 131.9, 129.8, 129.7, 129.4,
127.3, 126.2, 117.8, 117.6, 116.7, 111.1, 107.6, 103.5, 101.0,
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19
+
[M + H ], 498.1336, found 498.1395.
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-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-phenyl-8-p-tolyl-7H- 97.3, 21.2, 20.0 ppm. HRMS (m/z) (ESI-TOF) calcd for
+
pyrano[2,3-e]indol-4-one (4l). Pale yellow solid (399 mg, 78%), C H NO [M + H ], 476.1492, found 476.1551.
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0
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Org. Biomol. Chem.
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