Paper
NJC
1
(8a–l) were prepared in a similar manner but by replacing 740; H NMR (400 MHz, DMSO-d6): 3.72 (s, 3H), 3.80 (s, 3H),
malononitrile (2) with cyclohexadienone or dimedone (7).
4.94 (s, 1H), 6.62 (dd, 1H, J = 7.32 Hz, J = 1.83 Hz), 6.79 (br s, 2H),
6.85–6.93 (m, 3H), 7.06–7.10 (m, 1H), 7.20–7.22 (m, 1H), 7.29
(d, 1H, J = 7.93 Hz), 7.35 (d, 1H, J = 7.93 Hz); 13C NMR (100 MHz,
Spectral data for selected indolo-chromenes
2-Amino-4-(5-methoxy-1H-indol-3-yl)-4H-chromene-3-carbonitrile DMSO-d6): 32.23, 32.31, 55.64, 56.10, 109.83, 110.30, 118.12,
(5c). IR (cmÀ1, film): 3442, 3314, 2937, 2191, 1654, 1581, 1485, 1395, 118.58, 120.27, 120.74, 121.08, 123.92, 124.47, 125.55, 127.18,
1
1348, 1262, 1220, 1171, 1106, 1025, 839, 755, 606; H NMR (400 137.12, 137.79, 146.87, 159.98; HRMS (ESI, m/z) calcd for
MHz, CDCl3): 3.73 (s, 3H), 4.56 (br s, 2H), 5.02 (s, 1H), 6.77–6.82 C20H18N3O2: 332.1394 (MH)+; found: 332.1391.
(m, 2H), 6.97–7.03 (m, 2H), 7.08–7.11 (m, 2H), 7.16–7.18 (m, 1H),
2-Amino-7-hydroxy-4-(2-methyl-1H-indol-3-yl)-4H-chromene-
7.20–7.22 (m, 1H), 7.95 (br s, 1H); ESI-MS (m/z): 318.13 (MH)+; anal. 3-carbonitrile (5k). IR (cmÀ1, film): 3482, 3427, 3345, 2185,
calcd for C19H15N3O2: C, 71.91; H, 4.76; N, 13.24; found: C, 71.99; H, 1653, 1507, 1459, 1400, 1324, 1295, 1146, 1108, 1044, 851, 752;
4.87; N, 13.19.
1H NMR (400 MHz, DMSO-d6): 2.40 (s, 3H), 4.90 (s, 1H), 6.37–
2-Amino-4-(1H-indol-3-yl)-8-methoxy-4H-chromene-3-carbonitrile 6.39 (m, 2H), 6.62 (br s, 2H), 6.67–6.69 (m, 1H), 6.74–6.77
(5f). IR (cmÀ1, film): 3408, 3344, 2940, 2840, 2190, 1637, 1579, 1480, (m, 1H), 6.89–6.92 (m, 1H), 6.97 (d, 1H, J = 7.93 Hz), 7.20
1
1414, 1326, 1268, 1217, 1125, 1076, 950, 745; H NMR (400 MHz, (d, 1H, J = 7.93 Hz), 9.55 (br s, 1H), 10.75 (br s, 1H); HRMS (ESI,
DMSO-d6): 3.81 (s, 3H), 4.94 (s, 1H), 6.61 (dd, 1H, J = 7.32 Hz, m/z) calcd for C19H16N3O2: 318.1237 (MH)+; found: 318.1232.
J = 1.22 Hz), 6.78 (br s, 2H), 6.83–6.92 (m, 3H), 6.98–7.02 (m, 1H),
Spectral data for indolo-xanthenes
7.22–7.25 (m, 2H), 7.31 (d, 1H, J = 7.93 Hz), 10.88 (br s, 1H);
13C NMR (100 MHz, DMSO-d6): 32.54, 55.65, 56.23, 110.28, 111.64,
9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one (8a).
118.39, 118.69, 120.32, 120.75, 120.94, 122.92, 123.90, 124.49, IR (cmÀ1, film): 2922, 2877, 1641, 1484, 1455, 1374, 1330,
125.19, 136.83, 137.84, 146.86, 159.96; ESI-MS (m/z): 318.12 (MH)+. 1238, 1131, 1061, 993, 858, 762, 630; 1H NMR (400 MHz, CDCl3):
2-Amino-8-methoxy-4-(2-methyl-1H-indol-3-yl)-4H-chromene- 1.88–2.08 (m, 2H), 2.30–2.41 (m, 2H), 2.59–2.78 (m, 2H), 5.34
3-carbonitrile (5g). IR (cmÀ1, film): 3468, 3390, 3325, 2935, 2835, (s, 1H), 6.95–7.00 (m, 2H), 7.06–7.18 (m, 5H), 7.24–7.27 (m, 1H),
2195, 1655, 1583, 1459, 1399, 1278, 1213, 1187, 1078, 954, 748, 7.39 (d, 1H, J = 7.79 Hz), 8.04 (br s, 1H); 13C NMR (100 MHz,
1
627; H NMR (400 MHz, DMSO-d6): 2.40 (s, 3H), 3.80 (s, 3H), CDCl3): 20.49, 27.93, 29.52, 37.15, 111.28, 114.14, 116.26,
5.00 (s, 1H), 6.44–6.46 (m, 1H), 6.70 (br s, 2H), 6.74–6.78 (m, 1H), 119.18, 119.47, 120.65, 121.69, 122.60, 125.00, 125.41, 125.83,
6.85–6.92 (m, 3H), 6.99 (d, 1H, J = 7.93 Hz), 7.19 (d, 1H, 127.50, 130.20, 136.58, 149.72, 166.13, 197.45; HRMS (ESI, m/z)
J = 7.93 Hz), 10.79 (br s, 1H); 13C NMR (100 MHz, DMSO-d6): calcd for C21H18NO2: 316.1332 (MH)+; found: 316.1332.
11.19, 30.99, 55.58, 56.05, 110.17, 110.54, 113.86, 117.35, 118.20,
9-(2-Methyl-1H-indol-3-yl)-2,3,4,9-tetrahydro-xanthen-1-one (8b).
119.93, 120.35, 120.68, 123.88, 124.18, 126.49, 131.96, 135.29, IR (cmÀ1, film): 3396, 2951, 2872, 1633, 1580, 1485, 1373, 1227,
137.94, 146.73, 159.52; ESI-MS (m/z): 332.15 (MH)+; anal. calcd 1180, 995, 863, 740, 665; H NMR (400 MHz, CDCl3): 1.90–2.02
1
for C20H17N3O2: C, 72.49; H, 5.17; N, 12.68; found: C, 72.51; (m, 2H), 2.28–2.31 (m, 2H), 2.60 (s, 3H), 2.71–2.78 (m, 2H), 5.24
H, 5.19; N, 12.75.
(s, 1H), 6.86–6.90 (m, 1H), 6.92–6.98 (m, 2H), 7.01–7.11 (m, 3H),
2-Amino-8-methoxy-4-(5-methoxy-1H-indol-3-yl)-4H-chromene- 7.13–7.15 (m, 1H), 7.19–7.21 (m, 1H), 7.78 (br s, 1H); ESI-MS (m/z):
3-carbonitrile (5h). IR (cmÀ1, film): 3463, 3318, 3184, 2937, 2837, 330.16 (MH)+; anal. calcd for C22H19NO2: C, 80.22; H, 5.81; N, 4.25;
2206, 1660, 1584, 1482, 1435, 1402, 1327, 1268, 1210, 1169, 1080, found: C, 80.31; H, 5.89; N, 4.33.
1
955, 843, 768, 636; H NMR (400 MHz, DMSO-d6): 3.63 (s, 3H),
9-(5-Methoxy-1H-indol-3-yl)-2,3,4,9-tetrahydro-xanthen-1-one
3.80 (s, 3H), 4.90 (s, 1H), 6.63–6.69 (m, 2H), 6.75–6.76 (m, 1H), (8c). IR (cmÀ1, film): 3432, 2931, 2826, 1647, 1487, 1457, 1373,
6.79 (br s, 2 H), 6.85–6.93 (m, 2H), 7.15–7.17 (m, 1H), 7.20 (d, 1H, 1224, 1171, 1057, 993, 797, 759, 622; 1H NMR (400 MHz, CDCl3):
J = 9.16 Hz), 10.70 (br s, 1H); 13C NMR (100 MHz, DMSO-d6): 32.42, 1.90–2.02 (m, 2H), 2.29–2.38 (m, 2H), 2.58–2.71 (m, 2H), 3.74
55.09, 55.68, 56.09, 100.90, 110.31, 110.39, 112.13, 118.59, 120.33, (s, 3H), 5.32 (s, 1H), 6.73 (dd, 1H, J = 8.54 Hz, J = 2.44 Hz), 6.87
120.81, 123.43, 123.91, 124.61, 125.56, 131.96, 137.92, 146.88, (d, 1H, J = 1.83 Hz), 6.99–7.02 (m, 1H), 7.09–7.20 (m, 5H), 7.89
152.70, 160.13; HRMS (ESI, m/z) calcd for C20H18N3O3: 348.1343 (br s, 1H); HRMS (ESI, m/z) calcd for C22H20NO3: 346.1438
(MH)+; found: 348.1338.
(MH)+; found: 346.1425.
2-Amino-4-(5-bromo-1H-indol-3-yl)-8-methoxy-4H-chromene-
9-(1-Methyl-1H-indol-3-yl)-2,3,4,9-tetrahydro-xanthen-1-one (8d).
3-carbonitrile (5i). IR (cmÀ1, film): 3386, 3327, 2935, 2837, 2188, IR (cmÀ1, film): 3414, 2922, 2825, 1638, 1466, 1375, 1229, 1174,
1
1720, 1654, 1586, 1406, 1332, 1214, 1187, 1090, 1041, 958, 885, 1131, 992, 857, 747, 618; H NMR (400 MHz, CDCl3): 1.89–2.07
1
791; H NMR (400 MHz, DMSO-d6): 3.79 (s, 3H), 4.93 (s, 1H), (m, 2H), 2.32–2.37 (m, 2H), 2.62–2.78 (m, 2H), 3.68 (s, 3H), 5.32
6.57 (d, 1H, J = 7.33 Hz), 6.86–6.92 (m, 4H), 7.11 (dd, 1H, (s, 1H), 6.94–6.99 (m, 3H), 7.07–7.14 (m, 3H), 7.17–7.20 (m, 2H), 7.39
J = 8.70 Hz, J = 1.83 Hz), 7.28 (d, 1H, J = 8.70 Hz), 7.31 (d, 1H, (d, 1H, J = 7.93 Hz); ESI-MS (m/z): 330.15 (MH)+; anal. calcd for
J = 2.29 Hz), 7.34 (d, 1H, J = 1.83 Hz), 11.12 (br s, 1H); ESI-MS (m/z): C22H19NO2: C, 80.22; H, 5.81; N, 4.25; found: C, 80.29; H, 5.93; N, 4.31.
396.04 (MH)+, 398.03 (MH + 2)+; anal. calcd for C19H14BrN3O2: C,
57.59; H, 3.56; N, 10.60; found: C, 57.63; H, 3.59; N, 10.66.
9-(5-Bromo-1H-indol-3-yl)-2,3,4,9-tetrahydro-xanthen-1-one (8e).
IR (cmÀ1, film): 3299, 2925, 2861, 1630, 1457, 1376, 1225, 1180,
2-Amino-8-methoxy-4-(1-methyl-1H-indol-3-yl)-4H-chromene- 1135, 1101, 996, 882, 754, 620; 1H NMR (400 MHz, CDCl3):
3-carbonitrile (5j). IR (cmÀ1, Film): 3439, 3321, 2937, 2840, 2189, 1.95–2.05 (m, 2H), 2.35–2.47 (m, 2H), 2.61–2.79 (m, 2H), 5.29
1647, 1581, 1479, 1399, 1328, 1279, 1203, 1184, 1082, 947, 764, (s, 1H), 6.98–7.02 (m, 1H), 7.09–7.20 (m, 6H), 7.51–7.53 (m, 1H),
New J. Chem.
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015