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A.-L. Gerard et al. / Tetrahedron 61 (2005) 6082–6087
6084
(C-phenyl), 128.65 (C-phenyl), 128.08 (C-phenyl), 124.34
(C-5), 114.24 (C-3a), 111.13 (C-7). MS m/z: 223.1.
C14H9NO2 (223.23); calcd: C, 75.33; H, 4.06; N, 6.27;
found: C, 75.27; H, 4.12; N, 6.31.
6.96 (d, 1H, H5, JZ8 Hz), 3.77 (s, 1H, OCH3). 13C NMR
(DMSO-d6): 184.46 (C-3), 159.55 (C-2), 158.90 (C-40),
149.39 (C-7a), 135.93 (C-6), 134.68 (C0-5), 131.09 (C-10),
127.35 (C-4), 121.89 (C-7), 118.37 (C-3 and C-50), 114.40
(C-3a), 112.60 (OCH3), 55.17 (OCH3). MS m/z: 253.1.
C15H11NO3 (253.26); calcd: C, 71.14; H, 4.38; N, 5.53;
found: C, 70.96; H, 4.29; N, 5.43.
3.2.2. 4-(4-Methoxyphenyl)isatin (4b). 49%, red solid. Mp
214 8C. IR (KBr): 3335, 2921, 1754, 1719, 1612, 1519,
1
1469, 1303, 1252, 1194, 1101, 1026 and 789 cmK1. H
NMR (DMSO-d6): 11.09 (s, 1H, NH), 7.55 (t, 1H, H6, JZ
7.8 Hz), 7.50 (d, 2H, H2 and H6 , JZ8.3 Hz), 6.99 (d, 2H,
3.2.7. 5-(3,4,5-Trimethoxyphenyl)isatin (6c). 32%, orange
solid. Mp 113 8C. IR (KBr): 3471, 3289, 1739, 1625, 1582,
0
0
1
H3 and H5 , JZ8.3 Hz), 6.98 (d, 1H, H5 or H7, JZ7.8 Hz),
1482, 1411, 1348, 1242, 1121 and 986 cmK1. H NMR
0
0
6.82 (d, 1H, H5 or H7, JZ7.8 Hz), 3.80 (s, 3H, OCH3). 13
C
(DMSO-d6): 11,11 (s, 1H, NH), 7.92 (dd, 1H, H6, JZ8,
1.7 Hz), 7.83 (d, 1H, H4, JZ1.7 Hz), 6.96 (d, 1H, H7, JZ
NMR (DMSO-d6): 183.22 (C-3), 160.01 (C-2), 159.33
(C-400), 151.67 (C-10), 141.69 (C-7a), 138.02 (C-6), 130.55
(C-2 and C-60), 128.74 (C-4), 124.35 (C-5), 114.21 (C-3a),
113.71 (C-30 and C-50), 110.65 (C-7), 55.44 (OCH3). MS
m/z: 253.1. C15H11NO3 (253.26); calcd: C, 71.14; H, 4.38;
N, 5.53; found: C, 71.08; H, 4.29; N, 5.48.
0
0
8 Hz), 6.88 (s, 2H, H2 and H6 ), 3.85 (s, 6H, OCH3), 3.66 (s,
3H, OCH3). 13C NMR (DMSO-d6): 184.42 (C-3), 159.64
(C-2), 153.24 (C-30 and C-50), 149.80 (C-400), 137.09 (C-7a),
136.57 (C-6), 135.09 (C-5), 134.47 (C-1 ), 122.75 (C-4),
118.30 (C-3a), 112.40 (C-7), 103.72 (C-20 and C-60), 60.02
(OCH3), 55.98 (OCH3). MS m/z: 313.4. C17H15NO5
(313.31); calcd: C, 65.17; H, 4.83; N, 4.47; found: C,
65.02; H, 4.80; N, 4.35.
3.2.3. 4-(3,4,5-Trimethoxyphenyl)isatin (4c). 32%, orange
solid. Mp 231 8C. IR (KBr): 3242, 2922,1760, 1727, 1615,
1586, 1486, 1412, 1347, 1312, 1258, 1176, 1120, 987 and
797 cmK1. 1H NMR (DMSO-d6): 11.12 (s, 1H, NH), 7.57 (t,
1H, H6, JZ7.8 Hz), 7.10 (d, 1H, H5 or H7, JZ7.8 Hz), 6.88
3.2.8. 5-(2-Furyl)isatin (6d). 17%, purple solid. Mp 214 8C.
IR (KBr): 3285, 1757, 1730, 1621, 1503, 1477, 1282, 1200
1
(s, 2H, H2 and H6 ), 6.85 (d, 1H, H5 or H7, JZ7.8 Hz), 3.78
(s, 6H, OCH3), 3.70 (s, 3H, OCH3). 13C NMR (DMSO-d6):
182.33 (C-3), 159.04 (C-2), 152.40 (C-30 and C-50), 151.43
(C-4), 141.54 (C-40), 137.97 (C-7a), 137.65 (C-6), 131.54
(C-100), 124.16 0(C-5), 114.22 (C-3a), 110.90 (C-7), 106.57
(C-2 and C-6 ), 60.06 (OCH3), 55.96 (OCH3). MS m/z:
313.2. C17H15NO5 (313.31); calcd: C, 65.17; H, 4.83; N,
4.47; found: C, 65.12; H, 4.94; N, 4.53.
and 1120 cmK1. H NMR (DMSO-d6): 11.13 (s, 1H, NH),
0
0
7.89 (dd, 1H, H6, JZ8.2, 1.9 Hz), 7.78 (d, 1H, H4, JZ
1.9 Hz), 7.72 (s, 1H, Hfur), 6.97 (s, 1H, Hfur), 6.96 (d, 1H,
H7, JZ8.2 Hz), 6.57 (s, 1H, Hfur). 13C NMR (DMSO-d6):
183.97 (C-3), 159.49 (C-2), 151.81 (C-10), 149.39 (C-7a),
142.79 (C-fur), 132.74 (C-6), 125.41 (C-5), 119.36 (C-4),
118.34 (C-3a), 112.61 (C-fur), 112.12 (C-7), 105.48 (C-fur).
MS m/z: 213.0. C12H7NO3 (213.19); calcd: C, 67.61; H,
3.31; N, 6.57; found: C, 67.58; H, 3.30; N, 6.49.
3.2.4. 4-(2-Furyl)isatin (4d). 48%, red solid. Mp 241 8C. IR
(KBr): 3302, 3124, 1754, 1731, 1616, 1567, 1490, 1475,
3.2.9. 6-Phenylisatin (8a). 71%, orange solid. Mp 230 8C.
(Lit.13 230–235 8C). IR (KBr): 3271, 2923, 1765, 1733,
1
1250, 1190, 1027 and 923 cmK1. H NMR (DMSO-d6):
1
11.16 (s, 1H, NH), 7.94 (d, 1H, Hfur, JZ3.6 Hz), 7.90 (m,
1H, Hfur), 7.61 (t, 1H, H6, JZ7.9 Hz), 7.46 (d, 1H, H5 or H7,
JZ8 Hz), 6.79 (d, 1H, H5 or H7, JZ7.8 Hz), 6.72 (m, 1H,
Hfur). 13C NMR (DMSO-d6): 182.30 (C-3), 158.67 (C-2),
151.67 (C-7a), 149.25 (C-10), 144.75 (C-fur), 138.39 (C-6),
129.05 (C-4), 119.27 (C-fur), 114.12 (C-5), 112,49 (C-fur),
111.48 (C-7), 110.68 (C-3a). MS m/z: 213.1. C12H7NO3
(213.19); calcd: C, 67.61; H, 3.31; N, 6.57; found: C, 67.49;
H, 3.23; N, 6.48.
1622, 1455, 1433, 1325, 1181, 1107 and 893 cmK1. H
NMR (DMSO-d6): 11.13 (s, 1H, NH), 7.70 (d, 2H, Hphenyl
,
JZ8 Hz), 7.58 (d, 1H, H4, JZ7.8 Hz), 7.53–7.46 (m, 3H,
Hphenyl), 7.35 (d, 1H, H5, JZ7.8 Hz), 7.09 (br s, 1H, H7).
13C NMR (DMSO-d6): 183.70 (C-3), 159.77 (C-2), 151.38
(C-7a), 149.86 (C-6), 138.87 (C-10), 129.17 (C-phenyl),
129.12 (C-phenyl), 127.05 (C-4), 125.30 (C-phenyl), 121.33
(C-5), 116.81 (C-3a), 110.06 (C-7). MS m/z: 223.1.
3.2.10. 6-(4-Methoxyphenyl)isatin (8b). 24%, red solid.
Mp 250 8C. IR (KBr): 3408, 2962, 1757, 1706, 1627, 1597,
1568, 1392, 1258, 1179, 1115, 1017, 828 and 800 cmK1. 1H
3.2.5. 5-Phenylisatin (6a).3 26%, red solid. Mp 270 8C. IR
(KBr): 3435, 3052, 1603, 1494, 1442, 1345, 1306, 1178,
1086, 1024 and 700 cmK1. 1H NMR (DMSO-d6): 11.12 (s,
1H, NH), 7.90 (dd, 1H, H6, JZ8.0, 2.0 Hz), 7.76 (d, 1H, H4,
JZ2 Hz), 7.64 (d, 2H, Hphenyl, JZ7.0 Hz), 7.46 (m, 3H,
Hphenyl), 6.99 (d, 1H, H7, JZ8.0 Hz). 13C NMR (DMSO-
d6): 184.29 (C-3), 159.31 (C-2), 149.72 (C-7a), 138.68
(C-10), 136.43 (C-6), 134.86 (C-5), 128.97 (C-phenyl),
127.44 (C-phenyl), 126.18 (C-phenyl), 122.40 (C-4), 118.30
(C-3a), 112.63 (C-7). MS m/z: 223.1.
0
0
NMR (DMSO-d6): 7.68 (d, 2H, H2 and H6 , JZ8 Hz), 7.54
(d, 1H, H4, JZ7.9 Hz), 7.32 (d, 1H, H5, JZ7.9 Hz), 7.06 (d,
0
0
2H, H3 and H5 , JZ8 Hz,), 7.06 (br s, 1H, H7), 3.81 (s, 3H,
OCH3). 13C NMR (DMSO-d6): 183.50 (C-3), 160.26 (C-40),
159.97 (C-20), 151.520 (C-6), 149.57 (C-7a), 131.00 (C-10),
128.43 (C-2 and C-6 ), 125.36 (C-4), 120.59 (C-5), 116.17
(C-3a), 114.63 (C-30 and C-50), 109.68 (C-7), 55.32 (OCH3).
MS m/z: 253.2. C15H11NO3 (253.26); calcd: C, 71.14; H,
4.38; N, 5.53; found: C, 71.23; H, 4.40; N, 5.22.
3.2.6. 5-(4-Methoxyphenyl)isatin (6b). 21%, purple solid.
Mp 242 8C. IR (KBr): 3257, 2957, 1762, 1728, 1622, 1603,
3.2.11. 6-(3,4,5-Trimethoxyphenyl)isatin (8c). 24%,
orange solid. Mp 236 8C. IR (KBr): 3398, 3304, 1750,
1730, 1625, 1577, 1489, 1436, 1411, 1343, 1252, 1161,
1120, 983 and 800 cmK1. 1H NMR (DMSO-d6): 8.01 (s, 1H,
NH), 7.67 (d, 1H, H4 or H5, JZ8 Hz), 7.32 (d, 1H, H4 or H5,
1478, 1412, 1340, 1245, 1170, 1110, 1019 and 829 cmK1
.
1H NMR (DMSO-d6): 11.08 (s, 1H, NH), 7.84 (dd, 1H, H6,
0
JZ8, 1.8 Hz), 7.70 (d, 1H, H4, JZ1.8 Hz), 7.58 (d, 2H, H2
0
0
0
and H6 , JZ8.5 Hz), 6.99 (d, 2H, H3 and H5 , JZ8.5 Hz),