7.72–7.81 (m, 2H), 8.05 (d, J = 7.6 Hz, 2H), 8.18 (d, J = 8.0 Hz,
2H); 13C NMR: 13.8, 13.9, 14.0, 27.4, 28.0, 51.2, 51.3, 51.5, 51.8,
61.0, 61.8, 61.9, 61.9, 125.8, 125.8, 125.9, 125.9, 126.9, 128.8,
128.9, 128.9, 129.2, 129.3, 133.9, 134.7, 135.0, 135.3, 135.8,
138.2, 168.9, 169.2, 169.3, 169.7, 194.1, 194.4, 194.7, 195.1. IR
(cm-1): 2987, 2942, 1742, 1690, 1598, 1582, 1450, 1412, 1372,
1327, 1253, 1170, 1130, 1067, 1015, 963, 855, 690, 595. HR-MS:
m/z = 464.1409, calcd. for C24H23F3O6 [M]: 464.1447.
120.4, 120.7, 121.2, 123.9, 125.7, 127.9, 128.5, 128.5, 128.6,
130.2, 133.4, 133.7, 135.9, 136.4, 162.2, 169.8, 195.2. IR (cm-1):
3313, 2981, 1717, 1687, 1540, 1460, 1448, 1368, 1340, 1257,
1232, 1212, 1161, 1025, 741, 689. HR-MS: m/z = 394.1622,
calcd. for C23H24NO5 [M + H+]: 394.1654.
Ethyl a-(4-methylbenzoyl)-3-[2-(ethoxycarbonyl)-1H-indol-3-
yl]propanoate (7c). red solid, mp = 135–136 ◦C, 1H NMR
(CDCl3): 0.99 (t, J = 7.2 Hz, 3H), 1.35 (t, J = 6.8 Hz, 3H), 2.36 (s,
3H), 3.77 (ddd, Ja = 8.0 Hz, Jb = 13.6 Hz, Jc = 20.0 Hz, 2H), 3.96
(q, J = 7.2 Hz, 2H), 4.38 (dq, Ja = 1.2 Hz, Jb = 7.2 Hz, 2H), 4.86 (t,
J = 8.6 Hz, 1H), 7.12 (dt, Ja = 1.2 Hz, Jb = 6.4 Hz, 1H), 7.18 (d, J =
2.0 Hz, 2H), 7.24–7.34 (m, 2H), 7.76 (d, J = 8.4 Hz, 1H), 7.84 (d,
J = 8.0 Hz, 2H), 8.93 (bs, 1H); 13C NMR: 13.8, 14.4, 21.7, 24.3,
55.0, 61.0, 61.4, 111.6, 120.4, 120.8, 121.3, 123.8, 125.7, 128.0,
128.8, 129.2, 133.9, 135.7, 144.3, 162.0, 169.8, 194.6. IR (cm-1):
3319, 2980, 2934, 1715, 1688, 1607, 1537, 1455, 1371, 1339, 1257,
1214, 1168, 1100, 1019, 744. HR-MS: m/z = 430.1663, calcd. for
C24H25NNaO5 [M + Na+]: 430.1630.
Diethyl 2-◦benzoyl-4-(2-thenoyl)glutarate (5f). white solid,
1
mp = 82–83 C, H NMR (CDCl3): 1.10–1.27 (m, 6H), 2.56–
2.67 (m, 1.5H), 2.70–2.79 (m, 0.5H), 4.06–4.16 (m, 2H), 4.18–
4.28 (m, 2H), 4.42 (t, J = 7.2 Hz, 0.5H), 4.47 (dd, Ja = 6.0 Hz,
Jb = 9.2 Hz, 0.5H), 4.54 (t, J = 7.6 Hz, 0.5H), 4.62 (dd, Ja =
5.6 Hz, Jb = 8.8 Hz, 0.5H), 7.13 (dd, Ja = 4.0 Hz, Jb = 4.8 Hz,
0.5H), 7.18 (dd, Ja = 4.0 Hz, Jb = 4.8 Hz, 0.5H), 7.44–7.53 (m,
2H), 7.55–7.64 (m, 1H), 7.69 (dd, Ja = 0.8 Hz, Jb = 4.8 Hz,
0.5H), 7.73 (dd, Ja = 1.2 Hz, Jb = 5.2 Hz, 0.5H), 7.93 (dd, Ja =
0.8 Hz, Jb = 4.0 Hz, 0.5H), 7.96 (dd, Ja = 0.8 Hz, Jb = 3.6 Hz,
0.5H), 8.02–8.08 (m, 2H); 13C NMR: 13.9, 13.9, 14.0, 14.0, 27.8,
28.5, 51.2, 51.5, 52.5, 52.7, 61.7, 61.7, 61.8, 61.8, 128.5, 128.8,
128.8, 128.9, 133.8, 133.9, 134.0, 135.4, 135.4, 135.8, 142.7,
143.2, 168.9, 169.2, 169.3, 169.7, 187.4, 187.7, 194.8, 195.1. IR
(cm-1): 3094, 2982, 1735, 1660, 1516, 1447, 1412, 1369, 1355,
1252, 1188, 1159, 1094, 1059, 1030, 946, 852, 732, 692, 619, 590.
HR-MS: m/z = 402.1102, calcd. for C21H22O6S [M]: 402.1137.
Ethyl a-(4-chlorobenzoyl)-3-[2-(ethoxycarbonyl)-1H-indol-3-
yl]propanoate (7d). red solid, mp = 140–142 ◦C, 1H NMR
(CDCl3): 1.00 (t, J = 7.2 Hz, 3H), 1.36 (t, J = 7.2 Hz, 3H),
3.77 (q, J = 2.0 Hz, 2H), 3.98 (q, J = 7.2 Hz, 2H), 4.39 (q,
J = 6.8 Hz, 2H), 4.87 (t, J = 7.2 Hz, 1H), 7.12 (t, J = 7.2 Hz,
1H), 7.25–7.36 (m, 4H), 7.74 (d, J = 8.0 Hz, 1H), 7.85 (d, J =
8.4 Hz, 2H), 8.99 (bs, 1H); 13C NMR: 13.8, 14.4, 24.3, 55.0, 61.0,
61.5, 111.7, 120.4, 120.5, 121.2, 123.8, 125.8, 127.9, 128.0, 128.8,
130.0, 134.7, 135.7, 140.0, 161.9, 169.5, 194.1. IR (cm-1): 3313,
2979, 1718, 1689, 1590, 1537, 1459, 1399, 1368, 1338, 1283, 1254,
1211, 1161, 1096, 1026, 981, 899, 835, 745, 685. HR-MS: m/z =
428.1270, calcd. for C23H23ClNO5 [M + H+]: 428.1265.
1-Ethyl 5-methy◦l 2,4-bisbenzoylpentanedioate (5g). white
1
solid, mp = 86–88 C, H NMR (CDCl3): 1.10 (t, J = 6.8 Hz,
1.4H), 1.23 (t, J = 7.2 Hz, 1.6H), 2.52–2.65 (m, 1.5H), 2.71–2.80
(m, 0.5H), 3.63 (s, 1.5H), 3.75 (s, 1.5H), 4.05–4.15 (m, 1H), 4.16–
4.27 (m, 1H), 4.58 (td, Ja = 7.2 Hz, Jb = 20.4 Hz, 1H), 4.67 (quint,
J = 6.8 Hz, 1H), 7.44–7.54 (m, 4H), 7.55–7.64 (m, 2H), 8.06 (d,
J = 7.6 Hz, 4H); 13C NMR: 13.9, 14.0, 14.2, 27.8, 28.3, 51.0,
51.3, 51.3, 51.5, 52.7, 61.7, 61.7, 128.8, 133.9, 133.9, 133.9, 135.3,
135.4, 135.8, 135.8, 169.3, 169.7, 169.8, 170.2, 194.8, 195.1. IR
(cm-1): 2953, 1745, 1680, 1596, 1581, 1449, 1436, 1372, 1256,
1203, 1186, 1164, 1094, 1068, 1037, 962, 781, 725, 692, 617.
HR-MS: m/z = 382.1450, calcd. for C22H22O6 [M]: 382.1416.
Ethyl a-(4-methoxybenzoyl)-3-(1-methyl-2-phenylindol-3-yl)-
1
propanoate (7e). gum-like material, H NMR (CDCl3): 0.97
(t, J = 7.2 Hz, 3H), 3.38 (dd, Ja = 6.4 Hz, Jb = 10.8 Hz, 1H),
3.51 (s, 3H), 3.54 (dd, Ja = 6.4 Hz, Jb = 10.8 Hz, 1H), 3.81 (s,
3H), 3.84–3.96 (m, 2H), 4.46 (dd, Ja = 6.0 Hz, Jb = 7.6 Hz, 1H),
6.77 (td, Ja = 2.8 Hz, Jb = 8.8 Hz, 2H), 7.15 (t, J = 8.0 Hz, 1H),
7.23 (t, J = 8.4 Hz, 1H), 7.29 (d, J = 8.0 Hz, 1H), 7.34 (dd, Ja =
1.6 Hz, Jb = 8.0 Hz, 2H), 7.42–7.51 (m, 3H), 7.66 (td, Ja = 2.0 Hz,
Jb = 7.2 Hz, 2H), 7.70 (d, J = 8.0 Hz, 1H); 13C NMR: 13.8, 24.2,
30.7, 54.8, 55.5, 61.2, 109.3, 109.4, 113.7, 119.2, 119.5, 121.7,
127.5, 128.4, 128.6, 129.2, 130.7, 130.9, 131.9, 137.0, 138.7,
163.6, 169.8, 193.6. IR (cm-1): 3054, 2977, 2936, 2841, 1733,
1676, 1600, 1575, 1511, 1468, 1366, 1332, 1260, 1230, 1172,
1028, 912, 843, 742, 704, 560. HR-MS: m/z = 442.2053, calcd.
for C28H28NO4 [M + H+]: 442.2018.
Methyl a-benzoyl-3-[2-(ethoxycarbonyl)-1H-indol-3-yl]pro-
panoate (7a). red solid, mp = 140–141 ◦C, 1H NMR (CDCl3):
1.35 (t, J = 7.2 Hz, 3H), 3.53 (s, 3H), 3.79 (q, J = 4.4 Hz, 2H),
4.39 (dq, Ja = 2.0 Hz, Jb = 7.2, 2H), 4.29 (t, J = 7.2 Hz, 1H), 7.13
(td, Ja = 1.6 Hz, Jb = 6.0 Hz, 1H), 7.25–7.33 (m, 2H), 7.37 (t, J =
8.0 Hz, 2H), 7.50 (t, J = 7.6 Hz, 1H), 7.75 (d, J = 8.4 Hz, 1H),
7.91 (d, J = 7.2 Hz, 2H), 8.85 (bs, 1H); 13C NMR: 14.4, 24.5,
52.5, 54.8, 61.0, 111.6, 120.5, 120.6, 121.2, 123.9, 125.8, 127.9,
128.6, 128.6, 133.4, 135.7, 136.3, 161.9, 170.1, 195.0. IR (cm-1):
3314, 2943, 1725, 1687, 1541, 1461, 1435, 1340, 1282, 1256,
1232, 1210, 1159, 1020, 954, 779, 737, 692. HR-MS: m/z =
380.1493, calcd. for C22H22NO5 [M + H+]: 380.1498.
Ethyl a-(4-methoxybenzoyl)-3-(1-ethyl-2-phenylindol-3-yl)-
1
propanoate (7f). gum-like material, H NMR (CDCl3): 0.98
(t, J = 7.2 Hz, 3H), 1.13 (t, J = 6.8 Hz, 3H), 3.32 (dd, Ja
=
6.4 Hz, Jb = 10.8 Hz, 1H), 3.51 (dd, Ja = 6.4 Hz, Jb = 10.8 Hz,
1H), 3.80 (s, 3H), 3.87–3.99 (m, 4H), 4.46 (dd, Ja = 6.0 Hz, Jb =
8.0 Hz, 1H), 6.75 (td, Ja = 2.8 Hz, Jb = 10.0 Hz, 2H), 7.14 (t, J =
8.0 Hz, 1H), 7.21 (dt, Ja = 1.2 Hz, Jb = 8.0 Hz, 1H), 7.29–7.35
(m, 3H), 7.42–7.51 (m, 3H), 7.62 (td, Ja = 2.8 Hz, Jb = 9.6 Hz,
2H), 7.70 (d, J = 8.0 Hz, 1H); 13C NMR: 13.9, 15.4, 24.2, 38.5,
54.7, 55.5, 61.1, 109.5, 109.6, 113.6, 119.3, 119.4, 121.6, 127.8,
128.4, 128.7, 129.2, 130.7, 130.9, 132.1, 135.7, 138.2, 163.6,
169.8, 193.7. IR (cm-1): 3055, 2978, 2935, 2841, 1734, 1676,
Ethyl
a-benzoyl-3-[2-(ethoxycarbonyl)-1H-indol-3-yl]pro-
panoate (7b). red solid, mp = 118–119 ◦C, 1H NMR (CDCl3):
0.99 (t, J = 7.2 Hz, 3H), 1.33 (t, J = 7.2 Hz, 3H), 3.80 (dd, Ja =
3.2 Hz, Jb = 8.0 Hz, 2H), 3.98 (q, J = 8.8 Hz, 2H), 4.38 (dq, Ja =
1.6 Hz, Jb = 7.2 Hz, 2H), 4.90 (t, J = 7.2 Hz, 1H), 7.11 (td, Ja =
0.8 Hz, Jb = 7.6 Hz, 1H), 7.23–7.29 (m, 2H), 7.36 (t, J = 8.0 Hz,
2H), 7.45–7.50 (m, 1H), 7.75 (d, J = 8.0 Hz, 1H), 7.92 (d, J =
7.2 Hz, 2H), 9.19 (bs, 1H); 13C NMR: 55.1, 61.1, 61.4, 111.7,
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The Royal Society of Chemistry 2010
Green Chem., 2010, 12, 1772–1782 | 1781
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