Med Chem Res (2013) 22:3076–3084
3081
(CDCl3): d 6.87 (t, 1H, J = 8.83 Hz), 6.95 (d, 1H,
J = 8.03 Hz), 7.04 (t, 1H, J = 9.56 Hz), 7.13 (d, 2H,
J = 7.41 Hz), 7.26 (d, 2H, J = 8.12 Hz), 7.33 (m, 3H),
7.41 (t, 1H, J = 7.16 Hz), 7.46 (d, 1H, J = 7.79 Hz), 7.55
(s, 1H), 7.68 (d, 2H, J = 9.12 Hz). 13C-NMR (CDCl3): d
197.2, 144.2, 141.3, 139.6, 139.0, 135.8, 135.0, 134.6,
133.4, 131.3, 129.4, 128.5, 128.4, 128.0, 127.8, 127.5,
127.0, 126.7, 126.1, 125.8, 125.5, 124.4, 123.4, 37.7; FAB-
mass (m/z): 415 (M?).
(C=O str.), 1,678 (C=C str., alkene), 1,610, 1,579 (C=C
str., aromatic), 1,107 (C–N str.), 741 (OOP bending), 717
(C–Cl str.), 656. 1H-NMR (CDCl3): d 6.92 (d, 2H,
J = 7.15 Hz), 6.98 (s, 1H), 7.18 (t, 1H, J = 8.2 Hz), 7.22
(t, 1H, J = 7.11 Hz), 7.26 (t, 1H, J = 8.35 Hz), 7.31 (d,
2H, J = 7.68 Hz), 7.38 (d, 2H, J = 8.66 Hz), 7.41 (d, 1H,
J = 7.81 Hz), 7.44 (d, 1H, J = 8.14 Hz), 7.61 (s, 1H).
13C-NMR (CDCl3): d 197.2, 157.9, 144.2, 141.2, 139.8,
138.9, 135.3, 134.9, 129.6, 128.2, 128.0, 128.2, 127.3,
126.9, 126.4, 116.2, 37.9; FAB-mass (m/z): 381 (M?).
1-{[(2,6-Dichlorophenyl)-3-(4-chlorophenyl)]methylene}-
1,3-dihydro-indol-2-one (4g) Yield: 60 %, m.p. (oC):
164. Rf = 0.73. IR (KBr, cm-1): 1,713 (C=O str.), 1,680
(C=C str., alkene), 1,622, 1,545 (C=C str., aromatic), 1,164
(C–N str.), 757 (C–Cl str.), 734 (OOP bending), 679.
1H-NMR (CDCl3): d 6.72 (t, 1H, J = 8.79 Hz), 7.08
(m, 4H), 7.24 (d, 2H, J = 9.11 Hz), 7.41 (m, 3H), 7.62
(d, 1H, J = 8.42 Hz), 7.73 (s, 1H). 13C-NMR (CDCl3): d
197.0, 144.0, 141.0, 139.6, 138.9, 135.7, 134.9, 133.8,
133.6, 129.4, 128.9, 128.6, 128.2, 127.8, 127.6, 127.0,
126.6, 37.7; FAB-mass (m/z): 400 (M?).
1-{[(2,6-Dichlorophenyl)-3-(4-(dimethylamino)phenyl)]-methy-
lene}-1,3-dihydro-indol-2-one (4k) Yield: 46 %, m.p. (°C):
220–222. Rf = 0.42. IR (KBr, cm-1): 2,912, 2,856 (C–H
str.), 1710 (C=O str.), 1,620 (C=C str., alkene), 1,589,
1,536 (C=C str., aromatic), 1,222 (C–N str.), 785 (OOP
bending), 780 (C–Cl str.) 678. 1H-NMR (CDCl3): d 3.11 (s,
6H), 6.83 (d, 2H, J = 8.10 Hz), 6.88 (t, 1H, J = 9.32 Hz),
6.98 (t, 1H, J = 7.18 Hz), 7.06 (t, 1H, J = 7.83 Hz), 7.18
(dd, 2H, J = 9.03 Hz), 7.31 (d, 1H, J = 8.47 Hz), 7.38 (d,
1H, J = 8.35 Hz), 7.44 (m, 2H), 7.61 (s, 1H). 13C-NMR
(CDCl3): d 197.2, 149.0, 144.3, 141.2, 139.7, 139.2, 135.4,
134.0, 129.5, 128.8, 128.2, 127.8, 127.2, 126.9, 126.4,
124.8, 114.7, 40.8, 37.7; FAB-mass (m/z): 408 (M?).
1-{[(2,6-Dichlorophenyl)-3-(4-methoxyphenyl)]methylene}-1,3-
dihydro-indol-2-one (4h) Yield: 57 %, m.p. (°C): 175.
Rf = 0.44. IR (KBr, cm-1): 1,718 (C=O str.), 1,688 (C=C
str., alkene), 1,610, 1,536 (C=C str., aromatic), 1,216 (C–N
str.), 766 (C–Cl str.), 723 (OOP bending). 1H-NMR
(CDCl3): d 3.86 (s, 3H), 6.68 (d, 2H, J = 9.82 Hz), 6.82 (t,
1H, J = 7.86 Hz), 6.97 (t, 1H, J = 8.33 Hz), 7.10 (d, 2H,
J = 9.12 Hz), 7.23 (d, 1H, J = 8.56 Hz), 7.47 (m, 3H),
7.74 (d, 1H, J = 8.71 Hz), 7.91 (s, 1H). 13C-NMR
(CDCl3): d 197.2, 160.0, 144.2, 141.4, 138.9, 139.5, 135.2,
134.8, 129.5, 128.3, 128.0, 127.7, 127.4, 127.0, 126.2,
114.6, 66.6, 37.5; FAB-mass (m/z): 395 (M?).
1-{[(2,6-Dichlorophenyl)-3-(3-chlorophenyl)]methylene}-1,3-
dihydro-indol-2-one (4l) Yield: 55 %, m.p. (°C): 144.
Rf = 0.64. IR (KBr, cm-1): 1,703 (C=O str.), 1,668 (C=C
str., alkene), 1,618, 1,570 (C= str., aromatic), 1,208 (C–N
1
str.), 811 (C–Cl str.), 760 (OOP bending), 679. H-NMR
(CDCl3): d 6.73 (t, 1H, J = 9.29 Hz), 6.94 (t, 1H,
J = 8.74 Hz), 7.15 (d, 1H, J = 8.82 Hz), 7.43 (d, 2H,
J = 7.90 Hz), 7.58 (t, 1H, J = 9.76 Hz), 7.71 (m, 4H),
7.83 (d, 1H, J = 7.81 Hz), 7.96 (s, 1H). 13C-NMR
(CDCl3): d 197.0, 144.3, 140.9, 139.5, 138.8, 136.4, 135.4,
135.0, 134.6, 130.5, 129.7, 128.6, 128.4, 128.0, 127.4,
127.0, 126.4 126.1, 124.5, 37.8; FAB-mass (m/z): 400
(M?).
1-{[(2,6-Dichlorophenyl)-3-(4-fluorophenyl)]methylene}-
1,3-dihydro-indol-2-one (4i) Yield: 56 %, m.p. (°C):
152. Rf = 0.47. IR (KBr, cm-1): 1720 (C=O str.), 1,639
(C=C str., alkene), 1,598, 1,564 (C=C str., aromatic), 1,234
(C–F str.), 1,157 (C–N str.), 817 (OOP bending), 786
1-{[(2,6-Dichlorophenyl)-3-(3-bromobenzylidene)]methy-
lene}-1,3-dihydro-indol-2-one (4m) Yield: 52 %, m.p.
(°C): 149–151. Rf = 0.67. IR (KBr, cm-1): 1,702 (C=O str.),
1,650 (C=C str., alkene), 1,613, 1,577 (C=C str., aromatic),
1,214 (C–N str.), 743 (OOP bending), 718 (C–Cl str.). 617.
1H-NMR (CDCl3): d 6.87 (t, 1H, J = 9.29 Hz), 7.04 (t, 1H,
J = 7.81 Hz), 7.13 (t, 1H, J = 8.07 Hz), 7.24 (m, 3H), 7.41
(t, 1H, J = 8.51 Hz), 7.47 (d, 1H, J = 8.86 Hz), 7.58
(m, 3H), 7.66 (s, 1H). 13C-NMR (CDCl3): d 197.2, 144.1,
141.2, 139.5, 138.4, 137.6, 135.4, 134.9, 131.3, 130.0, 129.4,
128.7, 128.2, 127.6, 126.7, 126.3, 125.5, 123.2, 37.8; FAB-
mass (m/z): 444 (M?).
(C–Cl str.). 1H-NMR (CDCl3):
d
6.42 (d, 1H,
J = 7.80 Hz), 6.95 (m, 1H), 7.15–7.25 (m, 2H), 7.39 (dd,
1H, J = 7.30, 1.47 Hz), 7.52 (d, 2H, J = 7.63 Hz),
7.68–7.75 (m, 4H), 7.91 (s, 1H). 13C-NMR (CDCl3): d
196.7, 162.5, 144.2, 140.4, 139.6, 138.9, 135.5, 135.0,
131.4, 129.6, 128.4, 128.2, 127.8, 127.3, 126.9, 126.4,
115.7, 37.8; FAB-mass (m/z): 383 (M?).
1-{[(2,6-Dichlorophenyl)-3-(4-hydroxyphenyl)]methylene}-1,3-
dihydro-indol-2-one (4j) Yield: 60 %, m.p. (°C): 218.
Rf = 0.61. IR (KBr, cm-1): 3,418, (O–H str.), 1,688
123