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128.9, 128.6, 128.2, 127.6, 127.8, 127.0, 126.6, 37.7; FAB-mass
(m/z): 400 (Mþ).
str.), 1157 (CeN str.), 1639 (C]C str., alkene), 1598, 1564
(C]C str., aromatic), 1234 (CeF str.), 817 (OOP bending),
786 (CeCl str.); 1H NMR (CDCl3) d ¼ 6.42 (d, 1H,
J ¼ 7.80 Hz), 6.95 (m, 1H), 7.15e7.25 (m, 2H), 7.39 (dd, 1H,
J ¼ 7.30, 1.47 Hz), 7.52 (d, 2H, J ¼ 7.63 Hz), 7.68e7.75 (m,
4H), 7.91 (s, 1H); 13C NMR (CDCl3) d ¼ 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
(Mþ).
2.1.5.6. 1-(2,6-Dichlorophenyl)-3-((2,4-dichlorophenyl)methy-
lene)-1,3-dihydro-indol-2-one (4f). IR (KBr, cmꢀ1): 1712
(C]O str.), 1182 (CeN str.), 1635 (C]C str., alkene),
1606, 1577 (C]C str., aromatic), 817, 864 (OOP bending),
778 (CeCl str.); 1H NMR (CDCl3) d ¼ 6.40 (d, 1H, J ¼
7.60 Hz), 6.92 (tt, 1H, J ¼ 7.49, 1.20 Hz), 7.21 (tt, 1H,
J ¼ 7.49, 1.18 Hz), 7.39 (m, 3H), 7.52 (m, 2H), 7.76 (d, 2H,
J ¼ 8.34 Hz), 7.89 (s, 1H); 13C NMR (CDCl3) d ¼ 196.9,
144.2, 140.9, 135.7, 135.3, 139.7, 138.9, 135.3, 132.8,
131.7, 130.7, 129.6, 129.4, 128.9, 128.3, 127.7, 127.0,
126.7, 37.7; FAB-mass (m/z): 435 (Mþ).
2.1.5.11. 1-(2,6-Dichlorophenyl)-3-((3-bromobenzylidene)methy-
lene)-1,3-dihydro-indol-2-one (4k). IR (KBr, cmꢀ1): 1702
(C]O str.), 1214 (CeN str.), 1650 (C]C str., alkene), 1613,
1577 (C]C str., aromatic), 617, 743 (OOP bending), 718
1
(CeCl str.); H NMR (CDCl3) d ¼ 6.87 (t, 1H, J ¼ 9.29 Hz),
2.1.5.7. 1-(2,6-Dichlorophenyl)-3-((2,6-dichlorophenyl)methy-
lene)-1,3-dihydro-indol-2-one (4g). IR (KBr, cmꢀ1): 1694
(C]O str.), 1142 (CeN str.), 1667 (C]C str., alkene),
1652, 1605 (C]C str., aromatic), 656, 772 (OOP bending),
7.04 (t, 1H, J ¼ 7.81 Hz), 7.13 (t, 1H, J ¼ 8.07 Hz), 7.24 (m,
3H), 7.41 (t, 1H, J ¼ 8.51 Hz), 7.47 (d, 1H, J ¼ 8.86 Hz), 7.58
(m, 3H), 7.66 (s, 1H); 13C NMR (CDCl3) d ¼ 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 (Mþ).
1
812 (CeCl str.); H NMR (CDCl3) d ¼ 6.93 (m, 2H), 7.12
(d, 1H, J ¼ 7.89 Hz), 7.27 (d, 2H, J ¼ 8.83 Hz), 7.39 (d, 2H,
J ¼ 8.77 Hz), 7.48 (m, 1H), 7.79 (d, 1H, J ¼ 8.14 Hz), 7.87
(d, 1H, J ¼ 8.91 Hz), 8.04 (s, 1H); 13C NMR (CDCl3)
d ¼ 197.1, 144.0, 141.2, 139.8, 138.9, 136.0, 135.7, 135.0,
132.9, 131.3, 129.5, 128.8, 128.0, 127.5, 127.0, 126.5, 37.7;
FAB-mass (m/z): 435 (Mþ).
2.1.5.12. 1-(2,6-Dichlorophenyl)-3-((3-phenoxyphenyl)methy-
lene)-1,3-dihydro-indol-2-one (4l). IR (KBr, cmꢀ1): 1722
(C]O str.), 1138 (CeN str.), 1690 (C]C str., alkene),
1625, 1545 (C]C str., aromatic), 667, 759 (OOP bending),
810 (CeCl str.); 1H NMR (CDCl3) d ¼ 6.59 (t, 1H,
J ¼ 9.36 Hz), 6.74 (t, 1H, J ¼ 7.78 Hz), 6.91 (dd, 2H,
J ¼ 8.41 Hz), 7.07 (m, 5H), 7.19 (d, 2H, J ¼ 8.06 Hz), 7.23
(t, 1H, J ¼ 8.92 Hz), 7.39 (d, 1H, J ¼ 9.14 Hz), 7.46 (d, 2H,
J ¼ 8.17 Hz), 7.58 (d, 1H, J ¼ 7.93 Hz), 7.66 (s, 1H); 13C
NMR (CDCl3) d ¼ 197.3, 144.3, 157.5, 157.1, 140.9, 139.7,
139.0, 135.4, 135.3, 135.2, 129.9, 128.7, 128.6, 128.6,
127.8, 126.7, 122.4, 119.9, 117.8, 116.9, 114.2, 37.2; FAB-
mass (m/z): 457 (Mþ).
2.1.5.8. 1-(2,6-Dichlorophenyl)-3-((4-methoxyphenyl)methylene)-
1,3-dihydro-indol-2-one (4h). IR (KBr, cmꢀ1): 1718 (C]O
str.), 1216 (CeN str.), 1688 (C]C str., alkene), 1610, 1536
(C]C str., aromatic), 723 (OOP bending), 766 (CeCl str.);
1H NMR (CDCl3) d ¼ 3.86 (s, 3H), 6.68 (d, 2H,
J ¼ 9.82 Hz), 6.82 (t, 1H, J ¼ 7.86 Hz), 6.97 (t, 1H, J ¼
8.33 Hz), 7.10 (d, 2H, J ¼ 9.12 Hz), 7.23 (d, 1H,
J ¼ 8.56 Hz), 7.47 (m, 3H), 7.74 (d, 1H, J ¼ 8.71 Hz), 7.91
(s, 1H); 13C NMR (CDCl3) d ¼ 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
(Mþ).
2.1.5.13. 1-(2,6-Dichlorophenyl)-3-((4-hydroxyphenyl)methy-
lene)-1,3-dihydro-indol-2-one (4m). IR (KBr, cmꢀ1): 3418
(OeH str.), 1688 (C]O str.), 1107 (CeN str.), 1678 (C]C
str., alkene), 1610, 1579 (C]C str., aromatic), 656, 741
1
2.1.5.9. 1-(2,6-Dichlorophenyl)-3-((2-nitrophenyl)methylene)-
1,3-dihydro-indol-2-one (4i). IR (KBr, cmꢀ1): 1720 (C]O
str.), 1174 (CeN str.), 1645 (C]C str., alkene), 1608, 1568
(C]C str., aromatic), 1523 (NO2 str.), 742 (OOP bending),
792 (CeCl str.); 1H NMR (CDCl3) d ¼ 6.40 (d, 1H,
J ¼ 7.89 Hz), 6.83 (t, 1H, J ¼ 7.04 Hz), 6.94 (d, 1H, J ¼
7.32 Hz), 7.18 (tt, 1H, J ¼ 7.90 Hz), 7.39 (dd, 1H, J ¼
7.31 Hz), 7.53 (d, 2H, J ¼ 7.59 Hz), 7.67 (tt, 1H, J ¼ 7.82,
1.45 Hz), 7.76 (tt, 1H, J ¼ 6.00, 1.17 Hz), 7.83 (d, 1H,
J ¼ 6.76 Hz), 8.19 (s, 1H), 8.34 (dd, 1H, J ¼ 8.10, 1.21 Hz);
13C NMR (CDCl3) d ¼ 197.3, 146.5, 144.2, 140.9, 139.5,
138.3, 135.2, 134.9, 130.5, 129.5, 129.0, 128.5, 128.2,
127.9, 127.5, 126.8, 126.4, 120.7, 37.9; FAB-mass (m/z):
410 (Mþ).
(OOP bending), 717 (CeCl str.); H NMR (CDCl3) d ¼ 6.92
(d, 2H, J ¼ 7.15 Hz), 6.98 (s, 1H), 7.18 (t, 1H, J ¼ 8.20 Hz),
7.22 (t, 1H, J ¼ 7.11 Hz), 7.26 (t, 1H, J ¼ 8.35 Hz), 7.31 (d,
2H, J ¼ 7.68 Hz), 7.38 (d, 2H, J ¼ 8.66 Hz), 7.41 (d, 1H,
J ¼ 7.81 Hz), 7.44 (d, 1H, J ¼ 8.14 Hz), 7.61 (s, 1H); 13C
NMR (CDCl3) d ¼ 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 (Mþ).
2.1.5.14. 1-(2,6-Dichlorophenyl)-3-((3,4-dimethoxyphenyl)methy-
lene)-1,3-dihydro-indol-2-one (4n). IR (KBr, cmꢀ1): 2977, 2845
(CeH str.), 1693 (C]O str.), 1147 (CeN str.), 1612 (C]C
str., alkene), 1600, 1566 (C]C str., aromatic), 885, 775
(OOP bending), 1024 (CeOeC str.); 1H NMR (CDCl3)
d ¼ 3.94 (s, 3H), 3.96 (s, 3H), 6.39 (d, 1H, J ¼ 7.65 Hz), 6.91
(d, 1H, J ¼ 8.34 Hz), 7.11 (tt, 1H, J ¼ 7.92 Hz), 7.19 (tt, 1H,
J ¼ 7.28 Hz), 7.37 (dd, 1H), 7.53 (d, 2H, J ¼ 9.00 Hz), 7.61
2.1.5.10. 1-(2,6-Dichlorophenyl)-3-((4-fluorophenyl)methylene)-
1,3-dihydro-indol-2-one (4j). IR (KBr, cmꢀ1): 1720 (C]O