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S.K. Sridhar et al. / European Journal of Medicinal Chemistry 36 (2001) 615–625
4.1.1.2. 3-(4-Chloro-phenylimino)-1,3-dihydro-indol-2-
one (2) [26]
(CꢁN), 1480, 1440 (CꢁC), 1320 (NꢁO), 1250 (NꢀH), 730,
1
680 (ArꢀH). H-NMR (CDCl3, l, ppm): 2.50–3.62 (s,
IR (KBr, cm−1): 3220 (enolic OꢀH), 1625 (CO), 1590
(CꢁN), 1440 (CꢁC), 815, 780, 740 (ArꢀH), 660 (CꢀCl).
1H-NMR (CDCl3, l, ppm): 6.45–7.18 (m, 5H,
4,5,6,2%,6%H), 7.18–7.56 (m, 3H, 7,3%,5%,H), 8.92–9.39 (s,
1H, NH).
3H, 5-CH3), 6.12–6.35 (d, 1H, 2%H), 6.66–6.92 (d, 2H,
4%,5%H), 6.93–7.12 (d, 1H, 8%H), 7.12–7.60 (m, 6H,
4,6,7,3%,6%,7%H), 7.60–7.98 (s, 1H, NH).
4.1.1.9. 3-(1-Naphthylimino)-5-methyl-1,3-dihydro-
indol-2-one (9)
4.1.1.3. 3-(4-Bromo-phenylimino)-1,3-dihydro-indol-2-
one (3) [26]
IR (KBr, cm−1): 3200 (enolic OꢀH), 1660 (CO), 1590
1
(CꢁN), 1460 (CꢁC), 1300 (CꢀH), 780, 760 (ArꢀH). H-
IR (KBr, cm−1): 3220 (enolic OꢀH), 1625 (CO), 1590
(CꢁN), 1440 (CꢁC), 815, 780, 740 (ArꢀH), 660 (CꢀBr).
1H-NMR (CDCl3, l, ppm): 6.64–7.01 (m, 5H,
4,5,6,2%,6%H), 7.17–7.81 (m, 3H, 7,3%,5%,H), 8.95–9.30 (s,
1H, NH).
NMR (CDCl3, l, ppm): 1.10–2.63 (s, 3H, 5-CH3), 6.47–
6.66 (d, 2H, 2%,6%H), 6.68–6.85 (d, 1H, 7H), 6.87–7.00
(d, 1H, 6H), 7.04–7.34 (d, 2H, 3%,5%H), 7.38–7.48 (s, 1H,
4H), 7.48–7.62 (s, 1H, NH).
4.1.1.10. 3-(4-Bromo-phenylimino)-5-methyl-1,3-
dihydro-indol-2-one (10)
4.1.1.4. 3-(4-Methoxy-phenylimino)-1,3-dihydro-indol-2-
one (4) [26]
IR (KBr, cm−1): 3100(enolic OꢀH), 1700 (CO),
1590(CꢁN), 1470 (CꢁC), 1290 (CꢀH), 800, 720 (ArꢀH),
IR (KBr, cm−1): 3150 (enolic OꢀH), 1620 (CO), 1590
(CꢁN), 1440 (CꢁC), 1315 (CꢀH), 1230 (CꢀO), 815, 740
1
1
630 (CꢀBr). H-NMR (CDCl3, l, ppm): 1.02–1.90 (s,
(ArꢀH). H-NMR (CDCl3, l, ppm): 3.68–3.95 (s, 3H,
3H, 5-CH3), 6.52–6.71 (t, 2H, 4,6H), 6.73–6.87 (d, 1H,
7H), 6.92–7.05 (d, 2H, 2%,6%H), 7.06–7.19 (d, 2H,
3%,5%H), 8.12–8.67 (s, 1H, NH).
4%-OCH3), 6.63–7.52 (m, 8H, 4,5,6,7,2%,3%,5%,6%H), 8.42–
8.90 (s, 1H, NH).
4.1.1.5. 3-(4-Methyl-phenylimino)-1,3-dihydro-indol-2-
one (5) [26]
4.1.1.11. 3-(4-Chloro-phenylimino)-5-methyl-1,3-
dihydro-indol-2-one (11) [30]
IR (KBr, cm−1): 3200 (enolic OꢀH), 1630 (CO), 1590
1
IR (KBr, cm−1): 3000 (enolic OꢀH), 1690 (CO), 1590
(CꢁN), 1440 (CꢁC), 1290 (CꢀH), 800, 720 (ArꢀH), 620
(CꢁN), 1440 (CꢁC), 1310 (CꢀH), 810, 735 (ArꢀH). H-
NMR (CDCl3, l, ppm): 2.26–2.53 (s, 3H, 4%-CH3),
6.60–7.44 (m, 8H, 4,5,6,7,2%,3%,5%,6%H), 9.09–9.42 (s, 1H,
NH).
1
(CꢀCl). H-NMR (CDCl3, l, ppm): 1.02–1.90 (s, 3H,
5-CH3), 6.52–6.71 (t, 2H, 4,6H), 6.73–6.87 (d, 1H, 7H),
6.920–7.05 (d, 2H, 2%,6%H), 7.06–7.19 (d, 2H, 3%,5%H),
8.12–8.67 (s, 1H, NH).
4.1.1.6. Indole-2,3-dione-3-phenyl hydrazone (6) [27]
IR (KBr, cm−1): 3100 (enolic OꢀH), 1660 (CO), 1530
(CꢁN), 1470, 1440 (CꢁC), 1220 (NꢀH), 735, 680 (ArꢀH).
1H-NMR (CDCl3, l, ppm): 6.80–7.17 (m, 3H, 5,6,7H),
7.17–7.51 (m, 5H, 2%,3%,4%,5%,6%H), 7.51–7.74 (d, 1H, 4H),
7.80–8.13 (s, 1H, NH), 12.54–12.86 (s, 1H, ꢀNꢁNH).
4.1.1.12. 3-(1-Naphthylimino)-5-nitro-1,3-dihydro-indol-
2-one (12)
IR (KBr, cm−1): 3300 (enolic OꢀH), 1685 (CO), 1600
1
(CꢁN), 1490 (CꢁC), 1310 (NꢁO), 780, 755 (ArꢀH). H-
NMR (CDCl3, l, ppm): 6.67–6.87 (d, 1H, 8%H), 7.39–
7.52 (m, 3H, 4,6,7H), 7.52–8.09 (m, 6H,
2%,3%,4%,5%,6%,7%H), 8.09–8.38 (s, 1H, NH).
4.1.1.7. Indole-2,3-dione-3-thiosemicarbazone (7) [28]
IR (KBr, cm−1): 3290 (NꢀH), 3100 (enolic OꢀH), 1650
(CO), 1600, 1570 (CꢁN), 1440 (CꢁC), 1185 (NꢀH), 1110
(CꢁS), 750, 730 (ArꢀH). 1H-NMR (CDCl3, l, ppm):
6.84–7.04 (m, 3H, 5,6,7H), 7.07–7.23 (d, 1H, 4H),
7.48–7.75 (s, 2H, ꢀNH2), 7.77–8.05 (s, 1H, NH), 12.45–
13.04 (s, 1H, ꢀNꢁNH).
4.1.1.13. 3-(4-Bromo-phenylimino)-5-nitro-1,3-
dihydro-indol-2-one (13) [30]
IR (KBr, cm−1): 3190 (enolic OꢀH), 1685 (CO), 1600
(CꢁN), 1470 (CꢁC), 1315 (NꢁO), 805, 740 (ArꢀH), 630
1
4.1.1.8. 3-[(2,4-Dinitrophenylimino)-hydrazono]-1,3-
dihydro-indol-2-one (8) [29]
(CꢀBr). H-NMR (CDCl3, l, ppm): 6.42–6.67 (s, 1H,
NH), 6.80–7.32 (m, 3H, 4,6,7H), 7.34–7.90 (d, 2H,
3%,5%H), 7.93–9.03 (d, 2H, 2%,6%H).
IR (KBr, cm−1): 3200 (enolic OꢀH), 1590 (CO), 1560