S. Ahadi et al. / Tetrahedron 67 (2011) 3954e3958
3957
6.66e7.92 (11H, m, HeAr), 10.66 (1H, s, NH). 13C NMR (75 MHz,
DMSO-d6): dC¼40.4, 55.9, 57.0, 112.3, 112.5, 113.1, 123.0, 124.8, 127.4,
127.9, 131.8, 136.6, 141.9, 142.5, 142.7, 149.9, 177.6, 197.2, 197.9. MS
(EI, 70 eV) m/z: 476 (Mþ), 474 (Mþ). Anal. Calcd for C25H19BrN2O3: C,
63.17; H, 4.03; N, 5.89. Found: C, 63.10; H, 4.11; N, 5.98%.
143.2, 149.8, 198.2, 201.0. MS (EI, 70 eV) m/z: 431 (Mþ). Anal. Calcd
for C29H21NO3: C, 80.72, H, 4.91; N, 3.25. Found: C, 80.65; H, 4.99;
N, 3.32%.
4.1.11. 2-(4-(Dimethylamino)phenyl)-1H,10H-2,20-biindene-
1,10,3,30(2H,20H)-tetraone (10). Yellow powder (0.41 g, 60%); mp
291 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3243, 3078, 1716, 1702. 1H NMR
(300 MHz, DMSO-d6): dH¼2.86 (6H, s, 2CH3), 4.76 (1H, s, CH),
6.64e7.99 (12H, m, HeAr). 13C NMR (75 MHz, DMSO-d6): dC¼40.4,
57.7, 109.7, 112.6, 120.0, 123.3, 123.8, 126.6, 127.9, 130.6, 135.8, 136.8,
141.6, 142.4, 142.7, 149.8, 150.1, 197.0, 197.4, 198.3, 199.9. MS (EI,
70 eV) m/z: 409 (Mþ). Anal. Calcd for C26H19NO4: C, 76.27, H, 4.68;
N, 3.42. Found: C, 76.16; H, 4.60; N, 3.51%.
4.1.5. 2-(3-(4-(Dimethylamino)phenyl)-5-nitro-2-oxoindolin-3-yl)-
1H-indene-1,3(2H)-dione (4e). Cream powder (0.44 g, 91%); mp
215 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3451, 3184, 1742, 1706, 1612. 1H
NMR (300 MHz, DMSO-d6): dH¼2.88 (6H, s, 2CH3), 5.00 (1H, s,
CH), 6.66e8.15 (11H, m, HeAr), 11.29 (1H, s, NH). 13C NMR
(75 MHz, DMSO-d6): dC¼40.5, 56.4, 57.3, 110.5, 112.6, 120.3, 123.2,
124.3, 126.6, 127.9, 131.3, 136.8, 141.7, 142.1, 142.7, 149.7, 150.0,
178.4, 197.1, 197.6. MS (EI, 70 eV) m/z: 441 (Mþ). Anal. Calcd for
C25H19N3O5: C, 68.02; H, 4.34; N, 9.52. Found: C, 67.91; H, 4.28; N,
9.43%.
Acknowledgements
We gratefully acknowledge financial support from the Research
Council of Shahid Beheshti University.
4.1.6. 2-(3-(4-(Dimethylamino)phenyl)-5-methyl-2-oxoindolin-3-
yl)-1H-indene-1,3(2H)-dione (4f). Cream powder (0.41 g, 94%); mp
239 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3362, 3190, 1742, 1721, 1690. 1H
NMR (300 MHz, DMSO-d6): dH¼1.96 (3H, s, CH3), 2.87 (6H, s, 2CH3),
4.69 (1H, s, CH), 6.47e7.90 (11H, m, HeAr), 10.36 (1H, s, NH). 13C
NMR (75 MHz, DMSO-d6): dC¼21.0, 40.5, 55.6, 57.2, 110.0, 112.4,
122.9, 125.5, 128.1, 129.3, 129.7, 130.2, 136.3, 136.4, 140.8, 141.9,
149.8, 178.0, 198.0. MS (EI, 70 eV) m/z: 410 (Mþ). Anal. Calcd for
C26H22N2O3: C, 76.08, H, 5.40; N, 6.82. Found: C, 75.99; H, 5.46; N,
6.77%.
Supplementary data
Supplementary data associated with this article can be found in
References and notes
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4.1.7. 2-(3-(4-(Dimethylamino)phenyl)-5-fluoro-2-oxoindolin-3-yl)-
1H-indene-1,3(2H)-dione (4g). Cream powder (0.41 g, 98%); mp
252 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3398, 1737, 1711, 1705. 1H NMR
(300 MHz, DMSO-d6): dH¼2.87 (6H, s, 2CH3), 4.78 (1H, s, CH),
6.53e7.91 (11H, m, HeAr), 10.54 (1H, s, NH). 13C NMR (75 MHz,
DMSO-d6): dC¼40.5, 56.2, 56.9, 111.1, 112.1, 112.5, 115.3, 123.1, 124.8,
128.0, 136.6, 139.4, 141.9, 142.8, 149.9, 177.9, 197.3, 197.8. MS (EI,
70 eV) m/z: 414 (Mþ). Anal. Calcd for C25H19FN2O3: C, 72.45, H, 4.62;
N, 6.76. Found: C, 72.55; H, 4.68; N, 6.69%.
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Dubac, J. Tetrahedron Lett. 1997, 38, 8871; (b) Repichet, S.; Le Roux, C.; Dubac, J.;
4.1.8. 2-(5-Bromo-3-(4-(dimethylamino)phenyl)-1-methyl-2-ox-
oindolin-3-yl)-1H-indene-1,3(2H)-dione (4h). Cream powder (0.49 g,
90%); mp 220 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3420,1742,1715,1701. 1H
NMR (300 MHz, DMSO-d6): dH¼2.50 (6H, s, 2CH3), 3.12 (3H, s, CH3),
4.91 (1H, s, CH), 6.65e8.31 (11H, m, HeAr).13C NMR (75 MHz, DMSO-
d6): dC¼26.9, 40.4, 55.1, 57.5, 111.4, 112.5, 113.9, 123.1, 123.2, 127.1,
128.0, 131.7, 132.0, 136.7, 141.7, 142.7, 150.6, 176.0, 197.2, 197.7. MS (EI,
70 eV) m/z: 490 (Mþ), 488 (Mþ). Anal. Calcd for C26H21BrN2O3: C,
63.81, H, 4.33; N, 5.72. Found: C, 63.70; H, 4.25; N, 5.61%.
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4.1.9. 2-(3-(4-(Dimethylamino)phenyl)-1-ethyl-5-nitro-2-ox-
oindolin-3-yl)-1H-indene-1,3(2H)-dione (4i). Yellow powder (0.47 g,
85%); mp 220 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3085, 1748, 1732, 1711.
1H NMR (300 MHz, DMSO-d6): dH¼1.19 (3H, t, J¼6.8 Hz, CH3), 2.87
(6H, s, 2CH3), 3.77e3.81 (2H, m, CH2), 5.09 (1H, s, CH), 6.65e8.23
(11H, m, HeAr). 13C NMR (75 MHz, DMSO-d6): dC¼12.3, 35.4, 40.4,
54.6, 57.7, 109.7, 112.6, 120.0, 123.3, 123.6, 126.6, 127.9, 130.6, 136.8,
136.8, 141.6, 142.4, 142.7, 149.8, 150.1, 176.6, 197.0, 197.4. MS (EI,
70 eV) m/z: 469 (Mþ). Anal. Calcd for C27H23N3O5: C, 69.07, H, 4.94;
N, 8.95. Found: C, 69.13; H, 4.99; N, 8.87.
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4.1.10. 2-(1-(4-(Dimethylamino)phenyl)-2-oxo-1,2-dihydroacenaph-
thylen-1-yl)-1H-indene-1,3(2H)-dione (9). Yellow powder (0.43 g,
73%); mp 284 ꢀC dec; IR (KBr) (nmax, cmꢁ1): 3278, 3075, 1717, 1654.
1H NMR (300 MHz, DMSO-d6): dH¼2.81 (6H, s, 2CH3), 5.19 (1H, s,
CH), 6.58e8.21 (14H, m, HeAr). 13C NMR (75 MHz, DMSO-d6):
dC¼40.4, 58.3, 60.0, 112.4, 121.9, 122.9, 123.1, 125.3, 125.5, 128.3,
128.9, 129.4, 130.6, 131.9, 132.2, 136.4, 136.7, 138.9, 141.2, 141.6,