10.1002/cbdv.201900670
Chemistry & Biodiversity
Chem. Biodiversity
Yellow solid; Yield: 67%. mp: 181.6-182.9 oC. Rf = 0.66 (DCM:MeOH = 14:1). IR (KBr, cm-1):3215 (N-H); 2986, 2903 (CH, CH2); 1720 (C=O);
1694 (C=N); 1611 (C=C). 1H-NMR (500 MHz, DMSO-d6, ppm): δ 11.84 (s, NH-isatin, 1H); 10.89 (s, CONH, 1H); 8.36 (s, H2, 1H); 8.32 (s, H4’, 1H);
8.02 (t, J = 2.00, H5, 1H); 7.82 (dd, J = 7.75, J’ = 2.25, H7, 1H); 7.69-7.67 (m, H8, 1H); 7.36 (d, J = 6.5, H7’, 1H); 6.83 (dd, J = 7.50, J’ = 1.50, H6’, 1H);
5.23 (s, NCH2CO, 2H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 171.56, 164.58, 159.78, 149.40, 147.29, 143.18, 135.23, 132.62, 132.02, 130.10,
127.30, 126.42, 126.25, 125.51, 123.08, 120.89, 116.66, 112.48, 48.02. HR-MS (ESI) m/z calculated for C18H11Cl2N5O3, {[M-H]-, (35Cl, 35Cl)}
414.0238, {[M-H]-, (37Cl, 35Cl)} 416.0238, {[M-H]-, (37Cl, 37Cl)} 418.0238. Found, 414.0164, 416.0164, 418.0164.
2-(6-Chloro-4-oxoquinazolin-3(4H)-yl)-N'-(5-methyl-2-oxoindolin-3-ylidene)acetohydrazide (5k)
Yellow solid; Yield: 69%. mp: 180.5-182.2 oC. Rf = 0.61 (DCM:MeOH = 14:1). IR (KBr, cm-1):3318, 3210 (N-H); 2970, 2905 (CH, CH2); 1721
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(C=O); 1674 (C=N); 1607 (C=C). H-NMR (500 MHz, DMSO-d6, ppm): δ 11.53 (s, NH-isatin, 1H); 10.64 (s, CONH, 1H); 8.35 (s, H2, 1H); 8.02-
8.01 (m, H5, H4’, 2H); 7.82 (dd, J = 9.00, J’ = 2.50, H7, 1H); 7.68 (d, J = 8.50, H8, 1H); 7.12 (d, J = 8.00, H7’, 1H); 6.72 (d, J = 8.00, H6’, 1H); 5.21 (s,
NCH2CO, 2H); 2.20 (s, CH3, 3H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.79, 159.76, 149.46, 147.30, 142.10, 135.29, 135.21, 133.53, 132.87,
132.29, 132.09, 132.00, 131.27, 130.09, 127.15, 125.50 ,123.10 ,123.01, 115.66, 110.83, 20.92. HR-MS (ESI) m/z calculated for C19H14ClN5O3,
394.0785 {[M-H]-, 35Cl}, 396.0785 {[M-H]-, 37Cl}. Found, 394.0711, 396.0711.
2-(6-Bromo-4-oxoquinazolin-3(4H)-yl)-N'-(2-oxoindolin-3-ylidene)acetohydrazide (5l)
Yellow solid; Yield: 62%. mp: 182.1-183.0 oC. Rf = 0.62 (DCM:MeOH = 14:1). IR (KBr, cm-1):3343, 3244 (N-H); 2990, 2887 (CH, CH2); 1717
(C=O); 1668 (C=N); 1603 (C=C). 1H-NMR (500 MHz, DMSO-d6, ppm): δ 11.62 (s, NH-isatin, 1H); 10.77 (s, CONH, 1H); 8.37 (s, H2, 1H); 8.16 (d, J
= 2.50, H5, 1H); 8.09 (d, J = 7.50, H4’, 1H); 7.94 (dd, J = 8.75, J’ = 2.25, H7, 1H); 7.60 (d, J = 8.50, H8, 1H); 7.32 (t, J = 7.50, H6’, 1H); 6.96 (s, H7’,
1H); 6.83 (d, J = 7.50, H5’, 1H); 5.23 (s, NCH2CO, 2H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.65, 149.55, 147.56, 144.49, 137.95, 133.33,
130.22, 128.61, 126.70, 123.44, 123.16, 122.24, 120.17, 115.55, 111.17, 48.05. HR-MS (ESI) m/z calculated for C18H12BrN5O3, 424.0123 {[M-H]-,
79Br}, 426.0123 {[M-H]-, 81Br}. Found, 424.0042, 426.0042.
2-(6-Bromo-4-oxoquinazolin-3(4H)-yl)-N'-(5-chloro-2-oxoindolin-3-ylidene)acetohydrazide (5m)
Yellow solid; Yield: 65%. mp: 180.9-181.5 oC. Rf = 0.69 (DCM:MeOH = 14:1). IR (KBr, cm-1): 3325 (N-H); 3061, 2984, 2905 (CH, CH2); 1721
(C=O); 1670 (C=N); 1609 (C=C). 1H-NMR (500 MHz, DMSO-d6, ppm): δ 11.84 (s, NH-isatin, 1H); 10.89 (s, CONH, 1H); 8.38 (s, H4’, 1H); 8.36 (s,
H2, 1H); 8.16 (d, J = 2.50, H5, 1H); 7.94 (dd, J = 8.75, J’ = 2.25, H7, 1H); 7.61 (d, J = 9.00, H8, 1H); 7.37 (d, J = 7.00, H6’, 1H); 6.84 (d, J = 8.50, H7’,
1H); 5.23 (s, NCH2CO, 2H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 171.56, 164.58, 159.78, 149.40, 147.29, 143.18, 135.23, 132.62, 132.02,
130.10, 127.30, 126.42, 126.25, 125.51, 123.08, 120.89, 116.66, 112.48, 48.02. HR-MS (ESI) m/z calculated for C18H11BrClN5O3, 457.9733 {[M-
H]-, (35Cl, 79Br)}, 459.9733 {[M-H]-, (35Cl, 81Br), (37Cl, 79Br)}, 461.9733 {[M-H]-, (37Cl, 81Br)}. Found, 457.9650, 459.9630, 461.9616.
2-(6-Bromo-4-oxoquinazolin-3(4H)-yl)-N'-(5-methyl-2-oxoindolin-3-ylidene)acetohydrazide(5n)
Yellow solid; Yield: 68%. mp: 179.3-180.1 oC. Rf = 0.57 (DCM:MeOH = 14:1). IR (KBr, cm-1): 3099, 2986, 2905 (CH, CH2); 1711 (C=O); 1682
(C=N); 1607 (C=C). 1H-NMR (500 MHz, DMSO-d6, ppm): δ 11.54 (s, NH-isatin, 1H); 10.65 (s, CONH, 1H); 8.37 (s, H2, 1H); 8.15 (d, J = 2.50, H5,
1H); 7.99 (s, H4’, 1H); 7.93 (dd, J = 8.75, J’ = 2.25, H7, 1H); 7.60 (d, J = 8.50, H8, 1H); 7.12 (d, J = 7.50, H7’, 1H); 6.72 (d, J = 8.00, H6’, 1H); 5.23 (s,
NCH2CO, 2H); 2.20 (s, CH3, 3H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 171.24, 164.83, 159.65, 149.54, 147.55, 142.15, 137.93, 133.56, 131.31,
130.21, 129.61, 127.15, 123.43, 120.17, 115.58, 110.84, 48.02, 20.91. HR-MS (ESI) m/z calculated for C19H14BrN5O3 , {[M+H]+, 79Br}, 440.0280,
{[M+H]+, 81Br}, 442.0280. Found, 440.0345, 442.0325.
2-(6-Iodo-4-oxoquinazolin-3(4H)-yl)-N'-(2-oxoindolin-3-ylidene)acetohydrazide (5o)
Yellow solid; Yield: 58%. mp: 179.7-180.5 oC. Rf = 0.62 (DCM:MeOH = 14:1). IR (KBr, cm-1):3262, 3148 (N-H); 3086, 2972, 2899, 2833 (CH,
CH2); 1724 (C=O); 1680 (C=N); 1603 (C=C). 1H-NMR (500 MHz, DMSO-d6, ppm): δ 11.62 (s, NH-isatin, 1H); 10.77 (s, CONH, 1H); 8.35 (s, H2, H5,
2H); 8.08 (dd, J = 8.50, J’ = 2.00, H4’, H7, 2H); 7.44 (d, J = 8.50, H8, 1H); 7.32 (t, J = 7.25, H6’, 1H); 6.97 (s, H7’, 1H); 6.84 (d, J = 8.00, H5’, 1H); 5.22
(s, NCH2CO, 2H). 13C NMR (125 MHz, DMSO-d6, ppm): δ 159.46, 149.60, 147.84, 144.50, 143.46, 134.77, 133.36, 129.98, 126.72, 123.63,
122.25, 115.56, 111.18, 92.81, 48.09. HR-MS (ESI) m/z calculated for C18H12IN5O3, [M+H]+ 473.9984. Found, 474.1527
N'-(5-Chloro-2-oxoindolin-3-ylidene)-2-(6-iodo-4-oxoquinazolin-3(4H)-yl)acetohydrazide (5p)
Yellow solid; Yield: 53%. mp: 178.2-179.1 oC. Rf = 0.61 (DCM:MeOH = 14:1). IR (KBr, cm-1):3294, 3211 (N-H); 3084, 2986, 2903 (CH, CH2);
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1719 (C=O); 1692 (C=N); 1609 (C=C). H-NMR (500 MHz, DMSO-d6, ppm): δ 11.83 (s, NH-isatin, 1H); 10.89 (s, CONH, 1H); 8.37 – 8.31 (m, H4’,
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