S. M. Saad et al.
(C=N), 1529 (C=C), 702 (C–Cl) cm-1; EI-MS: m/z
(%) = 364 ([M ? 2]?, 40), 362 ([M]?, 100), 346 (8),
327 (25), 312 (9).
References
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3-(6-Chloro-4-phenylquinazolin-2-yl)phenol
(8, C20H13ClN2O)
Yield: quantitative; m.p.: 105–106 °C; Rf = 0.33 (ethyl
acetate/hexane, 1:9); 1H NMR (300 MHz, DMSO-d6):
d = 9.63 (s, 1H, 30-OH), 8.16 (d, 1H, J8,7 = 9.0 Hz, H-8),
8.04 (m, 3H, H-7, H-5, H-60), 7.99 (s, 1H, H-20), 7.87 (m,
2H, H-200, H-600), 7.67 (m, 3H, H-400, H-300, H-500), 7.38 (t,
1H, J5 (4 ,6 ) = 8.1 Hz, H-50), 6.95 (d, 1H, J4 ,5 = 7.5 Hz,
H-40) ppm; 13C NMR (75 MHz, DMSO-d6): d = 196.78,
150.50, 139.19, 133.94, 132.06, 131.28, 128.46, 128.37,
0
0
0
0
0
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(2010) Bioorg Med Chem 18:4317
ꢀ
118.90, 116.99, 116.94 ppm; IR (KBr): m = 3420 (O–H),
1582 (C=N), 1535 (C=C), 1151 (C–O), 702 (C–Cl) cm-1
;
EI-MS: m/z (%) = 334 ([M ? 2]?, 33), 332 ([M]?, 97),
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EE, El-Subbagh HI (2013) Eur J Med Chem 63:33
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col 6:511
331 (100), 297 (96), 255 (6).
6-Chloro-2-(3-methoxyphenyl)-4-phenylquinazoline
(9, C21H15ClN2O)
Yield: quantitative; m.p.: 16–164 °C; Rf = 0.83 (ethyl
acetate/hexane, 1:9); 1H NMR (300 MHz, DMSO-d6):
d = 8.19 (d, 2H, J2 ,3 = J6 ,5 = 8.7 Hz, H-200, H-600),
8.11 (m, 2H, H-8, H-7), 8.01 (s, 1H, H-5), 7.89 (m, 2H, H-
300, H-500), 7.67 (m, 3H, H-50, H-20, H-400), 7.51 (t, 1H,
00 00
00 00
J6 (5 ,4 ) = 7.8 Hz, H-60), 7.16 (d, 1H, J4 ,5 = 6.3 Hz, H-40),
3.86 (s, 3H, 30-OCH3) ppm; 13C NMR (100 MHz, DMSO-
d6): d = 167.36, 159.64, 159.14, 149.76, 138.54, 136.35,
134.92, 131.97, 130.99, 130.37, 129.89, 128.79, 125.43,
121.77, 120.66, 116.76, 113.20, 55.22 ppm; IR (KBr):
0
0
0
0
0
¨
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ꢀ
m = 1599 (C=N), 1535 (C=C), 1159 (C–O), 704 (C–Cl)
cm-1; EI-MS: m/z (%) = 348 ([M ? 2]?, 31), 346 ([M]?,
93), 345 (100), 330 (4), 317 (18), 311 (24) 281 (5).
6-Chloro-2-(2-methoxyphenyl)-4-phenylquinazoline
(15, C21H15ClN2O)
Yield: quantitative; m.p.: 144–146 °C; Rf = 0.39 (ethyl
acetate/hexane, 1:9); 1H NMR (300 MHz, DMSO-d6):
d = 8.09 (m, 3H, H-8, H-7, H-5), 7.82 (m, 2H, H-200,
H-600), 7.62 (m, 4H, H-60, H-400, H-300, H-500), 7.46 (m, 1H,
H-40), 7.17 (d, 1H, J3 ,4 = 7.2 Hz, H-30), 7.06 (m, 1H,
H-50), 3.77 (s, 3H, 20-OCH3) ppm; 13C NMR (100 MHz,
DMSO-d6): d = 166.69, 161.44, 157.48, 149.60, 136.25,
134.71, 132.04, 131.21, 130.91, 130.30, 129.97, 128.75,
128.64, 125.25, 121.11, 120.29, 112.45, 55.87 ppm; IR
0
0
ꢀ
(KBr): m = 1589 (C=N), 1533 (C=C), 1178 (C–O), 706
(C–Cl) cm-1; EI-MS: m/z (%) = 348 ([M ? 2]?, 34), 346
([M]?, 100), 331 (5), 317 (36), 281 (28), 241 (14).
Acknowledgments The authors are thankful to the OPCW, The
Netherlands, for their financial support for project No. L/ICA/ICB/
173681/12 and DAAD (Deutscher Akademischer Austauschdienst),
Bonn (Germany) granting fellowship to Prof. Dr. Khalid M. Khan.
123