, CDCl 3 ) 8.13 (d, 2H, J¼ 8.10 Hz, H-3 00 and H-5 00 ), 7.98 (s, 1H, H-4), 7.82 (d, 1H, J¼ 9.00 Hz, H-5), 7.79 (d, 2H, J¼ 8.10 Hz, H-3 0 and H-5 0 ), 7.50 (d, 2H, J¼ 8.10 Hz, H-2 00 and H-6 00 ), 7.42 (d, 1H, J¼ 2.40 Hz, H-8), 7.41 (d, 2H, J¼ 8.10 Hz, H-2 0 and H-6 0 ), 7.33 (dd, 1H, J¼ 9
, 13C NMR d (75 MHz, CDCl 3 ) 159.9, vol.142, pp.130-133
, C-6), vol.129, p.0
,
, CDCl 3 ) 8.14 (d, 2H, J¼ 8.40 Hz, H-3 00 and H-5 00 ), 8.00 (d, 1H, J¼ 9, 30 Hz, H-8), 7.94 (s, 1H, H-4), 7.74 (d, 2H, J¼ 8.40 Hz, H-3 0 and H-5 0 ), vol.7
, C-4a), 140.0 (C-1 0 ), 13C NMR d (75 MHz, CDCl 3 ) 161.9, vol.151, p.0
, , pp.568-407
, Pale-yellow oil (96%)
, 7.96 (d, 1H, J¼ 9.00 Hz, H-8), 7.89 (s, 1H, H-4), 7.71 (d, 2H, J¼ 8.10 Hz, H-3 0 and H-5 0 ), 7.45 (d, 2H, J¼ 8.10 Hz, H-2 00 and H-6 00 ), 7.38 (d, 2H, J¼ 8.40 Hz, H-2 0 and H-6 0 ), 7.10 (d, 1H, J¼ 2.40 Hz, H-5), 7.04 (dd, 1H, J¼ 9.00 and 2.40 Hz, p.0
, C-4a), 140.0 (C-1 0 ), 13C NMR d (75 MHz, CDCl 3 ) 161.9, vol.160, p.0
-methylpiperazin-1-yl)butyl)aminomethyl]phenylgisoquinoline (2k) Yellow oil (97%); 1 H NMR d (300 MHz, 30 Hz, H-8), 7.91 (s, 1H, H-4), 7.71 (d, 2H, J¼ 8.10 Hz, H-3 0 and H-5 0 ), 7.44 (d, 2H, J¼ 8.10 Hz, H-2 00 and H-6 00 ), 7.38 (d, 2H, J¼ 8.10 Hz, H-2 0 and H-6 0 ), vol.7 ,
, C-4a), 140.0 (C-1 0 ), 139.8 (C-1 00 ), 131.6 (C-2 0 and C-6 0 ), 13C NMR d (75 MHz, CDCl 3 ) 161.9, vol.151, p.0
Yellow oil (59%); 1 H NMR d (300 MHz, CDCl 3 ) 8.14 (d, 2H, J¼ 8.20 Hz, H-3 00 and H-5 00 ), 8.00 (d, 1H, J¼ 9.20 Hz, H-8), 7.95 (s, 1H, H-4), 7.74 (d, 2H, J¼ 8.20 Hz, H-3 0 and H-5 0 ), 7.48 (d, 2H, J¼ 8.20 Hz, H-2 00 and H-6 00 ), 7.42 (d, 2H, J¼ 8.20 Hz, H-2 0 and H-6 0 ), 7.16 (d, 1H, J¼ 2.50 Hz, H-5), 7.10 (dd, 1H, J¼ 9.20 and 2.50 Hz ,
, C-4a), 140.0 (C-1 0 ), 152.0 (C-1), vol.142, p.0
89 (d, 2H, J¼ 8.10 Hz, H-2 00 and H-6 00 ), 7.63 (d, 2H, CDCl 3 ) 8.69 (d, 2H, J¼ 8.10 Hz, H-2 0 and H-6 0 ), 8.17 (dd, 1H, J¼ 8.40 and 1.20 Hz, H-8), 8.14 (dd, 1H, J¼ 8.40 and 1.20 Hz, H-5), 7.91 (ddd, 1H, J¼ 8.40, 7.00 and 1.20 Hz, H-7), vol.7, p.0 ,
,
, C-3 00 and C-5 00 , C-2 0 and C-6 0 , C-2 00 and C-6 00 ), 123.7 (C-4a), 105.7 (C-5), vol.138, p.0
-dimethylaminopropyl)aminomethyl]phenylgquinazoline (3i) Yellow oil (97%); 1 H NMR d (300 MHz, 30 Hz, H-8), 7.80 (d, 2H, J¼ 8.25 Hz, H-2 0 and H-6 0 ), 7.48 (d, 2H, J¼ 8.25 Hz, H-3 00 and H-5 00 ), 7.43 (dd, 1H, J¼ 9.30 and 2.80 Hz, H-7), 7.40 (d, 2H, J¼ 8.25 Hz, H-3 0 and H-5 0 ), vol.7 ,
, 13C NMR d (75 MHz, CDCl 3 ) 167.6 (C-6), 159.8 (C-2), 159.2 (C-4), 149.4 (C-8a), vol.143, p.0
,
, 82 (d, 2H, J¼ 8.15 Hz, H-2 0 and H-6'), 7.51 (d, 2H, J¼ 8.15 Hz, H-3 00 and H-5 00 ), 7.44 (dd, 1H, J¼ 9.00 and 2.60 Hz, H-7), 7.42 (d, 2H, J¼ 8.15 Hz, H-3 0 and H-5 0 ), 7.32 (d, 1H, J¼ 2.60 Hz, H-5), vol.7
, 13C NMR d (75 MHz, CDCl 3 ) 167.7 (C-6), vol.159, p.0
-methylpiperazin-1-yl)propyl)aminomethyl]phenylgquinazoline (3k) Yellow oil (97%); 1 H NMR d (300 MHz, 7.47 (dd, 1H, J¼ 9.20 and 2.80 Hz, H-7), 7.39 (d, 2H, J¼ 8.30 Hz, H-3 0 and H-5 0 ), vol.7, p.0 ,
, CDCl 3 ) 167.6 (C-6), 159.8 (C-2), 159.3 (C-4), 149.5 (C-8a), 13C NMR d (75 MHz, vol.143, p.0
, 123.7 (C-4a), 105.7 (C-5), vol.129, pp.127-131
-methylpiperazin-1-yl)ethyl)aminomethyl]phenylgquinazoline (3l) Yellow oil (96%); 1 H NMR d (300 MHz, 20 Hz, H-8), 7.87 (d, 2H, J¼ 8.20 Hz, H-2 0 and H-6 0 ), 7.55 (d, 2H, J¼ 8.30 Hz, H-3 00 and H-5 00 ), 7.52 (dd, 1H, J¼ 9.20 and 2.80 Hz, H-7), vol.7 ,
, 13C NMR d (75 MHz, CDCl 3 ) 167.7 (C-6), 159.8 (C-2), vol.159, p.0
m) Pale yellow oil (89%); 1 H NMR d (300 MHz, CDCl 3 ) 8.61 (d, 2H, J¼ 7.95 Hz, H-2 00 and H-6 00 ), 7.99 (d, 1H, J¼ 9.15 Hz, H-5), 7.82 (d, 2H, J¼ 7.95 Hz, H-2 0 and H-6 0 ), 7.53 (d, 2H, J¼ 7.95 Hz, H-3 00 and H-5 00 ), 7.46 (d, 2H, J¼ 7.95 Hz, H-3 0 and H-5 0 ), 7.41 (d, 1H, J¼ 2.10 Hz, H-8), vol.7 ,
-dimethylaminopropyl)aminomethyl]phenylgquinazoline (3n) Yellow oil (96%); 1 H NMR d (300 MHz, 20 Hz, H-5), 7.80 (d, 2H, J¼ 8.20 Hz, H-2 0 and H-6'), 7.51 (d, 2H, J¼ 8.20 Hz, H-3 00 and H-5 00 ), 7.44 (d, 2H, J¼ 8.20 Hz, H-3 0 and H-5 0 ), 7.40 (d, 1H, J¼ 2.50 Hz, H-8), 7.11 (dd, 1H, J¼ 9.20 and 2.50 Hz ,
, 155.8 (C-8a), vol.144, p.0
,
, 79 (d, 2H, J¼ 8.25 Hz, H-2' and H-6'), 7.51 (d, 2H, J¼ 8.25 Hz, H-3'' and H-5''), 7.45 (d, 2H, J¼ 8.25 Hz, H-3' and H-5'), 7.38 (d, 1H, J¼ 2.50 Hz, H-8), 7.10 (dd, 1H, J¼ 9.20 and 2.50 Hz, H-6), vol.7
, C-6), 118.4 (C-4a), 108.0 (C-8, 155.8 (C-8a), vol.144, p.0
,
, CDCl 3 ) 8.52 (d, 2H, J¼ 8.30 Hz, H-2 00 and H-6 00 ), 7.89 (d, 1H, J¼ 9.30 Hz, H-5), 7.72 (d, 2H, J¼ 8.30 Hz, H-2 0 and H-6 0 ), 7.44 (d, 2H, J¼ 8.30 Hz, H-3 00 and H-5 00 ), 7.38 (d, 2H, J¼ 8.30 Hz, H-3 0 and H-5 0 ), 7.30 (d, 1H, J¼ 2.30 Hz, H-8), 7.02 (dd, 1H, J¼ 9.30 and 2.30 Hz
, 13C NMR d (75 MHz, CDCl 3 ) 168.1 (C-7), vol.164, p.0
,
, CDCl 3 ) 8.55 (d, 2H, J¼ 8.20 Hz, H-2 00 and H-6 00 ), 7.92 (d, 1H, J¼ 9.10 Hz, H-5), 7.75 (d, 2H, J¼ 8.20 Hz, H-2 0 and H-6 0 ), 7.46 (d, 2H, J¼ 8.20 Hz, H-3 00 and H-5 00 ), 7.39 (d, 2H, J¼ 8.20 Hz, H-3 0 and H-5 0 ), 7.34 (d, 1H, J¼ 2.50 Hz, H-8), 7.05 (dd, 1H, J¼ 9.10 and 2.50 Hz
, C-4), 155.8 (C-8a), 13C NMR d (75 MHz, CDCl 3 ) 168.3 (C-7), 165.0 (C-2), vol.162, pp.129-136
, C-4a), vol.129, pp.121-124
-methylpiperazin-1-yl)ethyl)aminomethyl]phenylgquinazoline (3r) Yellow oil (89%); 1 H NMR d (300 MHz, 30 Hz, H-5), 7.83 (d, 2H, J¼ 8.40 Hz, H-2 0 and H-6 0 ), 7.53 (d, 2H, J¼ 8.40 Hz, H-3 00 and H-5 00 ), 7.46 (d, 2H, J¼ 8.40 Hz, H-3 0 and H-5 0 ), vol.7 ,
, 13C NMR d (75 MHz, CDCl 3 ) 168.4 (C-7), 165.1 (C-2), 162.1 (C-4), 155.8 (C-8a), vol.144, p.0
-dimethylaminopropyl)aminomethyl]phenylgquinazoline (3 s) Yellow oil (60%); 1 H NMR d (300 MHz, .13 (m, 2H, H-6 0 and H-2 0 ), 7.91 (dd, 1H, J¼ 8.20 and 1.20 Hz, H-5), 7.80 (dd, 1H, J¼ 1.40 and 1.40 Hz, H-2 00 ), 7.72 (ddd, 1H, J¼ 8.20, 7.00 and 1.20 Hz, H-7, vol.8, pp.17-25 ,
, C-8a), vol.150, pp.127-133
-methylpiperazin-1-yl)propyl)aminomethyl]phenylg quinazoline(3t) Pale-yellow oil (88%); 1 H NMR d (300 MHz, 20 Hz, H-8), 8.06 (dd, 1H, J¼ 8.40 and 1.20 Hz, H-5), 7.84 (ddd, 1H, J¼ 8.40, 7.20 and 1.20 Hz, H-7), 7.81 (dd, 1H, J¼ 1.40 and 1.40 Hz, p.0 ,
, 13C NMR d (75 MHz, CDCl 3 ) 169.8 (C-2), 161.5 (C-4), 153.2 (C-8a), vol.142, p.0
CDCl 3 ) 8.58 (dd, 1H, J¼ 1.50 and 1.50 Hz, H-2 0 ), 8.56 (ddd, 1H, J¼ 7.80, 1.50 and 1.50 Hz, H-6 0 ), dd, 1H, J¼ 8.70 and 1.10 Hz, H-8), 8.08 (dd, 1H, J¼ 8.70 and 1.10 Hz, H-5), 7.87 (ddd, 1H, J¼ 8.70, 7.20 and 1.10 Hz, H-7), 7.81 (dd, 1H, J¼ 1.50 and 1.50 Hz, vol.8, p.0 ,
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