6.71 (d, J=8.7 Hz, 2H), 3.04 (s, 6H), 2.40 (s, 6H); 13C NMR (75 MHz, CDCl3) δ: 189.0, 152.2, 146.6,
142.9, 141.2, 139.7, 138.0, 133.3, 132.1, 131.7, 130.7, 130.2, 123.1, 122.4, 120.7, 116.0, 111.8, 110.7,
40.1, 20.7, 20.3.
4-Dimethylamino-4’-(1-triazolyl)chalcone (8). yellow solid; 1H NMR (300MHz, CDCl3) δ: 8.67 (s, 1H),
8.17 (s, 1H), 8.14 (s, 2H), 7.85 (d, J=15.6 Hz, 1H), 7.84 (d, J=8.7 Hz, 2H), 7.57 (d, J=8.7 Hz, 2H), 7.35
13
(d, J=15.6 Hz, 1H), 6.71 (d, J=8.7 Hz, 2H), 3.05 (s, 6H); C NMR (75 MHz, CDCl3) : 188.8, 152.9,
152.3, 146.6, 141.0, 139.4, 138.5, 130.6, 130.1, 122.4, 119.4, 116.1, 111.8, 40.1; HRMS: m/z calcd for
C19H19N4O (M+H)+ 319.1553, found 319.1554.
1
4-Dimethylamino-4’-(1-piperazinyl)chalcone (9). brown solid; H NMR (300 MHz, CDCl3) δ: 8.01 (d,
J=9.0 Hz, 2H), 7.80 (d, J=15.3 Hz, 1H), 7.56 (d, J=9.0 Hz, 2H), 7.41 (d, J=15.6 Hz, 1H), 6.92 (d, J=9.0
Hz, 2H), 6.70 (d, J=9.0 Hz, 2H), 3.33 (t, J=4.8 Hz, 4H), 3.01-3.04 (m, 10H), 2.12 (s, 1H); 13C NMR (75
MHz, CDCl3) : 188.3, 154.2, 151.8, 144.1, 130.3, 130.1, 129.1, 123.0, 116.8, 113.6, 111.8, 48.5, 45.9,
40.2; HRMS: m/z calcd for C21H26N3O (M+H)+ 336.2070, found 336.2072.
4-Dimethylamino-4’-(N-methyl-1-piperazinyl)chalcone (10). Brown solid; 1H NMR (300 MHz, CDCl3 )
δ: 8.00 (d, J=9.0 Hz, 2H), 7.80 (d, J=15.6 Hz, 1H), 7.55 (d, J=8.7 Hz, 2H), 7.39 (d, J=15.6 Hz, 1H), 6.92
(d, J=8.7 Hz, 2H), 6.70 (d, J=9.0 Hz, 2H), 3.38 (t, J=5.1 Hz, 4H), 3.01 (s, 6H), 2.57 (t, J=5.1 Hz, 4H),
2.34 (s, 3H); 13C NMR (75 MHz, CDCl3) : 188.3, 153.8, 151.8, 144.1, 130.3, 130.1, 129.2, 123.1, 116.9,
113.7, 111.9, 54.8, 47.3, 46.1, 40.1.
4-Dimethylamino-4’-(N-(2-pyrimidyl)-1-Piperazinyl)chalcone (11). Yellow solid; 1H NMR (300 MHz,
CDCl3 ) δ: 8.35 (d, J=4.8 Hz, 2H), 8.03 (d, J=8.7 Hz, 2H), 7.81 (d, J=15.6 Hz, 1H), 7.56 (d, J=8.7 Hz,
2H), 7.40 (d, J=15.3 Hz, 1H), 6.96 (d, J=9.0 Hz, 2H), 6.70 (d, J=9.0 Hz, 2H), 6.55 (t, J=4.8 Hz, 1H), 4.01
(t, J=5.4 Hz, 4H), 3.47 (t, J=5.4 Hz, 4H), 3.02 (s, 6H); 13C NMR (75 MHz, CDCl3) : 188.4, 161.6, 157.8,
153.7, 151.8, 144.2, 130.4, 130.1, 129.4, 123.1, 116.9, 113.8, 111.9, 110.3, 47.3, 43.3, 40.1.
4-Dimethylamino-4’-(1-pyrazolyl)chalcone (12). Yellow solid; 1H NMR (300 MHz, CDCl3 ) δ: 8.14 (d,
J=8.7 Hz, 2H), 8.02 (d, J=2.1 Hz, 1H), 7.77-7.85 (m, 4H), 7.58 (d, J=8.7 Hz, 2H), 7.38 (d, J=15.3 Hz,
13
1H), 6.70 (d, J=8.7 Hz, 2H), 6.52 (t, J=1.8 Hz, 1H), 3.04 (s, 6H); C NMR (75 MHz, CDCl3) : 189.0,
152.1, 146.0, 142.7, 141.9, 136.7, 130.5, 129.9, 126.9, 122.5, 118.4, 116.3, 111.8, 108.4, 40.1; HRMS:
m/z calcd for C20H20N3O (M+H)+ 318.1601, found 318.1603.
1
4-Dimethylamino-4’-(3,5-dimethyl-1-pyrazolyl)chalcone (13). Yellow solid; H NMR (300 MHz,
CDCl3 ) δ: 8.11 (d, J=8.7 Hz, 2H), 7.84 (d, J=15.6 Hz, 1H), 7.59 (d, J=6.6 Hz, 2H),, 7.57 (d, J=7.2 Hz,
2H), 7.36 (d, J=15.6 Hz, 1H), 6.71 (d, J=8.7 Hz, 2H), 6.04 (s, 1H), 3.04 (s, 6H), 2.38 (s, 3H), 2.32 (s, 3H);
13C NMR (75 MHz, CDCl3) : 189.6, 152.1, 149.8, 146.3, 142.9, 139.6, 137.2, 130.5, 129.3, 123.8, 122.5,
116.6, 111.8, 108.1, 40.1, 13.6, 12.8.