Molecules 2007, 12
2422
5
7
”), 6.9 (H-3”), 7.35 (H-4”), 7.35 (H-6”), 7.4 (H-4’), 7.48 ( H-3’), 7.56 (H-6), 7.6 (H-8), 7.6 (H-7),
13
.81 (H-2’), 8.36 (H-5), 9.19 (s, 1H, H-C=N), 9.99 (OH, H-bonded), 7.8 Hz (J ); C-NMR: 116.42
5
6
(C-1”), 117.50 (C-3’’), 119.69 (C-5”), 121.46 (C-4a), 127.32 (C-8), 127.39 (C-6), 128.00 (C-2’),
1
1
28.97 (C-5), 130.34 (C-3’), 132.5 (C-6”), 133.33 (C-4’), 134.19 (C-4”), 134.84 (C-7), 146.37 (C-8a),
53.63 (C-2), 159.14 (C-4), 159.74 ( =C(OH)-, C-2”), 164.75 (H-C=N), C-1’ quaternary peak not
observed; Anal. Calcd. for C H N O : C, 73.89%; H, 4.45%; N, 12.31%; found: C, 74.10%; H,
2
1
15
3
2
4
.45%; N, 12.28%.
3
-{[(4-Methoxyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one (3b). Yield 75%; m.p. 140°C;
-1
1
R
f
0.75; IR (cm ): 1679.9, 1602.7, 1448.4, 1494.7, 1257.5, 1170.7; FAB MS (m/z): 356(M+1); H-
NMR: 3.84 (s, 3H, methoxy protons), 7.37 (H-3’/ H-4’), 7.40 (H-3”), 7.46 (H-8), 7.53 (H-6), 7.78 (H-
1
3
2
”), 7.80 (H-7), 7.84 (H-2’), 8.36 (H-5), 8.87 (1H, s, H-C=N-N); C-NMR: 55.40 (-O-CH ), 114.34
3
(
(
(
C-3”), 121.48 (C-4a), 125.89 (C-1”), 126.90 (C-8), 127.26 (C-2’), 127.70 (C-6), 127.88 (C-5), 129.89
C-2”), 129.90 (C-4’), 130.75 (C-3’), 134.39 (C-7), 134.67 (C-1’), 146.50 (C-8a), 159.40 (C-4), 163.08
=C(OCH )-,C-4”), 164.0 (C-2), 166.55 (H-C=N); Anal. Calcd. for C H N O : C, 74.35%, H, 4.82%,
3
22 17
3
2
N, 11.82%; found: C, 74.40%, H, 4.90%, N, 11.78%.
3
0
3
2
-{[(4-Fluorophenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one (3c). Yield 68%; m.p. 166°C; R
f
-1
.73; IR (cm ): 1674.1, 1614.3, 1593.1, 1554.5, 1537.2, 1469.7, 1373.2, 1184.2; FAB MS (m/z):
1
44(M+1); H-NMR: 7.1 (H-4”), 7.41 (H-3’), 7.45 (H-4’), 7.49 (H-6), 7.53 (H-8), 7.54 (H-2”), 7.7 (H-
’), 7.8 (H-7), 8.3 (H-5), 9.04 (s, 1H, H-C=N); 7.8 Hz (J56), 0.9 Hz (J57), 0Hz (J58), 6.3 Hz (J67), 1.8 Hz
1
3
(
J
68), 8.7 Hz (J2”3”); C-NMR: 166.30 (=C(F)-, C-4”), 164.84 (H-C=N), 153.97 (C-4), 153.90 (C-2),
46.60 (C-8a), 134.55 (C-1’), 134.15 (C-7), 131.00 (C-2”), 130.89 (C-4’), 130.50 (C-1”), 129.30 (C-
’), 128.98 (C-3’), 127.68 (C-6), 127.20 (C-5), 126.79 (C-8), 121.50 (C-4a), 116.33 (C-3”); Anal.
1
2
Calcd. for C21
H
14
N
3
OF: C, 73.46%, H, 4.11%, N, 12.24%; found: C, 73.50%, H, 4.10%, N, 12.18%.
3
-{[4-Dimethylaminophenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one (3d). Yield 70%; m.p.
-1
1
78°C; R
f
0.8; IR (cm ): 1681.8, 1589.2, 1556.4, 1508.2, 1456.2, 1375.2, 1328.9, 1313.4; FAB MS
1
(
m/z): 344(M+1); H-NMR: 3.04 (-N-CH
3
), 6.66 (H-3”), 7.40 (H-3’ and H-4’), 7.58 (H-6 and H-2”),
7
7
.79 (H-8 and H-2’), 7.80 (H-7), 8.36 (H-5), 8.67 (s, 1H. H-C=N); 8.7 Hz (J ), 0.9 Hz (J ), 0 Hz (J ),
56 57 58
13
.5 Hz (J67), 9.0 Hz (J2”3”); C-NMR: 187.65 (H-C=N), 159.80 (C-4), 154.07 (C-2), 153.06
), C-4”), 146.66 (C-8a), 134.80 (C-1’), 134.15 (C-7), 130.72 (C-2”), 129.70 (C-4’),
(=C(N(CH
3
)
2
1
29.30 (C-2’), 127.89 (C-3’), 127.68 (C-3), 127.20 (C-5), 126.79 (C-8), 121.58 (C-1”), 120.30 (C-4a),
11.52 (C-3”), 40.13 (-N-CH3); Anal. Calcd. for C H N O: C, 74.98%, H, 5.47%, N, 15.2%; found:
1
2
3
20
4
C, 74.99%, H, 5.50%, N, 15.13%.
3
-{[4-Chloroyphenyl)methylene]amino}-2-phenylquinazolin-4(3H)-one (3e). Yield 72%; m.p. 162°C;
-1
1
R
f
0.81; IR (cm ): 1679.9, 1591.2, 1554.5, 1377.1; FAB MS (m/z): 360(M+1); H-NMR: 7.37 (H-3’),
7
.42 (H-4’), 7.49 (H-6), 7.53 (H-8), 7.54 (H-3”), 7.68 (H-2”), 7.80 (H-7), 7.82 (H-2’), 8.36 (H-5), 9.10
13
(
s, 1H, H-C=N); C-NMR: 121.47 (C-4a), 127.16 (C-8), 127.33 (C-2’), 127.88 (C-6), 127.93 (C-5),
29.24 (C-3’), 129.77 (C-3”), 129.92 (C-4’), 130.00 (C-2”), 131.36 (C-1”), 134.36 (C-1”), 134.78 (C-
1