Med Chem Res
1
4
4
28.27 (aromatic ↓), and 124.94 (aromatic ↑); MS m/z (%):
6 ↓), 124.89 (C-8 ↑), 123.82 (C-7 ↑), 121.55 (C-10 ↑),
119.67 (C-4a ↓), 115.98 (CN ↓), 53.97 (C-3 ↓), 38.52 (C-4
+
+
+
06 (M +6, 1.10), 404 (M +4, 9.55), 402 (M +2, 30.10),
+
+
+
00 (M , 30.80) with a base peak at 255 (100); anal. calcd
↑); MS m/z (%): 406 (M +6, 1.49), 404 (M +4, 14.47),
+
+
for C H Cl N O: C, 59.80; H, 2.76; N, 6.97. Found: C,
402 (M +2, 44.45), 400 (M ,45.66) with a base peak at
2
0
11
3 2
5
9.75; H, 2.72; N, 6.93%.
255 (100); anal. calcd for C H Cl N O: C, 59.80; H, 2.76;
2
0
11
3 2
N, 6.97. Found: C, 59.77; H, 2.73; N, 6.94%.
2
-Amino-6-chloro-4-(2,4-dichlorophenyl)-4H-benzo[h]
chromene-3-carbonitrile (3e)
2-Amino-6-chloro-4-(2,6-dichlorophenyl)-4H-benzo[h]
chromene-3-carbonitrile (3g)
Pale yellow crystals from ethanol/benzene; Yield 84%; m.p.
−
1
2
(
45–246 °C; IR (KBr, υmax cm ): 3469, 3334, 3200
Pale yellow crystals from ethanol/benzene; Yield 84%; m.p.
1
−1
NH ), 3055, 2970, 2947 (CH), 2195 (CN); H NMR δ:
.34–7.10 (m, 8H, aromatic), 7.33 (bs, 2H, NH ), 5.39 (s,
315–316 °C; IR (KBr, υmax cm
): 3470, 3330, 3196
2
1
8
1
1
1
1
1
(NH ), 3059, 2973, 2949 (CH), and 2198 (CN); H NMR δ:
2
2
1
3
H, H-4); C NMR δ: 160.09 (C-2), 140.45 (C-10b),
29.38 (C-6a), 128.48 (C-9), 128.18 (C-5), 125.77 (C-10a),
24.97 (C-8), 123.82 (C-6), 123.77 (C-7), 121.50 (C-10),
19.66 (C-4a), 116.46 (CN), 54.30 (C-3), 37.80 (C-4),
42.47, 133.08, 132.78, 132.68, 129.49, and 127.83 (aro-
matic); MS m/z (%): 406 (M +6, 0.45), 404 (M +4, 4.05),
02 (M +2, 12.57), 400 (M ,12.97) with a base peak at
8.32–6.93 (m, 8H, aromatic), 7.39 (bs, 2H, NH ), 5.95 (s,
2
1
3
1H, H-4); C NMR δ: 160.41 (C-2), 136.58 (C-10b),
130.87 (C-6a), 130.24 (C-9), 128.79 (C-5), 128.46 (C-10a),
125.62 (C-8), 124.09 (C-6), 123.85 (C-7), 121.43 (C-10),
119.44 (C-4a), 114.80 (CN), 52.14 (C-3), 36.73 (C-4),
143.01, 134.93, 129.53, and 127.87 (aromatic); MS m/z
+
+
+
+
+
+
+
4
2
(%): 406 (M +6, 0.45), 404 (M +4, 4.05), 402 (M +2,
+
55 (100); anal. calcd for C H Cl N O: C, 59.80; H, 2.76;
12.57), 400 (M ,12.97) with a base peak at 255 (100); anal.
2
0
11
3 2
N, 6.97. Found: C, 59.85; H, 2.80; N, 7.02%.
calcd for C H Cl N O: C, 59.80; H, 2.76; N, 6.97. Found:
2
0
11
3 2
C, 59.85; H, 2.80; N, 7.02%.
2
-Amino-6-chloro-4-(2,5-dichlorophenyl)-4H-benzo[h]
chromene-3-carbonitrile (3f)
2-Amino-6-chloro-4-(3,4-dichlorophenyl)-4H-benzo[h]
chromene-3-carbonitrile (3h)
Pale yellow crystals from ethanol/benzene; Yield 84%; m.p.
−
1
2
(
8
1
1
1
1
1
75–276 °C; IR (KBr, υmax cm ): 3457, 3321, 3196
Pale yellow crystals from ethanol/benzene; Yield 84%; m.p.
1
−1
NH ), 3058, 2964, 2949 (CH), and 2197 (CN); H NMR δ:
.33–7.07 (m, 8H, aromatic), 7.34 (bs, 2H, NH ), 5.34 (s,
253–254 °C; IR (KBr, υmax cm ): 3469, 3324, 3196
2
1
(NH ), 3057, 2977, 2945 (CH), and 2196 (CN); H NMR
2
2
1
3
H, H-4); C NMR δ: 160.20 (C-2), 142.52 (C-10b),
31.12 (C-6a), 130.86 (C-9), 128.47 (C-5), 127.81 (C-10a),
25.79 (C-6), 124.89 (C-8), 123.82 (C-7), 121.55 (C-10),
19.67 (C-4a), 115.98 (CN), 53.97 (C-3), 38.52 (C-4),
43.13, 132.36, 131.89, 129.55, 129.18, and 128.26 (aro-
(500 MHz, DMSO-d ) δ: 8.34–6.93 (m, 8H, aromatic), 7.36
6
1
3
(bs, 2H, NH ), 5.01 (s, 1H, H-4); C NMR (125 MHz,
2
DMSO-d ) δ: 160.05 (C-2), 142.17 (C-10b), 129.60 (C-9),
6
129.46 (C-6a), 128.26 (C-5), 128.16 (C-10a), 125.82 (C-6),
125.62 (C-8), 123.83 (C-7), 121.53 (C-10), 119.90 (C-4a),
117.37 (CN), 55.22 (C-3), 39.35 (C-4), 146.06, 131.31,
1
3
matic);
C NMR-DEPT spectrum at 135° CH, CH (↑),
3
CH (↓), imply signals at δ: 131.89 (aromatic ↑), 130.86
1
3
131.15, 129.91, 128.45, and 127.79 (aromatic); C NMR-
2
(
(
1
C-9 ↑), 129.18 (aromatic ↑), 128.47 (C-5 ↑), 128.26
aromatic ↑), 124.89 (C-8 ↑), 123.82 (C-7 ↑), 121.55 (C-
0 ↑), and 38.52 (C-4 ↑); In the DEPT spectrum at 90°
DEPT spectrum at 135° CH, CH (↑), CH (↓), imply
3
2
signals at δ: 131.31 (aromatic ↑), 129.60 (C-9 ↑), 128.26
(C-5 ↑), 128.45 (aromatic ↑), 127.79 (aromatic ↑), 125.62
(C-8 ↑), 123.83 (C-7 ↑), 121.53 (C-10 ↑), and 39.35 (C-4
↑). In the DEPT spectrum at 90° only CH signals are
positive (↑) and showed δ: 131.31 (aromatic ↑), 129.60 (C-
9 ↑), 128.26 (C-5 ↑), 128.45 (aromatic ↑), 127.79 (aro-
matic ↑), 125.62 (C-8 ↑), 123.83 (C-7 ↑), 121.53 (C-10 ↑),
only CH signals are positive (↑), and showed δ: 131.89
(
(
aromatic ↑), 130.86 (C-9 ↑), 129.18 (aromatic ↑), 128.47
C-5 ↑), 128.26 (aromatic ↑), 124.89 (C-8 ↑), 123.82 (C-7
↑
), 121.55 (C-10 ↑), 38.52 (C-4 ↑). In the DEPT spectrum
at 45° (CH, CH and CH ↑) imply signals at δ: 131.89
2
3
(
(
↑
aromatic ↑), 130.86 (C-9 ↑), 129.18 (aromatic ↑), 128.47
C-5 ↑), 128.26 (aromatic ↑), 124.89 (C-8 ↑), 123.82 (C-7
), 121.55 (C-10 ↑), 38.52 (C-4 ↑); CNMR-APT spec-
39.35 (C-4 ↑). In the DEPT spectrum at 45° (CH, CH , and
2
CH ↑) revealed signals at δ: 131.31 (aromatic ↑), 129.60
3
1
3
(C-9 ↑), 128.26 (C-5 ↑), 128.45 (aromatic ↑), 127.79
(aromatic ↑), 125.62 (C-8 ↑), 123.83 (C-7 ↑), 121.53 (C-
trum CH, CH (↑), CH , Cq (↓), imply signals at δ: 160.20
3
2
1
3
(C-2 ↓), 143.13 (aromatic ↓), 142.52 (C-10b ↓), 132.36
(aromatic ↓),131.12 (C-6a ↓), 131.89 (aromatic ↑), 130.86
(C-9 ↑), 129.55 (aromatic ↓), 129.18 (aromatic ↑), 128.47
(C-5 ↑), 128.26 (aromatic ↑), 127.81 (C-10a ↓), 125.79 (C-
10 ↑), and 39.35 (C-4 ↑); CNMR-APT spectrum CH,
CH (↑), CH , Cq (↓), imply signals at δ: 160.05 (C-2 ↓),
3
2
146.06 (aromatic ↓), 142.17 (C-10b ↓), 131.31 (aromatic ↑),
131.15 (aromatic ↓), 129.91 (aromatic ↓), 129.60 (C-9 ↑),