R. Teimuri-Mofrad et al.
(
100 MHz, DMSO-d ): d 33.17, 57.81, 116.01, 116.78, 120.38, 123.46, 124.05,
6
1
24.81, 125.06, 126.66, 127.19, 128.46, 129.64, 130.08, 130.75, 146.33, 150.25,
60.30 ppm; Anal. Calc. for C H N OS (%): C, 71.03; H, 3.97; N, 9.20; S, 10.53;
1
found: C, 71.08; H, 4.12; N, 9.43; S, 10.34.
1
8 12 2
3
-Amino-1-(5-methylfuran-2-yl)-1H-benzo[f]chromene-2-carbonitrile (4l) Brown
solid; m.p. 152–156 °C; FT-IR (KBr) m 3429, 3326, 3068, 2921, 2182, 1644, 1587,
-
1 1
1
5
411 cm ; H NMR (400 MHz, DMSO-d ): d 2.07 (3H, s, CH ), 5.41 (1H, s, CH),
6
3
.89 (1H, d, J = 1.95 Hz, Ar–H), 6.10 (1H, d, J = 2.97 Hz, Ar–H), 7.08 (2H, s,
NH ), 7.28 (1H, d, J = 8.94 Hz, Ar–H), 7.44–7.47 (1H, m, Ar–H), 7.50–7.54 (1H,
2
1
3
m, Ar–H), 7.90–7.93 (2H, m, Ar–H), 8.06 (1H, d, J = 8.41 Hz, Ar–H) ppm;
C
NMR (100 MHz, DMSO-d ): d 13.42, 31.84, 54.43, 106.44, 106.60, 113.77, 116.90,
6
1
20.50, 123.39, 125.06, 127.14, 128.45, 129.49, 130.26, 130.66, 146.88, 150.78,
54.33, 160.94 ppm; Anal. Calc. for C H N O (%): C, 75.48; H, 4.67; N, 9.27;
found: C, 75.72; H, 4.76; N, 9.21.
1
1
9 14 2 2
3
-Amino-8-bromo-1-(4-isopropylphenyl)-1H-benzo[f]chromene-2-carbonitrile (4n)
Brown solid; m.p. 211–213 °C; FT-IR (KBr) m 3419, 3354, 3173, 2878, 2187, 1651,
-
1 1
1
CH ), 2.73–2.78 (1H, m, CH), 5.25 (1H, s, CH), 6.98 (2H, s, NH ), 7.05–7.13 (4H,
532, 1417 cm ; H NMR (400 MHz, DMSO-d ): d 1.11 (6H, d, J = 6.78 Hz,
6
3
2
m, Ar–H), 7.38 (1H, d, J = 8.98 Hz, Ar–H), 7.53–7.55 (1H, m, Ar–H), 7.79 (1H, d,
J = 9.04 Hz, Ar–H), 7.91 (1H, d, J = 8.99 Hz, Ar–H), 8.19 (1H, s, Ar–H) ppm;
1
3
C NMR (100 MHz, DMSO-d ): d 23.73, 23.77, 32.96, 37.49, 57.91, 116.33,
6
1
1
18.15, 120.48, 125.95, 126.67, 126.81, 127.26, 128.66, 128.85, 129.91, 130.25,
32.14, 142.89, 146.68, 147.09, 159.58, 159.62 ppm; Anal. Calc. for C H BrN O
2
3
19
2
(
%): C, 65.88; H, 4.57; N, 6.68; found: C, 65.97; H, 4.64; N, 6.59.
3
-Amino-8-bromo-1-(4-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrile
(4o)
White solid; m.p. 258–262 °C; FT-IR (KBr) m 3455, 3301, 3068, 2867, 2199,
-
1
1
1
663, 1590, 1403 cm ; H NMR (400 MHz, DMSO-d ): d 5.35 (1H, s, CH),
6
7
J = 8.94 Hz, Ar–H), 7.53–7.55 (1H, m, Ar–H), 7.75 (1H, d, J = 9.06 Hz, Ar–H),
.01–7.10 (4H, m, NH , Ar–H), 7.18–7.21 (2H, m, Ar–H), 7.39 (1H, d,
2
1
.92 (1H, d, J = 9.02 Hz, Ar–H), 8.19 (1H, s, Ar–H) ppm; C NMR (100 MHz,
3
7
DMSO-d ): d 37.06, 57.63, 115.44, 115.65, 115.85, 118.21, 118.23, 120.30, 125.93,
6
1
28.79, 128.82, 128.90, 128.93, 129.96, 130.33, 132.19, 141.71, 141.73, 147.10,
59.49, 159.53, 159.57, 159.67, 162.09 ppm; Anal. Calc. for C H BrFN O (%):
C, 60.78; H, 3.06; N, 7.09; found: C, 60.71; H, 2.97; N, 6.91.
1
2
0
12
2
3
-Amino-8-bromo-1-(3-bromophenyl)-1H-benzo[f]chromene-2-carbonitrile
(4p)
Light-brown solid; m.p. 198–201 °C; FT-IR (KBr) m 3444, 3319, 3173, 2964,
-
1 1
2
185, 1655, 1587, 1408 cm ; H NMR (400 MHz, DMSO-d ): d 5.37 (1H, s, CH),
6
7
.08–7.14 (3H, m, NH , Ar–H), 7.18–7.22 (1H, m, Ar–H), 7.33 (1H, d,
2
J = 8.04 Hz, Ar–H), 7.38 (2H, d, J = 8.99 Hz, Ar–H), 7.53–7.55 (1H, m, Ar–H),
.75 (1H, d, J = 9.1 Hz, Ar–H), 7.91 (1H, d, J = 9.04 Hz Ar–H), 8.16 (1H, d,
7
1
3
J = 1.51 Hz, Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 37.38, 57.25, 115.29,
6
1
18.36, 120.17, 122.03, 125.80, 126.07, 128.73, 129.09, 129.53, 129.74, 130.09,
1
23