S. Sadjadi et al.
physisorption using a Quantachrome Chem-BET 3000 sorption analyzer (Mi-
cromeritics) at 77 K.
Melting points of the synthesized 2-amino-4H-chromene derivatives were
measured by using the capillary tube method with an Electrothermal 9200
apparatus and FTIR spectroscopy. All known products were identified by
comparison of physical and spectroscopic data with those of previously reported
authentic samples.
Physical and spectral data for selected organic compounds
To confirm the formation of the final products, spectral data were obtained for
selected products, as presented below, showing results in good agreement with
previous reports [26, 35–39], thereby proving the formation of the final products.
1
-Amino-3-cyano-4-phenyl-4H-benzo[h]chromene (4a) H-NMR [400 MHz,
2
dimethyl sulfoxide (DMSO)]: d = 4.90 (1H, s, H-4), 7.10 (2H, s, NH ),
2
0 0 0 0 0
7
d, J = 8.4 Hz, H-7), 8.23 (1H, d, J = 8.4 Hz, H-10) ppm; C-NMR (100 MHz,
.07–7.12 (6H, m, H-5, 2 , 3 , 4 , 5 , 6 ), 7.56–7.66 (3H, m, H-6, 8, 9), 7.94 (1H,
1
3
DMSO): d = 41.3, 54.3, 115.5, 120.8, 121.3, 121.7, 122.4, 123.0, 125.4, 126.3,
1
3
27.4, 127.8, 128.4, 130.5, 131.7, 140.4, 142.7, 158.3 ppm. IR (KBr): 3454, 3318,
-
1
020, 2932, 2205, 1656, 1600, 1572, 1450, 1372, 1267, 1100, 1022, 811, 744 cm
.
1
(4b) H-NMR
2
-Amino-3-cyano-4-(4-chlorophenyl)-4H-benzo[h]chromene
(
J = 8 Hz), 7.21–7.33 (4H, m, Ar), 7.40–7.45 (3H, m, Ar), 7.56 (1H, d, H-7,
400 MHz, DMSO): d = 4.55 (1H, s, H-4), 6.70 (2H, s, NH ), 7.1 (1H, d, H-5,
2
1
J = 8 Hz), 8.15 (1H, d, H-10, J = 8 Hz) ppm; C-NMR (100 MHz, DMSO):
3
d = 42.6, 55.6, 119.8, 120.6, 122.1, 122.4, 123.7, 125.4, 125.9, 126.5, 127.6, 128.8,
1
1
30.2, 132.8, 133.9, 142.4, 147.6, 160.8 ppm. 132.8, 133.9, 142.4, 147.6,
-
1
60.8 ppm. IR (KBr): 3421, 3253, 2208, 1662, 1596, 1436, 1380, 1139, 805 cm
.
1
-Amino-3-cyano-4-(4-nitrophenyl)-4H-benzo[h]chromene (4c) H-NMR (400 MHz,
2
DMSO): d = 5.12 (1H, s, H-4), 7.29 (2H, s, NH ), 7.05 (1H, d, J = 8.4 Hz, H-5),
2
0 0
7
.5–7.7 (3H, m, H-6, 8, 9), 7.52 (d, 2H, H-2 , 6 ), 7.90 (1H, d, J = 8.4 Hz, H-7),
0
0
13
.15 (2H, d, H-3 , 5 ), 8.27 (1H, d, J = 8.4 Hz, H-10) ppm; C-NMR (100 MHz,
8
DMSO): d = 43.1, 54.8, 119.3, 125.7, 121.1, 122.6, 123.6, 124.9, 126.5, 127.2,
1
28.6, 129.3, 130.6, 133.7, 136.3, 140.9, 146.2, 160.7 ppm. IR (KBr): 3460, 3335,
-
1
2
196, 1665, 1600, 1575, 1536, 1500, 1346, 1270, 1195, 1100, 805, 770 cm
.
1
-Amino-3-cyano-4-(4-methoxyphenyl)-4H-benzo[h]chromene (4d) H-NMR
2
(
500 MHz, DMSO): d = 3.90 (3H, s, OCH ), 4.54 (1H, s, H-4), 6.82 (2H, s, NH ),
3
2
7
d, H-7, J = 8 Hz), 8.15 (1H, d, H-10, J = 8 Hz); C-NMR (125 MHz, DMSO):
.0 (1H, s, H-5, J = 8 Hz), 7.10–7.22 (4H, m, Ar), 7.40–7.45 (3H, m, Ar), 7.56 (1H,
1
3
d = 40.8, 55.1, 56.3, 118.7, 121.9, 122.2, 122.8, 123.5, 124.7, 125.1, 126.9, 127.7,
1
1
28.2, 129.4, 131.7, 133.4, 143.5, 148.3, 161.2 ppm. IR (KBr): 3430, 3337, 2200,
1
-
678, 1592, 1436, 1383, 1123, 794 cm
.
1
-Amino-4-(3-nitrophenyl)-4H-benzo[h]chromene-3-carbonitrile (4e) H-NMR
2
(
500 MHz, DMSO): d = 5.24 (1H, s, H-4), 7.17 (2H, s, NH ), 7.22 (1H, d,
2
1
23