spectrum, δ, ppm (J, Hz): 7.36 (1H, d, J = 8.0, H-7); 7.39 (2H, d, J = 8.5, H-3',5'); 7.42 (1H, t, J = 8.0, H-9);
7.53 (2H, d, J = 8.5, H-2',6'); 7.68 (1H, dt, 3J = 8.0, 4J = 1.5, H-8); 8.19 (2H, br. s, NH2); 8.38 (1H, dd, 3J = 8.0,
4J = 1.5, H-10). Mass spectrum, m/z (Irel, %): 349 [M+2]+ (22), 347 [M]+ (67), 346 (100), 330 (5), 318 (5), 228
(5), 201 (5). Found, %: C 65.58; H 2.87; N 12.05. C19H10ClN3O2. Calculated, %: C 65.62; H 2.90; N 12.08.
2-Amino-4-(2-bromophenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3f). Yield 1.80 g
(85%). Mp 242-244°C. IR spectrum, , cm-1: 3323, 3469 (NH2), 3213 (C–H), 2214 (CN), 1727 (C=O). 1H NMR
spectrum, δ, ppm (J, Hz): 7.36-7.39 (2H, m, H-7,4'); 7.42-7.46 (2H, m, H-9,6'); 7.61-7.70 (3H, m, H-8,3',5');
3
4
8.15 (2H, br. s, NH2); 8.38 (1H, dd, J = 8.0, J = 1.5, H-10). Mass spectrum, m/z (Irel, %): 393/391 [M]+ (66),
392 (100), 312 (33), 228 (17), 201 (20), 76 (32), 63 (32). Found, %: C 58.14; H 2.50; N 10.75. C19H10BrN3O2.
Calculated, %: C 58.18; H 2.57; N 10.71.
2-Amino-4-(3-bromophenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3g). Yield 1.48 g
(70%). Mp 244-246°C. IR spectrum, , cm-1: 3321, 3463 (NH2), 3218 (C–H), 2212 (CN), 1726 (C=O). 1H NMR
spectrum, δ, ppm (J, Hz): 7.37-7.39 (2H, m, H-7,2'); 7.41 (1H, dt, 3J = 8.0, 4J = 1.5, H-6'); 7.45 (1H, t, J = 8.0,
H-9); 7.51 (1H, t, J = 7.5, H-5'); 7.68 (1H, t, J = 8.0, H-8); 7.74 (1H, d, J = 8.0, H-4'); 8.05 (2H, br. s, NH2);
8.38 (1H, dd, 3J = 8.0, 4J = 1.5, H-10). Mass spectrum, m/z (Irel, %): 393/391 [M]+ (64), 312 (100), 284 (5), 125
(5). Found, %: C 58.15; H 2.52; N 10.68. C19H10BrN3O2. Calculated, %: C 58.18; H 2.57; N 10.71.
2-Amino-4-(4-bromophenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3h). Yield 1.59 g
(75%). Mp 290-292°C. IR spectrum, , cm-1: 3393, 3489 (NH2), 3100 (C–H), 2219 (CN), 1722 (C=O). 1H NMR
spectrum, δ, ppm (J, Hz): 7.33 (2H, d, J = 9.0, H-2',6'); 7.37 (1H, d, J = 8.0, H-7); 7.42 (1H, t, J = 8.5, H-9);
7.66 (1H, t, J = 8.0, H-8); 7.68 (2H, d, J = 9.0, H-3',5'); 8.10 (2H, br. s, NH2); 8.37 (1H, d, J = 8.0, H-10). Mass
spectrum, m/z (Irel, %): 393/391 [M]+ (63), 392 (100), 312 (9), 284 (7), 228 (8), 201 (9). Found, %: C 58.13;
H 2.53; N 10.64. C19H10BrN3O2. Calculated, %: C 58.18; H 2.57; N 10.71.
2-Amino-4-(2-methoxyphenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3i). Yield 0.65 g
(35%). Mp 209-211°C. IR spectrum, , cm-1: 3349, 3431 (NH2), 3214 (C–H), 2223 (CN), 1722 (C=O). 1H NMR
spectrum, δ, ppm (J, Hz): 4.07 (3H, s, OCH3); 7.12 (1H, d, J = 8.0, H-3'); 7.47-7.53 (2H, m, H-5',6'); 7.68-7.76
(3H, m, H-7,9,4'); 8.03 (1H, t, J = 8.0, H-8); 8.20 (2H, br. s, NH2); 8.32 (1H, d, J = 8.0, H-10). Mass spectrum,
m/z (Irel, %): 343 [M]+ (19), 300 (6), 167 (25), 149 (100), 105 (75), 76 (50), 43 (25). Found, %: C 69.92; H 3.78;
N 12.22. C20H13N3O3. Calculated, %: C 69.96; H 3.82; N 12.24.
2-Amino-4-(3-methoxyphenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3j). Yield 1.44 g
1
(78%). Mp 260-262°C. IR spectrum, , cm-1: 3374 (NH2), 3181 (C–H), 2192 (CN), 1707 (C=O). H NMR
spectrum, δ, ppm (J, Hz): 4.76 (3H, s, OCH3); 6.88 (1H, d, J = 8.0, H-6'); 6.92 (1H, s, H-2'); 7.01 (1H, dt,
4
3J = 8.0, J = 2.0, H-4'); 7.34 (1H, d, J = 8.0, H-7); 7.38 (1H, t, J = 8.0, H-5'); 7.41 (1H, t, J = 8.0, H-9); 7.66
3
4
3
4
(1H, dt, J = 8.0, J = 1.5, H-8); 8.05 (2H, br. s, NH2); 8.37 (1H, dd, J = 8.0, J = 1.5, H-10). Mass spectrum,
m/z (Irel, %): 343 [M]+ (100), 328 (23), 312 (23), 300 (31), 270 (10), 201 (13), 190 (20), 76 (23), 63 (67). Found,
%: C 69.92; H 3.79; N 12.24. C20H13N3O3. Calculated, %: C 69.96; H 3.82; N 12.24.
2-Amino-4-(4-methoxyphenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3k). Yield 1.39 g
1
(75%). Mp 259-261°C. IR spectrum, , cm-1: 3349, 3431 (NH2), 3239 (C–H), 2214 (CN), 1734 (C=O). H NMR
spectrum, δ, ppm (J, Hz): 3.83 (3H, s, OCH3); 7.00 (2H, d, J = 8.5, H-2',6'); 7.30 (2H, d, J = 8.5, H-3',5'); 7.33 (1H,
d, J = 8.0, H-7); 7.40 (1H, t, J = 8.0, H-9); 7.65 (1H, t, J = 8.0, H-8); 8.10 (2H, br. s, NH2); 8.37 (1H, d, J = 8.0,
13
H-10). C NMR spectrum, δ, ppm: 55.1; 94.2; 105.2; 113.3 (2C); 115.3; 116.6; 118.3; 124.3; 125.3; 129.0 (2C);
129.2; 133.4; 153.1; 155.1; 157.3; 159.5; 160.0; 160.9. Mass spectrum, m/z (Irel, %): 343 [M]+ (100), 328 (3), 314
(2), 300 (13), 271 (2), 201 (2), 190 (3). Found, %: C 69.85; H 3.89; N 12.20. C20H13N3O3. Calculated, %: C 69.96; H
3.82; N 12.24.
2-Amino-4-(2-methylphenyl)-5-oxo-5H-chromeno[4,3-b]pyridine-3-carbonitrile (3l). Yield 1.15 g
(65%). Mp 270-272°C. IR spectrum, , cm-1: 3331, 3468 (NH2), 3218 (C–H), 2211 (CN), 1730 (C=O). 1H NMR
spectrum, δ, ppm (J, Hz): 2.05 (3H, s, CH3); 7.10 (1H, d, J = 6.5, H-3'); 7.26 (1H, t, J = 6.5, H-4'); 7.31-7.33
(2H, m, H-5',6'); 7.35 (1H, d, J = 8.0, H-7); 7.44 (1H, t, J = 8.0, H-9); 7.67 (1H, t, J = 8.0, H-8); 8.10
1842