An efficient synthesis
2-Amino-3,5-dicarbonitrile-6-ethoxy-4-(4-methoxyphenyl)pyridine (4f)
M.p. [280 °C; IR (KBr, v, cm-1): 3,415, 3,342, 3,241, 2,967, 2,936, 2,842, 2,214,
1,652, 1,608, 1,543, 1,517, 1,381, 1,340, 1,299, 1,244, 1,180, 1,021, 924, 840, 786,
663, 611 cm-1; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 1.43 (3H, t, J = 7.2 Hz,
CH3), 3.86 (3H, s, OCH3), 4.46 (2H, q, J = 7.2 Hz, CH2), 5.64 (2H, s, NH2), 7.03
(2H, d, J = 8.7 Hz, ArH), 7.51 (2H, d, J = 8.7 Hz, ArH); 13C NMR (300 MHz,
CDCl3) (d, ppm): 14.53, 55.64, 64.45, 83.90, 114.60, 114.65, 115.23, 116.28,
125.75, 130.42, 130.47, 160.66, 161.16, 161.78, 166.70. HRMS m/z calculated for
C16H14N4O2 [M ? Na]?: 317.1014, found: 317.1016.
2-Amino-3,5-dicarbonitrile-4-(3,4-dimethylphenyl)-6-ethoxypyridine (4g)
M.p. 198–200 °C; IR (KBr, v, cm-1): 3,472, 3,324, 3,219, 2,980, 2,922, 2,226,
1,623, 1,581, 1,552, 1,436, 1,378, 1,343, 1,301, 1,252, 1,178, 1,029, 833,
1
784 cm-1; H NMR (300 MHz, CDCl3) (d, ppm): 1.43 (3H, t, J = 7.2 Hz, CH3),
2.32 (3H, s,CH3), 2.33 (3H, s,CH3), 4.47 (2H, q, J = 7.2 Hz, CH2), 5.60 (2H, s,
NH2), 7.28 (3H, s, ArH); 13C NMR (300 MHz, CDCl3) (d, ppm): 14.53, 20.08,
64.43, 84.11, 115.05, 126.08, 129.60, 130.36, 130.49, 131.16, 137.55, 140.09,
161.03, 161.28. HRMS m/z calculated for C17H16N4O [M ? Na]?: 315.1222,
found: 315.1228.
2-Amino-3,5-dicarbonitrile-4-(3,4-dimethoxyphenyl)-6-ethoxypyridine (4h)
M.p. 213–215 °C; IR (KBr, v, cm-1): 3,443, 3,334, 3,231, 2,222, 1,634, 1,567,
1,519, 1,435, 1,384, 1,342, 1,325, 1,265, 1,177, 1,144, 1,021 cm-1 1H NMR
;
300 MHz, CDCl3) (d, ppm): 1.43 (3H, t, J = 6.9 Hz, CH3), 3.94 (3H, s, OCH3),
3.94 (3H, s, OCH3), 4.47 (2H, q, J = 6.9 Hz, CH2), 5.61 (2H, s, NH2), 7.00
(1H, d, J = 8.4 Hz, ArH), 7.07 (1H, s, ArH), 7.17–7.20 (1H, m, ArH); 13C NMR
(300 MHz, CDCl3) (d, ppm): 14.56, 56.20, 56.32, 64.47, 83.92, 111.32, 111.85,
115.23, 116.30, 122.09, 125.78, 149.12, 151.33, 160.57, 161.14, 161.16. HRMS
m/z calculated for C17H16N4O3 [M ? Na]?: 347.1120, found: 347.1132.
2-Amino-3,5-dicarbonitrile-4-(benzo[d][1,3]dioxol-4-yl)-6-ethoxypyridine (4i)
M.p. 189–191 °C; IR (KBr, v, cm-1): 3,456, 3,356, 3,237, 2,908, 2,210, 1,648,
1,637, 1,573, 1,544, 1,504, 1,449, 1,429, 1,384, 1,384, 1,345, 1,252, 1,187, 1,101,
;
1,036, 932, 876, 821, 781 cm-1 1H NMR (300 MHz, CDCl3) (d, ppm): 1.43
(3H, t, J = 7.2 Hz, CH3), 4.46 (2H, q, J = 7.2 Hz, CH2), 5.63 (2H, s, NH2), 6.06
(2H, s, CH2), 6.94 (1H, d, J = 7.8 Hz, ArH), 6.99 (1H, s, ArH), 7.03 (1H, dd,
J = 1.2 Hz, J = 7.8 Hz, ArH); 14.51, 64.52, 84.08, 102.05, 104.32, 109.04,
109.09, 114.96, 116.02, 123.40, 123.45, 127.14, 148.28, 150.05, 160.55, 161.07,
166.63. HRMS m/z calculated for C16H12N4O3 [M ? Na]?: 331.0807, found:
331.0810.
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