J IRAN CHEM SOC
2-Amino-4-(4-bromophenyl)-6-(4-methoxy-
2-Amino-4-phenyl-6-(4-bromo-phenylsulfanyl)-pyridine-
phenylsulfanyl)-pyridine-3,5-dicarbonitrile (4l)
3,5-dicarbonitrile (4p)
Yellow solid, M.Pt. 162–164 °C; IR (KBr, mmax): 3,469,
Yellow solid, M.Pt. 202–204 °C; IR (KBr, mmax): 3,450,
3,327, 2,217, 1,618, 1,549, 1,263, 1,007, 811, 757,
706 cm-1; 1H NMR (CDCl3, 400 MHz) dH: 5.48 (br s, 2H,
NH2), 7.30–7.35 (m, 5H, Ar–H), 7.38 (d, J = 8.6 Hz, 2H,
Ar–H), 7.42 (d, J = 8.6 Hz, 2H, Ar–H) ppm; 13C NMR
(CDCl3, 100 MHz) dC: 87.64, 96.35, 118.32, 121.49, 128.41,
129.05, 131.04, 132.18, 135.68, 137.27, 159.04, 168.25 ppm.
3,346, 2,218, 1,624, 1,590, 1,248, 1,025, 828, 798 cm-1
;
1H NMR (CDCl3, 400 MHz) dH: 3.78 (s, 3H, OCH3), 5.48
(br s, 2H, NH2), 6.80 (d, J = 7.8 Hz, 2H, Ar–H), 6.96 (d,
J = 7.8 Hz, 2H, Ar–H), 7.36 (d, J = 8.6 Hz, 2H, Ar–H),
7.46 (d, J = 8.6 Hz, 2H, Ar–H) ppm; 13C NMR (CDCl3,
100 MHz) dC: 54.85, 85.95, 93.58, 114.36, 114.69, 116.95,
123.18, 124.63, 129.59, 131.60, 131.99, 136.74, 156.46,
160.50, 168.80, 183.67 ppm.
2-Amino-4-(4-chlorophenyl)-6-(4-bromo-phenylsulfanyl)-
pyridine-3,5-dicarbonitrile (4q)
2-Amino-4-(3-hydroxyphenyl)-6-(4-methoxy-
Yellow solid, M.Pt. 184–186 °C; IR (KBr, mmax): 3,481,
phenylsulfanyl)-pyridine-3,5-dicarbonitrile (4m)
3,351, 2,927, 2,214, 1,630, 1,544, 1,257, 1,090, 811 cm-1
;
1H NMR (CDCl3, 400 MHz) dH: 6.51 (br s, 2H, NH2), 7.20
(d, J = 8.0 Hz, 2H, Ar–H), 7.36 (d, J = 8.4 Hz, 2H, Ar–
H), 7.59 (d, J = 8.4 Hz, 2H, Ar–H), 7.68 (d, J = 8.2 Hz,
2H, Ar–H) ppm; 13C NMR (CDCl3, 100 MHz) dC: 86.58,
93.54, 115.57, 120.85, 125.81, 128.76, 129.41, 131.63,
131.88, 135.06, 136.58, 156.61, 159.23, 167.02 ppm.
Yellow solid, M.Pt. 138–142 °C; IR (KBr, mmax): 3,465,
3,328, 2,214, 1,620, 1,551, 1,251, 1,028, 814, 774,
640 cm-1; 1H NMR (CDCl3, 400 MHz) dH: 3.02 (br s, 1H,
OH), 3.63 (s, 3H, OCH3), 6.20 (br s, 2H, NH2), 6.64 (m,
1H, Ar–H), 6.70–6.75 (m, 3H, Ar–H), 7.04 (d, J = 7.8 Hz,
2H, Ar–H), 7.22 (d, J = 7.8 Hz, 2H, Ar–H) ppm; 13C
NMR (CDCl3, 100 MHz) dC: 54.95, 86.59, 94.03, 114.42,
114.94, 115.01, 117.28, 117.54, 118.74, 124.76, 129.52,
134.17, 136.85, 157.11, 159.24, 160.44, 168.52,
184.78 ppm.
2-Amino-4-(4-methylphenyl)-6-(4-bromo-phenylsulfanyl)-
pyridine-3,5-dicarbonitrile (4r)
Yellow solid, M.Pt. 216–218 °C; IR (KBr, mmax): 3,453, 3,274,
2,927, 2,207, 1,646, 1,536, 1,264, 1,084, 821 cm-1; 1H NMR
(CDCl3, 400 MHz)dH: 2.31(s, 3H, CH3), 6.62 (br s, 2H, NH2),
6.76 (d, J = 8.0 Hz, 2H, Ar–H), 6.93 (d, J = 8.0 Hz, 2H, Ar–
H), 7.10 (d, J = 7.8 Hz, 2H, Ar–H), 7.32 (d, J = 7.8 Hz, 2H,
Ar–H) ppm; 13C NMR (CDCl3, 100 MHz) dC: 20.76, 88.56,
93.49, 114.55, 118.45, 125.42, 127.72, 128.65, 129.69, 131.41,
133.63, 137.77, 152.58, 164.76, 183.75 ppm.
2-Amino-4-(3-nitrophenyl)-6-(4-methoxy-phenylsulfanyl)-
pyridine-3,5-dicarbonitrile (4n)
Yellow solid, M.Pt. 196–200 °C; IR (KBr, mmax): 3,407,
3,330, 2,213, 1,645, 1,551, 1,250, 1,029, 828, 735 cm-1
;
1H NMR (CDCl3, 400 MHz) dH: 3.85 (s, 3H, OCH3), 6.47
(d, J = 8.0 Hz, 2H, Ar–H), 6.84 (d, J = 8.0 Hz, 2H, Ar–
H), 7.56–7.67 (m, 3H, Ar–H), 7.94 (s, 1H, Ar–H), 8.20 (br
s, 2H, NH2) ppm; 13C NMR (CDCl3, 100 MHz) dC: 55.24,
83.53, 86.60, 92.80, 114.93, 116.91, 123.35, 124.96,
130.51, 134.94, 135.29, 136.86, 147.61, 157.92, 159.47,
161.13, 167.69 ppm.
2-Amino-4-(4-methoxyphenyl)-6-(4-bromo-
phenylsulfanyl)-pyridine-3,5-dicarbonitrile (4s)
Yellow solid, M.Pt. 222–224 °C; IR (KBr, mmax): 3,466,
3,348, 2,920, 2,210, 1,642, 1,544, 1,262, 1,113, 803 cm-1
;
1H NMR (CDCl3, 400 MHz) dH: 3.67 (s, 3H, OCH3), 6.68
(br s, 2H, NH2), 6.80 (d, J = 7.4 Hz, 2H, Ar–H), 6.98 (d,
J = 7.6 Hz, 2H, Ar–H), 7.13 (d, J = 8.0 Hz, 2H, Ar–H),
7.30 (d, J = 8.0 Hz, 2H, Ar–H) ppm; 13C NMR (CDCl3,
100 MHz) dC: 55.46, 88.16, 92.42, 113.61, 116.52, 119.23,
126.54, 128.28, 129.65, 130.76, 132.65, 157.33, 160.67,
166.48, 185.43 ppm.
2-Amino-4-(2-thienyl)-6-(4-methoxy-phenylsulfanyl)-
pyridine-3,5-dicarbonitrile (4o)
Yellow solid, M.Pt. 204–208 °C; IR (KBr, mmax): 3,448,
3,338, 2,209, 1,638, 1,544, 1,286, 1,020, 824, 710 cm-1
;
1H NMR (CDCl3, 400 MHz) dH: 3.68 (s, 3H, OCH3), 6.19
(br s, 2H, NH2), 6.66–6.79 (m, 3H, Ar–H), 7.38 (d,
J = 8.0 Hz, 2H, Ar–H), 7.47 (d, J = 8.0 Hz, 2H, Ar–H)
ppm; 13C NMR (CDCl3, 100 MHz) dC: 55.01, 86.10,
93.64, 114.49, 117.22, 123.03, 124.58, 125.32, 127.37,
127.47, 130.71, 132.52, 136.92, 149.96, 160.55, 161.12,
169.35, 186.06 ppm.
2-Amino-4-phenyl-6-(2-amino-phenylsulfanyl)-pyridine-
3,5-dicarbonitrile (4t)
Yellow solid, M.Pt. 224–226 °C [40]; IR (KBr, mmax):
3,462, 3,358, 2,924, 2,213, 1,609, 1,264, 1,158, 747 cm-1
;
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