RSC Advances
Paper
87.1, 95.1, 112.3, 112.7, 114.7, 126.5, 128.2, 130.4, 132.6, 133.4,
133.6, 133.7, 134.5, 141.0, 147.1, 157.5, 157.5, 159.8, 160.7,
160.8, 167.9; HRMS (ESI): m/z [M + H]+ calcd for C19H17N4F2S:
371.1137; found mass: 371.1136.
2-Amino-6-[(4-methoxyphenyl)sulfanyl]-4-(2,6-dimethylphenyl)-
pyridine-3,5-dicarbonitrile, 5k. Pale yellow solid; mp 243–
245 ꢀC; 1H-NMR (DMSO-d6, 300 MHz): 2.08 (s, 6H), 3.82 (s, 3H),
7.06 (d, 2H, J ¼ 8.7 Hz), 7.23 (d, 2H, J ¼ 7.5 Hz), 7.32 (t, 1H, J ¼
8.4 Hz), 7.56 (d, 2H, J ¼ 8.7 Hz), 7.85 (s, 2H); 13C-NMR (DMSO-
d6, 75 MHz): 19.6, 55.9, 87.5, 114.8, 115.6, 117.4, 128.4, 129.9,
134.1, 134.9, 137.5, 159.2, 160.2, 161.1, 168.1 ppm.
Acknowledgements
Authors S. S. K. and U. V. D. are thankful to UGC, New Delhi, for
the junior research fellowship and nancial assistance [F. No.
43-221/2014 (SR)], respectively.
2-Amino-4-(2,6-dimethoxyphenyl)-6-(phenylsulfanyl)pyridine-
1
ꢀ
3,5-dicarbonitrile, 5l. Off white solid; mp 196–198 C; H-NMR
(DMSO-d6, 300 MHz): 3.78 (s, 6H), 6.81 (s, 1H), 7.5 (d, 7H),
7.85–8.00 (broad signal, 2H); HRMS (ESI): m/z [M + H]+ calcd for
C
21H17O2N4S: 389.1067; found mass: 389.1063 [due to very poor
References
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2-Amino-6-[(4-chlorophenyl)sulfanyl]-4-(2,6-dimethoxyphenyl)-
pyridine-3,5-dicarbonitrile, 5m. Off white solid; mp 208–210 ꢀC;
1H-NMR (DMSO-d6, 300 MHz): 3.77 (s, 6H), 6.77 (d, 2H, J ¼ 7.2
Hz), 7.44–7.48 (m, 4H), 7.58 (d, 2H, J ¼ 7.2 Hz), 7.85–7.95 (m,
1H); 13C-NMR (DMSO-d6, 75 MHz): 56.4, 89.7, 104.8, 111.2,
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2-Amino-4-(2,6-dimethoxyphenyl)-6-[(4-methylphenyl)sulfanyl]-
pyridine-3,5-dicarbonitrile, 5n. Off white solid; mp 194–196 ꢀC;
1H-NMR (DMSO-d6, 300 MHz): 2.35 (s, 3H), 3.77 (s, 6H), 6.71 (s,
2H), 7.23 (d, 3H, J ¼ 6.3 Hz), 7.42 (d, 2H, J ¼ 7.5 Hz), 7.83 (broad
singlet, 1H); 13C-NMR (DMSO-d6, 75 MHz): 21.4, 56.2, 89.6,
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2-Amino-4-(2,6-diuorophenyl)-6-(phenylsulfanyl)pyridine-
3,5-dicarbonitrile, 5o. Grey solid; mp 274–276 ꢀC; 1H-NMR
(DMSO-d6, 300 MHz): 7.36 (t, 2H), 7.5 (s, 3H), 7.61–7.86 (m,
3H), 8.00 (broad singlet, 2H); 13C-NMR (DMSO-d6, 75 MHz):
88.6, 94.5, 112.7, 113.0, 114.4, 114.6, 127.2, 129.8, 130.2, 131.5,
134.2, 135.4, 147.7, 159.8, 167.0 ppm; HRMS (ESI): m/z [M + H]+
calcd for C19H11N4F2S: 365.0667; found mass: 365.0665.
2-Amino-6-[(4-chlorophenyl)sulfanyl]-4-(2,6-diuorophenyl)
pyridine-3,5-dicarbonitrile, 5p. Grey solid; mp 280–282 C; H-
NMR (DMSO-d6, 300 MHz): 7.23 (s, 2H), 7.46–7.56 (m, 4H),
7.83 (s, 2H), 8.03 (s, 1H); 13C-NMR (DMSO-d6, 75 MHz): 88.8,
94.6, 112.4, 112.7, 114.4, 125.9, 129.7, 133.8, 135.6, 137.0, 147.6,
159.8, 166.6 ppm; HRMS (ESI): m/z [M + H]+ calcd for C19H10-
N4ClF2S: 399.0277; found mass: 399.0276.
2-Amino-4-(2,6-diuorophenyl)-6-[(4-methylphenyl)sulfanyl]
pyridine-3,5-dicarbonitrile, 5q. Light grey solid; mp 196–198 ꢀC;
1H-NMR (DMSO-d6, 300 MHz): 2.37 (s, 3H), 7.28–7.34 (m, 4H),
7.48 (d, 2H, J ¼ 7.5 Hz), 7.69–7.73 (m, 1H), 7.85–8.02 (m, 2H);
13C-NMR (DMSO-d6, 75 MHz): 21.4, 88.5, 94.3, 112.7, 113.0,
114.5, 114.6, 123.5, 130.6, 131.5, 135.5, 140.14, 147.6, 159.8,
167.4 ppm; HRMS (ESI): m/z [M + H]+ calcd for C20H13N4F2S:
379.0823; found mass: 379.0820.
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1
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Frijtag
Drabbe
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2-Amino-6-(cyclohexylsulfanyl)-4-(2,6-diuorophenyl)pyridine-
3,5-dicarbonitrile, 5r. Light grey solid; mp 164–166 ꢀC; 1H-NMR
(DMSO-d6, 300 MHz): 1.48–2.02 (m, 11H), 3.95 (s, 1H), 7.20–7.89
(m, 5H); 13C-NMR (DMSO-d6, 75 MHz): 25.5, 25.9, 32.7, 43.7,
38882 | RSC Adv., 2017, 7, 38877–38883
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