Organic & Biomolecular Chemistry
Paper
7.83–7.87 (m, 1H), 7.95 (s, 1H), 8.38 (d, J = 8.0 Hz, 1H), 8.70 (d,
J = 4.4 Hz, 1H); 13C NMR (100 MHz, DMSO): δ 87.9, 109.0,
116.6, 121.1, 124.8, 127.9, 128.6, 129.4, 136.8, 137.1, 149.2,
153.8, 154.8, 157.2, 160.6; Anal. Calcd for C17H12N4: C, 74.98;
H, 4.44; N, 20.58. Found: C, 74.65; H, 4.39; N, 20.31.
4 S. Erić, S. Ke, T. Barata, T. Solmajer, J. A. Stanković,
Z. Juranić, V. Savića and M. Zloh, Bioorg. Med. Chem., 2012,
20, 5220.
5 S. A. Laufer, W. Zimmermann and K. J. Ruff, J. Med. Chem.,
2004, 47, 6311.
2-Amino-5-methyl-4,6-diphenylnicotinonitrile
(2s). White
6 H. Ji, S. L. Delker, H. Li, P. Martásek, L. J. Roman,
T. L. Poulos and R. B. Silverman, J. Med. Chem., 2010, 53,
7804.
7 (a) J. S. Yang, Y. H. Lin and C. S. Yang, Org. Lett., 2002, 4,
777; (b) K. Araki, T. Mutai, Y. Shigemitsu, M. Yamada,
T. Nakajima, S. Kuroda and I. Shimao, J. Chem. Soc., Perkin
Trans. 2, 1996, 613.
8 (a) B. K. Langlotz, H. Wadepohl and L. H. Gade, Angew.
Chem., Int. Ed., 2008, 47, 4670; (b) Ö. Öztopcu, K. Mereiter,
M. Puchberger and K. A. Kirchner, Dalton Trans., 2011, 40,
7008.
9 R. Zong, H. Zhou and R. P. Thummel, J. Org. Chem., 2008,
73, 4334.
solid: mp 203–205 °C; 1H NMR (400 MHz, CDCl3): δ 1.95 (s,
3H), 5.18 (s, 2H), 7.32–7.34 (m, 2H), 7.40–7.53 (m, 8H); 13C
NMR (100 MHz, CDCl3): δ 16.9, 91.1, 116.5, 119.0, 128.2, 128.6,
128.6, 128.7, 128.9, 136.8, 139.9, 155.7, 157.2, 162.0; IR (KBr):
ν = 3475, 3290, 3153, 2210, 1632, 1556, 754, 704 cm−1; Anal.
Calcd for C19H15N3: C, 79.98; H, 5.30; N, 14.73. Found: C,
79.65; H, 5.37; N, 14.58.
2-Amino-6-methyl-4-phenylnicotinonitrile (2t). Yellow solid:
mp 183–185 °C; 1H NMR (400 MHz, DMSO): δ 2.36 (s, 3H),
6.61 (s, 1H), 6.84 (s, 2H), 7.51–7.56 (m, 5H); 13C NMR
(100 MHz, DMSO): δ 24.4, 85.0, 112.2, 117.1, 128.1, 128.8,
129.5, 137.0, 154.0, 160.9, 162.2; Anal. Calcd for C13H11N3: C,
74.62; H, 5.30; N, 20.08. Found: C, 74.35; H, 5.26; N, 20.01.
10 G. Bentabed-Ababsa, S. C. S. Ely, S. Hesse, E. Nassar,
F. Chevallier, T. T. Nguyen, A. Derdour and F. Mongin,
J. Org. Chem., 2010, 75, 839.
3,6-Diphenylpyridin-2-amine
(2u). White
solid:
mp
153–154 °C; 1H NMR (400 MHz, DMSO): δ 5.66 (s, 2H), 7.25 (d,
J = 7.6 Hz, 1H), 7.39–7.50 (m, 9H), 8.04 (d, J = 7.2 Hz, 1H); 13C 11 H. Wang, Y. Wang, D. Liang, L. Liu, J. Zhang and Q. Zhu,
NMR (100 MHz, DMSO): δ 109.6, 119.6, 126.3, 127.4, 128.5,
Angew. Chem., Int. Ed., 2011, 50, 5678.
128.5, 128.6, 129.0, 138.1, 138.6, 138.9, 153.6, 156.1; Anal. 12 (a) J. Chen, Q. Pang, Y. Sun and X. Li, J. Org. Chem., 2011,
Calcd for C17H14N2: C, 82.90; H, 5.73; N, 11.37. Found: C,
80.43; H, 5.65; N, 11.46.
76, 3523; (b) J. Chen, G. Song, C. L. Pan and X. Li, Org.
Lett., 2010, 12, 5426.
13 A. E. Chichibabin and O. A. Zeide, J. Russ. Phys. Chem. Soc.,
1914, 46, 1216.
14 S. Thomas, S. Roberts, L. Pasumansky, S. Gamsey and
B. Singaram, Org. Lett., 2003, 5, 3867.
Acknowledgements
15 G. A. Grasa, M. S. Viciu, J. Huang and S. P. Nolan, J. Org.
Chem., 2001, 66, 7729.
16 A. Shafir and S. L. Buchwald, J. Am. Chem. Soc., 2006, 128,
8742.
17 (a) J. Yin, B. Xiang, M. A. Huffman, C. E. Raab and
I. W. Davies, J. Org. Chem., 2007, 72, 4554;
(b) A. T. Londregan, S. Jennings and L. Wei, Org. Lett.,
2010, 12, 5254; (c) P. J. Manley and M. T. Bilodeau, Org.
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Financial support of this research by the National Natural
Science Foundation of China (51073150, and 21172211) and
“Hundred Talents Program” of the Chinese Academy of
Sciences and the Department of Science and Technology of
Jilin Province (20111802) is greatly acknowledged.
Notes and references
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Org. Biomol. Chem., 2013, 11, 1001–1006 | 1005