JOURNAL OF CHEMICAL RESEARCH 2013 505
J = 9.0 Hz), 8.51−8.50 (m, 1H), 8.38 (d, 1H, J = 3.0 Hz), 8.27 (d,
1H, J = 7.5 Hz), 8.09 (s, 1H), 7.82 (d, 1H, J = 9.0 Hz), 7.75 (d, 2H,
J = 8.0 Hz), 7.67 (d, 1H, J = 8.5 Hz), 7.59−7.57 (m, 1H), 7.51 (t, 1H,
J = 7.5 Hz), 7.45 (d, 2H, J = 8.0 Hz), 7.30−7.26 (m, 3H), 4.47 (t, 2H,
J = 7.0 Hz), 2.50 (t, 3H, J = 1.5 Hz), 1.84−1.78 (m, 2H), 1.38−1.31
(m, 2H), 0.91 (t, 3H, J = 7.5 Hz). Anal. Calcd for C37H30N4, C, 83.74;
H, 5.70; N, 10.56. Found: C, 83.72; H, 5.83; N, 10.68%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-methoxyphenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5c): Yellow powder; IR (KBr) νmax 3310, 3053,
2950, 2927, 2870, 2212 (CN), 1609, 1570, 1524, 1511, 1489, 1457,
1365, 1253, 1211, 1178, 1135, 1032, 834, 745 cm−1; 1H NMR
(500 MHz, DMSO-d6): δ 11.82 (s, 1H), 9.21 (s, 1H), 8.55 (dd, 1H,
J = 1.5 Hz and J = 8.5 Hz), 8.53−8.51 (m, 1H), 8.40 (d, 1H, J =
2.5 Hz), 8.28 (d, 1H, J = 8.0 Hz), 8.08 (s, 1H), 7.84−7.80 (m, 3H),
7.66 (d, 1H, J = 8.0 Hz), 7.60−7.58 (m, 1H), 7.51 (t, 1H, J = 8.0 Hz),
7.31−7.28 (m, 3H), 7.21−7.19 (m, 2H), 4.46 (t, 2H, J = 7.0 Hz), 3.89
(s, 3H), 1.83−1.77 (m, 2H), 1.38−1.31 (m, 2H), 0.91 (t, 3H, J =
7.5 Hz). Anal. Calcd for C37H30N4O, C, 81.29; H, 5.53; N, 10.25.
Found: C, 81.32; H, 5.42; N, 10.38%.
3-Cyano-2-(1H-indol-3-yl)-4-(3-methoxyphenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5d): Pale yellow powder; IR (KBr) νmax 3282, 3046,
2953, 2227 (CN), 1565, 1526, 1488, 1455, 1378, 1365, 1205, 1140,
1051, 815, 752, 742 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.82 (s,
1H), 9.21 (s, 1H), 8.56 (d, 1H, J = 8.5 Hz), 8.51 (t, 1H, J = 5.0 Hz),
8.39 (d, 1H, J = 3.0 Hz), 8.28 (d, 1H, J = 8.0 Hz), 8.13 (s, 1H), 7.82
(d, 1H, J = 8.5 Hz), 7.67 (d, 1H, J = 8.0 Hz), 7.59−7.49 (m, 3H), 7.40
(d, 2H, J = 7.0 Hz), 7.29−7.27 (m, 3H), 7.18−7.16 (m, 1H), 4.47 (t,
2H, J = 7.0 Hz), 3.90 (s, 3H), 1.81 (t, 2H, J = 8.0 Hz), 1.37−1.32 (m,
2H), 0.91 (t, 3H, J = 7.5 Hz). Anal. Calcd for C37H30N4O, C, 81.29; H,
5.53; N, 10.25. Found: C, 81.25; H, 5.63; N, 10.18%.
3-Cyano-2-(1H-indol-3-yl)-4-(1-naphthyl)-6-(9-butylcarbazol-3-
yl)pyridine (5i): Pale yellow powder; IR (KBr) ν 3297, 3052, 2954,
2928, 2870, 2225 (CN), 1561, 1542, 1522, 1485, 1430, 1358, 1323,
1213, 1123, 777, 742 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.83
(s, 1H), 9.21 (s, 1H), 8.63−8.60 (m, 2H), 8.38 (d, 1H, J = 3.0 Hz), 8.22
(d, 1H, J = 8.0 Hz), 8.19 (s, 1H), 8.17 (t, 1H, J = 6.0 Hz), 8.12 (d, 1H,
J = 8.5 Hz), 7.82 (d, 1H, J = 9.0 Hz), 7.75−7.73 (m, 3H), 7.67−7.57
(m, 4H), 7.49 (t, 1H, J = 7.5 Hz), 7.31 (t, 2H, J = 3.5 Hz), 7.23 (t, 1H,
J = 7.5 Hz), 4.47 (t, 2H, J = 7.0 Hz), 1.83−1.77 (m, 2H), 1.36−1.32
(m, 2H), 0.90 (t, 3H, J = 7.5 Hz). Anal. Calcd for C40H30N4, C, 84.78;
H, 5.34; N, 9.89. Found: C, 84.67; H, 5.41; N, 9.92%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-chlorophenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5j): Pale yellow powder; IR (KBr) νmax 3297, 3049,
2954, 2930, 2870, 2214 (CN), 1592, 1570, 1524, 1467, 1441, 1243,
1211, 1137, 1011, 747 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.84
(s, 1H), 9.21 (s, 1H), 8.57−8.55 (m, 1H), 8.52−8.50 (m, 1H), 8.39 (d,
1H, J = 3.0 Hz), 8.26 (d, 1H, J = 8.0 Hz), 8.13 (s, 1H), 7.87−7.81 (m,
5H), 7.67 (d, 1H, J = 8.5 Hz), 7.59−7.57 (m, 1H), 7.53−7.49 (m, 1H),
7.29−7.26 (m, 3H), 4.47 (t, 2H, J = 7.5 Hz), 1.84−1.78 (m, 2H),
1.38−1.31 (m, 2H), 0.91 (t, 3H, J = 7.0 Hz).Anal. Calcd for C36H27ClN4,
C, 78.46; H, 4.94; N, 10.17. Found: C, 78.52; H, 5.03; N, 10.29%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-bromophenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5k): Pale yellow powder; IR (KBr) νmax 3301, 3049,
2954, 2928, 2873, 2214 (CN), 1571, 1525, 1491, 1440, 1365, 1243,
1211, 1138, 1123, 1088, 799, 744 cm−1; 1H NMR (500 MHz, DMSO-
d6): δ 11.84 (s, 1H), 9.20 (s, 1H), 8.56−8.51 (m, 2H), 8.39 (d, 1H,
J = 3.0 Hz), 8.26 (d, 1H, J = 7.5 Hz), 8.12 (s, 1H), 7.88 (d, 2H, J =
8.5 Hz), 7.81 (d, 1H, J = 8.5 Hz), 7.72−7.66 (m, 2H), 7.59−7.58 (m,
1H), 7.52−7.49 (m, 2H), 7.29−7.26 (m, 3H), 4.46 (t, 2H, J = 7.0 Hz),
1.83−1.77 (m, 2H), 1.38−1.30 (m, 2H), 0.90 (t, 3H, J = 7.0 Hz). Anal.
Calcd for C36H27BrN4, C, 72.61; H, 4.57; N, 9.41. Found: C, 72.69; H,
4.43; N, 9.38%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-isopropylphenyl)-6-(9-butylcar-
bazol-3-yl)pyridine (5e): Pale yellow powder; IR (KBr) νmax 3300,
3051, 2952, 2869, 2220 (CN), 1562, 1524, 1494, 1442, 1379, 1320,
1
1247, 1201, 1140, 810, 741 cm−1; H NMR (500 MHz, DMSO-d6):
This work was partially supported by the Hebei Province
Science and Technology Support Plan Project (No. 12211406,
12211405) and Natural Science Foundation of Hebei Province
(No. B2012208051).
δ 11.82 (s, 1H), 9.21 (s, 1H), 8.57−8.55 (m, 1H), 8.51 (t, 1H, J =
4.5 Hz), 8.39 (d, 1H, J = 3.0 Hz), 8.27 (d, 1H, J = 8.0 Hz), 8.11 (s,
1H), 7.82−7.77 (m, 3H), 7.66 (d, 1H, J = 8.0 Hz), 7.59−7.58 (m, 1H),
7.52−7.49 (m, 3H), 7.29−7.25 (m, 3H), 4.46 (t, 2H, J = 7.0 Hz),
3.08−3.00 (m, 1H), 1.83−1.77 (m, 2H), 1.36−1.30 (m, 8H), 0.90 (t,
3H, J = 7.5 Hz). Anal. Calcd for C39H34N4, C, 83.84; H, 6.13; N, 10.03.
Found: C, 83.68; H, 6.26; N, 10.11%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-tert-butylphenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5f): Pale yellow powder; IR (KBr) νmax 3308, 3048,
2959, 2869, 2221 (CN), 1565, 1537, 1470, 1379, 1245, 1212, 1140,
1122, 838, 809, 739 cm−1; 1H NMR (500 MHz, DMSO-d6): δ 11.82 (s,
1H), 9.22 (s, 1H), 8.57−8.52 (m, 2H), 8.40 (d, 1H, J = 3.0 Hz), 8.27
(d, 1H, J = 8.0 Hz), 8.11 (s, 1H), 7.80−7.77 (m, 3H), 7.66−7.63 (m,
3H), 7.60−7.58 (m, 1H), 7.50 (t, 1H, J = 8.0 Hz), 7.29−7.25 (m, 3H),
4.45 (t, 2H, J = 7.0 Hz), 1.82−1.76 (m, 2H), 1.38 (s, 9H), 1.36−1.31
(m, 2H), 0.90 (t, 3H, J = 7.5 Hz). Anal. Calcd for C40H36N4, C, 83.88;
H, 6.34; N, 9.78. Found: C, 83.71; H, 6.47; N, 9.69%.
3-Cyano-2-(1H-indol-3-yl)-4-(4-dimethylaminophenyl)-6-(9-butyl-
carbazol-3-yl)pyridine (5g): Yellow powder; IR (KBr) νmax 3408,
3297, 3052, 2924, 2214 (CN), 1609, 1568, 1526, 1517, 1493, 1440,
1360, 1211, 1136, 1123, 813, 744 cm−1; 1H NMR (500 MHz, DMSO-
d6): δ 11.79 (s, 1H), 9.18 (s, 1H), 8.54−8.52 (m, 1H), 8.50−8.48 (m,
1H), 8.37 (d, 1H, J = 3.0 Hz), 8.28 (d, 1H, J = 7.5 Hz), 8.04 (s, 1H),
7.80 (d, 1H, J = 9.0 Hz), 7.75 (d, 2H, J = 8.5 Hz), 7.66 (d, 1H, J =
8.5 Hz), 7.58−7.56 (m, 1H), 7.52−7.49 (m, 1H), 7.29−7.26 (m, 3H),
6.92 (d, 2H, J = 9.0 Hz), 4.47 (t, 2H, J = 7.0 Hz), 3.04 (s, 6H),
1.83−1.77 (m, 2H), 1.38−1.30 (m, 2H), 0.90 (t, 3H, J = 7.5 Hz). Anal.
Calcd for C38H33N5, C, 81.54; H, 5.94; N, 12.51. Found: C, 81.60; H,
5.83; N, 12.68%.
Received 5 May 2013; accepted 9 June 2013
Paper 1301932 doi: 10.3184/174751913X13736278296459
Published online: 9 August 2013
References
1
2
3
4
5
P. Kundu, K.R. Justin Thomas, J.T. Lin, Y.T. Tao and C.H. Chien, Adv.
Funct. Mater., 2003, 13, 445.
B.E. Koene, D.E. Loy and M.E. Thompson, Chem. Mater., 1998, 10,
2235.
S. Wakim, J. Bouchard, N. Blouin, A. Michaud and M. Leclerc, Org. Lett.,
2004, 6, 3413.
J.F. Morin, M. Leclerc, D. Ades and A. Siove, Macromol. Rapid Commun.,
2005, 26, 761.
A.Van Dijken, J.J.A.M. Bastiaansen, N.M.M. Kiggen, B.M.W. Langeveld,
C. Rothe, A. Monkman, I. Bach, P. Stoessel and K. Brunner, J. Am. Chem.
Soc., 2004, 126, 7718.
6
K.R. Justin Thomas, M. Velusamy, J.T. Lin, Y.T. Tao and C.H. Chien, Adv.
Funct. Mater., 2004, 14, 387.
7
8
9
A. Strecker, Liebigs Ann. Chem., 1850, 75, 27.
A. Nefzi, J.M. Ostresh and R.A. Houghten, Chem. Rev., 1997, 97, 449.
L.A. Thompson, Curr. Opin. Chem. Bio., 2000, 4, 324.
10 M.C. Bagley, J.W. Cale and J. Bower, Chem. Commun., 2002, 16, 1682.
11 D. Dallinger, N.Y. Gorobets and C.O. Kappe, Org. Lett., 2003, 5, 1205.
12 S. Kumar, P. Sharma, K.K. Kapoor and M.S. Hundal, Tetrahedron, 2008,
64, 536.
13 K.K. Pasunooti, H. Chai, C.N. Jensen, B.K. Gorityala, S. Wang and X.W.
Liu, Tetrahedron Lett., 2011, 52, 80.
14 Z.L. Shen, X.P. Xu and S.J. Ji, J. Org. Chem., 2010, 75, 1162.
15 P. Thirumurugan and P.T. Perumal, Tetrahedron Lett., 2009, 50, 4145.
16 S.L. Zhu, S.J. Ji, X.M. Su, C. Sun and Y. Liu, Tetrahedron Lett., 2008, 49,
1777.
17 L.J. Geng, G.L. Feng and J.G. Yu, J. Chem. Res., 2010, 34, 333.
18 L.J. Geng, G.L. Feng, J.G. Yu and H.L. Zhang, J. Chem. Res., 2011, 35,
74.
3-Cyano-2-(1H-indol-3-yl)-4-(4-hydroxyphenyl)-6-(9-butylcarba-
zol-3-yl)pyridine (5h): Yellow powder; IR (KBr) νmax 3405, 3378,
3322, 3059, 2955, 2873, 2218 (CN), 1569, 1515, 1435, 1355, 1238,
1
1211, 1130, 1113, 837, 745 cm−1; H NMR (500 MHz, DMSO-d6):
δ 11.81 (s, 1H), 10.00 (s, 1H), 9.19 (s, 1H), 8.55−8.49 (m, 2H), 8.38
(d, 1H, J = 2.5 Hz), 8.28 (d, 1H, J = 7.5 Hz), 8.06 (s, 1H), 7.80 (d, 1H,
J = 8.5 Hz), 7.72 (d, 2H, J = 8.5 Hz), 7.66 (d, 1H, J = 8.5 Hz),
7.59−7.57 (m, 1H), 7.51 (t, 1H, J = 7.0 Hz), 7.29−7.26 (m, 3H), 7.01
(d, 2H, J = 8.5 Hz), 4.46 (t, 2H, J = 7.0 Hz), 1.83−1.77 (m, 2H),
1.38−1.30 (m, 2H), 0.90 (t, 3H, J = 7.0 Hz).Anal. Calcd for C36H28N4O,
C, 81.18; H, 5.30; N, 10.52. Found: C, 81.09; H, 5.43; N, 10.48%.
19 J. Slatt, I. Romero and J. Bergman, Synthesis, 2004, 2760.
20 H.Y. Wang, G. Chen, X.P. Xu, H. Chen and S.J. Ji, Dyes Pigm., 2010, 86,
238.
21 D. Philippe and D. Fanny, U.S. Pat. 20120039804, 2012.