PAPER
Synthesis of 4′-Aryl-2,2′:6′,2′′-terpyridines and 2,4,6-Triarylpyridines
3049
Anal. Calcd for C23H14Cl3N: C, 67.26; H, 3.44; N, 3.41. Found: C,
67.20; H, 3.45; N, 3.54.
ridyl-H), 7.51–7.58 (m, 2 H, ArH), 7.22–7.24 (m, 2 H, ArH), 7.10–
7.12 (m, 4 H, ArH), 3.86 (s, 6 H, OCH3).
Anal. Calcd for C27H22N2O2: C, 79.78; H, 5.46; N, 6.89. Found: C,
79.85; H, 5.66; N, 6.78.
2l
IR (KBr): 1610, 1541, 1474, 1433, 1398, 1085, 1052, 1034, 987,
890 cm–1.
3a
1H NMR (400 MHz, DMSO-d6): d = 8.85 (s, 2 H, pyridyl-H), 7.79–
7.82 (m, 4 H, ArH), 7.61–7.67 (m, 2 H, ArH), 7.57–7.60 (m, 2 H,
ArH), 7.51–7.54 (m, 2 H, ArH).
IR (KBr): 3512, 1599, 1563, 1518, 1460, 842, 771, 773 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 9.31 (s, 1 H, OH), 8.11 (d,
J = 7.2 Hz, 2 H, 5,6-H), 7.64 (d, J = 7.6 Hz, 2 H, Aryl 5,6-H), 7.51
(t, J = 7.2 Hz, 2 H, 3,8-H), 7.44 (t, J = 7.2 Hz, 2 H, 4,7-H), 7.23 (s,
1 H, ArH), 7.20 (d, J = 8.0 Hz, 1 H, 2-H), 6.97 (d, J = 7.6 Hz, 1 H,
9-H), 3.97 (s, 4 H, 1,10-H), 3.84 (s, 3 H, OCH3).
Anal. Calcd for C23H12Cl5N: C, 57.60; H, 2.52; N, 2.92. Found: C,
57.62; H, 2.49; N, 2.89.
2m
Anal. Calcd for C27H20O2: C, 86.14; H, 5.36; Found: C, 86.22; H,
5.46.
IR (KBr): 1600, 1571, 1541, 1473, 1422, 1364, 888, 835, 811 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 8.03 (s, 2 H, pyridyl-H), 7.88–
7.90 (m, 2 H, ArH), 7.78–7.81 (m, 4 H, ArH), 7.74–7.76 (m, 2 H,
ArH), 7.58–7.61 (m, 2 H, ArH).
3b
IR (KBr): 1612, 1561, 1517, 1464, 1440, 1288, 1025, 859, 831, 776
cm–1.
Anal. Calcd for C23H12BrCl4N: C, 52.71; H, 2.31; N, 2.67. Found:
C, 52.67; H, 2.40; N, 2.81.
1H NMR (400 MHz, DMSO-d6): d = 8.11 (d, J = 7.2 Hz, 2 H, 5,6-
H), 7.76 (d, J = 8.0 Hz, 2 H, Aryl 2,6-H), 7.63 (d, J = 7.2 Hz, 2 H,
2,9-H), 7.51 (t, J = 7.2 Hz, 2 H, 3,8-H), 7.45 (t, J = 7.2 Hz, 2 H, 4,7-
H), 7.14 (d, J = 8.0 Hz, 2 H, Aryl 3,5-H), 3.95 (s, 4 H, 1,10-H), 3.87
(s, 3 H, OCH3).
2n
IR (KBr): 1605, 1577, 1540, 1490, 1459, 1423, 1384, 1361, 819
cm–1.
1H NMR (400 MHz, DMSO-d6): d = 8.27 (d, J = 8.0 Hz, 2 H, ArH),
8.06 (s, 2 H, pyridyl-H), 8.00 (d, J = 8.0 Hz, 2 H, ArH), 7.75 (d,
J = 8.0 Hz, 2 H, ArH), 7.08 (d, J = 8.0 Hz, 2 H, ArH), 7.08 (d,
J = 8.0 Hz, 2 H, ArH), 3.85 (s, 6 H, 2 OCH3).
Anal. Calcd for C27H20O: C, 89.97; H, 5.59; Found: C, 90.02; H,
5.48.
3c
IR (KBr): 3292, 1573, 1559, 1491, 767, 794, 738 cm–1.
Anal. Calcd for C25H20BrNO2: C, 67.27; H, 4.52; N, 3.14. Found: C,
67.32; H, 4.46; N, 3.08.
1H NMR (400 MHz, DMSO-d6): d = 11.68 (s, 1 H, NH), 8.13 (d,
J = 7.6 Hz, 2 H, 5,6-H), 7.96 (s, 1 H, indolyl 2-H), 7.62 (d, J = 7.6
Hz, 2 H, 2,9-H), 7.57 (s, 1 H, indolyl 7-H), 7.55 (s, 1 H, indolyl 4-
H), 7.51 (t, J = 7.2 Hz, 2 H, 5,6-H), 7.44 (t, J = 7.2 Hz, 2 H, 3,8-H),
7.23 (t, J = 7.2 Hz, 1 H, indolyl 6-H), 7.10 (t, J = 7.2 Hz, 1 H, in-
dolyl 5-H), 3.94 (s, 4 H, 1,10-H).
2o
IR (KBr): 1597, 1556, 1541, 1474, 1411, 1368, 816 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 8.06 (s, 2 H, pyridyl-H), 7.91–
7.93 (m, 2 H, ArH), 7.79–7.82 (m, 4 H, ArH), 7.50–7.61 (m, 5 H,
ArH).
Anal. Calcd for C28H19N: C 91.03; H 5.18; N 3.79; Found: C, 91.00;
H, 5.32; N, 3.68.
Anal. Calcd for C23H13Cl4N: C, 62.05; H, 2.94; N, 3.15; Found: C,
62.10; H, 2.87; N, 3.24.
4a
IR (KBr): 3446, 2926, 2836, 1594, 1511, 1464, 1471, 1266, 1238,
2p
1034, 766 cm–1.
IR (KBr): 1598, 1557, 1538, 1471, 1414, 1363, 1050, 872, 813
cm–1.
1H NMR (400 MHz, DMSO-d6): d = 9.17 (s, 1 H, OH), 8.44 (d,
J = 7.6 Hz, 2 H, 6,7-H), 7.41 (d, J = 7.6 Hz, 2 H, 5,8-H), 7.34 (t,
J = 7.6 Hz, 2 H, 4,9-H), 7.28 (d, J = 7.2 Hz, 2 H, 3,10-H), 6.67–6.93
(3 H, m, Ar-H), 3.81 (s, 3 H, OCH3), 2.83–2.92 (m, 4 H, 1,12-H),
2.32–2.70 (m, 4 H, 2,11-H).
1H NMR (400 MHz, DMSO-d6): d = 7.87 (s, 2 H, pyridyl-H), 7.79–
7.82 (m, 4 H, ArH), 7.75–7.53 (m, 1 H, ArH), 7.68–7.70 (m, 1 H,
ArH), 7.58–7.61 (m, 3 H, ArH).
Anal. Calcd for C23H11Cl6N: C, 53.74; H, 2.16; N, 2.72. Found: C,
53.62; H, 2.10; N, 2.81.
Anal. Calcd for C29H24O2: C, 86.11; H, 5.98; Found: C, 86.21; H,
5.88.
2q
4b
IR (KBr): 1665, 1603, 1551, 1473, 1420, 1389, 1363, 1322, 993,
IR (KBr): 2949, 2834, 1611, 1549, 1512, 1456, 1274, 1036, 840,
857, 813 cm–1.
759 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 7.79–7.82 (m, 5 H, ArH), 7.78
(s, 2 H, pyridyl-H), 7.57–7.71 (m, 5 H, ArH), 7.37–7.48 (m, 3 H,
ArH).
1H NMR (400 MHz, DMSO-d6): d = 8.43 (d, J = 7.6 Hz, 2 H, 6,7-
H), 7.41 (d, J = 7.6 Hz, 2 H, 5,8-H), 7.35 (t, J = 7.2 Hz, 2 H, 4,9-H),
7.28 (d, J = 7.2 Hz, 2 H, 3,10-H), 7.24 (d, J = 8.4 Hz, 2 H, Aryl 2,6-
H), 7.09 (d, J = 8.4 Hz, 2 H, Aryl 3,5-H), 3.84 (3 H, s, OCH3), 2.79–
2.83 (m, 4 H, 1,12-H), 2.60–2.64 (m, 4 H, 2,11-H).
Anal. Calcd for C23H11Cl6N: C, 53.74; H, 2.16; N, 2.72. Found: C,
53.70; H, 2.21; N, 2.63.
Anal. Calcd for C29H24O: C, 89.66; H, 6.23. Found: C, 89.49; H,
6.34.
2r
IR (KBr): 3135, 3105, 2829, 1599, 1512, 1458, 1421, 1342, 880,
801 cm–1.
4c
1H NMR (400 MHz, DMSO-d6): d = 11.75 (s, 1 H, indolyl-NH),
8.24–8.27 (m, 5 H, ArH), 8.08–8.11 (m, 1 H, ArH), 8.08 (s, 2 H, py-
IR (KBr): 2931, 2887, 1549, 1502, 1489, 1239, 1038, 759 cm–1.
1H NMR (400 MHz, DMSO-d6): d = 8.42 (d, J = 7.6 Hz, 2 H, 6,7-
H), 7.41 (d, J = 7.2 Hz, 2 H, 5,8-H), 7.34 (t, J = 7.2 Hz, 2 H, 4,9-H),
Synthesis 2005, No. 18, 3045–3050 © Thieme Stuttgart · New York