S. Tu et al. / Tetrahedron 63 (2007) 381–388
385
1088, 1040, 991, 790, 779, 749 cmꢁ1; 1H NMR (400 MHz,
DMSO-d6) d 8.81 (d, J¼5.2 Hz, 2H, 6,600-H), 8.51 (s, 2H,
30,50-H), 8.47 (d, J¼8.0 Hz, 2H, 3,300-H), 8.27 (dd,
J1¼8.4 Hz, J2¼8.0 Hz, 2H, 4,400-H), 8.05 (dd, J1¼8.4 Hz,
J2¼5.2 Hz, 2H, 5,500-H), 7.70–7.50 (m, 4H, ArH). Anal.
Calcd for C21H14ClN3: C, 73.36; H, 4.10; N, 12.22. Found:
C, 73.29; H, 4.11; N, 12.24.
1075, 993, 885, 781, 733 cmꢁ1
;
1H NMR (400 MHz,
DMSO-d6) d 8.83 (d, J¼5.6 Hz, 2H, 6,600-H), 8.77 (s, 2H,
30,50-H), 8.68 (d, J¼8.0 Hz, 2H, 3,300-H), 8.64 (s, 1H,
ArH), 8.63 (d, J¼8.0 Hz, 1H, ArH), 8.42 (d, J¼8.4 Hz,
1H, ArH), 8.04 (dd, J1¼8.0 Hz, J2¼7.2 Hz, 2H, 4,400-H),
7.88 (dd, J1¼8.4 Hz, J2¼8.0 Hz, 1H, ArH), 7.55 (dd,
J1¼7.2 Hz, J2¼5.6 Hz, 2H, 5,500-H). Anal. Calcd for
C21H14N4O2: C, 71.18; H, 3.98; N, 15.81. Found: C,
71.26; H, 4.02; N, 15.70.
4.2.4. 40-(4-Fluorophenyl)-2,20:60,200-terpyridine (1d). A
white solid; IR (KBr) 1585, 1567, 1552, 1512, 1466, 1416,
1386, 1225, 1161, 1039, 991, 832, 788, 733 cmꢁ1
;
1H
4.2.10. 40-(4-Hydroxy-3-nitrophenyl)-2,20:60,200-terpyri-
dine (1j). A white solid; IR (KBr) 1576, 1558, 1539, 1473,
NMR (400 MHz, DMSO-d6) d 8.77 (d, J¼5.2 Hz, 2H,
6,600-H), 8.70 (s, 2H, 30,50-H), 8.67 (d, J¼8.4 Hz, 2H, 3,300-
H), 8.05 (dd, J1¼8.8 Hz, J2¼8.4 Hz, 2H, 4,400-H), 7.99
(dd, J1¼8.8 Hz, J2¼5.2 Hz, 2H, 5,500-H), 7.53 (d,
J¼8.8 Hz, 2H, ArH), 7.40 (d, J¼8.8 Hz, 2H, ArH). Anal.
Calcd for C21H14FN3: C, 77.05; H, 4.31; N, 12.84. Found:
C, 69.97; H, 4.34; N, 12.87.
1420, 1340, 1060, 941, 898, 737 cmꢁ1
;
1H NMR
(400 MHz, DMSO-d6) d 10.29 (s, 1H, OH), 8.80 (s, 1H,
ArH), 8.30 (d, J¼7.2 Hz, 2H, 6,600-H), 8.08 (s, 2H, 30,50-
H), 7.83 (d, J¼8.4 Hz, 2H, 3,300-H), 7.30 (dd, J1¼8.8 Hz,
J2¼4.0 Hz, 2H, 4,400-H), 7.21 (d, J¼8.8 Hz, 2H, 5,500-H),
6.90 (m, 1H, ArH), 6.69 (m, 1H, ArH). Anal. Calcd for
C21H14N4O3: C, 68.10; H, 3.81; N, 15.13. Found: C,
68.21; H, 3.92; N, 15.21.
4.2.5. 40-(2,4-Dichlorophenyl)-2,20:60,200-terpyridine (1e).
A white solid; IR (KBr) 1583, 1568, 1544, 1468, 1402,
993, 816, 793 cmꢁ1
;
1H NMR (400 MHz, DMSO-d6)
4.2.11. 40-Phenyl-2,20:60,200-terpyridine (1k). A white
solid; IR (KBr) 1583, 1567, 1550, 1468, 1392, 993, 892,
d 8.81 (d, J¼6.0 Hz, 2H, 6,600-H), 8.77 (d, J¼8.0 Hz, 2H,
3,300-H), 8.48 (s, 2H, 30,50-H), 8.05 (dd, J1¼8.4 Hz,
J2¼8.0 Hz, 2H, 4,400-H), 7.70 (dd, J1¼8.4 Hz, J2¼6.0 Hz,
2H, 5,500-H), 7.51–7.54 (m, 3H, ArH). Anal. Calcd for
C21H13Cl2N3: C, 66.68; H, 3.46; N, 11.11. Found: C,
66.73; H, 3.51; N, 11.20.
796 cmꢁ1 1H NMR (400 MHz, DMSO-d6) d 8.82 (d,
;
J¼4.8 Hz, 2H, 6,600-H), 8.72 (s, 2H, 30,50-H), 8.68 (d,
J¼8.0 Hz, 2H, 3,300-H), 8.04 (dd, J1¼8.0 Hz, J2¼6.4 Hz,
2H, 4,400-H), 7.93 (dd, J1¼6.4 Hz, J2¼4.8 Hz, 2H, 5,500-H),
7.63–7.52 (m, 5H, ArH). Anal. Calcd for C21H15N3: C,
81.53; H, 4.89; N, 13.58. Found: C, 81.50; H, 4.87; N, 13.63.
4.2.6. 40-(3,4-Methylenedioxylphenyl)-2,20:60,200-terpyri-
dine (1f). A white solid; IR (KBr) 1585, 1567, 1545, 1453,
1400, 1359, 1110, 991, 856, 786, 731, 640 cmꢁ1; 1H NMR
(400 MHz, DMSO-d6) d 8.76 (d, J¼4.8 Hz, 2H, 6,600-H),
8.67 (d, J¼8.0 Hz, 2H, 3,300-H), 8.64 (s, 2H, 30,50-H), 8.06–
8.02 (m, 2H, 4,400-H), 7.53 (dd, J1¼7.0 Hz, J2¼4.8 Hz, 2H,
5,500-H), 7.51 (d, J¼1.6 Hz, 2H, ArH), 7.13 (d, J¼8.4 Hz,
1H, ArH), 6.15 (s, 2H, CH2). Anal. Calcd for C22H15N3O2:
C, 74.78; H, 4.28; N, 11.89. Found: C, 74.69; H, 4.36;
N, 11.95.
4.2.12. 4-(4-Chlorophenyl)-2,6-bis(3-nitrophenyl)pyri-
dine (2a). A yellow solid; IR (KBr) 1602, 1493, 1437,
1
1386, 881, 819, 755, 729, 715 cmꢁ1; H NMR (400 MHz,
DMSO-d6) d 9.14 (s, 2H, ArH), 8.82 (d, J¼8.0 Hz, 2H,
ArH), 8.51 (s, 2H, Pyridine-H), 8.36 (d, J¼8.0 Hz,
2H, ArH), 8.21 (d, J¼8.0 Hz, 2H, ArH), 7.85–7.90 (m,
2H, ArH), 7.66 (d, J¼8.0 Hz, 2H, ArH). Anal. Calcd for
C23H14ClN3O4: C, 63.97; H, 3.27; N, 9.73. Found: C,
64.04; H, 3.17; N, 9.88.
4.2.7. 40-(3,4,5-Trimethoxyphenyl)-2,20:60,200-terpyridine
(1g). A white solid; IR (KBr) 1586, 1568, 1546, 1469,
4.2.13. 4-(4-Chlorophenyl)-2,6-di p-tolylpyridine (2b). A
yellow solid; IR (KBr) 1602, 1578, 1542, 1492, 1421,
1
1441, 1416, 1389, 1086, 1008, 827, 788, 659 cmꢁ1; H
1384, 875, 786 cmꢁ1 1H NMR (400 MHz, DMSO-d6)
;
NMR (400 MHz, DMSO-d6) d 8.79 (d, J¼3.6 Hz, 2H,
6,600-H), 8.69 (s, 2H, 30,50-H), 8.67 (d, J¼8.0 Hz, 2H, 3,300-
H), 8.07–8.03 (m, 2H, 4,400-H), 7.56–7.52 (m, 2H, 5,500-H),
7.14 (s, 2H, ArH), 3.98 (s, 3H, OCH3), 3.94 (s, 3H, OCH3),
3.76 (s, 3H, OCH3). Anal. Calcd for C24H21N3O3: C,
72.16; H, 5.30; N, 10.52. Found: C, 72.23; H, 5.21; N, 10.43.
d 8.22 (d, J¼8.0 Hz, 4H, ArH), 8.13 (s, 2H, Pyridine-H),
8.08 (d, J¼8.4 Hz, 2H, ArH), 7.79–7.77 (m, 2H, ArH),
7.61 (d, J¼8.0 Hz, 2H, ArH), 7.35 (d, J¼8.0 Hz, 2H,
ArH), 2.39 (s, 6H, 2ꢂCH3). Anal. Calcd for C25H20ClN:
C, 81.18; H, 5.45; N, 3.79. Found: C, 81.26; H, 5.50; N,
3.87.
4.2.8. 40-(4-Nitrophenyl)-2,20:60,200-terpyridine (1h). A
white solid; IR (KBr) 1584, 1567, 1550, 1415, 1386, 1350,
4.2.14. 2,6-Bis(2-chlorophenyl)-4-(4-chlorophenyl)pyri-
dine (2c). A yellow solid; IR (KBr) 1605, 1577, 1545,
1
1
1107, 991, 854, 789, 754, 694 cmꢁ1; H NMR (400 MHz,
1494, 1476, 1441, 1386, 890, 824, 768 cmꢁ1; H NMR
DMSO-d6) d 8.85 (d, J¼6.4 Hz, 2H, 6,600-H), 8.74 (s,
2H, 30,50-H), 8.66 (d, J¼8.4 Hz, 2H, 3,300-H), 8.63 (d,
J¼9.2 Hz, 2H, ArH), 8.20 (d, J¼9.2 Hz, 2H, ArH), 8.04
(dd, J1¼8.4 Hz, J2¼7.25 Hz, 2H, 4,400-H), 7.53 (dd,
J1¼7.2 Hz, J2¼6.4 Hz, 2H, 5,500-H). Anal. Calcd for
C21H14N4O2: C, 71.18; H, 3.98; N, 15.81. Found: C,
71.08; H, 4.08; N, 15.80.
(400 MHz, DMSO-d6) d 7.98–7.95 (m, 2H, ArH), 7.80 (s,
2H, Pyridine-H), 7.75–7.73 (m, 2H, ArH), 7.63–7.59 (m,
4H, ArH), 7.52–7.48 (m, 4H, ArH). Anal. Calcd for
C23H14Cl3N: C, 67.26; H, 3.44; N, 3.41. Found: C, 67.42;
H, 3.54; N, 3.47.
4.2.15. 4-(4-Chlorophenyl)-2,6-bis(4-fluorophenyl)pyri-
dine (2d). A yellow solid; IR (KBr) 1607, 1546, 1493,
4.2.9. 40-(3-Nitrophenyl)-2,20:60,200-terpyridine (1i). A
white solid; IR (KBr) 1585, 1567, 1527, 1470, 1390, 1348,
1423, 1384, 828, 780, 750 cmꢁ1 1H NMR (400 MHz,
;
DMSO-d6) d 8.41–8.37 (m, 2H, ArH), 8.21 (s, 2H,