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A. K. Verma et al. / Tetrahedron 63 (2007) 8715–8722
m), 7.38–7.50 (4H, m), 7.53 (2H, d, J 8.5 Hz), 7.60 (1H, s),
7.63 (2H, d, J 8.5 Hz), 8.01 (2H, ddd, J 8.6, 3.3, 1.0 Hz). 13C
NMR (CDCl3): dC 34.10, 120.6, 125.4, 126.9, 127.6, 128.1,
128.2, 128.5, 130.1, 131.2, 132.4, 133.2, 139.5, 152.9, 154.4,
157.1. HREIMS: m/z (rel int.) 425.2185 (M+) (42) (calcd for
C32H27N, 425.2143), 348 (100%), 334 (45), 322 (20), 232
(25), 220 (45), 129 (55), 116 (25), 105 (47), 91 (70). Anal.
CHN (%), found: C, 89.89; H, 6.51; N, 3.57. Calcd: C,
90.31; H, 6.39; N, 3.29.
(2H, d, J 8.7 Hz), 7.56 (2H, d, J 8.7 Hz), 7.61 (1H, s), 7.62
(2H, d, J 8.7 Hz), 7.68 (2H, d, J 8.7 Hz), 8.01 (2H, ddd,
J 8.6, 3.2, 1.0 Hz). 13C NMR (CDCl3): dC 36.7, 121.3, 125.4,
125.6, 127.5, 127.8, 128.4, 128.6, 128.7, 129.5, 130.3, 131.4,
131.5, 131.9, 132.1, 139.9, 141.6, 145.2, 154.4, 154.8.
HREIMS: m/z (rel int.) 553.0104, 557.0100 (M+) (22, 32)
(calcd for C30H21Br2N, 553.0041, 557.0001), 476 (100%),
452 (31), 399 (21), 350 (63), 297 (53), 194 (59), 181 (41),
170 (44), 156 (72). Anal. CHN (%), found: C, 65.09; H,
3.69; N, 2.69. Calcd: C, 64.89; H, 3.81; N, 2.52.
4.5.3. 4-(4-Nitrophenyl)-3-[(4-nitrophenyl)methyl]-2,6-
diphenylpyridine, 3c. Colorless cubes, mp 128–129 ꢀC.
IR: nmax 3038, 3012, 1615, 1495, 1478, 1452, 1373, 1247,
4.5.7. 4-(4-Methoxyphenyl)-3-[(4-methoxyphenyl)-
methyl]-2,6-diphenylpyridine, 3g. Colorless cubes, mp
123–125 ꢀC. IR: nmax 3035, 3004, 1618, 1500, 1470, 1455,
1
1052, 967 cmꢂ1. H NMR (300 MHz, CDCl3): d 4.36 (2H,
1
s), 7.33–7.46 (8H, m), 7.50 (2H, d, J 8.7 Hz), 7.55 (2H, d,
J 8.7 Hz), 7.63 (1H, s), 8.01 (2H, ddd, J 8.6, 3.2, 1.0 Hz),
8.19 (2H, d, J 8.7 Hz), 8.25 (2H, d, J 8.7 Hz). 13C NMR
(CDCl3): dC 40.5, 120.1, 126.5, 126.9, 127.9, 128.6, 128.7,
137.0, 138.0, 140.4, 140.7, 142.6, 143.4, 146.4, 148.1,
154.4, 157.3, 158.5. HREIMS: m/z (rel int.) 487.1548 (M+)
(38) (calcd for C30H21N3O4, 487.1533), 410 (100%), 384
(30), 365 (24), 288 (38), 263 (30), 160 (58), 147 (56), 136
(38), 122 (87). Anal. CHN (%), found: C, 74.31; H, 4.49,
N, 8.70. Calcd: C, 73.91; H, 4.34; N, 8.62.
1430, 1371, 1294, 1050, 967 cmꢂ1. H NMR (300 MHz,
CDCl3): d 3.56 (3H, s), 3.58 (3H, s), 4.01 (2H, s), 6.84 (2H,
d, J 8.4 Hz), 6.85 (2H, d, J 8.4 Hz), 7.23–7.36 (4H, m), 7.25
(2H, dd, J 8.7, 2.7 Hz), 7.37–7.49 (4H, m), 7.60 (1H, s), 8.07
(2H, dd, J 9.6, 2.3, 1.0 Hz). 13C NMR (CDCl3): dC 34.13,
55.1, 55.3, 113.3, 113.6, 120.9, 126.9, 127.7, 127.9, 128.6,
128.7, 129.1, 132.4, 133.2, 139.5, 141.4, 151.2, 151.9,
154.4, 157.4, 159.2. HREIMS: m/z (rel int.) 457.2068 (M+)
(21) (calcd for C32H27NO2, 457.2042), 380 (100), 354
(41), 350 (66), 252 (25), 248 (42), 145 (55), 132 (28), 121
(54), 107 (67). Anal. CHN (%), found: C, 84.50; H, 6.19;
N, 3.31. Calcd: C, 84.00; H, 5.95; N, 3.15.
4.5.4. 4-(4-Fluorophenyl)-3-[(4-fluorophenyl)methyl]-
2,6-diphenylpyridine, 3d. Colorless cubes, mp 113–
114 ꢀC. IR: nmax 3004, 1618, 1500, 1470, 1455, 1430,
4.5.8. 2-{3-[(2-Hydroxyphenyl)methyl]-2,6-diphenyl-4-
pyridyl}phenol, 3h. Colorless plates, mp 172–173 ꢀC. IR:
nmax 3460, 3430, 3050, 1605, 1550, 1485, 1380, 1345,
1280, 1140, 1096, 1050, 920, 750 cmꢂ1. 1H NMR (300 MHz,
CDCl3): d 4.15 (2H, s), 7.01 (1H, dd, J 7.3, 7.7 Hz), 7.10 (2H,
dd, J 7.3, 7.7 Hz), 7.19 (1H, d, J 8.7 Hz), 7.23 (1H, d,
J 8.7 Hz), 7.30–7.51 (4H, m), 7.35 (2H, dd, J 8.7, 2.3 Hz),
7.38 (2H, dd, J 7.8, 2.3 Hz), 7.42 (1H, dd, J 7.8, 2.3 Hz),
7.53–7.67 (4H, m), 7.59 (1H, s), 8.10 (2H, ddd, J 8.6, 3.0,
1.0 Hz), 10.16 (1H, s, exch. D2O), 10.90 (1H, s, exch.
D2O). 13C NMR (CDCl3): dC 34.20, 118.3, 118.7, 119.1,
119.9, 120.4, 120.8, 126.9, 127.1, 127.6, 128.3, 128.6, 129.5,
130.2, 130.4, 133.7, 145.7, 145.9, 154.6, 157.8, 158.5.
HREIMS: m/z (rel int.) 429.1768 (M+) (13) (calcd for
C30H23NO2, 429.1729), 352 (100), 36 (42), 326 (46), 234
(54), 224 (25), 131 (75), 118 (25), 107 (35), 93 (78). Anal.:
not done.
1398, 1371, 1294, 1253, 1030, 967 cmꢂ1 1H NMR
.
(300 MHz, CDCl3): d 4.80 (2H, s), 7.12 (2H, dd, J 8.8,
8.7 Hz), 7.26 (2H, dd, J 8.8, 8.7 Hz), 7.73 (2H, dd, J 8.8,
5.4 Hz), 7.76 (2H, dd, J 8.8, 5.4 Hz). 13C NMR (CDCl3):
dC 39.4, 116.4 (d, J 8.2 Hz), 117.2 (d, J 8.2 Hz), 117.4 (d,
J 8.2 Hz), 118.3 (d, J 8.2 Hz), 112.6, 126.8, 126.9, 127.6,
128.6, 128.7, 129.1 (d, J 8.2 Hz), 130.0 (d, J 8.2 Hz), 151.9,
155.3, 157.6, 163.9, 164.7. HREIMS: m/z (rel int.) 433.1666
(M+) (42) (calcd for C30H21F2N, 433.1642) 356 (100%), 338
(29), 330 (50), 236 (66), 228 (46), 133 (23), 109 (37), 95
(73). Anal. CHN (%), found: C, 83.42; H, 5.09; N, 3.36.
Calcd: C, 83.12; H, 4.88; N, 3.23.
4.5.5. 4-(4-Chlorophenyl)-3-[(4-chlorophenyl)methyl]-
2,6-diphenylpyridine, 3e. Colorless prisms, mp 120–
121 ꢀC. IR: nmax 3025, 1610, 1495, 1475, 1385, 1350,
1
1140, 1090, 1072, 1050, 926 cmꢂ1. H NMR (300 MHz,
CDCl3): d 4.52 (2H, s), 7.35–7.49 (4H, m), 7.40 (2H, d,
J 8.4 Hz), 7.49 (2H, d, J 8.4 Hz), 7.50–7.67 (4H, m), 7.61
(1H, s), 7.61 (1H, s), 7.65 (2H, dd, J 8.4, 3.8 Hz), 7.72
(2H, dd, J 8.6, 3.8 Hz), 8.01 (2H, ddd, J 8.6, 3.3, 1.0 Hz).
13C NMR (CDCl3): dC 34.30, 120.5, 127.0, 127.7, 128.2,
128.3, 128.4, 128.5, 129.5, 130.2, 130.4, 132.1, 132.2,
136.9, 137.1, 139.6, 141.3, 152.1, 154.3, 157.9. HREIMS:
m/z (rel int.) 465.1023, 469.0989 (M+) (49, 37) (calcd for
C30H21Cl2N, 465.1051, 469.0996), 388 (100%), 363 (22),
354.5 (56), 261 (33), 252 (13), 149 (45), 136 (39), 125
(14), 111 (67). Anal. CHN (%), found: C, 77.76; H, 4.38;
N, 3.29. Calcd:. C, 77.36; H, 4.54; N, 3.10.
4.5.9. 2-{3-[(2-Hydroxy-4-methylphenyl)methyl]-2,6-di-
phenyl(4-pyridyl)}-5-methylphenol, 3i. Colorless plates,
mp 165–166 ꢀC. IR: nmax 3478, 3466, 3050, 1610, 1555,
1480, 1385, 1340, 1270, 1145, 1096, 1050, 920, 730 cmꢂ1
.
1H NMR (300 MHz, CDCl3): d 2.36 (3H, s), 2.39 (3H, s),
3.95 (2H, s), 6.85 (1H, dd, J 8.0, 0.91 Hz), 6.88 (1H, d,
J 8.0 Hz), 6.92 (1H, br s), 7.20 (1H, d, J 8.0 Hz), 7.25
(1H, d, J 8.0 Hz), 7.50–7.53 (4H, m), 7.53–7.68 (4H, m),
7.67 (1H, s), 8.01 (2H, ddd, J 8.6, 2.2, 1.0 Hz), 10.18 (2H,
s, exch. D2O). 13C NMR (CDCl3): dC 114.6, 117.6, 120.7,
121.0, 127.1, 127.3, 127.5, 128.5, 130.1, 130.4, 145.1,
147.9, 154.6, 157.1. HREIMS: m/z (rel int.) 457.2091 (M+)
(24) (calcd for C32H27NO2, 457.2042), 380 (100), 354
(39), 350 (56), 252 (23), 248 (34), 145 (35), 132 (15), 121
(79). Anal.: not done.
4.5.6. 4-(4-Bromophenyl)-3-[(4-bromophenyl)methyl]-
2,6-diphenylpyridine, 3f. Colorless needles, mp 123–
125 ꢀC. IR: nmax 3026, 1612, 1497, 1477, 1386, 1351, 1142,
1090, 1073, 1050, 928 cmꢂ1. 1H NMR (300 MHz, CDCl3):
d 4.20 (2H, s), 7.30–7.46 (4H, m), 7.47–7.52 (4H, m), 7.54
4.5.10. 2,6-Bis(4-nitrophenyl)-4-(4-bromophenyl)-3-[(4-
bromophenyl)methyl]pyridine, 3j. Colorless prisms, mp