October 2001
1317
Table 4. 1H-NMR and IR Spectral Data for the Final Products
Compound
1H-NMR (CDCl3) d
IR (neat) cmϪ1
1Aa
1Ab
1Ac
1Ba
2Aa
3Aa
4Aa
5Aa
6Aa
7Aa
8Aa
2.04—2.18 (2H, m), 2.20—2.41 (3H, br), 2.41—2.56 (6H, m), 2.84—3.10 (3H, br), 3.44 (4H, t, Jϭ5.1 Hz),
6.52—6.62 (2H, m), 7.22—7.48 (11H, m), 8.11—8.17 (1H, m)
2.44—2.60 (6H, m), 2.60—2.71 (2H, m), 3.52 (4H, t, Jϭ5.1 Hz), 6.57—6.66 (2H, m), 7.22—7.52 (11H, m),
8.14—8.22 (1H, m)
2.58 (6H, m), 2.80—2.91 (2H, m), 3.58 (4H, t, Jϭ5.1 Hz), 6.58—6.70 (2H, m), 7.15—7.35 (5H, m),
7.43—7.53 (1H, m), 8.16—8.24 (1H, m)
1630
2240
1600, 1490
1640
1.78—1.91 (2H, m), 2.14—2.48 (7H, m), 2.48—2.60 (2H, m), 2.60—2.72 (2H, m), 2.82—3.10 (3H, br), 3.49—3.59
(2H, m), 3.59—3.68 (2H, m), 6.40 (1H, d, Jϭ8.8 Hz), 6.43—6.50 (1H, m), 7.18—7.44 (11H, m), 8.05—8.12 (1H, m)
2.07—2.17 (2H, m), 2.20—2.41 (3H, br), 2.41—2.56 (6H, m), 2.80—3.07 (3H, br), 3.13 (4H, t, Jϭ5.0 Hz),
7.11 (1H, d, Jϭ3.0 Hz), 7.12 (1H, d, Jϭ3.0 Hz), 7.33—7.47 (8H, m), 8.05 (1H, t, Jϭ3.0 Hz), 8.25 (1H, s)
2.06—2.16 (2H, m), 2.22—2.41 (3H, br), 2.41—2.52 (6H, m), 2.88—3.10 (3H, br), 3.23 (4H, t, Jϭ5.0 Hz),
6.59 (2H, d, Jϭ6.8 Hz), 7.22—7.47 (10 H, m), 8.22 (2H, d, Jϭ6.8 Hz)
2.06—2.17 (2H, m), 2.22—2.41 (3H, br), 2.41—2.54 (6H, m), 2.88—3.08 (3H, br), 3.39 (4H, t, Jϭ5.1 Hz),
6.52 (1H, d, Jϭ3.7 Hz), 7.16 (1H, d, Jϭ3.7 Hz), 7.16 (1H, d, Jϭ3.7 Hz), 7.23—7.33 (2H, m), 7.33—7.46 (8H, m)
2.06—2.19 (2H, m), 2.22—2.40 (3H, br), 2.40—2.53 (6H, m), 2.86—3.08 (3H, br), 3.50 (4H, t, Jϭ5.0 Hz), 7.24—7.33
(2H, m), 7.33—7.46 (8H, m), 7.80 (1H, d, Jϭ2.6 Hz), 8.02 (1H, dd, Jϭ2.6, 1.5 Hz), 8.07 (1H, d, Jϭ1.5 Hz)
2.06—2.17 (2H, m), 2.24—2.43 (3H, br), 2.38 (4H, t, Jϭ5.0 Hz), 2.44—2.53 (2H, m), 2.86—3.10 (3H, br),
3.72 (4H, t, Jϭ5.0 Hz), 6.43 (1H, t, Jϭ4.9 Hz), 7.22—7.32 (2H, m), 7.33—7.46 (8H, m), 8.26 (2H, d, Jϭ4.9 Hz)
2.08—2.18 (2H, m), 2.22—2.40 (3H, br), 2.40—2.60 (6H, m), 2.86—3.12 (3H, br), 3.12—3.24 (4H, m),
7.24—7.34 (2H, m), 7.34—7.47 (8H, m), 8.30 (2H, d, Jϭ2.9 Hz), 8.65 (1H, d, Jϭ2.9 Hz)
2.07—2.19 (2H, m), 2.20—2.43 (3H, br), 2.43—2.57 (6H, m), 2.90—3.12 (3H, br), 3.66 (4H, t, Jϭ5.1 Hz),
6.91 (1H, d, Jϭ9.2 Hz), 7.18 (1H, t, Jϭ7.7 Hz), 7.22—7.32 (2H, m), 7.32—7.46 (8H, m),
7.49 (1H, t, Jϭ7.7 Hz), 7.55 (1H, d, Jϭ7.7 Hz), 7.66 (1H, d, Jϭ7.7 Hz), 7.83 (1H, d, Jϭ9.2 Hz)
2.14—2.26 (2H, m), 2.26—2.46 (3H, br), 2.46—2.56 (2H, m), 2.60—2.72 (4H, br), 2.84—3.10 (3H, br),
3.10—3.24 (4H, br), 6.77 (1H, d, Jϭ5.0 Hz), 7.24—7.34 (3H, m), 7.24—7.34 (8H, m), 7.63 (1H, t, Jϭ8.5 Hz),
7.97 (1H, d, Jϭ8.5 Hz), 8.02 (1H, d, Jϭ8.5 Hz), 8.69 (1H, d, Jϭ5.0 Hz)
1640
1635
1640
1640
1630 (KBr)
1630 (KBr)
1630
9Aa
1630
1640
10Aa
2.14—2.26 (2H, m), 2.26—2.46 (3H, br), 2.46—2.58 (2H, m), 2.58—2.78 (4H, br), 2.82—3.08 (3H, br),
3.08—3.22 (4H, br), 7.23—7.34 (2H, m), 7.34—7.50 (8H, m), 7.56 (1H, t, Jϭ8.0 Hz), 7.65 (1H, t, Jϭ8.0 Hz),
7.92 (1H, d, Jϭ8.0 Hz), 8.05 (1H, d, Jϭ8.0 Hz), 8.14 (1H, s), 8.93 (1H, s)
11Aa
11Ba
12Aa
12Ba
13Aa
13Ba
2.07—2.18 (2H, m), 2.22—2.42 (3H, br), 2.42—2.58 (6H, m), 2.86—3.06 (3H, br), 3.10 (4H, t, Jϭ5.0 Hz),
6.80 (1H, t, Jϭ7.2 Hz), 6.87 (2H, d, Jϭ8.0 Hz), 7.16—7.32 (4H, m), 7.32—7.47 (8H, m)
1.78—1.96 (2H, m), 2.14—2.48 (7H, m), 2.48—2.60 (2H, m), 2.63—2.76 (2H, m), 2.84—3.08 (3H, br),
2.32—3.50 (4H, m), 6.56—6.68 (3H, m), 7.10—7.22 (2H, m), 7.22—7.46 (10H, m)
2.12—2.25 (2H, m), 2.25—2.46 (3H, br), 2.46—2.58 (2H, m), 2.58—2.78 (4H, br), 2.86—3.20 (7H, m),
7.03 (1H, dd, Jϭ7.4, 1.1 Hz), 7.22—7.56 (14H, m), 7.74—7.84 (1H, m), 8.08—8.18 (1H, m)
2.08—2.46 (5H, m), 2.60—2.80 (4H, m), 2.90—3.10 (3H, br), 3.10—3.62 (8H, m), 7.13 (1H, d, Jϭ7.4 Hz),
7.16—7.52 (13H, m), 7.56 (1H, d, Jϭ8.0 Hz), 7.74—7.86 (1H, m), 8.08—8.18 (1H, m )
2.09—2.22 (2H, m), 2.24—2.44 (3H, br), 2.44—2.70 (6H, m), 2.87—3.14 (3H, br), 3.14—3.34 (4H, br),
7.05 (1H, s), 7.10—7.55 (13H, m), 7.55—7.76 (3H, m)
1630
1640
1625
1625
1625
1625
1.95—2.37 (5H, m), 2.37—2.63 (4H, m), 2.63—3.05 (7H, m), 3.56 (2H, d, Jϭ6.6 Hz), 3.60—3.80 (2H, m),
6.83 (1H, d, Jϭ2.5 Hz), 7.01 (1H, dd, Jϭ8.8, 2.5 Hz), 7.18 (1H, t, Jϭ7.5 Hz), 7.22—7.50 (11H, m),
7.59 (1H, d, Jϭ8.8 Hz), 7.62—7.70 (2H, m)
14Aa
15Aa
16Aa
17Aa
2.10—2.18 (2H, m), 2.23 (3H, s), 2.26—2.40 (3H, br), 2.43—2.58 (6H, m), 2.85 (4H, t, Jϭ4.6 Hz), 2.91—3.05 (3H, br),
6.90—6.99 (2H, m), 7.07—7.15 (2H, m), 7.24—7.30 (2H, m), 7.33—7.46 (8H, m)
2.07—2.16 (2H, m), 2.23—2.40 (3H, br), 2.28 (3H, s), 2.42—2.55 (6H, m), 2.88—3.13 (7H, m),
6.60—6.71 (3H, m), 7.10 (1H, t, Jϭ7.8 Hz), 7.23—7.45 (10H, m)
2.08—2.16 (2H, m), 2.23 (3H, s), 2.26—2.38 (3H, br), 2.43—2.55 (6H, m), 2.90—3.10 (7H, m),
6.78 (2H, d, Jϭ8.8 Hz), 7.02 (2H, d, Jϭ8.8 Hz), 7.23—7.29 (2H, m), 7.32—7.46 (8H, m)
2.09—2.17 (2H, m), 2.27—2.39 (3H, br), 2.43—2.58 (6H, m), 2.81 (4H, t, Jϭ4.4 Hz), 2.93—3.05 (3H, br),
6.81 (1H, dt, Jϭ7.8, 1.2 Hz), 6.89 (1H, dd, Jϭ7.8, 1.2 Hz), 7.02 (1H, dt, Jϭ7.8, 1.2 Hz),
7.11 (1H, dd, Jϭ7.8, 1.2 Hz), 7.25—7.32 (2H, m), 7.34—7.46 (8H, m)
1635
1635
1645
3330, 1645
18Aa
19Aa
20Aa
21Aa
2.09—2.18 (2H, m), 2.27—2.37 (3H, br), 2.43—2.54 (6H, m), 2.91—3.06 (7H, m), 6.17—6.25 (2H, m),
6.34 (1H, d, Jϭ8.0 Hz), 6.97 (1H, t, Jϭ8.0 Hz), 7.21—7.43 (10H, m)
2.08—2.17 (2H, m), 2.28—2.36 (3H, br), 2.45—2.56 (6H, m), 2.93—3.02 (7H, br), 6.72 (4H, dd, Jϭ9.3, 4.9 Hz),
7.24—7.30 (2H, m), 7.33—7.42 (8H, m)
2.10—2.19 (2H, m), 2.27—2.39 (3H, br), 2.44—2.60 (6H, m), 2.90—3.09 (7H, m), 3.80 (3H, s),
6.81 (1H, d, Jϭ8.3 Hz), 6.84—6.90 (2H, m), 6.91—6.98 (1H, m), 7.22—7.30 (2H, m), 7.32—7.45 (8H, m)
2.08—2.14 (2H, m), 2.28—2.37 (3H, br), 2.43—2.52 (6H, m), 2.93—3.02 (3H, br), 3.10 (4H, t, Jϭ4.9 Hz),
3.76 (3H, s), 6.37 (1H, dd, Jϭ7.8, 2.0 Hz), 6.40 (1H, t, Jϭ2.0 Hz), 6.47 (1H, dd, Jϭ7.8, 2.0 Hz),
7.12 (1H, t, Jϭ7.8 Hz), 7.24—7.30 (2H, m), 7.33—7.45 (8H, m)
3285, 1620
3275, 1620
1635
1630
22Aa
23Aa
24Aa
25Aa
26Aa
27Aa
2.08—2.15 (2H, m), 2.28—2.38 (3H, br), 2.43—2.55 (6H, m), 2.93—3.04 (7H, m), 3.74 (3H, s),
6.80 (2H, d, Jϭ2.4 Hz), 6.84 (2H, d, Jϭ2.4 Hz), 7.24—7.30 (2H, m), 7.33—7.45 (8H, m)
2.10—2.19 (2H, m), 2.26—2.40 (3H, br), 2.45—2.61 (6H, m), 2.88—3.07 (4H, m), 6.91 (1H, t, Jϭ8.0 Hz),
6.99 (1H, d, Jϭ8.0 Hz), 7.17 (1H, t, Jϭ8.0 Hz), 7.23—7.46 (11H, m)
2.06—2.16 (2H, m), 2.24—2.39 (3H, br), 2.41—2.52 (6H, m), 2.88—3.02 (3H, br), 3.05—3.12 (4H, m), 6.70 (1H, d,
Jϭ8.5 Hz), 6.73 (1H, d, Jϭ8.5 Hz), 6.79 (1H, s), 7.10 (1H, t, Jϭ8.5 Hz), 7.23—7.30 (2H, m), 7.32—7.46 (8H, m)
2.07—2.16 (2H, m), 2.23—2.40 (3H, br), 2.41—2.54 (6H, m), 2.88—3.10 (7H, m), 6.76 (4H, d, Jϭ9.0 Hz),
7.13 (4H, d, Jϭ9.0 Hz), 7.22—7.30 (2H, m), 7.31—7.45 (8H, m)
2.10—2.18 (2H, m), 2.28—2.39 (3H, br), 2.43—2.58 (6H, m), 2.92—3.07 (7H, m), 7.24—7.31 (2H, m),
7.34—7.45 (8H, m)
2.08—2.17 (2H, m), 2.28—2.39 (3H, br), 2.42—2.57 (6H, m), 2.90—3.10 (7H, m), 6.78—6.85 (2H, m),
6.87—6.96 (2H, m), 7.24—7.31 (2H, m), 7.33—7.46 (8H, m)
1645 (KBr)
1635
1630
1645
1635
1635