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M. I. Hegab et al.
Arch. Pharm. Chem. Life Sci. 2007, 340, 396–403
Table 2. IR, 1H-, 13C-NMR, and mass spectra for the new compounds.
Compd.
2c
IR (cm– 1
)
1H- and13C-NMR (d ppm)
MS m/z (%)
2972, 2929,1631, 1605,
1480, 1453, 1249, 752
1.02 (t, J = 7.3 Hz, 3H, CH3CH2), 1.44 (s, 3H, CH3), 1.78
(q, J = 7.3 Hz, 2H, CH3CH2), 5.75 (s, 1H, 3-H), 6.84 (d, J =
8.2 Hz, 1H, ArH), 6.91-6.99 (m, 1H, ArH), 7.18–7.29
(m, 1H, ArH), 7.47 (dd, J = 7.4 Hz, 1.2 Hz, 1H, ArH).
3c
4a
2970, 2932, 1673, 1600, 0.92 (t, J = 7.4 Hz, 3H, CH3CH2), 1.60 (s, 3H, CH3),
1559, 1454, 1293, 756
1.70–1.88 (m, 1H, CH3CHaHb), 2.23-2.41 (m, 1H,
CH3CHaHb), 6.85 (d, J = 8.2 Hz, 1H, ArH), 6.97–7.04
(m, 1H, ArH), 7.21–7.42 (m, 1H, ArH), 7.70 (d, J =
7.8 Hz, 1H, ArH), 10.29 (s, 1H, CHO).
2959, 2925, 1728, 1602, 1.78 (s, 6H, 2 CH3), 6.99 (d, J = 8.1 Hz, 1H, ArH),
261 (M, 20), 245 (M – CH3, 100), 230 (2),
217 (16), 149 (8), 123 (10), 109 (10).
1459, 1263
7.14–7.17 (m, 1H, ArH), 7.35–7.38 (m, 1H, ArH),
7.49–7.51 (m, 1H, ArH), 7.67–7.80 (m, 1H, ArH), 7.92
(s, 1H, ArH), 8.13 (d, J = 8.4 Hz, 1H, ArH), 8.50–8.53
(m, 1H, ArH), 7.78 (d, J = 8.1 Hz, 1H, ArH).
4b
4c
2928, 2855, 1602, 1488, 1.19–2.26 (m, 10H, 5 CH2), 6.96–7.10 (m, 2H, ArH),
301 (M, 26), 300 (M –H, 31), 272 (11),
1457, 1262
7.26–7.44 (m, 2H, ArH), 7.57–7.72 (m, 2H, ArH), 7.86 257 (100), 245 (14), 216 (17), 188 (5).
(s, 1H, ArH), 8.05 (d, J = 8.6 Hz, 1H, ArH), 8.39–8.44
(m, 1H, ArH).
2969, 2937, 1602, 1490, 0.84–0.91 (m, 3H, CH3CH2), 1.68 (s, 3H, CH3), 1.75–
275 (M, 10), 260 (M – CH3, 6), 246 (M –
C2H5, 100), 217 (13), 123 (8).
1457, 1241
1.89 (m, 1H, CHaHbCH3), 1.96-2.14 (m, 1H,
CHaHbCH3), 6.90 (d, J = 8.0 Hz, 1H, ArH), 7.00–7.07
(m, 1H, ArH), 7.17–7.44 (m, 2H, ArH), 7.57–7.78
(m, 2H, ArH), 8.04 (d, J = 8.4 Hz, 1H, ArH), 8.41 (d, J =
7.6 Hz, 1H, ArH), 7.78 (s, 1H, ArH).
4d
4e
2963, 1446, 1261
1.77 (s, 6H, 2 CH3), 6.99 (d, J = 8.1 Hz, 1H, ArH), 7.14 279 (M, 23), 264 (M – CH3, 100), 235 (12),
(t, J = 7.5 Hz, 1H, ArH), 7.35–7.38 (m, 1H, ArH), 7.48– 149 (2).
7.51 (m, 1H, ArH), 7.67–7.76 (m, 1H, ArH), 7.86 (s, 1H,
ArH), 8.09–8.14 (m, 1H, ArH), 7.47 (d, J = 7.8 Hz, 1H,
ArH).
2928, 2858, 1608, 1494, 1.18–1.90 (m, 8H, 4 CH2), 2.21 (d, J = 14.0 Hz, 2H,
1457, 1298, 1262
319 (M, 34), 275 (M – C3H8, 100), 262
(13), 234 (11).
CH2), 6.95–7.09 (m, 2H, ArH), 7.18 (s, 1H, ArH),
7.25–7.42 (m, 2H, ArH), 7.80 (s, 1H, ArH), 7.99–8.06
(m, 1H, ArH), 8.36 (dd, J = 7.8, 1.8 Hz, 1H, ArH)/ 21.41,
25.28, 35.17, 78.43, 110.68 (d, JC-F = 21.75 Hz), 117.87,
119.46 (d, JC-F = 25.50 Hz), 121.95, 123.04, 125.26,
128.38 (d, JC-F = 10.50 Hz), 129.01, 131.59 (d, JC-F
=
9.00 Hz), 131.68, 134.80, 144.60, 147.76, 154.71,
160.23 (d, JC-F = 246.00 Hz).
4f
3047, 2971, 2925, 2876, 0.85-0.90 (m, 3H, CH3CH2), 1.70 (s, 3H, CH3), 1.76–
293 (M, 23), 264 (M – C2H5, 100), 235
(11), 132 (7).
1601, 1498,1460, 1215
1.89 (m, 1H, CHaHbCH3), 2.01–2.11 (m, 1H,
CHaHbCH3), 7.00 (d, J = 8.1 Hz, 1H, ArH), 7.12 (t, J =
7.4 Hz, 1H, ArH), 7.38–7.43 (m, 1H, ArH), 7.63–7.78
(m, 2H, ArH), 8.09 (d, J = 8.1 Hz, 1H, ArH), 8.30–8.34
(m, 2H, ArH).
4g
4h
3745, 2963, 2923, 1492, 1.78 (s, 6H, 2 CH3), 7.00 (d, J = 8.1 Hz, 1H, ArH),
1460, 1252
277 (M, 37), 262 (M – CH3, 100), 233 (7),
7.14–7.18 (m, 2H, ArH), 7.30 (d, J = 8.4 Hz, 1H, ArH), 117 (9).
7.36–7.40 (m, 2H, ArH), 7.93 (s, 1H, ArH), 8.2 (bs, 1H,
OH exchangeable with D2O), 8.43 (d, J = 7.8 Hz, 1H,
ArH).
3445, 2924, 2854, 2364, 0.89-1.81 (m, 10H, 5 CH2), 6.99–7.05 (m, 1H, ArH),
1629, 1543, 1485, 1454, 7.12–7.18 (m, 1H, ArH), 7.38–7.47 (m, 3H, ArH),
273 (M – C3H8, 70), 154 (56), 96 (40), 55
(100).
1254
7.60–7.63 (m, 1H, ArH), 7.72–7.76 (m, 1H, ArH),
8.04 (dd, J = 7.8, 1.2 Hz, 1H, ArH), 11.42 (bs, 1H, OH
exchangeable with D2O).
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