1386
Vol. 54, No. 10
Table 3. 1H-NMR, IR Spectroscopic and Elemental Analysis Data of Synthesized Compounds (1a—k, 2a—k)
Compound code
Spectrum data
1a
1H-NMR (d/ppm in CDCl3): 5.0 (s, 1H, 2ꢀ-OH), 7.14 (dd, Jꢂ7.9, 1.8 Hz, 1H, 4ꢁ-H), 7.21 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.30 (d,
Jꢂ7.9 Hz, 2H, 2ꢁ, 6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.64 (m, Jꢂ8.3 Hz, 4H, Ar-H), 7.90 (s, 1H, –CHꢂCH–). IR (KBr/cmꢃ1): 3480
(–OH), 1748—1716 (–CO), 1670 (–CHꢂCH–), 1616, 1558 (aromatic), 754, 697 (monosubstituted benzene).
1H-NMR (d/ppm in CDCl3): 5.0 (s, 1H, 2ꢀ-OH), 5.1 (s, 1H, 4ꢁ-OH), 6.68 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.13 (d, Jꢂ8.0 Hz, 2H, 2ꢁ, 6ꢁ-
H), 7.64—6.92 (m, Jꢂ8.3 Hz, 4H, Ar-H), 7.56 (s, 1H, –CHꢂCH–), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3480, 3345 (–OH),
1771, 1732 (–CO), 1682 (–CHꢂCH–), 1603, 1575 (aromatic), 834 (p-disubstituted benzene).
1b
1c
1d
1H-NMR (d/ppm in CDCl3): 3.73 (s, 3H, 4ꢁ-OCH3), 5.0 (s, 1H, 2ꢀ-OH), 6.72 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.19 (d, Jꢂ7.9 Hz, 2H, 2ꢁ,
6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.64—6.92 (m, Jꢂ8.1 Hz, 4H, Ar-H), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3480, 3446 (–OH),
1748, 1716 (–CO), 1670 (–CHꢂCH–), 1605, 1575 (aromatic), 834 (p-disubstituted benzene).
1H-NMR (d/ppm in CDCl3): 2.8 (s, 6H, 4ꢁ-NMe2), 5.0 (s, 1H, 2ꢀ-OH), 6.54 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.12 (d, Jꢂ8.0 Hz, 2H, 2ꢁ, 6ꢁ-
H), 7.56 (s, 1H, –CHꢂCH–), 7.64—6.92 (m, Jꢂ7.9 Hz, 4H, Ar-H), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3480, 3446 (–OH),
1748, 1716 (–CO), 1670 (–CHꢂCH–), 1621, 1558, 1521 (aromatic), 1312 (C–N stretching in Ar amines), 835 (p-disubstituted ben-
zene).
1e
1f
1H-NMR (d/ppm in CDCl3): 5.0 (s, 3H, 2ꢀ, 4ꢀ, 6ꢁ-OH), 6.68 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.13 (d, Jꢂ7.9 Hz, 2H, 2ꢁ, 4ꢁ-H), 7.39 (s, 1H,
–CHꢂCH–), 7.47—6.39 (m, Jꢂ8.2 Hz, 3H, Ar-H), 8.17 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3841 (–OH), 1732, 1698 (–CO), 1670
(–CHꢂCH–), 1616, 1558 (aromatic), 727, 652 (monosubstituted benzene).
1H-NMR (d/ppm in CDCl3): 2.85 (s, 6H, 4ꢁ-NMe2), 5.0 (s, 2H, 2ꢀ, 4ꢀ-OH), 6.54 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.12 (d, Jꢂ7.9 Hz, 2H,
2ꢁ, 6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.47—6.39 (m, Jꢂ8.1 Hz, 3H, Ar-H), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3480 (–OH),
1748, 1697 (–CO), 1670 (–CHꢂCH–), 1616, 1540 (aromatic), 1316 (C–N stretching in Ar. amines), 824 (p-disubstituted benzene).
1H-NMR (d/ppm in CDCl3): 5.0 (s, 2H, 2ꢀ, 6ꢁ-OH), 7.11—6.75 (m, Jꢂ8.2 Hz, 4H, Ar-H), 7.14 (dd, Jꢂ7.9, 1.8 Hz, 1H, 4ꢁ-H), 7.21 (d,
Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.30 (s, 1H, 2ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3391, 3209 (–OH),
1748, 1698 (–CO), 1653 (–CHꢂCH–), 1623, 1576 (aromatic), 728, 697 (monosubstituted benzene).
1g
1h
1i
1H-NMR (d/ppm in CDCl3): 5.0 (s, 3H, 2ꢀ, 5ꢀ, 6ꢁ-OH), 6.68 (d, Jꢂ7.9 Hz, 1H, 3ꢀ-H), 6.77 (dd, Jꢂ7.9, 1.8 Hz, 1H, 6ꢀ-H), 6.97 (dd,
Jꢂ7.9, 1.8 Hz, 1H, 4ꢀ-H), 7.11—6.75 (m, Jꢂ8.3 Hz, 4H, Ar-H), 7.39 (s, 1H, –CHꢂCH–), 8.17 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1):
3446 (–OH), 1748, 1698 (–CO), 1670, 1652 (–CHꢂCH–), 1616, 1540 (aromatic), 714, 673 (monosubstituted benzene).
1H-NMR (d/ppm in CDCl3): 5.0 (s, 3H, 2ꢀ, 5ꢀ, 4ꢁ-OH), 6.68 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.11—6.75 (m, Jꢂ8.3 Hz, 3H, Ar-H), 7.13
(d, Jꢂ7.9 Hz, 2H, 2ꢁ, 6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3244 (–OH), 1732, 1698 (–CO), 1683
(–CHꢂCH–), 1646, 1557 (aromatic), 834 (p-disubstituted benzene).
1j
1H-NMR (d/ppm in CDCl3): 3.73 (s, 3H, 4ꢁ-OCH3), 5.0 (s, 2H, 2ꢀ, 5ꢀ-OH), 6.72 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.11—6.75 (m,
Jꢂ8.3 Hz, 3H, Ar-H), 7.19 (d, Jꢂ7.9 Hz, 2H, 2ꢁ, 6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3244
(–OH), 1732, 1716 (–CO), 1683 (–CHꢂCH–), 1577, 1540 (aromatic), 834 (p-disubstituted benzene).
1k
2a
2b
1H-NMR (d/ppm in CDCl3): 2.85 (s, 6H, 4-NMe2), 5.0 (s, 2H, 2ꢀ, 5ꢀ-OH), 6.54 (d, Jꢂ7.9 Hz, 2H, 3ꢁ, 5ꢁ-H), 7.11—6.75 (m, Jꢂ8.3 Hz,
3H, Ar-H), 7.12 (d, Jꢂ7.9 Hz, 2H, 2ꢁ, 6ꢁ-H), 7.56 (s, 1H, –CHꢂCH–), 7.90 (s, 1H, –CHꢂCH–), IR (KBr/cmꢃ1): 3480 (–OH), 1748,
1697 (–CO), 1670 (–CHꢂCH–), 1616, 1540 (aromatic), 1315 (C–N stretching in Ar. amines), 824 (p-disubstituted benzene).
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 7.19 (s, 5H, –C6H5), 7.78—6.85 (m,
Jꢂ7.9 Hz, 2H, 6-, 7-Ar-H), 7.78 (dd, Jꢂ7.9, 1.8 Hz, 2H, 5, 8-H), IR (KBr/cmꢃ1): 2930 (–CH2), 1748, 1683 (–CO), 1616, 1520 (aro-
matic), 778, 696 (monosubstituted benzene), elemental analysis: Calcd (Found): C: 80.34 (79.18), H:5.39 (5.36).
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.0 (s, 1H, 4ꢀ-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.66 (d, Jꢂ7.9 Hz,
2H, 3ꢀ, 5ꢀ-H), 7.02 (d, Jꢂ7.9 Hz, 2H, 2ꢀ, 6ꢀ-H), 7.78 (d, Jꢂ7.9 Hz, 1H, 5-H), 7.78—6.85 (m, Jꢂ8.3 Hz, 3H, 6-, 7-, 8-Ar-H), IR
(KBr/cmꢃ1): 2925 (–CH2), 1748, 1698 (–CO–), 1636, 1517 (aromatic), 834 (disubstituted benzene), elemental analysis: Calcd.
(Found): C: 74.99 (74.97), H: 5.03 (4.94).
2c
2d
2e
2f
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 3.73 (s, 3H, 4ꢀ-OCH3), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.70 (d,
Jꢂ7.9 Hz, 2H, 3ꢀ, 5ꢀ-H), 7.08 (d, Jꢂ7.9 Hz, 2H, 2ꢀ, 6ꢀ-H), 7.78—6.85 (m, Jꢂ8.3 Hz, 3H, 6, 7, 8-H, Ar-H), 7.78 (d, Jꢂ8.0 Hz, 1H, 5-
H), IR (KBr/cm1ꢃ): 2840 (–CH2), 1670, 1636 (–CO–), 1558, 1520 (aromatic), 830, 804 (disubstituted benzene), elemental analysis:
Calcd (Found): C: 75.88 (75.02), H: 5.55 (5.04).
1H-NMR (d/ppm in CDCl3): 2.85 (s, 6H, 4ꢀ-NMe2), 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.52 (d,
Jꢂ7.9 Hz, 2H, 3ꢀ, 5ꢀ-H), 7.01 (d, Jꢂ7.9 Hz, 2H, 2ꢀ, 6ꢀ-H), 7.78—6.85 (m, Jꢂ8.3 Hz, 3H, 6, 7, 8-Ar-H), 7.78 (d, Jꢂ7.6 Hz, 1H, 5-H),
IR (KBr/cmꢃ1): 2908, 2821 (–CH2), 1670, 1617 (–CO–), 1558, 1521 (aromatic), 1339 (Tert. Ar. amine), 835 (disubstituted benzene),
elemental analysis: Calcd (Found): C: 76.38 (75.35), H: 6.41 (6.05), N: 5.24 (5.22)
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.0 (s, 2H, 7, 6ꢀ-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.32 (s, 1H, H-8),
6.37 (d, Jꢂ7.9 Hz, 1H, H-6), 7.1 (d, Jꢂ7.8 Hz, 1H, 2ꢀ-H), 7.61 (d, Jꢂ7.8 Hz, 1H, H-5), 7.78—6.85 (m, Jꢂ8.3 Hz, 3H, 6, 7, 8-Ar-H),
IR (KBr/cmꢃ1): 3480, 3446 (–OH), 2914 (–CH2), 1670, 1635 (–CO–), 1558, 1521 (aromatic), 754, 684 (monosubstituted benzene), el-
emental analysis: Calcd (Found): C: 70.31 (69.10), H: 4.72 (4.01).
1H-NMR (d/ppm in CDCl3): 2.85 (s, 6H, 4-NMe2), 3.26—2.50 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.0 (s, 1H, 7-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-
H), 6.32 (s, 1H, H-8), 6.37 (d, Jꢂ7.7 Hz, 1H, H-6), 6.52 (d, Jꢂ7.7 Hz, 2H, 3ꢀ, 5ꢀ-H), 7.01 (d, Jꢂ7.9 Hz, 2H, 2ꢀ, 6ꢀ-H), 7.61 (d,
Jꢂ7.9 Hz, 1H, H-5), IR (KBr/cmꢃ1): 3480, 3446 (–OH), 2926 (–CH2), 1670, 1636 (–CO–), 1576, 1540 (aromatic), 1375, 1317 (Tert.
Ar. amine), 824 (disubstituted benzene), elemental analysis: Calcd (Found): C: 72.07 (71.09), H: 6.05 (5.96), N: 4.94 (4.94).
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.3 Hz, 2H, 3-H), 5.0 (s, 1H, 6ꢀ-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.68 (s, 1H, H-8),
6.80 (d, Jꢂ7.9 Hz, 1H, H-7), 7.19 (m, Jꢂ8.5 Hz, 4H, 2ꢀ, 3ꢀ, 4ꢀ, 5ꢀ, Ar-H), 7.25 (d, Jꢂ7.9 Hz, 1H, H-5), 7.61 (d, Jꢂ7.9 Hz, 1H, H-6),
IR (KBr/cmꢃ1): 3237 (–OH), 2348 (–CH2), 1669, 1635 (–CO–), 1575, 1540 (aromatic), 731, 698 (monosubstituted benzene), elemen-
tal analysis: Calcd (Found): C: 74.99 (74.98), H: 5.03 (4.92).
2g
2h
2i
1H-NMR (d/ppm in CDCl3): 3.26—2.59 (d, Jꢂ6.2 Hz, 2H, 3-H), 5.0 (s, 2H, 6-, 6ꢀ-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.68 (d,
Jꢂ7.9 Hz, 1H, H-8), 6.68 (d, Jꢂ7.5 Hz, 1H, 3ꢀ-H), 6.80 (d, Jꢂ7.9 Hz, 1H, H-7), 7.02 (q, Jꢂ8.3 Hz, 2H, 4ꢀ, 2ꢀ-H), 7.25 (d, Jꢂ7.9 Hz,
1H, H-5), 7.31 (d, Jꢂ7.9 Hz, 1H, 5ꢀ-H), IR (KBr/cmꢃ1): 3480, 3447 (–OH), 3216 (–CH2), 1748, 1683 (–CO–), 1616, 1521 (aromatic),
760, 697 (monosubstituted benzene), elemental analysis: Calcd (Found): C: 70.31 (69.82), H: 4.72 (4.56).
1H-NMR (d/ppm in CDCl3): 3.26—2.50 (d, Jꢂ6.3 Hz, 2H, 3-H), 5.0 (s, 2H, 6, 4ꢀ-OH), 5.51 (t, Jꢂ6.0 Hz, 1H, 2-H), 6.66 (d,
Jꢂ7.7 Hz, 2H, 3ꢀ, 5ꢀ-H), 6.68 (bs, 1H, H-8), 6.80 (d, Jꢂ7.9 Hz, 1H, H-7), 7.02 (dd, Jꢂ7.9, 1.8 Hz, 2H, 2ꢀ, 6ꢀ-H), 7.25 (d, Jꢂ8.0 Hz,
1H, H-5), IR (KBr/cmꢃ1): 3446 (–OH), 3065 (–CH2), 1748, 1698 (–CO–), 1617, 1540 (aromatic), 822 (disubstituted benzene), ele-
mental analysis: Calcd (Found): C: 70.31 (69.70), H: 4.72 (4.61).