3006
Wang et al.
Compound 2a. M.p.: 59–628C (lit.[7] 60–638C). nmax (KBr)/cm21: 3430,
3155, 2927, 2852, 1667, 1599. dH (CDCl3): 8.42 (1H, s), 7.05–7.50 (5H, m),
3.59–3.70 (2H, m), 2.78 (1H, br, s), 2.44 (2H, t, J 6.8 Hz), 1.87–1.89 (2H, m).
Compound 2b. M.p.: 98–1008C. nmax (KBr)/cm21: 3329, 2960, 2933,
2864, 1673. dH (CDCl3): 7.59 (1H, s), 7.35 (2H, d, J 8.0 Hz), 7.09 (2H, d, J
8.0 Hz), 3.73 (2H, t, J 5.6 Hz), 2.73 (1H, br, s), 2.49 (2H, t, J 6.8 Hz), 2.29
(3H, s), 1.91–1.96 (2H, m). 13C NMR (100 MHz, CDCl3): 171.8, 135.2,
134.0, 129.5, 120.1, 62.2, 34.7, 28.0, 20.9. m/z (%): 193 (Mþ, 8.54), 107
(100), 106 (46.87). Anal. Calcd. for C11H15NO2: C, 68.37; H, 7.82; N, 7.25.
Found C, 68.43; H, 7.85; N, 7.22%.
Compound 2c. M.p.: 73–748C. nmax (KBr)/cm21: 3278, 3071, 2944,
2879, 1653. dH (CDCl3): 7.69–7.73 (1H, m), 7.42 (1H, s), 7.06–7.34 (3H,
m), 3.75–3.77 (2H, m), 2.80 (1H, br, s), 2.57 (2H, t, J 6.8 Hz), 2.25 (3H, s),
1.96–1.98 (2H, m). 13C NMR (100 MHz, CDCl3): 173.2, 135.5, 130.5,
126.7, 125.5, 123.6, 62.1, 34.5, 28.1, 17.8. m/z (%): 193 (Mþ, 11.46), 107
(100), 106 (39.18). Anal. Calcd. for C11H15NO2: C, 68.37; H, 7.82; N, 7.25.
Found C, 68.42; H, 7.79; N, 7.28%.
Compound 2d. Viscous oil. nmax (KBr)/cm21: 3340, 2923, 2853, 1650. dH
(CDCl3): 7.60 (1H, s), 7.18–7.36 (4H, m), 3.75 (2H, t, J 5.6 Hz), 2.78 (1H, br, s),
2.52 (2H, t, J 6.8 Hz), 2.34 (3H, s), 1.90–2.00 (2H, m). 13C NMR (100MHz,
CDCl3): 172.8, 140.5, 138.0, 130.3, 125.7, 122.5, 116.6, 62.0, 34.2, 28.1, 19.0.
m/z (%): 193 (Mþ, 8.12), 107 (100), 106 (48.18). Anal. Calcd. for
C11H15NO2: C, 68.37; H, 7.82; N, 7.25. Found C, 68.47; H, 7.86; N, 7.21%.
Compound 2e. M.p.: 107–1098C. nmax (KBr)/cm21: 3282, 3181, 3123,
3073, 2956, 2926, 2883, 1664. dH (CDCl3): 7.64 (1H, s), 7.46 (2H, d, J 8.8 Hz),
7.27 (2H, d, J 8.8 Hz), 3.77 (2H, t, J 6.0 Hz), 2.54 (2H, t, J 6.8 Hz), 2.31 (1H,
br, s), 1.95–2.05 (2H, m). 13C NMR (100 MHz, CDCl3): 172.3, 139.1, 129.0,
121.0, 62.3, 34.8, 27.7. m/z (%): 215 (Mþ, 3.07), 213 (9.58), 129 (32.03), 127
(100). Anal. Calcd. for C10H12ClNO2: C, 56.21; H, 5.66; N, 6.56. Found C,
56.12; H, 5.63; N, 6.54%.
Compound 3a. M.p.: 99–1028C (lit.[8] 1048C). nmax (KBr)/cm21: 3253,
3128, 2924, 1660, 1614. dH (CDCl3): 8.08 (1H, s), 7.30–7.57 (5H, m),
6.27–6.46 (2H, m), 5.69 (1H, d, J 11.2 Hz).
Compound 3b. M.p.: 151–1538C (lit.[9] 154–1568C). nmax (KBr)/cm21
:
3261, 3104, 2920, 1637. dH (CDCl3): 7.89 (1H, d, J 15.6Hz), 734–7.56 (11H,
m), 6.65 (1H, d, J15.6Hz).
Compound 3c: M.p.: 114–1168C (lit.[9] 1148C). nmax (KBr)/cm21: 3265,
3145, 2919, 1660, 1625. dH (CDCl3): 7.76 (1H, d, J 15.6Hz), 737–7.54 (8H,
m), 724–7.27 (1H, m), 6.95 (1H, s), 6.57 (1H, d, J 15.6Hz), 2.36 (3H, s).
Compound 4a. M.p.: 200–2028C (lit.[10] 201–2028C). nmax (KBr)/
cm21: 3042, 2917, 1715. dH (CDCl3): 7.95–7.97 (2H, m), 7.78–7.81 (2H,
m), 7.27–7.32 (4H, m), 2.42 (3H, s).