JOURNAL OF CHEMICAL RESEARCH 2008 161
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J = 5.5 Hz); Anal: Calcd. for C13H15ClO3 C, 61.30; H, 5.94. Found C,
61.36; H, 5.90%.
3db: Oil. IR (film)/cm-1: 2954, 2840, 1722, 1610, 1088, 825; H
NMR (500 MHz, CDCl3) δ (ppm): 7.26 (d, 2H, J = 7.0 Hz), 6.85 (d, 2H,
J = 7.5 Hz), 6.30 (t, 1H, J = 1.25 Hz), 5.94 (t, 1H, J = 1.5 Hz), 5.19
(s, 1H), 3.79 (s, 3H), 3.69 (s, 3H), 3.49–3.42 (m, 2H), 1.20 (t, 3H,
J = 6.5 Hz); Anal: Calcd. for C14H18O4 C, 67.18; H, 7.25; Found C,
67.25; H, 7.20%.
3ag: IR (film)/cm-1: 2951, 2868, 1722, 1630, 1604, 739, 699;
1H NMR (500 MHz, CDCl3) 7.40–7.26 (m, 10H), 6.35 (s, 1H), 6.02
(m, 1 Hz), 5.34 (s, 1H), 4.47 (s, 2H), 3.66 (s, 3H); 13C NMR (125
MHz, CDCl3) δ (ppm): 166.33, 141.32, 139.64, 138.21, 128.44,
128.41, 128.02, 127.82, 127.73, 127.67, 125.30, 78.63, 70.84, 51.86;
Anal: Calcd. for C18H18O3 C, 76.57; H, 6.43; Found C, 76.46; H,
6.49%.
4db: Oil. IR (film)/cm-1: 2951, 2872, 1711, 1628, 1603, 1089,
841; 1H NMR (500 MHz, CDCl3) δ (ppm): 7.89 (s, 1H), 7.54 (q, 2H,
J = 4.5 Hz), 6.93 (q, 2H, J = 4.5 Hz), 4.30 (s, 2H), 3.83 (s, 3H), 3.82
(s, 3H), 3.62 (q, 2H, J = 6.0 Hz), 1.28 (t, 3H, J = 6.0 Hz); Anal:
Calcd. for C14H18O4 C, 67.18; H, 7.25; Found C, 67.12; H, 7.32%.
3dc: Oil. IR (film)/cm-1: 2970, 1722, 1610, 1586, 1061, 839; 1H NMR
(500 MHz, CDCl3) δ (ppm): 7.276 (d, 2H, J = 7.5 Hz), 6.87 (d, 2H,
J = 7.5 Hz), 6.30 (d, 1H, J = 1.0 Hz), 5.91 (t, 1H, J = 1.5 Hz), 5.32
(s, 1H), 3.79 (s, 3H), 3.70 (s, 3H), 3.61–3.56 (m, 1H), 1.18 (d, 3H,
J = 6.0 Hz), 1.14 (d, 3H, J = 6.0 Hz);Anal: Calcd. for C15H20O4 C, 68.16;
H, 7.63; Found C, 68.21; H, 7.57%.
4ag: Oil. IR (film)/cm-1: 3029, 1715, 1632, 1577, 1068, 741, 698;
1 H NMR (500 MHz, CDCl3) 7.93 (s, 1H) 7.39–7.24 (m, 10H), 4.62
(s, 2H), 4.34 (s, 2H), 3.06 (s, 3H); Anal: Calcd. for C18H18O3 C,
76.57; H, 6.43; Found C, 76.55; H, 6.44%.
3bb: Oil. IR (film)/cm-1: 2976, 2952, 2873, 1725, 1631, 1512, 814;
1H NMR (500 MHz, CDCl3) δ (ppm): 7.24 (d, 2H, J = 8.0 Hz), 7.12
(d, 2H, J = 8.0 Hz), 6.30 (m, 1H), 5.93 (s, 1H), 5.21 (s, 1H), 3.67 (s,
3H), 3.45 (q, 2H, J = 7.5 Hz), 2.32 (s, 3H), 1.19 (t, 3H, J = 7.0 Hz);
13C NMR (125 MHz, CDCl3) δ (ppm): 166.44, 141.62, 137.44, 137.04,
129.02, 127.50, 124.70, 78.86, 64.59, 51.74, 21.17, 15.32; Anal: Calcd.
for C14H18O3 C, 71.77; H, 7.74; Found C, 71.80; H, 7.72%.
4dc: Oil. IR(film)/cm-1: 2971, 1712, 1629, 1604, 1055, 839; 1H
NMR (500 MHz, CDCl3) δ (ppm):, 7.88 (s, 1H), 7.58–7.56 (m,
2H), 6.93 (q, 2H, J = 4.5 Hz), 4.30 (s, 2H), 3.83 (s, 3H), 3.82 (s,
3H), 3.77–3.71 (m, 1H), 1.18 (d, 6H, J = 6.5 Hz); Anal: Calcd. for
C15H20O4 C, 68.16; H, 7.63; Found C, 68.20; H, 7.59%.
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4bb: Oil. IR (film)/cm-1: 2872, 1715, 1631, 1091, 814; H NMR
(500 MHz, CDCl3) δ (ppm): 7.90 (s, 1H), 7.45 (d, 2H, J = 8.0 Hz),
7.21 (d, 2H, J = 8.5 Hz), 4.29 (s, 2H), 3.82 (s, 3H), 3.60 (q, 2H,
J = 6.5 Hz), 2.37 (s, 3H), 1.28 (t, 3H, J = 6.0 Hz); Anal: Calcd. for
C14H18O3 C, 71.77; H, 7.74; Found C, 71.79; H, 7.68%.
3dg: Oil. IR (film)/cm-1: 3030, 1721, 1629, 1608, 1067, 827; 1H NMR
(500 MHz, CDCl3) 7.34–7.26 (m, 7H), 6.88–6.87 (q, 2H, J = 1.0 Hz),
6.34 (t, 1H, J = 1.25 Hz), 6.04 (t, 1H, J = 1.75 Hz), 5.28 (s, 1H), 4.46 (d,
2H, J = 3.0 Hz), 3.80 (s, 3H), 3.68 (s, 3H); Anal: Calcd. for C19H20O4 C,
73.06; H, 6.45; Found C, 73.18; H, 6.26%.
3bc: Oil. IR (film)/cm-1: 2972, 2927, 1725, 1631, 1512, 813; 1H NMR
(500 MHz, CDCl3) δ (ppm): 7.24 (d, 2H, J = 8.0 Hz), 7.12 (d, 2H,
J = 8.0 Hz), 6.30 (q, 1H, J = 1.0 Hz), 5.90 (t, 1H, J = 1.5 Hz), 5.34 (s,
1H), 3.70 (s, 3H), 3.58 (m, 1H), 2.32 (s, 3H), 1.19 (d, 3H, J = 6.0 Hz),
1.14 (d, 3H, J = 7.0 Hz); Anal: Calcd. for C15H20O3 C, 72.55; H, 8.12;
Found C, 72.50; H, 8.14%.
4dg: Oil. IR (film)/cm-1: 3030, 1709, 1269, 1603, 1066, 782, 741,
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700; H NMR (500 MHz, CDCl3) δ (ppm): 7.89 (s, 1H), 7.50 (dd,
2H, J = 7.0 Hz), 7.41–7.30 (m, 5H), 6.86 (dd, 2H, J = 7.0 Hz), 4.64
(s, 2H), 4.37 (s, 2H), 3.81 (s, 3H), 3.68 (s, 3H); Anal: Calcd. for
C19H20O4 C, 73.06; H, 6.45; Found C, 72.88; H, 6.58%.
4bc: Oil. IR (film)/cm-1: 2972, 1716, 1632, 1375, 1122, 812; 1H NMR
(500 MHz, CDCl3) δ (ppm): 7.89 (s, 1H), 7.48 (d, 2H, J = 8.0 Hz), 7.20
(d, 2H, J = 8.0 Hz), 4.28 (s, 2H), 3.81 (s, 3H), 3.76-3.69 (m, 1H), 2.37
(s, 3H), 1.25 (t, 6H, J = 6.0 Hz); Anal: Calcd. for C15H20O3 C, 72.55; H,
8.12; Found C, 72.59; H, 8.09%.
3eb: Oil. IR (film)/cm-1: 2964, 2870, 1725, 1631, 1091, 823; 1H NMR
(500 MHz, CDCl3) δ (ppm): 7.33 (d, 2H, J = 8.5 Hz), 7.27 (d, 2H,
J = 8.0 Hz), 6.31 (t, 1H, J = 0.5 Hz), 5.94 (t, 1H, J = 1.5 Hz), 5.24 (s, 1H),
3.69 (s, 3H), 3.52–3.42 (m, 2H), 1.29 (s, 9H), 1.20 (t, 3H, J = 7.0 Hz);
Anal: Calcd. for C17H24O3 C, 73.88; H, 8.75; Found C, 73.93; H,
8.77%.
3bg: Oil. IR (film)/cm-1: 2950, 2922, 2865, 1722, 1630, 819; 1H NMR
(500 MHz, CDCl3) 7.30–7.13 (m, 9H), 6.33 (s, 1H), 6.02 (t, 1H, J = 1.25
Hz), 5.30 (s, 1H), 4.45 (q, 2H, J = 1.5 Hz), 3.64 (s, 3H), 2.32 (s, 3H);
Anal: Calcd. for C19H20O3 C, 77.00; H, 6.80; Found C, 76.95; H, 6.88%.
4bg: Oil. IR (film)/cm-1: 2975, 2894, 2839, 1723, 1631, 712, 788;
1H NMR (500 MHz, CDCl3) δ (ppm): 7.90 (s, 1H), 7.42–7.19 (m,
9H), 4.62 (s, 2H), 4.35 (s, 2H), 3.81 (s, 3H), , 2.35 (s, 3H); Anal:
Calcd. for C19H20O3 C, 77.00; H, 6.80; Found C, 77.22; H, 6.76%.
3cb: Oil. IR (film)/cm-1: 2975, 2894, 2839, 1723, 1631, 712, 788;
1H NMR (500 MHz, CDCl3) δ (ppm): 7.26–7.22 (m, 1H), 6.95–6.90
(m, 2H), 6.82–6.80 (m, 1H), 6.32 (t, 1H, J = 1.0 Hz), 5.90 (t, 1H,
J = 1.25 Hz), 5.23 (s, 1H), 3.79 (s, 3H), 3.71 (s, 3H), 3.52–3.45 (m,
2H), 1.21 (t, 3H, J = 7.0 Hz); Calcd. for C14H18O4 C, 67.18; H, 7.25;
Found C, 67.21; H, 7.31%.
4eb: Oil. IR (film)/cm-1: 2967, 1716, 1632, 1609, 1366, 836;
1H NMR (500 MHz, CDCl3) δ (ppm): 7.91 (s, 1H), 7.50 (d, 2H,
J = 8.5 Hz), 7.44 (t, 2H, J = 8.0 Hz), 4.30 (s, 2H), 3.82 (s, 3H), 3.64–
3.60 (m, 2H), 1.34 (s, 9H), 1.28 (m, 3H); Anal: Calcd. for C17H24O3
C, 73.88; H, 8.75; Found C, 73.76; H, 8.79%.
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3ec: Oil. IR (film)/cm-1: 2977, 2871, 1726, 1631, 1462, 820; H
NMR (500 MHz, CDCl3) δ (ppm): 7.32 (d, 2H, J = 8.0 Hz), 7.26
(d, 2H, J = 8.0 Hz), 6.30 (d, 1H, J = 2.5 Hz), 5.91 (t, 1H, J = 2.5
Hz), 5.37 (s, 1H), 3.69 (s, 3H), 3.64–3.57 (m, 1H), 1.29 (s, 9H), 1.18
(d, 3H, J = 6.5 Hz), 1.15 (d, 3H, J = 6.5 Hz); 13C NMR (125 MHz,
CDCl3) δ (ppm): 166.73, 150.47, 142.17, 137.50, 127.21, 125.28,
125.26, 76.00, 69.63, 51.83, 34.58, 31.46, 22.74, 21.99; Anal: Calcd.
for C18H26O3 C, 74.45; H, 9.02; Found C, 74.42; H, 9.23%.
4ec: Oil. 1H NMR (500 MHz, CDCl3) δ (ppm): 7.89 (s, 1H, ), 7.26
(d, 2H, J = 8.5 Hz), 7.43 (d, 2H, J = 8.5 Hz), 4.30 (t, 1H, J = 4.5 Hz),
3.83 (s, 3H), 1.33 (s, 9H), 1.26 (d, 6H, J = 6.0 Hz); Anal: Calcd. for
C18H26O3 C, 74.45; H, 9.02; Found C, 74.38; H, 9.15. 3eg: 1H NMR
(500 MHz, CDCl3) 7.36–7.26 (m, 9H), 6.35 (d, 1H, J = 1.0 Hz), 6.03
(t, 1H, J = 1.5 Hz), 5.33 (s, 1H), 4.47 (m, 2H), 3.67 (s, 3H), 1.30 (s,
9H); Anal: Calcd. for C22H26O3 C, 78.07; H, 7.74; Found C, 78.20;
H, 7.63%.
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4cb: Oil. H NMR (500 MHz, CDCl3) δ (ppm):7.90 (s, 2H), 7.32
(t, 1H, J = 7.75 Hz), 7.16 (d, 1H, J = 7.5 Hz), 7.11 (d, 1H, J = 7.5 Hz),
6.95–6.93 (m, 1H), 4.29 (s, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 3.62 (q,
2H, J = 10.5 Hz), 1.28 (t, 3H, J = 7.0 Hz); Anal: Calcd. for C14H18O4
C, 67.18; H, 7.25; Found C, 67.33; H, 7.31%.
3cc: Oil. IR (film)/cm-1: 2972, 1723, 1630, 1603, 1379, 1150, 758,
711; 1H NMR (500MHz, CDCl3) δ (ppm): 7.26–7.22 (m, 1H), 6.95–
6.91 (m, 2H), 6.81–6.79 (m, 1H), 6.30 (d, 1H, J = 0.5 Hz), 5.87 (t,
1H, J = 2.5 Hz), 5.36 (s, 1H), 3.79 (s, 3H), 3.71 (s, 3H), 3.62–3.55
(m, 1H), 1.20 (d, 3H, J = 6.0 Hz), 1.15 (d, 3H, J = 6.0 Hz); Calcd. for
C15H20O4 C, 68.16; H, 7.63; Found C, 68.13; H, 7.67%.
4eg: Oil. IR (film)/cm-1: 3030, 1715, 1629, 1608, 1109, 839, 737,
699; H NMR (500 MHz, CDCl3) δ (ppm): 7.92 (s, 1H), 7.46–7.33
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4cc: Oil. IR (film)/cm-1: 2971, 1715, 1633, 1375, 792, 693; 1H NMR
(500MHz, CDCl3) δ(ppm): 7.88 (s, 1H), 7.32 (t, 1H, J = 8.0 Hz), 7.18–
7.13 (m, 2H), 4.30 (s, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 3.77–3.72 (m,
1H), 1.24 (d, 6H, J = 6.0 Hz); Anal: Calcd. for C15H20O4 C, 68.16; H,
7.63; Found C, 68.25; H, 7.69%.
(m, 9H), 4.63 (s, 2H), 4.36 (s, 2H), 3.81 (s, 3H), 1.33 (s, 9H); Anal:
Calcd. for C22H26O3 C, 78.07; H, 7.74; Found C, 78.21; H, 7.69%.
3fb: Oil. IR (film)/cm-1: 2973, 2828, 2896, 1724, 1631, 1596,
818; 1H NMR (500 MHz, CDCl3) δ (ppm): 7.29 (s, 4H), 6.33 (t, 1H,
J = 1.0 Hz), 5.96 (t, 1H, J = 1.5 Hz), 5.20 (s, 1H), 3.70 (s, 3H), 3.52–
3.40 (m, 2H), 1.20 (t, 3H, J = 7.0 Hz); Anal: Calcd. for C13H15ClO3
C, 61.30; H, 5.94; Found C, 61.26; H, 6.03%.
3cg: Oil. IR (film)/cm-1: 2951, 2837, 1717, 1633, 1602, 775, 738,
700; 1H NMR (500 MHz, CDCl3) δ (ppm): 7.34–7.22 (m, 7H), 6.98
(d, 1H, J = 7.5 Hz), 6.94 (d, 1H, J = 7.5 Hz), 6.84–6.81 (m, 1H),
6.35 (t, 1H, J = 1.0 Hz), 6.00 (t, 1H, J = 1.5 Hz), 5.32 (s, 1H), 4.51–
4.46 (m, 2H), 3.78 (s, 3H), 3.68 (s, 3H); 13C NMR (125MHz, CDCl3)
δ (ppm):166.35, 159.71, 141.25, 141.23, 138.20, 129.44, 128.41,
127.78, 127.68, 125.48, 120.24, 113.48, 113.19, 78.49, 70.93, 55.26,
51.89; Anal: Calcd. for C19H20O4 C, 73.06; H, 6.45; Found C, 73.17;
H, 6.58%.
4fb:Oil.IR(film)/cm-1:2958,2925,1718,1632,1091,815;1HNMR
(500 MHz, CDCl3) δ (ppm): 7.87 (s, 1H), 7.49 (dd, 2H, J = 8.5 Hz),
7.49 (dd, 2H, J = 8.5 Hz), 4.25 (s, 2H), 3.84 (s, 3H), 3.63–3.57 (m,
2H), 1.26 (t, 3H, J = 7.0 Hz); Anal: Calcd. for C13H15ClO3 C, 61.30;
H, 5.94; Found C, 61.36; H, 6.01%.
3fc:Oil. IR(film)/cm-1:2972, 2929, 1721, 1630, 1596, 818;1HNMR
(500 MHz, CDCl3) δ (ppm): 7.29 (s, 4H), 6.31 (t, 1H, J = 1.0 Hz),
5.92 (t, 1H, J = 1.25 Hz), 5.33 (s, 1H), 3.70 (s, 3H), 3.62–3.55 (m,
1H), 1.18 (d, 3H, J = 6.0 Hz), 1.12 (d, 3H, J = 6.5 Hz); Anal: Calcd.
for C14H17ClO3 C, 62.57; H, 6.38; Found C, 62.41; H, 6.47%.
4cg: Oil. IR (film)/cm-1: 3029, 1710, 1632, 1067, 850, 738; 1H NMR
(500 MHz, CDCl3) δ (ppm): 7.92 (s, 1H), 7.39–7.25 (m, 7H), 7.14–7.09
(m, 2H), 4.63 (s, 2H), 4.36 (s, 2H), 3.83 (s, 3H), 3.78 (s, 3H); Anal:
Calcd. for C19H20O4 C, 73.06; H, 6.45; Found C, 73.17; H, 6.26%.
PAPER: 07/4855