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P.-C. Lv et al. / European Journal of Medicinal Chemistry 44 (2009) 1779e1787
2H); 7.28 (m, 2H); 7.39 (m, 2H). 13C NMR (DMSO-d6,
d ppm): 170.8, 163.8, 160.8, 149.2, 131.8, 130.9, 128.6,
127.2, 126.3, 122.8, 107.5, 106.1, 55.8, 51.8, 35.9. MS
(ESI): 305.0 (C18H19O6, [M þ H]þ). Anal. Calcd for
C18H18O6: C, 65.45; H, 5.49%; Found: C, 65.41; H, 5.53%.
129.1, 128.9, 128.4, 128.2, 127.1, 126.2, 122.6, 121.8,
121.5, 118.9, 115.0, 60.6, 60.1, 48.0, 35.5, 14.3. MS (ESI):
377.0 (C18H18BrO4, [M þ H]þ). Anal. Calcd for
C18H17BrO4: C, 57.31; H, 4.54%; Found: C, 57.37; H, 4.59%.
4.3.2.19. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(3-methoxyphenyl)
acetate (C19). Light yellow oil. Yield 86%, 1H NMR
(300 MHz, d6-DMSO): 1.14 (t, J ¼ 7.1 Hz, 3H); 3.52 (s,
2H); 3.76 (s, 3H); 3.91 (s, 3H); 4.03 (q, J ¼ 6.9 Hz, 2H);
6.89 (m, 2H); 7.12 (d, J ¼ 7.9 Hz, 1H); 7.30 (m, 4H). 13C
NMR (DMSO-d6, d ppm): 170.3, 169.5, 159.6, 149.2, 135.3,
131.7, 131.2, 129.7, 128.4, 127.1, 126.1, 122.6, 121.9,
115.4, 112.7, 60.5, 55.1, 35.5, 14.3. MS (ESI): 377.0
(C19H21O5, [M þ H]þ). Anal. Calcd for C19H20O5: C, 69.50;
H, 6.14%; Found: C, 69.54; H, 6.17%.
4.3.2.14. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(4-fluorophenyl)
acetate (C14). Light yellow oil. Yield 84%, 1H NMR
(300 MHz, d6-DMSO): 3.15 (t, J ¼ 9.1 Hz, 3H); 3.52 (s,
2H); 3.96 (s, 2H); 4.02 (q, J ¼ 8.1 Hz, 2H); 7.14 (t,
J ¼ 4.0 Hz, 2H); 7.22 (t, J ¼ 6.6 Hz, 2H); 7.32 (m, 2H); 7.42
(q, J ¼ 5.2 Hz, 2H). 13C NMR (DMSO-d6, d ppm): 170.3,
169.6, 163.2, 160.0, 149.1, 131.7, 131.6, 130.2, 128.4,
128.2, 127.1, 126.1, 122.6, 115.5, 115.2, 60.5, 35.5, 14.1.
MS (ESI): 305.0 (C18H18FO4, [M þ H]þ). Anal. Calcd for
C18H17FO4: C, 68.35; H, 5.42%; Found: C, 68.39; H, 5.48%.
4.3.2.20. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(3,4-dimethoxyphe-
nyl)acetate (C20). Light yellow oil. Yield 85%, 1H NMR
(300 MHz, d6-DMSO): 1.16 (t, J ¼ 7.1 Hz, 3H); 3.53 (s,
2H); 3.74 (s, 3H); 3.76 (s, 3H); 3.86 (s, 2H); 4.02 (q,
J ¼ 4.2 Hz, 2H); 6.94 (m, 3H); 7.11 (m, 1H); 7.22 (m, 1H);
7.32 (m, 1H). 13C NMR (DMSO-d6, d ppm): 170.4, 169.9,
149.2, 148.9, 148.2, 131.6, 131.2, 128.4, 128.2, 127.1,
126.2, 126.1, 122.6, 121.8, 118.9, 115.0, 113.4, 112.0, 60.5,
55.7, 35.5, 14.3. MS (ESI): 377.0 (C20H23O6, [M þ H]þ).
Anal. Calcd for C20H22O6: C, 67.03; H, 6.19%; Found: C,
67.09; H, 6.23%.
4.3.2.15. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(4-chlorophenyl)
acetate (C15). Light yellow oil. Yield 87%, 1H NMR
(300 MHz, d6-DMSO): 1.13 (t, J ¼ 8.1 Hz, 3H); 3.52 (s,
2H); 3.96 (s, 2H); 4.02 (q, J ¼ 8.4 Hz, 2H); 7.13 (d,
J ¼ 8.0 Hz, 1H); 7.22 (m, 1H); 7.32 (m, 2H); 7.42 (m, 4H).
13C NMR (DMSO-d6, d ppm): 170.3, 169.4, 149.1, 133.0,
132.2, 131.7, 128.6, 128.4, 127.1, 126.1, 122.6, 60.6, 35.6,
14.1. MS (ESI): 333.0 (C18H18ClO4, [M þ H]þ). Anal. Calcd
for C18H17ClO4: C, 64.97; H, 5.15%; Found: C, 64.91; H,
5.11%.
4.3.2.16. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(4-bromophenyl)
acetate (C16). Light yellow oil. Yield 82%, 1H NMR
(300 MHz, d6-DMSO): 1.14 (t, J ¼ 8.1 Hz, 3H); 3.52 (s,
2H); 3.96 (s, 2H); 4.01 (q, J ¼ 8.4 Hz, 2H); 7.13 (d,
J ¼ 8.4 Hz, 1H); 7.21 (t, J ¼ 7.5 Hz, 1H); 7.33 (t, J ¼ 8.0 Hz,
4H); 7.56 (d, J ¼ 8.4 Hz, 2H). 13C NMR (DMSO-d6,
d ppm): 170.3, 169.2, 149.1, 133.4, 132.0, 131.6, 131.5,
128.4, 127.1, 126.1, 122.6, 120.6, 60.6, 35.6, 14.2. MS
(ESI): 377.0 (C18H18BrO4, [M þ H]þ). Anal. Calcd for
C18H17BrO4: C, 57.31; H, 4.54%; Found: C, 57.38; H, 4.58%.
4.3.2.21. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(3,4-diethoxypheny-
l)acetate (C21). Yellow oil. Yield 81%, H NMR (300 MHz,
1
d6-DMSO): 1.13 (t, J ¼ 7.1 Hz, 3H); 1.31 (q, J ¼ 2.4 Hz,
3H); 1.33 (q, J ¼ 2.4 Hz, 3H); 3.50 (s, 2H); 3.82 (s, 2H);
3.99 (m, 6H); 6.84 (m, 1H); 6.93 (m, 2H); 7.11 (m, 1H);
7.22 (m, 1H); 7.32 (m, 1H). 13C NMR (DMSO-d6, d ppm):
170.3, 169.9, 149.2, 148.3, 147.6, 131.6, 128.4, 127.1,
126.3, 126.1, 122.6, 121.9, 115.1, 113.6, 64.0, 60.5, 35.5,
15.0, 14.1. MS (ESI): 387.1 (C22H27O6, [M þ H]þ). Anal.
Calcd for C22H26O6: C, 68.38; H, 6.78%; Found: C, 68.36;
H, 6.74%.
4.3.2.17. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(3-chlorophenyl)
acetate (C17). Light yellow oil. Yield 85%, 1H NMR
(300 MHz, d6-DMSO): 1.16 (t, J ¼ 8.6 Hz, 3H); 3.54 (s,
2H); 3.99 (s, 2H); 4.06 (q, J ¼ 10.0 Hz, 2H); 7.15 (d,
J ¼ 7.9 Hz, 1H); 7.22 (t, J ¼ 7.3 Hz, 1H); 7.37 (m, 5H); 7.48
(s, 1H). 13C NMR (DMSO-d6, d ppm): 170.3, 169.2, 149.1,
136.4, 133.2, 131.7, 131.1, 130.4, 129.7, 128.5, 128.4,
127.2, 127.1, 126.2, 122.6, 60.6, 35.5, 14.2. MS (ESI): 333.0
(C18H18ClO4, [M þ H]þ). Anal. Calcd for C18H17ClO4: C,
64.97; H, 5.15%; Found: C, 64.93; H, 5.12%.
4.3.2.22. 2-(2-Ethoxy-2-oxoethyl)phenyl 4-methylbenzoate
1
(C22). Yellow powder. Yield 85%, mp: 55e56 ꢀC, H NMR
(300 MHz, d6-DMSO): 1.01 (t, J ¼ 7.1 Hz, 3H); 2.43 (s,
3H); 3.64 (s, 2H); 3.91 (q, J ¼ 8.1 Hz, 2H); 7.28 (m, 2H);
7.41 (m, 4H); 7.99 (d, J ¼ 8.3 Hz, 2H). 13C NMR (DMSO-
d6, d ppm): 170.4, 166.9, 163.0, 149.0, 134.3, 132.9, 132.7,
132.0, 131.4, 131.0, 130.8, 130.6, 128.7, 127.7, 127.4,
127.2, 126.5, 122.7, 60.5, 36.0, 14.0. MS (ESI): 299.1
(C18H19O4, [M þ H]þ). Anal. Calcd for C18H18O4: C, 72.47;
H, 6.08%; Found: C, 72.43; H, 6.03%.
4.3.2.18. 2-(2-Ethoxy-2-oxoethyl)phenyl 2-(3-bromophenyl)
acetate (C18). Light yellow oil. Yield 83%, 1H NMR
(300 MHz, d6-DMSO): 1.17 (t, J ¼ 8.1 Hz, 3H); 3.55 (s,
2H); 3.99 (s, 2H); 4.06 (q, J ¼ 2.0 Hz, 2H); 7.11 (m, 2H);
7.23 (m, 2H); 7.35 (m, 2H); 7.50 (m, 2H). 13C NMR
(DMSO-d6, d ppm): 171.4, 170.0, 169.3, 155.6, 149.1,
136.7, 132.7, 131.7, 131.1, 130.7, 130.4, 130.1, 129.6,
4.3.2.23.
2-(2-Ethoxy-2-oxoethyl)phenyl
3-nitrobenzoate
1
(C23). White powder. Yield 88%, mp: 73e74 ꢀC, H NMR
(300 MHz, d6-DMSO): 0.99 (t, J ¼ 7.1 Hz, 3H); 3.71 (s,
2H); 3.94 (q, J ¼ 7.1 Hz, 3H); 7.31 (m, 1H); 7.42 (m, 3H);
7.93 (t, J ¼ 8.0 Hz, 1H); 8.52 (d, J ¼ 7.9 Hz, 1H); 8.59 (d,
J ¼ 8.3 Hz, 1H); 8.76 (m, 1H). 13C NMR (DMSO-d6,