H. Fu and H. Xu
159.0, 142.5, 134.9, 134.4, 129.9, 128.8, 125.5, 117.1, 114.2, 109.4, 44.8,
Compound 3m: Eluent: petroleum ether/EtOAc (4:1). White solid,
150 mg (98%). M.p. 124–1268C; H NMR (600 MHz, CDCl3): d=8.32 (d,
20.9, 11.4 ppm; MS (ESI): m/z: 228.3 [M+H]+, 250.2 [M+Na]+.
1
J=8.3 Hz, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.78 (d, J=8.3 Hz, 1H), 7.71–
7.67 (m, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.35–7.31 (m, 1H), 7.29–7.25 (m,
1H), 7.23–7.19 (m, 1H), 4.36 (t, J=7.6 Hz, 2H), 1.91–1.84 (m, 2H), 1.48–
1.37 (m, 4H), 0.92 ppm (t, J=7.6 Hz, 3H); 13C NMR (150 MHz, CDCl3):
d=159.2, 146.6, 142.6, 136.6, 134.5, 130.5, 129.9, 124.6, 124.0, 122.0, 119.1,
116.7, 114.1, 112.2, 43.6, 29.1, 27.2, 22.6, 14.1 ppm; MS (ESI): m/z: 306.2
[M+H]+, 328.1 [M+Na]+.
Compound 3d: Eluent: petroleum ether/EtOAc (2:1). White solid, 79 mg
(66%). M.p. 59–618C; 1H NMR (300 MHz, CDCl3): d=8.41–8.38 (m,
1H), 7.77–7.73 (m, 1H), 7.57 (d, J=8.3 Hz, 1H), 7.49 (d, J=1.4 Hz, 1H),
7.46–7.43 (m, 1H), 7.19 (d, J=1.4 Hz, 1H), 4.37–4.33 (m, 2H), 1.87–1.81
(m, 2H), 1.51–1.44 (m, 2H), 0.98 ppm (t, J=6.9 Hz, 3H); 13C NMR
(75 MHz, CDCl3): d=159.0, 142.4, 134.9, 134.4, 129.9, 128.9, 125.5, 117.1,
114.2, 109.4, 43.1, 29.7, 20.3, 13.9 ppm; MS (ESI): m/z: 242.3 [M+H]+,
264.1 [M+Na]+.
Compound 3n: Eluent: petroleum ether/EtOAc (4:1). White solid,
161 mg (80%). M.p. 80–828C; 1H NMR (300 MHz, CDCl3): d=8.46–8.42
(m, 1H), 8.17 (d, J=8.3 Hz, 1H), 7.98 (d, J=7.6 Hz, 1H), 7.86–7.75 (m,
2H), 7.48–7.29 (m, 3H), 4.44 (t, J=7.9 Hz, 2H), 1.95–1.84 (m, 2H), 1.53–
1.20 (m, 18H), 0.90–0.83 ppm (m, 3H); 13C NMR (75 MHz, CDCl3): d=
159.4, 146.9, 142.8, 136.9, 134.8, 130.8, 130.2, 124.9, 124.2, 122.2, 119.4,
116.9, 114.3, 112.5, 43.8, 32.0, 29.7, 29.6, 29.5, 29.4, 27.6, 27.0, 22.8,
14.2 ppm; MS (ESI): m/z: 404.3 [M+H]+.
Compound 3e: Eluent: petroleum ether/EtOAc (2:1). White solid, 83 mg
(65%). M.p. 40–428C; 1H NMR (300 MHz, CDCl3): d=8.41–8.36 (m,
1H), 7.78–7.71 (m, 1H), 7.56 (d, J=7.9 Hz, 1H), 7.50–7.41 (m, 2H), 7.18
(d, J=1.7 Hz, 1H), 4.37–4.30 (m, 2H), 1.90–1.78 (m, 2H), 1.46–1.34 (m,
4H), 0.90 ppm (t, J=6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=159.0,
142.5, 135.0, 134.5, 130.0, 128.9, 125.5, 117.2, 114.2, 109.4, 43.4, 29.1, 27.4,
22.6, 14.1 ppm; MS (ESI): m/z: 256.4 [M+H]+.
Compound 3o: Eluent: petroleum ether/EtOAc (4:1). White solid,
120 mg (75%). M.p. 159–1608C; H NMR (600 MHz, CDCl3): d=8.06 (d,
Compound 3 f: Eluent: petroleum ether/EtOAc (2:1). White solid, 85 mg
(62%). M.p. 154–1568C; 1H NMR (300 MHz, CDCl3): d=8.35 (d, J=
7.9 Hz, 1H), 7.72–7.56 (m, 3H), 7.51–7.34 (m, 3H), 7.33–7.20 (m, 3H),
7.17 (m, 1H), 5.53 ppm (s, 2H); 13C NMR (75 MHz, CDCl3): d=159.1,
142.5, 136.5, 135.0, 134.6, 130.0, 129.1, 128.9, 128.5, 127.8, 125.5, 117.1,
114.2, 109.6, 46.3 ppm; MS (ESI): m/z: 276.3 [M+H]+, 298.1 [M+Na]+.
1
J=8.9 Hz, 1H), 7.90 (d, J=8.3 Hz, 1H), 7.84 (d, J=2.8 Hz, 1H), 7.76 (d,
J=7.6 Hz, 1H), 7.38–7.34 (m, 2H), 7.32–7.28 (m, 1H), 4.45 (t, J=7.6 Hz,
2H), 3.91 (s, 3H), 1.91–1.86 (m, 2H), 1.54–1.47 (m, 2H), 1.00 ppm (t, J=
7.6 Hz, 2H); 13C NMR (150 MHz, CDCl3): d=159.3, 156.6, 146.4, 142.5,
131.0, 130.5, 123.9, 123.2, 122.0, 119.2, 117.9, 115.8, 112.1, 111.2, 55.9,
43.6, 29.6, 20.3, 14.0 ppm; MS (ESI): m/z: 322.6 [M+H]+, 344.5
[M+Na]+.
Compound 3g: Eluent: petroleum ether/EtOAc (2:1). White solid, 72 mg
(53%). M.p. 116–1188C; 1H NMR (600 MHz, CDCl3): d=7.82 (d, J=
2.8 Hz, 1H), 7.51 (d, J=8.9 Hz, 1H), 7.45 (d, J=1.4 Hz, 1H), 7.35–7.32
(m, 1H), 7.18 (d, J=1.4 Hz, 1H), 4.36 (t, J=7.6 Hz, 2H), 3.93 (s, 3H),
1.87–1.81 (m, 2H), 1.52–1.44 (m, 2H), 0.99 ppm (t, J=6.9 Hz, 3H);
13C NMR (150 MHz, CDCl3): d=158.9, 157.3, 141.9, 129.2, 128.5, 123.6,
118.1, 115.8, 110.6, 109.3, 56.0, 43.3, 29.8, 20.3, 13.9 ppm; MS (ESI): m/z:
272.3 [M+H]+.
Compound 3p: Eluent: petroleum ether/EtOAc (4:1). White solid,
1
150 mg (98%). M.p. 154–1568C; H NMR (300 MHz, CDCl3): d=8.16 (d,
J=1.4 Hz, 1H), 7.96 (d, J=8.6 Hz, 1H), 7.88 (d, J=7.6 Hz, 1H), 7.74–
7.70 (m, 1H), 7.57–7.52 (m, 1H), 7.37–7.24 (m, 2H), 4.41 (t, J=7.2 Hz,
2H), 2.44 (s, 3H), 1.93–1.80 (m, 2H), 1.55–1.42 (m, 2H), 0.99 ppm (t, J=
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=159.5, 146.7, 142.7, 135.5,
134.8, 134.7, 130.7, 129.8, 123.9, 122.0, 119.2, 116.6, 114.1, 112.3, 43.5,
29.6, 20.9, 20.3, 14.0 ppm; MS (ESI): m/z: 306.4 [M+H]+, 328.3
[M+Na]+.
Compound 3h: Eluent: petroleum ether/EtOAc (2:1). White solid, 68 mg
(54%). M.p. 98–1008C; 1H NMR (300 MHz, CDCl3): d=8.16 (s, 1H),
7.56–7.51 (m, 1H), 7.47–7.42 (m, 2H), 7.16 (d, J=1.4 Hz, 1H), 7.23–7.15
(m, 1H), 4.34 (t, J=7.6 Hz, 2H), 2.47 (s, 3H), 1.90–1.77 (m, 2H), 1.53–
1.39 (m, 2H), 0.98 ppm (t, J=6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3):
d=159.1, 142.3, 135.5, 135.4, 132.9, 129.6, 128.6, 116.9, 114.1, 109.3, 43.1,
29.7, 21.0, 20.3, 13.9 ppm; MS (ESI): m/z: 256.3 [M+H]+, 278.2
[M+Na]+.
Compound 3q: Eluent: petroleum ether/EtOAc (2:1). White solid,
1
152 mg (98%). M.p. 165–1678C; H NMR (300 MHz, CDCl3): d=8.38 (d,
J=2.8 Hz, 1H), 8.08 (d, J=8.6 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 7.79–
7.72 (m, 2H), 7.42–7.29 (m, 2H), 4.39 (t, J=7.6 Hz, 2H), 1.99–1.85 (m,
2H), 1.06 ppm (t, J=7.6 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=158.4,
146.6, 142.7, 135.3, 134.7, 130.7, 130.5, 129.7, 124.4, 122.5, 119.5, 118.3,
115.7, 112.2, 45.4, 20.8, 11.4 ppm; MS (ESI): m/z: 312.2 [M+H]+.
Compound 3i: Eluent: petroleum ether/EtOAc (2:1). White solid,
1
128 mg (98%). M.p. 165–1678C; H NMR (300 MHz, CDCl3): d=8.29 (d,
J=2.1 Hz, 1H), 7.70–7.64 (m, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.45 (d, J=
1.4 Hz, 1H), 7.17 (d, J=1.4 Hz, 1H), 4.28 (t, J=7.6 Hz, 2H), 1.94–1.79
(m, 2H), 1.03 ppm (t, J=6.9 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=
157.8, 142.2, 134.5, 133.4, 131.3, 129.4, 129.1, 118.3, 115.8, 109.5, 44.9,
20.8, 11.4 ppm; MS (ESI): m/z: 262.3 [M+H]+.
Compound 3r: Eluent: petroleum ether/EtOAc (2:1). White solid,
1
130 mg (80%). M.p. 163–1658C; H NMR (300 MHz, CDCl3): d=8.34 (d,
J=2.4 Hz, 1H), 8.02 (d, J=8.9 Hz, 1H), 7.83 (d, J=7.9 Hz, 1H), 7.74–
7.69 (m, 2H), 7.38–7.28 (m, 2H), 4.39 (t, J=7.6 Hz, 2H), 1.91–1.79 (m,
2H), 1.54–1.40 (m, 2H), 0.98 ppm (t, J=7.6 Hz, 3H); 13C NMR (75 MHz,
CDCl3): d=158.3, 146.5, 142.6, 135.2, 134.7, 130.6, 130.4, 129.6, 124.4,
122.5, 119.5, 118.2, 115.7, 112.2, 43.7, 29.5, 20.3, 13.9 ppm; MS (ESI): m/z:
326.2 [M+H]+.
Compound 3j: Eluent: petroleum ether/EtOAc (2:1). White solid, 63 mg
(55%). M.p. 106–1088C; 1H NMR (300 MHz, CDCl3): d=8.75–8.71 (m,
1H), 8.68–8.63 (m, 1H), 7.85 (d, J=1.7 Hz, 1H), 7.46–7.40 (m, 1H), 7.17
(d, J=1.7 Hz, 1H), 4.34–4.27 (m, 2H), 1.96–1.83 (m, 2H), 1.04 ppm (t,
J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=158.8, 153.7, 146.1,
142.6, 138.8, 128.7, 121.5, 112.5, 110.1, 44.9, 20.9, 11.4 ppm; MS (ESI): m/
z: 229.3 [M+H]+.
Compound 3s: Eluent: petroleum ether/EtOAc (2:1). White solid, 90 mg
(65%). M.p. 168–1708C; 1H NMR (300 MHz, CDCl3): d=8.76–8.72 (m,
1H), 8.60–8.55 (m, 2H), 7.65 (d, J=7.9 Hz, 1H), 7.37–7.23 (m, 3H), 4.35
(t, J=7.6 Hz, 2H), 2.00–1.86 (m, 2H), 1.07 ppm (t, J=7.6 Hz, 3H);
13C NMR (75 MHz, CDCl3): d=159.4, 153.7, 148.2, 146.4, 142.1, 138.3,
130.2, 124.6, 122.7, 120.5, 118.4, 115.3, 111.9, 45.1, 20.8, 11.4 ppm; MS
(ESI): m/z: 279.2 [M+H]+, 301.1 [M+Na]+.
Compound 3k: Eluent: petroleum ether/EtOAc (4:1). White solid,
113 mg (91%). M.p. 198–2008C; 1H NMR (300 MHz, CDCl3): d=8.41–
8.37 (m, 1H), 8.10–8.05 (m, 1H), 7.92–7.87 (m, 1H), 7.82–7.75 (m, 1H),
7.73–7.68 (m, 1H), 7.45–7.26 (m, 3H), 3.81 ppm (s, 3H); 13C NMR
(75 MHz, CDCl3): d=159.6, 147.1, 142.5, 136.7, 134.9, 134.8, 130.7, 130.0,
124.9, 124.3, 122.4, 119.3, 116.6, 114.2, 112.4, 30.0 ppm; MS (ESI): m/z:
250.5 [M+H]+, 272.3 [M+Na]+.
Compound 3t: Eluent: petroleum ether/EtOAc (4:1). White solid,
1
128 mg (92%). M.p. 236–2388C; H NMR (300 MHz, CDCl3): d=8.41 (d,
J=7.9 Hz, 1H), 8.13–8.05 (m, 1H), 7.87–7.78 (m, 1H), 7.67 (d, J=3.4 Hz,
1H), 7.49–7.39 (m, 2H), 3.81 (s, 3H), 2.43 (s, 3H), 2.37 ppm (s, 3H);
13C NMR (75 MHz, CDCl3) d=159.6, 146.6, 140.9, 136.9, 134.7, 133.1,
131.2, 130.0, 129.1, 124.6, 119.6, 116.6, 114.2, 112.9, 30.0, 20.8, 20.4 ppm;
MS (ESI): m/z: 278.3 [M+H]+, 300.2 [M+Na]+.
Compound 3l: Eluent: petroleum ether/EtOAc (4:1). White solid,
125 mg (95%). M.p. 168–1708C; 1H NMR (300 MHz, CDCl3): d=8.35–
8.30 (m, 1H), 7.96 (d, J=8.3 Hz, 1H), 7.79 (d, J=7.9 Hz, 1H), 7.74–7.63
(m, 2H), 7.37–7.18 (m, 3H), 4.44 (q, J=7.2 Hz, 2H), 1.46 ppm (t, J=
7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): d=159.0, 146.4, 142.6, 136.7,
134.6, 130.5, 129.9, 124.7, 124.1, 122.1, 119.1, 116.8, 114.1, 112.3, 38.8,
12.9 ppm; MS (ESI): m/z: 264.4 [M+H]+, 286.2 [M+Na]+.
Compound 3u: Eluent: petroleum ether/EtOAc (4:1). White solid,
150 mg (98%). M.p. 172–1748C; 1H NMR (300 MHz, CDCl3): d=8.44–
8.40 (m, 1H), 8.13 (d, J=8.6 Hz, 1H), 7.86–7.79 (m, 1H), 7.71 (s, 1H),
1184
ꢀ 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2012, 18, 1180 – 1186