G Model
CCLET-2632; No. of Pages 5
H.-Q. Liu et al. / Chinese Chemical Letters xxx (2013) xxx–xxx
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NMR (300 MHz, DMSO-d6): d 10.93 (s, 1H), 7.56–7.20 (m, 2H), 6.80 (d, J = 7.8 Hz,
1H). 6i: 25.7% yield, mp 201–201.2 8C; 1H NMR: (300 MHz, DMSO-d6): d 10.84 (s,
1H), 7.18 (dd, J = 8.5, 2.8 Hz, 1H), 7.07 (d, J = 2.7 Hz, 1H), 6.84 (d, J = 8.5 Hz, 1H). 6j:
77.5% yield, mp 131.6–132.3 8C; 1H NMR: (300 MHz, DMSO-d6): d 7.70 (t, 1H,
J = 3Hz), 7.69 (dd, 1H, J = 6 Hz, 3 Hz), 7.17 (d, 2H, J = 6 Hz), 3.17 (s, 3H); MS (ESI+)
m/z: 184 [M+Na]+. 6k: 81.2% yield, mp 129.4–130.3 8C; 1H NMR: (300 MHz,
DMSO-d6): d 7.28–7.36 (m,7H), 7.12 (t, 1H, J = 3 Hz), 6.97 (d, 1H, J = 6 Hz), 4.91
(s, 2H); MS (ESI+) m/z: 260 [M + Na]+. 6l: 72.7% yield, mp 191.3–194.0 8C; 1H NMR
(300 MHz, DMSO-d6): d 7.62(t, 1H, J = 3 Hz), 7.11 (t, 2H, J = 6 Hz), 3.14 (s, 3H); MS
(ESI+) m/z: 218 [M + Na]+. 6m: 79.3% yield, mp 165.8–166.5 8C; 1H NMR
(300 MHz, DMSO-d6): d 7.59(d, 1H, J = 3 Hz), 7.44 (d, 2H, J = 3 Hz),7.35 (t, 2H,
J = 6 Hz), 7.30 (d, 1H, J = 3 Hz), 7.13–7.18 (m, 2H), 4.93 (s, 2H); MS (ESI+) m/z: 294
[M + Na]+. 6n: 83.8% yield, mp 141.5–142.5 8C; 1H NMR (300 MHz, DMSO-d6): d
7.62 (t, 2H, J = 3 Hz), 7.43 (d, 2H, J = 6 Hz), 7.28–7.36 (m, 3H), 6.97 (d, 1H, J = 9 Hz),
7.49–7.39 (m, 3H), 7.26–7.20 (m, 2H), 6.89 (dd, 1H, J = 5.4, 3.0 Hz); MS (ESI+) m/
z 383 [M + Na]+. 1g: scarlet crystal; 51.2% yield, mp 213.6–214.2 8C; 1H NMR:
(300 MHz, DMSO-d6) d 10.69 (s, 1H), 8.91 (s, 1H), 7.63–7.39 (m, 7H), 6.84 (d, 1H,
J = 8.3 Hz); MS (ESI+) m/z: 383 [M + Na]+. 1h: yellow crystal; 43.7% yield, mp
221.3–221.6 8C; 1H NMR: (300 MHz, DMSO-d6) d 10.31 (s, 1H), 7.90 (s, 1H),
7.68–7.61 (m, 2H), 7.46–7.33 (m, 3H), 7.08–6.98 (m, 2H), 6.75–6.68 (m, 1H),
2.22 (s, 3H); MS (ESI+) m/z: 318 [M + Na]+. 1i: green crystal; 62.3% yield, mp
189.4–189.8 8C; 1H NMR (300 MHz, DMSO-d6): d 10.34 (s, 1H), 8.88 (s, 1H),
7.59–7.50 (m, 2H), 7.45 (d, 3H, J = 7.1 Hz), 7.09 (d, 1H, J = 2.2 Hz), 6.89 (dd, 1H,
J = 8.5, 2.8 Hz), 6.78 (d, 1H, J = 8.5 Hz), 3.72 (s, 3H); MS (ESI+) m/z: 334
[M + Na]+. 1j: scarlet crystal; 33.6% yield, mp 207–208.1 8C; 1H NMR
(300 MHz, DMSO-d6): d 8.84 (s, 1H), 7.71–7.27 (m, 8H), 7.24–6.94 (m, 2H),
3.14 (s, 3H); MS (ESI+) m/z 318 [M + Na]+. 1k: scarlet crystal; 57.2% yield, mp
156.7–157.2 8C; 1H NMR (300 MHz, DMSO-d6): d 9.03 (s, 1H), 7.63–7.56 (m,
3H), 7.51–7.43 (m, 3H), 7.38–7.28 (m, 6H), 7.12 (t, 1H, J = 7.5 Hz), 6.93 (d, 1H,
J = 7.8 Hz), 4.90 (s, 2H); MS (ESI+) m/z: 394 [M + Na]+. 1l: red crystal; 53.1%
yield, mp 193.7–194.0 8C; 1H NMR (300 MHz, DMSO-d6): d 8.69 (s, 1H), 7.59–
7.51 (m, 2H), 7.50–7.36 (m, 5H), 7.11 (dd, 3H, J = 21.7, 8.1 Hz), 3.33 (s, 2H); MS
(ESI+) m/z: 330 [M + H]+, 352 [M + Na]+. 1m: yellow crystal; 51.2% yield, mp
179.2–179.9 8C; 1H NMR (300 MHz, DMSO-d6): d 8.87 (s, 1H), 7.65–7.27 (m,
11H), 7.05 (dd, 1H, J = 54.6, 8.0 Hz), 4.95 (dd, 2H, J = 32.1, 16.0 Hz); MS (ESI+) m/
z: 406 [M + H]+, 428 [M + Na]+. 1n: orange crystal; 55.7% yield, mp 141.5–
142.5 8C; 1H NMR (300 MHz, DMSO-d6): d 9.06 (s, 1H), 7.59 (dd, 3H, J = 8.1,
1.6 Hz), 7.47 (dd, 3H, J = 7.1, 2.1 Hz), 7.44 7.34 (m, 5H), 6.97 (d, 1H, J = 7.8 Hz),
4.91 (d, 2H, J = 4.9 Hz); MS (ESI+) m/z: 406 [M + H]+, 428 [M + Na]+. 1o: red
crystal; 49.3% yield, mp 177.1–178.2 8C; 1H NMR (300 MHz, DMSO-d6): d 8.83
(s, 1H), 7.61–7.52 (m, 3H), 7.51–7.42 (m, 3H), 7.25 (d, 1H, J = 2.0 Hz), 7.18 (dd,
1H, J = 7.9, 1.9 Hz), 3.15 (s, 3H); MS (ESI+) m/z: 330 [M + H]+, 352 [M + Na]+. 1p:
orange crystal; 47.6% yield, mp 175.2–176.1 8C; 1H NMR (300 MHz, DMSO-d6):
d 9.02 (s, 1H), 7.66–7.54 (m, 4H), 7.51–7.42 (m, 4H), 7.40–7.28 (m, 7H), 7.19–
7.14 (m, 1H), 7.10 (d, 1H, J = 1.7 Hz), 4.92 (d, 2H, J = 4.3 Hz); MS (ESI+) m/z 406
[M + H]+, 428 [M + Na]+.
4.91 (s, 2H); MS (ESI+) m/z: 294 [M + Na]+. 6o: 80.6% yield, mp 177.1–178.2 8C; 1
H
NMR (300 MHz, DMSO-d6): d 7.54 (d, 1H, J = 3 Hz), 7.33 (s, 1H), 7.16 (d, 2H,
J = 3 Hz), 3.14 (s, 3H); MS (ESI+) m/z: 218 [M + Na]+. 6p: 85.1% yield, mp 175.2–
176.1 8C; 1H NMR (300 MHz, DMSO-d6): d 7.53 (t, 1H, J = 6 Hz), 7.43 (d, 2H,
J = 3 Hz), 7.28–7.36 (m, 3H), 7.11 (d, 1H, J = 3 Hz), 6.90 (d, 1H, J = 3 Hz), 4.91 (s,
2H); MS (ESI+) m/z: 294 [M + Na]+. 1a: yellow crystal; 39.3% yield, mp 208.8–
210.8 8C; 1H NMR (300 MHz, DMSO-d6): d 10.55 (s, 1H), 8.90 (s, 1H), 7.63–7.41 (m,
6H), 7.35–7.27 (m, 1H), 7.07 (t, 1H, J = 7.6 Hz), 6.88 (d, 1H, J = 7.8 Hz); MS (ESI+) m/
z 304 [M + Na]+. 1b: orange crystal; 43.5% yield, mp 198.1–198.9 8C; 1H NMR:
(300 MHz, DMSO-d6) d 10.84 (s, 1H), 8.71 (s, 1H), 7.55 (d, 2H, J = 6.0 Hz), 7.53–7.40
(m, 3H), 7.32 (t, 1H, J = 6.0 Hz), 7.07 (d, 1H, J = 9.0 Hz), 6.86 (d, 1H, J = 9.0 Hz); MS
(ESI+) m/z: 338 [M + Na]+. 1c: light yellow crystal; 53.9% yield, mp 210.4–
211.3 8C; 1H NMR (300 MHz, DMSO-d6): d 10.66 (s, 1H), 8.90 (s, 1H), 7.62–
7.31 (m, 7H), 6.88 (d, 1H, J = 8.3 Hz); MS (ESI+) m/z: 338 [M + Na]+. 1d: deep
orange crystal; 52.5% yield, mp 213–214.2 8C; 1H NMR (300 MHz, DMSO-d6): d
10.70 (s, 1H), 8.88 (s, 1H), 7.58–7.41 (m, 6H), 7.10 (dd, J = 8.0, 1.0 Hz, 1H), 6.89 (d,
J = 1.0 Hz, 1H); MS (ESI+) m/z 338 [M + Na]+. 1e: deep orange crystal; 61.0% yield,
mp 213.2–214.2 8C; 1H NMR: (300 MHz, DMSO-d6) d 11.01 (s, 1H), 8.93 (s, 1H),
7.62–7.53 (m, 2H), 7.45 (dt, J = 18.2, 7.4 Hz, 5H), 7.09 (t, J = 7.8 Hz, 1H); MS (ESI+)
m/z 338 [M + Na]+. 1f: light yellow crystal; 39.5% yield, mp 195.8–196.5 8C;
1H NMR (300 MHz, DMSO-d6): d 10.82 (s, 1H), 8.70 (s, 1H), 7.58–7.52 (m, 2H),
Please cite this article in press as: H.-Q. Liu, et al., Synthesis and biological evaluation of 50-phenyl-30H-spiro-[indoline-3,20-