846
Z.-Y. Kang et al.
(75 MHz, CD3COCD3) d (ppm): 158.3,
135.5, 132.2, 130.0, 128.5, 125.3, 121.2,
36.5.
124.5, 122.7, 116.1, 115.7, 113.1, 101.3,
55.9. HR-MS-ESI: m/z 330.1290 [M þ H]þ
(calcd for C22H17FNO, 330.1294).
3.4 General procedures for compounds
33A, 33B, 34A, 34B, 34C, 34D, 34E, and
34F
3.4.3 Compound 34A
1H NMR (300 MHz, CD3COCD3) d
(ppm): 8.50 (d, J ¼ 8.4 Hz, 1H), 8.35
(dd, J ¼ 7.2, 1.2 Hz, 1H), 8.03 (d,
J ¼ 7.8 Hz, 1H), 7.76 (s, 1H), 7.71 (dt,
J ¼ 7.2, 1.8 Hz, 1H), 7.65 (dt, J ¼ 7.2,
1.2 Hz, 1H), 7.37 (dt, J ¼ 7.8, 1.2 Hz, 2H),
7.09 (dt, J ¼ 0.6, 1.8 Hz, 1H), 6.90 (dd,
J ¼ 7.8, 1.2 Hz, 2H), 6.70 (ddd, J ¼ 1.2,
6.0, 7.8 Hz, 1H), 6.59 (dd, J ¼ 10.8, 6.0 Hz,
1H), 6.36 (d, J ¼ 10.8Hz, 1H), 4.15 (s, 3H).
13C NMR (75 MHz, CD3COCD3) d (ppm):
165.3, 157.8, 151.9, 140.6, 133.5, 132.0,
130.9, 130.1 (2C), 129.0, 128.7, 127.5,
127.3, 126.1 (2C), 125.8, 124.5, 123.1,
120.9 (2C), 105.2, 56.3. HR-ESI-MS: m/z
312.1387 [M þ H]þ (calcd for C22H18NO,
312.1388).
Compounds 33A, 33B, 34A, 34B, 34C,
34D, 34E, and 34F were synthesized by
the same procedure as compound 12.
Compounds 33A, 33B, 34A, 34B, and 34C
were isolated by HPLC in lower yield less
than 10%. Compounds 34D, 34E, and 34F
were prepared in quantitative yields.
3.4.1 Compound 33A
1H NMR (300 MHz, CD3COCD3) d
(ppm): 8.17 (dd, J ¼ 8.4, 1.2 Hz, 1H),
7.99 (dd, J ¼ 1.2, 0.6 Hz, 2H), 7.76 (d,
J ¼ 6.0 Hz, 1H), 7.52 (m, 1H), 7.49 (m,
3H), 7.41 (dt, J ¼ 8.4, 0.6 Hz, 1H), 6.90 (d,
J ¼ 11.4 Hz, 1H), 6.60 (s, 1H), 6.57 (d,
J ¼ 11.4 Hz, 1H), 6.40 (dd, J ¼ 11.4,
3.6 Hz, 1H), 6.36 (dd, J ¼ 11.4, 3.6 Hz,
1H), 4.02 (s, 3H). 13C NMR (75 MHz,
CD3COCD3) d (ppm): 167.4, 156.4, 151.4,
138.9, 136.8, 134.3, 132.6, 131.6, 131.2,
129.3 (3C), 128.8 (2C), 127.8, 124.8,
124.7, 123.9, 122.9, 113.2, 101.6, 56.1.
HR-MS-ESI: m/z 312.1388 [M þ H]þ
(calcd for C22H18NO, 312.1388).
3.4.4 Compound 34B
1H NMR (600 MHz, CD3COCD3) d
(ppm): 6.38 (d, J ¼ 11.7 Hz, 1H), 6.62
(dd, J ¼ 11.7, 6.6 Hz, 1H), 6.70 (ddd,
J ¼ 6.6, 3.6, 1.2, Hz, 1H), 8.02 (d,
J ¼ 11.4 Hz, 1H), 8.35 (dd, J ¼ 9.3,
1.5 Hz, 1H), 7.70 (m, 1H), 7.64 (m, 1H),
8.47 (d, J ¼ 5.7 Hz, 1H), 7.73 (s, 1H), 6.94
(m, 2H), 7.14 (t, J ¼ 8.0, 7.0 Hz, 2H), 4.14 (s,
3H). 13C NMR (150 MHz, CD3COCD3) d
(ppm): 165.2, 161.3 (F-C), 158.2 (F-C),
157.1, 156.2, 147.2, 139.7, 132.7, 131.4,
130.2, 128.0, 127.9, 126.8, 126.6, 126.5,
125.4, 125.0, 122.4, 121.9, 121.8, 116.0,
115.7, 104.4, 55.5. HR-MS-ESI: m/z
330.1290 [M þ H]þ (calcd for C22H17FNO,
330.1303).
3.4.2 Compound 33B
1H NMR (300 MHz, CD3COCD3) d
(ppm): 8.17 (d, J ¼ 7.5 Hz, 1H), 8.04
(dd, J ¼ 5.4, 2.1 Hz, 2H), 7.75 (d,
J ¼ 8.4 Hz, 1H), 7.50 (dt, J ¼ 8.4,
1.5 Hz, 1H), 7.41 (dt, J ¼ 7.5, 1.5, Hz,
1H), 7.24 (dd, J ¼ 5.4, 2.1 Hz, 2H), 6.90
(d, J ¼ 7.8 Hz, 1H), 6.60 (s, 1H), 6.56 (d,
J ¼ 11.1 Hz, 1H), 6.39 (dd, J ¼ 15.0,
3.6 Hz, 1H), 6.35 (dd, J ¼ 7.8, 3.6 Hz,
1H), 4.02 (s, 3H). 13C NMR (75 MHz,
CD3COCD3) d (ppm): 166.9, 156.2, 151.0,
137.0, 135.5, 135.3, 135.1, 134.1, 132.5,
130.7, 131.6, 130.1, 130.0, 127.6, 124.6,
3.4.5 Compound 34C
1H NMR (300 MHz, CD3COCD3) d
(ppm): 8.46 (d, J ¼ 8.4 Hz, 1H), 8.34
(dd, J ¼ 8.4, 1.5 Hz, 1H), 8.00 (d,
J ¼ 12.0 Hz, 1H), 7.73 (s, 1H), 7.68 (dd,