B. Sun et al. / Bioorg. Med. Chem. 18 (2010) 5352–5366
5361
4.2.27. (E)-4-(2-(Benzo[d][1,3]dioxol-5-yl)vinyl)benzenamine
(48)
4.2.33. 3,5-Dimethoxyl-30-amino-trans-stilbene (54)
This compound was prepared in 44% yield by following GP 2.
This compound was prepared in 75% yield by following GP 2.
Yellow solid: mp 132–133 °C. IR (film) 3368, 2924, 1606, 1516,
Yellow solid: mp 72–73 °C. IR (film) 3368, 1599, 1590, 1459,
1204, 1152, 1065, 960 cmꢀ1 1H NMR (300 MHz, CDCl3) d 7.16 (t,
;
1489, 1446, 1253, 1038, 960 cmꢀ1
;
1H NMR (500 MHz, CDCl3) d
J = 7.8 Hz, 1H), 7.00 (s, 2H), 6.93 (d, J = 7.8 Hz, 1H), 6.84 (t,
J = 2.1 Hz, 1H), 6.67 (d, J = 2.4 Hz, 2H), 6.61 (dd, J = 2.4 Hz, 8.4 Hz,
1H), 6.41 (t, J = 2.1 Hz, 1H), 3.84 (s, 6H); 13C NMR (75 MHz, CDCl3)
d 160.9, 146.6, 139.4, 138.1, 129.5, 129.3, 128.4, 117.3, 114.7,
112.8, 104.5, 99.8, 55.3; ESIMS m/z 256 (MH+). HRMS calcd for
7.30 (d, J = 8.4 Hz, 2H), 7.03 (d, J = 1.5 Hz, 1H), 6.89 (dd, J = 8.4 Hz,
1.5 Hz, 1H), 6.87 (d, J = 16.2 Hz, 1H), 6.82 (d, J = 16.2 Hz, 1H), 6.78
(d, J = 8.1 Hz, 1H), 6.66 (d, J = 8.4 Hz, 2H), 5.96 (s, 2H), 3.73 (br,
2H); 13C NMR (125 MHz, CDCl3) d 148.0, 146.6, 145.8, 132.4,
128.0, 127.4, 127.0, 124.7, 120.7, 115.1, 108.3, 105.2, 100.9; ESIMS
m/z 240 (MH+); HRMS calcd for C15H14O2N m/z 240.1025, found:
m/z 240.1022 (MH+).
C
16H17O2N m/z 256.1338, found: m/z 256.1341 (MH+).
4.2.34. 3,5-Dimethoxy-40-acetoxy-trans-stilbene (55)52
This compound was prepared in 50% yield by following GP 2.
White solid: mp 121–122 °C. IR (film) 3399, 1759, 1591, 1505,
4.2.28. 3-Nitro-40-nitro-trans-stilbene (49)49
1457, 1194, 1152, 968 cmꢀ1 1H NMR (300 MHz, CDCl3) d 7.49 (d,
;
This compound was prepared in 46% yield by following GP 2.
Yellow solid: mp 224–226 °C. IR (film) 1593, 1524, 1514, 1356,
J = 8.7 Hz, 2H), 7.09–7.02 (m, 3H), 6.96 (d, J = 16.5 Hz, 1H), 6.64
(d, J = 2.1 Hz, 2H), 6.39 (t, J = 2.4 Hz, 1H), 3.82 (s, 6H), 2.29 (s,
3H); 13C NMR (75 MHz, CDCl3) d 169.4, 160.9, 150.1, 139.1,
134.9, 128.9, 128.1, 127.5, 121.8, 104.5, 100.0, 55.3, 21.1; CIMS
m/z 299 (MH+).
1340, 972, 960, 868 cmꢀ1 1H NMR (300 MHz, CDCl3) d 8.40 (t,
;
J = 1.5 Hz, 1H), 8.25 (d, J = 9.0 Hz, 2H), 8.16 (d, J = 8.1 Hz, 1H),
7.82 (d, J = 7.8 Hz, 1H), 7.67 (d, J = 9.0 Hz, 2H), 7.57 (t, J = 7.8 Hz,
1H), 7.30 (d, J = 16.5 Hz, 1H), 7.24 (d, J = 16.5 Hz, 1H); 13C NMR
(75 MHz, CDCl3) d 148.7, 147.3, 142.5, 137.9, 132.6, 130.4, 129.8,
129.2, 127.2, 124.2, 123.0, 121.2; ESIMS m/z 271 (MH+).
4.2.35. 3,5-Dimethoxy-40-aminomethyl-trans-stilbene (56)
This compound was prepared in 50% yield by following GP 2.
White solid: mp 115–116 °C. IR (film) 3292, 2927, 1660, 1593,
4.2.29. 3-Nitro-40-amino-trans-stilbene (50)
1457, 1426, 1204, 1151, 1067, 963 cmꢀ1 1H NMR (300 MHz,
;
This compound was prepared in 39% yield by following GP 2.
Yellow solid: mp 177–178 °C. IR (film) 3469, 3390, 1620, 1527,
CDCl3) d 7.46 (d, J = 8.4 Hz, 2H), 7.26 (d, J = 8.4 Hz, 2H), 7.06 (d,
J = 16.5 Hz, 1H), 6.99 (d, J = 16.5 Hz, 1H), 6.65 (d, J = 2.1 Hz, 2H),
6.39 (t, J = 2.1 Hz, 1H), 5.92 (br, 1H), 4.47 (d, J = 6.0 Hz, 2H), 3.82
(s, 6H); 13C NMR (75 MHz, CDCl3) d 160.9, 139.0, 136.9, 136.6,
128.8, 128.4, 128.1, 126.8, 104.5, 100.0, 55.3, 41.8; ESIMS m/z
253 (MHꢀNH3)+; HRMS calcd for C17H17O2 m/z 253.1229, found:
m/z 253.1228 (MHꢀNH3)+.
1356, 970, 819 cmꢀ1 1H NMR (300 MHz, CDCl3) d 8.29 (s, 1H),
;
8.01 (d, J = 6.6 Hz, 1H), 7.72 (d, J = 7.8 Hz, 1H), 7.46 (t, J = 7.8 Hz,
1H), 7.34 (d, J = 8.4 Hz, 2H), 7.12 (d, J = 16.5 Hz, 1H), 6.91 (d,
J = 16.5 Hz, 1H), 6.67 (d, J = 8.4 Hz, 2H), 3.81 (s, 2H); 13C NMR
(75 MHz, CDCl3) d 150.4, 149.3, 141.1, 133.0, 132.6, 130.9, 129.2,
124.9, 121.6, 121.2, 120.7, 114.7; CIMS m/z 241 (MH+); HRMS calcd
for C14H12O2N2 m/z 240.0899, found: m/z 240.0898 (M+).
4.2.36. 3,5-Dimethoxy-40-fluoro-trans-stilbene (57)53
This compound was prepared in 56% yield by following GP 2.
White solid: mp 44–45 °C. IR (film) 1597, 1509, 1457, 1228,
4.2.30. 3-Methoxyl-40-amino-trans-stilbene (51)50
1204, 1157, 1067, 962 cmꢀ1 1H NMR (300 MHz, CDCl3) d 7.48–
;
This compound was prepared in 51% yield by following GP 2.
Yellow solid: mp 70–71 °C. IR (film) 2917, 1666, 1601, 1518,
7.43 (m, 2H), 7.06–7.00 (m, 3H), 6.93 (d, J = 16.2 Hz, 1H), 6.64 (d,
J = 2.4 Hz, 2H), 6.39 (t, J = 2.1 Hz, 1H), 3.82 (s, 6H); 13C NMR
(75 MHz, CDCl3) d 160.9, 139.1, 133.2, 128.3, 128.0, 127.9, 115.7,
115.4, 104.4, 99.8, 55.3; ESIMS m/z 259 (MH+).
1289, 965 cmꢀ1 1H NMR (300 MHz, CDCl3) d 7.37 (d, J = 8.4 Hz,
;
2H), 7.30 (t, J = 7.8 Hz, 1H), 7.14–7.05 (m, 3H), 6.95 (d,
J = 16.2 Hz, 1H), 6.83 (dd, J = 2.1 Hz, 7.8 Hz, 1H), 6.69 (d,
J = 7.8 Hz, 2H), 3.87 (s, 3H), 3.75 (br, 1H); 13C NMR (75 MHz, CDCl3)
d 159.8, 146.3, 139.4, 129.5, 129.0, 127.8, 124.8, 118.8, 115.2,
112.5, 111.3, 55.2; ESIMS m/z 226 (MH+).
4.2.37. 3,5-Dimethoxyl-40-chloro-trans-stilbene (58)54
This compound was prepared in 57% yield by following GP 2.
White solid: mp 65–66 °C. IR (film) 3369, 1587, 1455, 1347,
1206, 1151, 1057, 956 cmꢀ1 1H NMR (300 MHz, CDCl3) d 7.41 (d,
;
4.2.31. 3,5-Dinitro-40-nitro-trans-stilbene (52)
J = 8.7 Hz, 2H), 7.30 (d, J = 8.7 Hz, 2H), 7.02 (d, J = 16.8 Hz, 1H),
6.97 (d, J = 16.8 Hz, 1H), 6.64 (d, J = 2.4 Hz, 2H), 6.39 (t, J = 2.1 Hz,
1H), 3.81 (s, 6H); 13C NMR (75 MHz, CDCl3) d 160.9, 138.8, 135.5,
133.2, 129.2, 128.89, 127.8, 127.6, 104.5, 100.1, 55.3; ESIMS m/z
275 (MH+).
This compound was prepared in 42% yield by following GP 2.
Yellow solid: mp 281–282 °C. IR (film) 3368, 1533, 1506, 1343,
; d 8.90 (d,
1331, 961 cmꢀ1 1H NMR (300 MHz, DMSO-d6)
J = 2.1 Hz, 2H), 8.72 (t, J = 1.8 Hz, 1H), 8.29 (d, J = 9.0 Hz, 2H),
7.94–7.88 (m, 3H), 7.81 (d, J = 16.5 Hz, 1H); 13C NMR (75 MHz,
DMSO-d6) d 149.5, 147.9, 143.7, 141.0, 132.5, 130.0, 129.0, 127.6,
125.1, 118.4; negative ion ESIMS m/z 314 (MꢀH+)ꢀ; negative ion
HRMS calcd for C14H8O6N3 m/z 314.0413, found: m/z 314.0418
(MꢀH+)ꢀ.
4.2.38. 3,5-Dimethoxy-40-cyano-trans-stilbene (59)
This compound was prepared in 63% yield by following GP 2.
White solid: mp 106–107 °C. IR (film) 3400, 2223, 1602, 1586,
1458, 1427, 1206, 1154, 1061, 948 cmꢀ1 1H NMR (300 MHz,
;
CDCl3) d 7.60 (d, J = 8.1 Hz, 2H), 7.53 (d, J = 8.1 Hz, 2H), 7.11 (d,
J = 16.2 Hz, 1H), 7.02 (d, J = 16.2 Hz, 1H), 6.65 (d, J = 2.1 Hz, 2H),
6.42 (t, J = 2.1 Hz, 1H), 3.81 (s, 6H); 13C NMR (75 MHz, CDCl3) d
161.0, 141.5, 138.1, 132.4, 132.3, 127.1, 126.8, 118.9, 110.6,
104.9, 100.7, 55.3; CIMS m/z 266 (MH+); HRMS calcd for
4.2.32. 3,5-Dimethoxyl-40-amino-trans-stilbene (53)51
This compound was prepared in 67% yield by following GP 2.
Yellow solid: mp 134–135 °C. IR (film) 3368, 1588, 1509, 1462,
1336, 1205, 1164, 1064, 952 cmꢀ1 1H NMR (300 MHz, CDCl3) d
;
8.20 (d, J = 8.7 Hz, 2H), 7.61 (d, J = 8.7 Hz, 2H), 7.18 (d, J = 16.2 Hz,
1H), 7.09 (d, J = 16.2 Hz, 1H), 6.68 (d, J = 1.8 Hz, 2H), 6.43 (t,
J = 2.1 Hz, 1H), 3.83 (s, 6H); 13C NMR (75 MHz, CDCl3) d 160.7,
133.8, 129.7, 128.2, 126.8, 123.4, 106.6, 105.0, 100.9, 100.0, 55.2;
CIMS m/z 286 (MH+).
C
17H15O2N m/z 265.1103, found: m/z 265.1096 (M+).
4.2.39. 4-(3,5-Dimethoxyphenethyl)benzenamine (60)
This compound was prepared in 95% yield by following GP 4.
Yellow solid: mp 41–42 °C. IR (film) 3368, 2927, 2870, 1597,