2014
J. Potenziano, R. Spitale, and M. E. Janik
1
bs, 1H); 3.99 (s, 3H); 3.93 (s, 3H); 3.65 (s, 3H); C NMR (CDCl ) d 180.30,
3
(
3
1
1
2
64.25, 148.04, 144.58, 139.72, 138.86, 138.92, 136.34, 132.61, 129.11,
20.42, 112.88, 106.90, 61.08, 56.62, 56.58; IR 3540–3210 (broad), 3036,
21
980–2920, 1632, 1582, 1476, 1432, 1278, 1090cm ; GC: t ¼ 48.86 min,
R
purity . 99% (only one peak was observed); MS m/z (intensity %): 288
(
100), 260 (76), 245 (48), 227 (12), 213 (23), 199 (25), 185 (50), 183 (17),
59 (9), 145 (11), 128 (26), 115 (28).
1
0
0
0
2
-Methoxy-5-(2 4 -dimethoxy-3 -nitrophenyl)tropone 9c: mp: 171–1728C;
1
H NMR (CDCl ) d 7.41 (d, 1H, J ¼ 12.7Hz); 7.32 (d, 1H, J ¼ 8.8 Hz); 7.23
3
(
d, 1H, J ¼ 12.7 Hz); 7.20 (d, 1H, J ¼ 10.5 Hz); 6.84 (d, 1H, J ¼ 8.8 Hz);
6
.79 (d, 1H, J ¼ 10.5 Hz); 3.97 (s, 3H); 3.91 (s, 3H); 3.57 (s, 3H);
1
3
C NMR (CDCl ) d 179.83, 164.88, 151.39, 149.72, 147.62, 138.20,
3
1
5
36.29, 132.76, 132.19, 131.92, 130.11, 111.89, 107.97, 62.34, 56.64,
2
1
6.38; IR 3080, 2982–2890, 1628, 1592, 1496, 1422, 1376, 1242 cm
;
GC: t ¼ 47.13 min, purity . 99% (only one peak was observed); MS m/z
R
(
intensity %): 317 (10), 289 (100), 274 (42), 256 (22), 242 (37), 228 (62),
16 (10), 201 (18), 145 (49), 115 (31).
2
0
0
0
2
-Methoxy-5-(2 ,4 -dimethoxy-3 -methylphenyl)tropone 9d: mp: 142–1438C;
1
H NMR (CDCl ) d 7.39 (d, 1H, J ¼ 12.3 Hz); 7.28 (d, 1H, J ¼ 12.3 Hz); 7.19
3
(
d, 1H, J ¼ 10.2 Hz); 6.99 (d, 1H, J ¼ 8.3 Hz); 6.82 (d, 1H J ¼ 10.2 Hz); 6.74
d, 1H, J ¼ 8.3 Hz); 3.98 (s, 3H); 3.90 (s, 3H); 3.61 (s, 3H); 2.20 (s, 3H);
(
1
3
C NMR (CDCl ) d 180.24, 164.92, 152.02, 149.33, 143.88, 140.21,
3
1
5
1
38.44, 137.61, 131.45, 130.14, 125.70, 111.88, 108.82, 60.90, 56.93,
6.10, 29.20; IR 3050, 2984–2882, 1627, 1588, 1498, 1425, 1270,
2
1
096 cm ; GC: t ¼ 45.68 min, purity . 99% (only one peak was
R
observed); MS m/z (intensity %): 286 (100), 258 (72), 243 (29), 227 (4),
2
15 (33), 200 (16), 185 (11), 152 (8), 128 (53), 115 (14).
0 0 0
-Methoxy-5-(2 -t-butyldimethylsilyloxy-3 ,4 -dimethoxyphenyl)tropone 9e:
2
1
mp: 152–1538C; H NMR (CDCl ) d 7.48 (dd, 1H, J ¼ 12.6, J ¼ 2.2 Hz);
3
7
.26 (d, 1H, J ¼ 12.7 Hz); 7.16 (dd, 1H, J ¼ 10.9, J ¼ 2.2 Hz); 6.93 (d, 1H,
J ¼ 9.6 Hz); 6.78 (d, 1H, J ¼ 11.0 Hz); 6.63 (d, 1H, J ¼ 9.6 Hz); 3.99
1
3
s, 3H); 3.90 (s, 3H); 3.82 (s, 3H); 0.79 (s, 9H); 0.02 (s, 6H); C NMR
(
(CDCl ) d 180.24, 164.66, 153.92, 147.10, 140.92, 140.27, 136.22, 134.80,
3
1
33.10, 128.78, 124.74, 112.96, 105.52, 60.82, 56.58, 56.20, 25.60, 18.72,
4.08; IR 3040, 2976–2928, 1632, 1570, 1496, 1446, 1284, 1222,
2
2
1
1
observed); MS m/z (intensity %): 402 (6), 387 (9), 345 (100), 330 (18),
082 cm ; GC: t ¼ 51.22 min, purity . 99% (only one peak was
R
3
14 (36), 302 (39), 287 (20), 259 (16), 244 (12), 165 (19), 150 (11), 114 (10).
0
0
0
2
1
-Methoxy-5-(2 -hydroxy-3 ,4 -dimethoxyphenyl)tropone 9f: mp: 167–
1
688C; H NMR (CDCl ) d 7.53 (dd, 1H, J ¼ 12.4, J ¼ 1.8 Hz); 7.29
3
(
d, 1H, J ¼ 12.4 Hz); 7.23 (dd, 1H, J ¼ 10.2, J ¼ 1.8 Hz); 6.95 (d, 1H,