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Pharmacol. 1996, 50, 846.
180 (12%), 179 (100%), 175 (8%), 166 (11%), 165 (13%), 145
(7%). Compound 4b: beige solid; mp 180–184 °C; IR mmax
(KBr/cmꢀ1) 1785, 1721, 1707, 1676, 1609, 1505, 1491, 1436,
1274, 1175, 1143, 1034; 1H NMR (DMSO-d6): 3.72 (s, 3H),
3.83 (s, 3H), 5.23 (s, 2H), 6.22 (s, 2H), 6.62 (d, 1H,
3
3J = 16.0 Hz), 6.91 (d, 1H, J = 8.3 Hz), 6.93 (s, 1H), 7.34
(m, 2H), 7.53 (s, 1H), 7.60 (d, 1H, 3J = 16.0 Hz), 9.95 (s, 1H);
13C NMR (DMSO-d6): 45.1, 49.5, 58.8, 97.0, 98.3, 100.4,
105.9, 106.0, 109.4, 115.7, 117.7, 120.6, 138.2, 139.9, 140.8,
141.9, 144.8, 146.8, 160.7, 161.4, 181.7; IEMS (70 eV): 414
(M+Å, 12%), 221 (10%), 208 (10%), 207 (8%), 206 (40%), 189
(12%), 180 (11%), 179 (100%), 175 (9%), 166 (13%), 165
(14%), 161 (11%), 145 (7%). Compound 7a: white solid; mp
234 °C; IR mmax (KBr/cmꢀ1) 1722, 1640, 1600, 1505, 1487,
1455, 1430, 1352, 1306, 1261, 1196, 1175, 1156, 1133, 1070;
1H NMR (CDCl3): 3.79 (s, 3H), 3.87 (s, 3H), 6.02 (s, 2H),
6.38 (d, 1H, 3J = 16.0 Hz), 6.68 (s, 1H), 6.84 (s, 1H), 6.86 (s,
3
1H), 7.03 (d, 1H, J = 8.0 Hz), 7.10–7.13 (m, 2H), 7.65 (d,
1H, 3J = 16.0 Hz); 13C NMR (CDCl3): 51.8, 56.1, 98.2,
102.2, 104.4, 111.9, 112.5, 117.7, 120.4, 121.7, 122.2, 132.2,
140.2, 144.0, 145.2, 145.4, 147.3, 149.6, 150.8, 157.2, 167.2;
IEMS (70 eV): 397 (M+Å+H, 11%), 396 (M+Å, 45%), 365
(7%), 309 (10%), 204 (27%), 203 (100%), 177 (25%), 175
(14%). Compound 7b: beige solid; mp 199–203 °C; IR mmax
(KBr/cmꢀ1) 1716, 1637, 1599, 1519, 1488, 1451, 1329, 1263,
1
1223, 1176, 1164, 1132, 1023; H NMR (CDCl3): 3.75 (s,
3H), 3.82 (s, 3H), 6.02 (s, 2H), 6.26 (d, 1H,3J = 16.0 Hz),
6.66 (s, 1H), 6.76 (s, 1H), 6.82 (s, 1H), 6.99 (d, 1H,
3J = 8.6 Hz), 7.22 (s, 1H), 7.35 (d, 1H, 3J = 8.6 Hz), 7.60 (d,
1H, 3J = 16.0 Hz); 13C NMR (CDCl3): 45.4, 50.0, 92.0, 96.0,
98.2, 106.4, 106.8, 110.4, 113.4, 115.1, 120.5, 121.7, 134.4,
137.3, 137.5, 139.0, 141.0, 143.3, 146.3, 151.0, 161.1; IEMS
(70 eV): 397 (M+Å+H, 11%), 396 (M+Å, 49%), 365 (10%), 204
(21%), 203 (100%), 177 (24%), 175 (16%). Compound 8a:
brown solid; mp 248 °C (dec); IR mmax (KBr/cmꢀ1) 1670,
1605, 1523, 1444, 1406, 1346, 1278, 1262, 1228, 1217, 1136,
1100; 1H NMR (acetone-d6): 6.42 (d, 1H, 3J = 15.9 Hz),
6.84 (s, 1H), 7.01 (s, 1H), 7.09 (d, 1H, 3J = 8.4 Hz), 7.16 (dd,
1H, 3J = 8.4 Hz, 4J = 1.8 Hz), 7.28 (s, 1H), 7.30 (d, 1H,
4J = 1.8 Hz), 7.09 (d, 1H, 3J = 15.9 Hz); 13C NMR (ace-
tone-d6): 103.3, 112.1, 112.5, 117.1, 118.5, 120.6, 121.5,
124.8, 132.7, 140.0, 143.7, 144.9, 145.8, 146.8, 148.8, 149.2,
158.0, 167.8; IEMS (70 eV): 357 (M+Å+H, 16%), 356 (M+Å,
80%), 339 (7%), 338 (20%), 253 (8%), 192 (8%), 191 (100%),
178 (46%), 177 (94%), 166 (13%), 165 (26%), 163 (7%), 162
(27%), 150 (46%), 137 (10%), 121 (11%), 67 (11%). Com-
26. Abd-Elazem, I. S.; Chen, H. S.; Bates, R. B.; Huang, R. C.
C. Antiviral. Res. 2002, 55, 91.
27. (a) Maurin, C.; Bailly, F.; Cotelle, P. Tetrahedron 2004,
60, 6479; (b) Bailly, F.; Maurin, C.; Teissier, E.; Vezin, H.;
Cotelle, P. Bioorg. Med. Chem. 2004, 12, 5611.
28. (a) Nazeruddin, G. M.; Kelkar, S. L.; Wadia, M. S. Synth.
Commun. 1987, 17, 1383; (b) Mulay, B. D.; Kelkar, S. L.;
Wadia, M. S. Synth. Commun. 1987, 17, 535; (c) Salunke,
P. S.; Phadke, C. P.; Kelkar, S. L.; Wadia, M. S. Synthesis
1985, 111; (d) Phadke, C. P.; Kelkar, S. L.; Wadia, M. S.
Synthesis 1986, 413.
29. (a) Deshpande, A. R.; Paradkar, M. V. Synth. Commun.
1990, 20, 809; (b) Deshpande, A. R.; Thombe, H. M.;
Natu, A. D.; Paradkar, M. V. Indian J. Chem. 1992, 31B,
759.
pound 8b: black solid; mp 280 °C (dec); IR mmax (KBr/cmꢀ1
)
1666, 1620, 1572, 1513, 1456, 1435, 1411, 1284, 1215, 1184;
3
1H NMR (acetone-d6): 6.35 (d, 1H, J = 16.0 Hz), 6.81 (s,
1H), 6.88 (s, 1H), 7.03 (d, 1H, 3J = 8.4 Hz), 7.28 (s, 1H), 7.41
(dd, 1H, 3J = 8.4 Hz, 4J = 2.0 Hz), 7.49 (d, 1H, 4J = 2.0 Hz),
7.57 (d, 1H, 3J = 16.0 Hz), 8.38 (br s, 1H), 8.91 (br s, 1H),
9.00 (br s, 1H); 13C NMR (acetone-d6): 97.2, 106.0, 106.3,
110.7, 112.2, 114.2, 118.1, 120.9, 121.8, 134.3, 137.5, 138.0,
138.6, 140.5, 142.6, 145.1, 152.0, 161.8; IEMS (70 eV): 357
(M+Å+H, 11%), 356 (M+Å, 54%), 339 (8%), 338 (33%), 328
(7%), 312 (8%), 191 (45%), 178 (63%), 177 (90%), 165 (23%),
162 (61%), 150 (71%), 137 (9%).
30. Gallastegui, J.; Lago, J. M.; Palomo, C. J. Chem. Res. (S)
1984, 170.
31. (a) Smith, W. E. J. Org. Chem. 1972, 37, 3972; (b) Saito,
N.; Tashiro, K.; Maru, Y.; Yamaguchi, K.; Kubo, A.
J. Chem. Soc., Perkin Trans. 1 1997, 53.
32. Yamaguchi, S.; Saitoh, M.; Kawase, Y. J. Heterocycl.
Chem. 1991, 28, 125.
33. Compound 4a: beige solid; mp 163–167 °C; IR mmax (KBr/
cmꢀ1) 1794, 1701, 1670, 1638, 1623, 1518, 1478, 1438, 1309,
1268, 1202, 1186, 1167, 1137, 1078; 1H NMR (CDCl3): 3.80
(s, 3H), 3.93 (s, 3H), 5.05 (s, 2H), 6.09 (s, 2H), 6.34 (d, 1H,
34. Mahmood, N.; Moore, P. S.; De Tommasi, N.; De
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35. Pluymers, W.; Neamati, N.; Pannecouque, C.; Fikkert, V.;
Marchand, C.; Burke, T. R., Jr.; Pommier, Y.; Schols, D.;
De Clercq, E.; Debyser, Z.; Witvrouw, M. Mol. Pharma-
col. 2000, 58, 641.
36. Reinke, A. R.; Lee, D. J.; McDougall, B. R.; King, P. J.;
Victoria, J.; Mao, Y.; Lei, X.; Reinecke, M. G.; Robinson,
W. E., Jr. Virology 2004, 326, 203.
3
3J = 15.9 Hz), 6.67 (s, 1H), 7.02 (d, 1H, J = 8.3 Hz), 7.05
(m, 2H), 7.07 (m, 2H), 7.25 (d, 1H, 3J = 1.9 Hz), 7.63 (d, 1H,
3J = 15.9 Hz), 9.87 (s, 1H); 13C NMR (CDCl3): 51.7, 56.0,
66.2, 102.9, 104.3, 108.3, 110.8, 114.4, 116.5, 122.0, 122.1,
129.4, 144.3, 146.4, 147.9, 148.9, 149.8, 153.2, 167.2, 167.5,
186.7; IEMS (70 eV): 414 (M+Å, 12%), 207 (11%), 206 (26%),