Efficient Synthetic Method for the Title Compounds
1607
J ¼ 8.4 Hz, ArH). Found: C, 71.30; H, 4.64. C20H16O5 requires C, 71.42; H,
4.79%.
10-(2-Chlorophenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-3,4,5,6,9,10-hexa
hydroanthracene, 3c: IR (KBr, n): 3091, 1732, 1705, 1647, 1610, 1479,
1
1442, 1379, 1247, 1186, 1142, 1037, 972, 810, 756, 692 cm21; H NMR
(CDCl3, d): 2.24 (s, 6H, 2CH3), 5.07 (s, 1H, CH), 5.96 (s, 2H, 2C55CH),
7.14–7.53 (m, 4H, ArH). Found: C, 64.06; H, 3.60. C19H13ClO5 requires
C, 63.97; H, 3.67%.
10-(2-Bromophenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-3,4,5,6,9,10-hexa
hydroanthracene, 3d: IR (KBr, n): 3085, 1729, 1641, 1610, 1525, 1444,
;
1380, 1243, 1240, 1137, 1039, 968, 840, 794, 748 cm21 1H NMR
(CDCl3, d): 2.25 (s, 6H, 2CH3), 5.11 (s, 1H, CH), 5.96 (s, 2H, 2C55CH),
7.05–7.47 (m, 4H, ArH). Found: C, 56.98; H, 3.21. C19H13BrO5 requires
C, 56.88; H, 3.27%.
10-(4-Bromophenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-3,4,5,6,9,10-hexa
hydroanthracene, 3e: IR (KBr, n): 3085, 1749, 1718, 1639, 1604, 1490,
;
1375, 1242, 1186, 1132, 1075, 966, 815, 706, 698 cm21 1H NMR
(CDCl3, d): 2.25 (s, 6H, CH3), 4.79 (s, 1H, CH), 5.99 (s, 2H, C55CH),
7.21 (s, 2H, J ¼ 8.4 Hz, ArH), 7.34 (s, 2H, J ¼ 8.4 Hz, ArH). Found: C,
56.96; H, 3.34. C19H13BrO5 requires C, 56.88; H, 3.27%.
10-(4-Hydroxyphenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-3,4,5,6,9,10-hexah
ydroanthracene, 3f: IR (KBr, n): 3433, 3091, 1760, 1730, 1703, 1611, 1600, 150,
1
1438, 1377, 1242, 1201, 1186, 964, 916, 804, 742, 692, 670 cm21; H NMR
(CDCl3, d): 2.25 (s, 6H, 2CH3), 4.85 (s, 1H, CH), 5.99 (s, 2H, 2C55CH), 6.99
(s, 2H, J ¼ 8.4 Hz, ArH), 7.30 (s, 2H, J ¼ 8.4 Hz, ArH). Found: C, 67.58; H,
4.09. C19H14O6 requires C, 67.45; H, 4.17%.
10-(4-Hydroxy-3-methoxyphenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-
3,4,5,6,9,10-hexahydroanthracene, 3g: IR (KBr, n): 3415, 3097, 1768, 1728,
1640, 1602, 1500, 1442, 1377, 1241, 1137, 1029, 962, 900, 842 794, 702,
1
640 cm21; H NMR (CDCl3, d): 2.25(s, 6H, CH3), 3.85 (s, 3H, OCH3),
4.86 (s, 1H, CH), 5.99 (s, 2H, C55CH), 6.66–7.20 (m, 3H, ArH). Found: C,
65.32; H, 4.45. C20H16O7 requires C, 65.22; H, 4.38%.
10-(4-Nitrophenyl)-2,7-dimethyl-4,5-dioxo-3,6,9-trioxa-3,4,5,6,9,10-hexah
ydroanthracene, 3h: IR (KBr, n): 3085, 1722, 1639, 1608, 1515, 1440,
;
1348, 1245, 1188, 1136, 1035, 974, 839, 744, 692 cm21 1H NMR
(CDCl3, d): 2.27 (s, 6H, CH3), 4.92 (s, 1H, CH), 6.04 (s, 2H,
C55CH), 7.45 (s, 2H, J ¼ 8.6 Hz, ArH), 8.10 (s, 2H, J ¼ 8.6 Hz, ArH).
Found: C, 62.30; H, 3.46; N, 3.74. C19H13NO7 requires C, 62.13; H,
3.57; N, 3.81%.