C. M. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro
1-Methoxy-7-(4-methoxyphenyl)-6-phenyl-9H-xanthen-9-one (5o): 408 (6), 395 (13), 391 (12), 380 (6), 363 (6), 351 (8). C28H22O5
FULL PAPER
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M.p. 192–194 °C. H NMR: δ = 3.79 (s, 3 H, 4Ј-OCH3), 4.04 (s, 3
H, 8-OCH3), 6.78 (d, J = 8.8 Hz, 2 H, 3Ј,5Ј-H), 6.82 (d, J = 8.3 Hz,
1 H, 7-H), 7.08 (d, J = 8.8 Hz, 2 H, 2Ј,6Ј-H), 7.08 (dd, J = 8.3,
0.8 Hz, 1 H, 5-H), 7.18–7.21 (m, 2 H, 2ЈЈ,6ЈЈ-H), 7.27–7.29 (m, 3
H, 3ЈЈ,4ЈЈ,5ЈЈ-H), 7.46 (s, 1 H, 4-H), 7.62 (t, J = 8.3 Hz, 1 H, 6-H),
8.30 (s, 1 H, 1-H) ppm. 13C NMR: δ = 55.2 (4Ј-OCH3), 56.5 (8-
OCH3), 105.4 (C-7), 110.1 (C-5), 112.6 (C-8a), 113.4 (C-3Ј,5Ј),
118.9 (C-4), 121.9 (C-9a), 127.4 (C-4ЈЈ), 128.1 (C-3ЈЈ,5ЈЈ), 128.2 (C-
1), 129.6 (C-2ЈЈ,6ЈЈ), 131.0 (C-2Ј,6Ј), 132.4 (C-1Ј), 134.8 (C-6), 136.5
(C-2), 140.2 (C-1ЈЈ), 146.9 (C-3), 153.9 (C-4a), 158.2 (C-4b), 158.5
(C-4Ј), 160.8 (C-8), 176.4 (C-9) ppm. EI-MS: m/z (%) = 408 [M]+·
(100), 407 (23), 391 (14), 390 (9), 380 (10), 379 (41), 363 (14), 362
(32), 347 (10), 346 (6), 305 (5). C27H20O4 (408.45): calcd. for C
79.40, H 4.94; found C 79.42, H 4.91.
(438.47): calcd. for C 76.70, H 5.06; found C 76.73, H 5.27.
7-(3,4-Dimethoxyphenyl)-1-methoxy-6-phenyl-3,4-dihydro-9H-
xanthen-9-one (6p): Yellowish oil. 1H NMR: δ = 2.91 (dd, J = 17.3,
1.4 Hz, 1 H, 4trans-H), 3.60 (dd, J = 17.3, 9.1 Hz, 1 H, 4cis-H), 3.82
and 3.84 (2ϫs, 6 H, 3Ј,4Ј-OCH3), 3.99 (s, 3 H, 8-OCH3), 4.25 (dd,
J = 9.1, 1.4 Hz, 1 H, 3-H), 6.75 (d, J = 8.4 Hz, 1 H, 5Ј-H), 6.78
(dd, J = 8.4, 0.7 Hz, 1 H, 7-H), 6.90 (dd, J = 8.4, 0.7 Hz, 1 H, 5-
H), 6.95 (dd, J = 8.4, 2.1 Hz, 1 H, 6Ј-H), 7.07 (d, J = 2.1 Hz, 1 H,
2Ј-H), 7.18–7.31 (m, 5 H, 3-C6H5), 7.46 (s, 1 H, 1-H), 7.46 (t, J =
8.4 Hz, 1 H, 6-H) ppm. 13C NMR: δ = 36.1 (C-4), 41.9 (C-3), 55.74
and 55.84 (3Ј,4Ј-OCH3), 56.4 (8-OCH3), 106.3 (C-7), 108.7 (C-2Ј),
110.1 (C-5), 110.8 (C-5Ј), 114.5 (C-8a), 115.4 (C-1), 117.9 (C-9a),
118.2 (C-6Ј), 127.1 (C-4ЈЈ), 127.3 (C-2ЈЈ,6ЈЈ), 128.9 (C-3ЈЈ,5ЈЈ), 133.2
(C-1Ј), 133.0 (C-6), 135.6 (C-2), 141.1 (C-1ЈЈ), 148.7 and 148.8 (C-
3Ј, C-4Ј), 157.9 (C-4b), 159.7 (C-4a), 160.2 (C-8), 174.0 (C-9) ppm.
EI-MS: m/z (%) = 440 [M]+· (22), 439 (24), 408 (100), 423 (20),
395 (10), 391 (9), 363 (8). HRMS (EI): calcd. for C28H24O5 [M]+·
440.1624; found 440.1615.
1-Methoxy-7-(4-methoxyphenyl)-6-phenyl-7,8-dihydro-9H-xanthen-
9-one (6o): M.p. 168–170 °C. 1H NMR: δ = 2.89 (dd, J = 17.3,
1.5 Hz, 1 H, 4trans-H), 3.58 (dd, J = 17.3. 8.5 Hz, 1 H, 4cis-H), 3.76
(s, 3 H, 4Ј-OCH3), 3.98 (s, 3 H, 8-OCH3), 4.24 (brd, J = 8.5 Hz, 1
H, 3-H), 6.76 (d, J = 8.4 Hz, 1 H, 7-H), 6.80 (d, J = 8.9 Hz, 2 H,
3Ј,5Ј-H), 6.89 (dd, J = 8.4, 0.7 Hz, 1 H, 5-H), 7.17–7.30 (m, 5 H,
3-C6H5), 7.40 (d, J = 8.9 Hz, 2 H, 2Ј,6Ј-H), 7.44 (t, J = 8.4 Hz, 1
H, 6-H), 7.45 (s, 1 H, 1-H) ppm. 13C NMR: δ = 36.1 (C-4), 41.7
(C-3), 55.2 (8-OCH3), 56.3 (8-OCH3), 106.2 (C-7), 110.1 (C-5),
113.8 (C-3Ј,5Ј), 114.4 (C-8a), 115.1 (C-1), 117.9 (C-9a), 126.8 (C-
2Ј,6Ј), 127.0 (C-4ЈЈ), 127.3 (C-2ЈЈ,6ЈЈ), 128.9 (C-3ЈЈ,5ЈЈ), 131.7 (C-
1Ј), 132.9 (C-6), 134.4 (C-2), 140.9 (C-1ЈЈ), 157.8 (C-4b), 159.0 (C-
4Ј), 159.6 (C-4a), 160.1 (C-8), 173.9 (C-9) ppm. EI-MS: m/z (%) =
410 [M]+· (10), 409 (28), 408 (100), 407 (34), 391 (21), 390 (15), 380
(18), 379 (62), 363 (26), 362 (43), 347 (16), 305 (9), 153 (10), 152
(13), 137 (14), 121 (21), 99 (16), 78 (9). HRMS (EI): calcd. for
C27H22O4 [M]+· 410.1518; found 410.1505.
7-(3,4-Dimethoxyphenyl)-1-hydroxy-6-phenyl-9H-xanthen-9-one
(12p): M.p. 186–188 °C. 1H NMR: δ = 3.56 (s, 3 H, 4Ј-OCH3), 3.88
(s, 3 H, 3Ј-OCH3), 6.52 (d, J = 1.9 Hz, 1 H, 2Ј-H), 6.80 (d, J =
8.2 Hz, 1 H, 5Ј-H), 6.82 (d, J = 8.3 Hz, 1 H, 7-H), 6.84 (dd, J =
8.2, 1.9 Hz, 1 H, 6Ј-H), 6.95 (dd, J = 8.3, 0.7 Hz, 1 H, 5-H), 7.20–
7.24 (m, 2 H, 2ЈЈ,6ЈЈ-H), 7.28–7.32 (m, 3 H, 3ЈЈ,4ЈЈ,5ЈЈ-H), 7.52 (s,
1 H, 4-H), 7.61 (t, J = 8.3 Hz, 1 H, 6-H), 8.30 (s, 1 H, 1-H), 12.69
(s, 1 H, 8-OH) ppm. 13C NMR: δ = 55.5 (4Ј-OCH3), 55.7 (3Ј-
OCH3), 107.0 (C-5), 109.0 (C-8a), 110.5 (C-7), 110.7 (C-5Ј), 113.3
(C-2Ј), 119.3 (C-4), 119.4 (C-9a), 122.1 (C-6Ј), 127.0 (C-1), 127.7
(C-4ЈЈ), 128.2 (C-3ЈЈ,5ЈЈ), 129.4 (C-2ЈЈ,6ЈЈ), 132.0 (C-1Ј), 136.7 (C-
6), 136.9 (C-2), 139.9 (C-1ЈЈ), 148.09 and 148.12 (C-3Ј,4Ј), 148.4
(C-3), 155.0 (C-4a), 156.4 (C-4b), 161.9 (C-8) 182.1 (C-9) ppm. EI-
MS: m/z (%) = 424 [M]+· (100), 409 (20), 381 (10), 377 (14), 363
(10), 349 (13), 337 (10), 139 (10), 137 (14), 125 (12), 111 (16), 110
(13), 97 (19), 96 (13), 86 (13), 84 (19), 83 (15), 81 (16), 73 (12), 69
(17). C27H20O5 (424.45): calcd. for C 76.40, H 4.75; found C 76.11,
H 4.75.
1-Hydroxy-7-(4-methoxyphenyl)-6-phenyl-9H-xanthen-9-one (12o):
1
M.p. 126–128 °C. H NMR: δ = 3.79 (s, 3 H, 4Ј-OCH3), 6.77 (d, J
= 8.8 Hz, 2 H, 3Ј,5Ј-H), 6.81 (dd, J = 8.4, 0.7 Hz, 1 H, 7-H), 6.93
(dd, J = 8.4, 0.7 Hz, 1 H, 5-H), 7.07 (d, J = 8.8 Hz, 2 H, 2Ј,6Ј-H),
7.18–7.21 (m, 2 H, 2ЈЈ,6ЈЈ-H), 7.26–7.30 (m, 3 H, 3ЈЈ,4ЈЈ,5ЈЈ-H), 7.49
(s, 1 H, 4-H), 7.59 (t, J = 8.4 Hz, 1 H, 6-H), 8.25 (s, 1 H, 1-H),
12.70 (s, 1 H, 8-OH) ppm. 13C NMR: δ = 55.2 (4Ј-OCH3), 107.0
(C-5), 109.0 (C-8a), 110.5 (C-7), 113.5 (C-3Ј,5Ј), 119.35 (C-4),
119.38 (C-9a), 127.3 (C-4ЈЈ), 127.7 (C-1), 128.2 (C-3ЈЈ,5ЈЈ), 129.5
(C-2ЈЈ,6ЈЈ), 131.0 (C-2Ј,6Ј), 131.9 (C-1Ј), 136.7 (C-6), 136.9 (C-2),
139.8 (C-1ЈЈ), 148.4 (C-3), 155.0 (C-4a), 156.4 (C-4b), 158.7 (C-4Ј),
161.9 (C-8) 182.1 (C-9) ppm. EI-MS: m/z (%) = 394 [M]+· (100),
393 (15), 395 (25), 379 (15), 363 (15), 351 (10), 129 (17), 125 (11),
123 (10), 111 (17), 97 (22), 96 (13), 86 (14), 84 (16), 83 (21), 73 (12),
69 (12). HRMS (EI): calcd. for C27H22O4 [M]+· 394.1205; found
394.1204.
6-(3,4-Dimethoxyphenyl)-1-methoxy-7-phenyl-9H-xanthen-9-one
(5q): M.p. 188–190 °C. 1H NMR: δ = 3.52 (s, 3 H, 3ЈЈ-OCH3), 3.88
(s, 3 H, 4ЈЈ-OCH3), 4.04 (s, 3 H, 8-OCH3), 6.54 (d, J = 2.0 Hz, 1
H, 2ЈЈ-H), 6.82 (d, J = 8.4 Hz, 2 H, 5ЈЈ-H, 7-H), 6.90 (dd, J = 8.4,
2.0 Hz, 1 H, 6ЈЈ-H), 7.09 (dd, J = 8.4, 0.8 Hz, 1 H, 5-H), 7.17–7.20
(m, 2 H, 2Ј,6Ј-H), 7.23–7.27 (m, 3 H, 3Ј,4Ј,5Ј-H), 7.50 (s, 1 H, 4-
H), 7.62 (t, J = 8.4 Hz, 1 H, 6-H), 8.31 (s, 1 H, 1-H) ppm. 13C
NMR: δ = 55.5 (3ЈЈ-OCH3), 55.8 (4ЈЈ-OCH3), 56.5 (8-OCH3), 105.5
(C-7), 110.0 (C-5), 110.7 (C-5ЈЈ), 112.6 (C-8a), 113.3 (C-2ЈЈ), 118.3
(C-4), 121.6 (C-9a), 121.8 (C-6ЈЈ), 126.7 (C-4Ј), 128.1 (C-3Ј,5Ј),
128.4 (C-1), 129.9 (C-2Ј,6Ј), 132.3 (C-1ЈЈ), 134.6 (C-6), 136.8 (C-2),
140.4 (C-1Ј), 146.6 (C-3), 148.1 and 148.5 (C-3ЈЈ, C-4ЈЈ), 154.2 (C-
4a), 158.2 (C-4b), 160.8 (C-8), 176.3 (C-9) ppm. EI-MS: m/z (%) =
438 [M]+· (100), 437 (19), 422 (5), 421 (18), 420 (8), 410 (8), 409
(35), 393 (13), 392 (20), 377 (6), 376 (5), 361 (6), 333 (5). C28H22O5
(438.47): calcd. for C 76.70, H 506; found C 76.66, H 5.11.
7-(3,4-Dimethoxyphenyl)-1-methoxy-6-phenyl-9H-xanthen-9-one
1
(5p): M.p. 189–190 °C. H NMR: δ = 3.55 (s, 3 H, 3Ј-OCH3), 3.87
(s, 3 H, 4Ј-OCH3), 4.04 (s, 3 H, 8-OCH3), 6.53 (d, J = 1.9 Hz, 1 H,
2Ј-H), 6.80 (d, J = 8.3 Hz, 1 H, 5Ј-H), 6.83 (dd, J = 8.6, 0.9 Hz, 1
H, 7-H), 6.85 (dd, J = 8.3, 1.9 Hz, 1 H, 6Ј-H), 7.09 (dd, J = 8.6,
0.9 Hz, 1 H, 5-H), 7.19–7.22 (m, 2 H, 2ЈЈ,6ЈЈ-H), 7.27–7.31 (m, 3
6-(3,4-Dimethoxyphenyl)-1-methoxy-7-phenyl-7,8-dihydro-9H-
H, 3ЈЈ,4ЈЈ,5ЈЈ-H), 7.47 (s, 1 H, 4-H), 7.62 (t, J = 8.6 Hz, 1 H, 6-H), xanthen-9-one (6q): Yellowish oil. 1H NMR: δ = 2.91 (dd, J = 17.3,
8.35 (s, 1 H, 1-H) ppm. 13C NMR: δ = 55.5 (3Ј-OCH3), 55.8 (4Ј- 1.4 Hz, 1 H, 4trans-H), 3.58 (dd, J = 17.3, 8.6 Hz, 1 H, 4cis-H), 3.76
OCH3), 56.5 (8-OCH3), 105.4 (C-7), 110.1 (C-5), 110.7 (C-5Ј), (s, 3 H, 3ЈЈ-OCH3), 3.80 (s, 3 H, 4ЈЈ-OCH3), 3.99 (s, 3 H, 8-OCH3),
112.6 (C-8a), 113.5 (C-2Ј), 118.8 (C-4), 121.9 (C-9a), 122.1 (C-6Ј), 4.22 (dd, J = 8.6, 1.4 Hz, 1 H, 3-H), 6.72 (d, J = 8.2 Hz, 1 H, 5ЈЈ-
127.4 (C-4ЈЈ), 128.0 (C-1), 128.2 (C-3ЈЈ,5ЈЈ), 129.5 (C-2ЈЈ,6ЈЈ), 132.4 H), 6.79 (d, J = 8.4 Hz, 1 H, 7-H), 6.81 (d, J = 2.0 Hz, 1 H, 2ЈЈ-
(C-1Ј), 134.8 (C-6), 136.5 (C-2), 140.3 (C-1ЈЈ), 146.9 (C-3), 147.9
and 148.0 (C-3Ј, C-4Ј), 154.0 (C-4a), 158.2 (C-4b), 160.8 (C-8),
176.4 (C-9) ppm. EI-MS: m/z = 438 [M]+· (100), 424 (7), 423 (25),
H), 6.84 (dd, J = 8.2, 2.0 Hz, 1 H, 6ЈЈ-H), 6.92 (dd, J = 8.4, 0.7 Hz,
1 H, 5-H), 7.19–7.31 (m, 3 H, 3Ј,4Ј,5Ј-H), 7.46 (d, J = 8.4 Hz, 2 H,
2Ј,6Ј-H), 7.47 (t, J = 8.4 Hz, 1 H, 6-H), 7.53 (s, 1 H, 1-H) ppm.
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Eur. J. Org. Chem. 2009, 2642–2660