Page 19 of 29
The Journal of Organic Chemistry
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[1ꢀ(4ꢀMethoxyphenyl)ꢀ1Hꢀbenzo[f]chromenꢀ2ꢀyl](phenyl)methanone (10d). Yield: 85%,
485 mg. Colorless solid, mp 212–214 °C (ethanol). IR (KBr) υmax: 1639, 1593, 1508, 1462, 1381,
1319, 1312, 1257, 1227, 1177, 1037, 833, 810, 698 cm–1. 1H NMR (400 MHz, CDCl3) δ: 3.69 (s,
3H), 5.97 (s, 1H), 6.73 (d, J = 8.7 Hz, 2H), 7.28–7.32 (m, 3H), 7.36–7.51 (m, 6H), 7.54–7.56 (m,
2H), 7.75–7.80 (m, 2H), 7.99 (d, J = 8.5 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ: 35.7 (CH),
55.2 (СH3), 113.9 (2CH), 116.7 (C), 117.1 (CH), 120.7 (C), 123.9 (CH), 125.0 (CH), 127.1
(CH), 128.4 (2CH), 128.5 (CH), 128.9 (2CH), 129.1 (CH), 129.5 (2CH), 131.6 (C), 131.7 (CH),
131.8 (C), 137.3 (C), 138.8 (C), 147.7 (C), 152.4 (CH), 158.1 (C), 195.0 (C). Anal. Calcd (%)
for C27H20O3: C, 82.63; H, 5.14. Found (%): C, 82.52; H, 5.19.
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(1HꢀBenzo[f]chromenꢀ2ꢀyl)(2ꢀhydroxyphenyl)methanone (10e). Yield: 68%, 297 mg.
Colorless solid, mp 163–165 °C (ethanol). IR (KBr) υmax: 3300–2600, 1628, 1601, 1570, 1466,
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1443, 1400, 1354, 1308, 1265, 1231, 1142, 991, 822, 760, 687 cm–1. H NMR (400 MHz,
CDCl3) δ: 4.19 (s, 2H), 7.27 (d, J = 9.2 Hz, 1H), 7.32 (t, J = 7.8 Hz, 1H), 7.39 (t, J = 7.6 Hz,
1H), 7.43 (d, J = 8.3 Hz, 1H), 7.53 (ddd, J = 8.3, J = 6.9, J = 1.2 Hz, 1H), 7.64–7.69 (m, 2Н),
7.78 (d, J = 8.0 Hz, 1H), 7.97 (d, J = 8.5 Hz, 1H), 8.23 (dd, J = 8.0, J = 1.4 Hz, 1H), 8.38 (s, 1H),
10.15 (br s, 1H). 13C NMR (100 MHz, CDCl3) δ: 22.2 (CH2), 116.5 (C), 118.1 (CH), 121.0 (CH),
121.6 (CH), 122.9 (CH), 123.0 (C), 123.5 (C), 125.6 (CH), 126.1 (CH), 126.6 (CH), 129.1 (CH),
129.3 (CH), 129.6 (C), 133.1 (C), 134.4 (CH), 153.5 (C), 154.2 (CH), 156.6 (C), 180.2 (C).
Anal. Calcd (%) for C20H14O3: C, 79.46; H, 4.67. Found (%): C, 79.30; H, 4.56.
(1ꢀPhenylꢀ1Hꢀbenzo[f]chromenꢀ2ꢀyl)(pꢀtolyl)methanone (10f). Yield: 75%, 410 mg.
Colorless solid, mp 205–206 °C (ethanol). IR (KBr) υmax: 1639, 1601, 1508, 1454, 1416, 1377,
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1304, 1254, 1227, 1177, 1026, 988, 837, 810, 760, 698 cm–1. H NMR (400 MHz, CDCl3) δ:
2.38 (s, 3H), 6.02 (s, 1H), 7.08 (tt, J = 7.3, J = 1.2 Hz, 1H), 7.17–7.21 (m, 4H), 7.31 (d, J = 8.9
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Hz, 1H), 7.36–7.48 (m, 7H), 7.76–7.80 (m, 2H), 7.98 (d, J = 8.5 Hz, 1H). C NMR (100 MHz,
CDCl3) δ: 21.6 (CH3), 36.6 (CH), 116.4 (C), 117.1 (CH), 120.5 (C), 123.9 (CH), 125.0 (CH),
126.6 (CH), 127.1 (CH), 128.48 (2CH), 128.50 (CH), 128.6 (2CH), 129.1 (4CH), 129.2 (CH),
131.6 (C), 131.7 (C), 136.0 (C), 142.4 (C), 144.8 (C), 147.8 (C), 152.0 (CH), 194.7 (C). Anal.
Calcd (%) for C27H20O2: C, 86.14; H, 5.36. Found (%): C, 86.25; H, 5.32.
[1ꢀ(3ꢀNitrophenyl)ꢀ1Hꢀbenzo[f]chromenꢀ2ꢀyl](pꢀtolyl)methanone (10g). Yield: 60%, 365
mg. Lightꢀyellow solid, mp 188–190 °C (ethanol). IR (KBr) υmax: 1636, 1593, 1528, 1462, 1350,
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1315, 1227, 1180, 991, 922, 853, 826, 810, 756 cm–1. H NMR (400 MHz, CDCl3) δ: 2.39 (s,
3H), 6.11 (s, 1H), 7.21 (d, J = 7.3 Hz, 2H),7.35–7.46 (m, 6H), 7.56 (s, 1H), 7.81–7.88 (m, 4H),
7.96 (d, J = 8.0 Hz, 1H), 8.15 (s, 1H). 13C NMR (100 MHz, CDCl3) δ: 21.6 (CH3), 36.5 (CH),
115.0 (C), 117.3 (CH), 119.2 (C), 121.9 (CH), 123.3 (CH), 123.4 (CH), 125.3 (CH), 127.5 (CH),
128.8 (CH), 129.0 (2CH), 129.2 (2CH), 129.4 (CH), 130.0 (CH), 131.1 (C), 131.8 (C), 134.9
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