HETEROCYCLES, Vol. 81, No. 10, 2010
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arom.), 7.49-7.52 (m, 1H, arom.), 7.60-7.74 (m, 4H, arom.), 7.82-7.85 (m, 1H, arom.), 8.22 (d, J = 8.8 Hz,
1H, arom. 6-H), 8.86-8.90 (m, 1H, arom. 1-H). MS (CI) m/z: 277 (MH+, 100%).
Benzo[b]naphtho[2,3-f]thiepin-12(13H)-one21 (1b). This compound was obtained starting from 2b, light
yellow solid, 97%. IR (KBr) ν/cm-1: 3045, 1677 (C=O), 1620, 1574, 1468, 1428, 1316, 1250, 1217, 1142,
1134, 1075. 1H NMR (CDCl3) δ/ppm: 4.55 (s, 2H, CH2), 7.21 (dt, J = 7.5 Hz, 1,4 Hz, 1H, arom.), 7.36 (dt,
J = 7.5 Hz, 1.3 Hz, 1H, arom.), 7.44-7.50 (m, 2H, arom.), 7.53-7.59 (m, 1H, arom.), 7.70 (dd, J = 7.5 Hz,
1.0 Hz, 1H, arom.), 7.78 (d, J = 8.3 Hz, 1H, arom.), 7.91 (d, J = 8.1 Hz, 1H, arom.), 8.11 (s, 1H, arom.
6-H), 8.78 (s, 1H, arom. 11-H). MS (CI) m/z: 277 (MH+, 100%).
Benzo[b]naphtho[2,1-f]oxepin-7(8H)-one (1c). This compound was obtained starting from 2c, purified
by column chromatography (eluent hexane/EtOAc 2:1), yellow viscous oil, 84%. IR (film) ν/cm-1: 3061,
1674 (C=O), 1625, 1598, 1567, 1487, 1457, 1427, 1398, 1371, 1345, 1277, 1232, 1181, 1147, 1113, 1078,
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1025. H NMR (CDCl3) δ/ppm: 4.20 (s, 2H, CH2), 7.19-7.41 (m, 4H, arom.), 7.57 (d, J = 8.7 Hz, 1H,
arom. 5-H), 7.62-7.68 (m, 2H, arom.), 7.80-7.84 (m, 1H, arom.), 8.04 (d, J = 8.7 Hz, 1H, arom. 6-H),
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8.74-8.78 (m, 1H, arom. 1-H). C NMR (CDCl3) δ/ppm: 48.5 (CH2); 120.2, 123.4, 124.1, 125.0, 126.5,
126.9, 127.7, 128.3, 129.3, 129.8 (CH); 121.5, 127.2, 131.9, 137.2, 157.2, 158.0 (C); 190.6 (C=O). MS
(CI) m/z: 261 (MH+, 100%). Anal. Calcd for C18H12O2: C, 83.06; H, 4.65. Found: C, 83.45; H, 4.70.
1,2,3,4-Tetrahydrobenzo[b]naphtho[2,1-f]oxepin-7(8H)-one (1d). This compound was obtained starting
from 2d, purified by column chromatography (eluent hexane/EtOAc 3:1), pale yellow solid, 90%. IR
(KBr) ν/cm-1: 2934, 1678 (C=O), 1601, 1563, 1488, 1456, 1414, 1332, 1319, 1283, 1260, 1231, 1181,
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1112, 1069. H NMR (DMSO-d6) δ/ppm: 1.70-1.80 (m, 2H, tetralin), 1.80-1.89 (m, 2H, tetralinski),
2.76-2.81 (m, 2H, tetralin), 3.02-3.06 (m, 2H, tetralin), 4.08 (s, 2H, CH2C=O), 6.99 (d, J = 8.1 Hz, 1H,
arom. 5-H), 7.22-7.34 (m, 2H, arom.), 7.37-7.44 (m, 2H, arom.), 7.66 (d, J = 8.1 Hz, 1H, arom. 6-H). MS
(CI) m/z: 265 (MH+, 100%). Anal. Calcd for C18H16O2: C, 81.79; H, 6.10. Found: C, 81.55; H, 5.85.
Benzo[b]naphtho[2,3-f]oxepin-12(13H)-one (1e). This compound was obtained starting from 2e, distilled
under high vacuum, yellow solid, 69%, bp 195 ° C (10 mm Hg). IR (film) ν/cm-1: 3058, 1682 (C=O),
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1628, 1586, 1487, 1444, 1338, 1237, 1144, 1127. H NMR (DMSO-d6) δ/ppm: 4.26 (s, 2H, CH2),
7.26-7.30 (m, 1H, arom.), 7.36-7.56 (m, 4H, arom.), 7.63-7.67 (m, 1H, arom.), 7.99 (d, 1H, arom.), 8.00
(s, 1H, arom. 6-H), 8.12 (d, J = 8.2 Hz, 1H, arom.), 8.64 (s, 1H, arom. 11-H). MS (CI) m/z: 261 (MH+,
100%). Anal. Calcd for C18H12O2: C, 83.06; H, 4.65. Found: C, 83.01; H, 4.44.
7,8,9,10-Tetrahydrobenzo[b]naphtho[2,3-f]oxepin-12(13H)-one (1f). This compound was obtained
starting from 2f, distilled under high vacuum, light yellow solid, 44%, bp 180 °C (10 mm Hg). IR (KBr)
1
ν/cm-1: 2931, 1680 (C=O), 1612, 1586, 1480, 1456, 1416, 1316, 1275, 1231, 1177, 1129. H NMR
(DMSO-d6) δ/ppm: 1.70-1.73 (m, 4H, 2×CH2 tetralin), 2.68-2.74 (bm, 2H, tetralin), 2.76-2.82 (bm, 2H,
tetralin), 4.08 (s, 2H, CH2CO), 7.18 (s, 1H, arom. 6-H), 7.21-7.33 (m, 3H, arom.), 7.40-7.43 (m, 1H,