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HETEROCYCLES, Vol. 83, No. 7, 2011
tropolone-H), 7.72 (d, 1H, J=16.0 Hz, =CH), 7.8-8.08 (m, 2H, ben-H), 10.92 (s, br, 1H, OH); ESI-MS
m/z: 364.9, 366.9, 368.9 (M+1)+. Anal. Calcd for C16H10BrClO3: C, 52.56; H, 2.76. Found: C, 52.70; H,
2.67.
(E)-5-Bromo-3-[3-(4-cyanophenyl)acryloyl]tropolone (2e). This compound was obtained as orange
crystals, mp 273-274 oC. IR (KBr) ν/cm-1: 3211 (OH), 2240 (CN), 1663 (C=O), 1597 (C=O), 1546 (C=C),
1454, 1382, 1303, 1252, 1220; 1H NMR (CDCl3) δ (ppm): 7.16-7.21 (m, 2H, ArH), 7.38 (d, 1H, J=16.0
Hz, =CH), 7.44 (d, 1H, J=10.0 Hz, tropolone-H), 7.52-7.57 (m, 3H, ArH), 7.67 (d, 1H, J=16.0 Hz, =CH),
7.82 (d, 1H, J=10.0 Hz, tropolone-H), 11.01 (s, br, 1H, OH); ESI-MS m/z: 356.4, 358.4 (M+1)+. Anal.
Calcd for C17H10BrNO3: C, 57.33; H, 2.83. Found: C, 57.47; H, 2.89.
(E)-5-Bromo-3-[3-(2,4-dichlorophenyl)acryloyl]tropolone (2f). This compound was obtained as orange
crystals, mp 233-235 oC. IR (KBr) ν/cm-1: 3190 (OH), 1642 (C=O), 1602 (C=O), 1546 (C=C), 1450, 1382,
1235, 1207; 1H NMR (DMSO-d6) δ (ppm): 7.14-7.19 (m, 1H, ArH), 7.34 (d, 1H, J=16.0 Hz, =CH), 7.36
(s, 1H, ben-H), 7.50 (d, 1H, J=10.0 Hz, tropolone-H), 7.57-7.63 (m, 2H, ArH), 7.74 (d, 1H, J=16.0 Hz,
=CH), 7.97 (d, 1H, J=8.0 Hz, ben-H), 10.69 (s, br, 1H, OH); ESI-MS m/z: 398.9, 400.9, 402.9, 404.9
(M+1)+. Anal. Calcd for C16H9BrCl2O3: C, 48.04; H, 2.27. Found: C, 47.91; H, 2.34.
(E)-5-Bromo-3-[3-(2,4-dimethylphenyl)acryloyl]tropolone (2g). This compound was obtained as pale
o
yellow crystals, mp 189-190 C. IR (KBr) ν/cm-1: 3186 (OH), 1651 (C=O), 1607 (C=O), 1559 (C=C),
1507, 1458, 1346, 1259, 1187; 1H NMR (CDCl3) δ (ppm): 2.36 (s, 3H, Me), 2.42 (s, 3H, Me), 7.12-7.14
(m, 2H, ArH), 7.18 (d, 1H, J=16.0 Hz, =CH), 7.26-7.39 (m, 2H, ArH), 7.48 (d, 1H, J=10.0 Hz,
tropolone-H), 7.61 (d, 1H, J=16.0 Hz, =CH), 7.68 (d, 1H, J=10.0 Hz, tropolone-H), 10.64 (s, br, 1H,
OH); ESI-MS m/z: 359.1, 361.1 (M+1)+. Anal. Calcd for C18H15BrO3: C, 60.18; H, 4.21. Found: C, 60.09;
H, 4.39.
(E)-5-Bromo-3-[3-(3,4-dimethylphenyl)acryloyl]tropolone (2h). This compound was obtained as pale
o
yellow crystals, mp 182-184 C. IR (KBr) ν/cm-1: 3192 (OH), 1644 (C=O), 1625 (C=O), 1545 (C=C),
1508, 1400, 1345, 1256, 1183; 1H NMR (CDCl3) δ (ppm): 2.38 (s, 3H, Me), 2.43 (s, 3H, Me), 7.12-7.26
(m, 3H, ArH and =CH), 7.40-7.52 (m, 3H, ArH), 7.64 (d, 1H, J=16.0 Hz, =CH), 7.67 (d, 1H, J=10.0 Hz,
tropolone-H), 10.65 (s, br, 1H, OH); ESI-MS m/z: 359.0, 361.0 (M+1)+. Anal. Calcd for C18H15BrO3: C,
60.18; H, 4.21. Found: C, 59.93; H, 4.35.
(E)-5-Bromo-3-[3-(2,5-dimethoxylphenyl)acryloyl]tropolone (2i). This compound was obtained as
o
yellow crystals, mp 193-194 C. IR (KBr) ν/cm-1: 3190 (OH), 1642 (C=O), 1602 (C=O), 1545 (C=C),
1
1510, 1450, 1382, 1271, 1207; H NMR (CDCl3) δ (ppm): 3.79 (s, 3H, OMe), 3.82 (s, 3H, OMe),
6.86-6.90 (m, 2H, ArH), 7.08 (d, 1H, J=16.0 Hz, =CH), 7.18 (d, 1H, J=10.4 Hz, tropolone-H), 7.55-7.59
(m, 2H, ArH), 7.61 (d, 1H, J=16.0 Hz, =CH), 7.76 (d, 1H, J=10.0 Hz, tropolone-H), 10.88 (s, br, 1H,
OH); ESI-MS m/z: 391.2, 393.2 (M+1)+. Anal. Calcd for C18H15BrO5: C, 55.26; H, 3.86. Found: C, 55.40;