556
L. Wang, H. Zou, D. Ye, and D. Cao
Vol 50
dropwise and stirred for another 12 h. Then methanol was added
to the reaction mixture to give crude solids, which was purified
by recrystallization by use of dichloromethane/methanol to give
compounds 5a–5e.
Acknowledgments. The supports by the National Natural Science
Foundation of China (20904010) and the Fundamental Research
Funds for the Central Universities (2009ZM0170) are gratefully
acknowledged.
3-(4′-bromophenyl)-7-(N′-octyl-6′-bromo-3′-carbazolyl vinyl)
-2H-chromen-2-one (5a): orange solid in 60% yield. m. p. 210–213ꢁC.
IR(KBr, cmꢀ1) n = 3047, 2920, 2852, 1716, 1597, 1478, 1444,
1276 1133, 948, 516; 1H NMR(400 MHz, CDCl3): d = 8.39
(1H, s, Ar-H), 8.20 (1H, s, Ar-H), 7.80(1H, s, Ar-H), 7.72
(d, 1H, J = 8 Hz, Ar-H), 7.63–7.39 (m, 10H, Ar-H), 7.28(d, 1H,
J = 16 Hz, olefin H), 7.16(d, 1H, J = 16 Hz, olefin H), 4.27
(t, 2H, CH2), 1.87ꢀ1.84 (m, 2H, CH2), 1.33ꢀ1.23 (m, 10H, (CH2)5),
0.86 (t, 3H, CH3). Anal. Calc. for C37H33NO2Br2 (%): C, 65.02,
H, 4.87; N, 2.05. Found: C, 65.20; H, 4.60; N, 2.23.
3-(4′-bromophenyl)-7-(4′-methylphenyl vinyl) -2H-chromen-
2-one (5b): light yellow solid in 70% yield. m. p. 247–249ꢁC. IR
(KBr, cmꢀ1) n = 3058, 2922, 2854, 1712, 1597, 1462, 1422, 1262,
1163, 920, 508; 1H NMR(400 MHz, CDCl3): d = 7.80 (s, 1H,
Ar-H), 7.63–7.87 (m, 9H, Ar-H), 7.51(d, 2H, J = 8 Hz, Ar-H),
7.09(d, 2H, J = 16Hz, olefin H), 2.38 (s, 3H, CH3). Anal. Calc.
for C24H17O2Br (%): C, 69.08, H, 4.11. Found: C, 69.21; H, 4.22.
3-(4′-bromophenyl)-7-(4′-methoxylphenyl vinyl) -2H-chromen-
2-one (5c): light yellow solid in 65% yield. m. p. 235–237ꢁC. IR
(KBr,cmꢀ1) n = 3047, 2922, 2854, 1707, 1596, 1458, 1422,
1256, 1163, 954, 517; 1H NMR(400 MHz, CDCl3): d = 7.80
(s, 1H, Ar-H), 7.61–7.43 (m, 10H, Ar-H), 6.91(d, 1H, J = 8 Hz,
Ar-H), 7.01(d, 2H, J = 16 Hz, olefin H), 3.85 (s, 3H, OCH3). Anal.
Calc. for C24H17O3Br (%): C, 66.53, H, 3.95. Found: C, 66.43;
H, 3.82.
3-(4′-bromophenyl)-7-(2′-furyl vinyl) -2H-chromen-2-one
(5d): yellow solid in 72% yield. m. p. 182–184ꢁC. IR(KBr,
cmꢀ1) n = 3049, 2922, 2854, 1723, 1607, 1460, 1424, 1260,
1108, 943, 515; 1H NMR(400 MHz, CDCl3): d = 7.79 (s, 1H,
Ar-H), 7.62–7.56 (m, 5H, Ar-H), 7.46 (s, 1H, Ar-H), 7.41–7.39
(m, 2H, Ar-H), 7.04(d, 2H, J = 4 Hz, Ar-H), 6.47(s, 2H, olefin
H). Anal. Calc. for C21H13O3Br (%): C, 64.14, H, 3.33. Found:
C, 64.26; H, 3.56.
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3-(4′-bromophenyl)-7-(2′-thienyl vinyl) -2H-chromen-2-
one (5e): light yellow solid in 75% yield. m. p. 216–217ꢁC. IR
(KBr, cmꢀ1) n = 3061, 2921, 2852, 1714, 1597, 1483, 1418,
1266, 1128, 953, 509; 1H NMR(400 MHz, CDCl3): d = 7.81
(s, 1H, Ar-H), 7.50 (d, 2H, J= 12 Hz, Ar-H), 7.40 (d, 2H,
J= 12 Hz, Ar-H), 7.62–7.57 (m, 6H, Ar-H), 6.55(d, 1H, J=12Hz,
olefin H), 6.80(d, 1H, J=12Hz, olefin H). Anal. Calc. for
C21H13O2BrS (%): C, 61.62, H, 3.20. Found: C, 61.84; H, 3.39.
Determination of the fluorescence quantum yield. Fluorescence
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet