606 JOURNAL OF CHEMICAL RESEARCH 2014
MS (m/z): 406.6 (M+H+). Anal. calcd for C25H18N4O2: C, 73.88; H,
4.46; N, 13.78; found: C, 73.94; H, 4.43; N, 13.76%.
(E)-4-((3,5-Diphenyl-4H-1,2,4-triazol-4-ylimino)methyl)-7-
methoxy-2H-chromen-2-one (2b): Yield 65%; m.p. 206–208 °C; IR
(KBr, cm–1): 3018. 2987, 2889, 1679, 1601, 1508, 1461, 1382, 1234,
1
859, 731; H NMR (500 MHz, CDCl3): δ 8.35 (1H, s, CH=N), 7.87
(4H, m, ArH), 7.68 (1H, d, J=9.0 Hz, ArH), 7.55 (6H, m, ArH), 6.86
(1H, d, J=2.0 Hz, ArH), 6.77 (1H, m, ArH), 6.36 (1H, s, ArH), 3.89
(3H, s, OCH3); 13C NMR (500 MHz, CDCl3):δ 163.46, 161.93, 159.86,
156.19, 150.85, 142.33, 130.53, 129.19, 128.96, 126.51, 126.25, 116.31,
113.02, 109.11, 101.40, 55.89; MS (m/z): 422.6 (M+H+). Anal. calcd for
C25H18N4O3: C, 71.08; H, 4.29; N, 13.26; found: C, 71.14; H, 4.27; N,
13.22%.
(E)-8-((3,5-Diphenyl-4H-1,2,4-triazol-4-ylimino)methyl)-4-methyl-
7-hydroxy-2H-chromen-2-one (2c): Yield 56%; m.p. 262–264 °C;
IR (KBr, cm–1): 3014, 2991, 2879, 1680, 1607, 1496, 1464, 1377,
1
1228, 864, 725; H NMR (DMSO-d6):δ 11.38 (1H, s, OH), 8.99 (1H,
s, CH=N), 7.81 (4H, d, J=5.5 Hz, ArH), 7.68 (1H,d, J=9.0 Hz, ArH),
7.50 (6H, m, ArH), 7.00 (1H, d, J=9.0 Hz, ArH), 6.08 (1H, s, ArH),
2.37 (3H, s, CH3); 13C NMR (500 MHz, DMSO-d6): δ 165.31, 162.92,
158.55, 154.29, 152.36, 131.15, 130.41, 129.11, 128.71, 125.84, 114.14,
112.48, 112.08, 104.34, 18.80; MS, m/z: 422.6 (M+H+). Anal. calcd for
C25H18N4O3: C, 71.08; H, 4.29; N, 13.26; found: C, 71.15; H, 4.26; N,
13.23%.
Fig. 5 Job’s plot for determining the stoichiometry of receptor 2b and Zn2+
ion in CH3OH and DMF (v/v=9/1), I and I0 are the fluorescence intensity of
2b in the presence and absence of Zn2+, respectively, the total concentration
of 2b and Zn2+ ion is 0.1 mM (λex =398 nm).
Experimental
We acknowledge the financial support of the Key Laboratory
Project (2008S127) and the Initial Fund for Young Teachers of
University of Science and Technology Liaoning (008131).
3,5‑Diaryl‑4‑amino‑1,2,4‑triazol 1 12 and coumarin aldehydes 13 were
prepared according to the literature, other reagents were obtained
from Aladdin and used without further purification. TLC was carried
out on alumina‑backed plates coated with Merck gel F254. IR spectra
were obtained with a PerkinElmer spectrophotometer. Mass spectral
data were obtained on an Agilent 1100 LC/MS. 1H NMR and 13C NMR
were recorded at room temperature on a Bruker Avance‑500 NMR
spectrometer. CDCl3 and DMSO‑d6 were used as solvent and TMS
as internal standard. Elemental analyses were made with a CHN
CODRDER MT‑3. UV‑Vis absorption spectra were recorded at
room temperature on a Lambda‑900 spectrometer. The fluorescence
emission spectra were measured on a LS‑55 spectrometer.
Received 19 August 2014; accepted 10 September 2014
Paper 1402839 doi: 10.3184/174751914X14115551312011
Published online: 17 October 2014
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3,5‑Diaryl‑4‑amino‑1,2,4‑triazole (1) (0.02 mol) was added to a
mixture of coumarin aldehydes (0.02 mol), glacial acetic acid (20 mL)
and the mixture was refluxed for 8 h, cooled and filtered, the products
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products (2a–c).
(E)-4-((3,5-Diphenyl-4H-1,2,4-triazol-4-ylimino)methyl)-6-methyl-
2H-chromen-2-one (2a): Yield 69%; m.p. 246–248 °C; IR (KBr,
cm–1): 3025, 2976, 2892, 1684, 1609, 1513, 1457, 1378, 1242, 868, 724;
1H NMR (500 MHz, CDCl3): δ 8.426 (1H, s, CH=N), 7.87 (4H, m,
ArH), 7.55 (6H, m, ArH), 7.38 (2H, m, ArH), 7.27 (1H, d, J=7.0 Hz,
ArH), 6.53 (1H, s, ArH), 2.27 (3H, s, CH3); 13C NMR (500 MHz,
CDCl3): δ 161.52, 159.61, 152.23, 150.86, 142.38, 134.71, 133.85,
130.59, 129.25, 129.03, 126.22, 124.90, 119.08, 117.30, 115.47, 20.85;
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