KOVGANKO et al.
1816
OCH2, J = 7 Hz), 6.33 s (1H, 4-H), 7.00 d (2H, Harom
,
13C NMR spectrum (C5D5N), δC, ppm: 14.23 (CH3);
22.82, 31.47, 31.71, 35.73 (CH2); 126.25, 127.19,
127.65, 129.50 (Carom).
J = 9 Hz), 7.88 d (2H, Harom, J = 9 Hz). 13C NMR
spectrum (C5D5N), δC, ppm: 10.47 (CH3); 22.68, 69.49
(CH2); 87.07 (C4); 115.17, 126.95 (Carom); 159.26.
REFERENCES
Compounds VIIb–VIId were synthesized in a sim-
ilar way.
1. Petrov, V.F., Liq. Cryst., 2001, vol. 28, p. 217.
3-(4-Heptyloxyphenyl)-1H-pyrazol-5(4H)-one
(VIIb). Yield 95%, mp 223°C (from propan-2-ol).
UV spectrum: λmax 265 nm. IR spectrum, ν, cm–1:
2800–2000, 3600–3300 br (N–H); 3125 (C–Harom);
2955, 2928, 2856 (C–Haliph); 1619 (C=O); 1552, 1514,
1496 (C=Carom); 1248, 1180 (C–O). 1H NMR spectrum
(C5D5N), δ, ppm: 0.76 t (3H, CH3, J = 7 Hz), 1.06–
1.19 m (6H, CH2), 1.30 quint (2H, CH2, J = 7 Hz),
1.63 quint (2H, CH2, J = 7 Hz), 3.85 t (2H, OCH2, J =
7 Hz), 6.34 s (1H, 4-H), 7.05 d (2H, Harom, J = 9 Hz),
7.90 br.d (2H, Harom, J = 9 Hz), 12.4–13.4 br.m (OH,
NH). 13C NMR spectrum (C5D5N), δC, ppm: 14.30
(CH3); 22.90, 26.32, 29.33, 29.60, 32.03, 68.29 (CH2);
87.27 (C4); 115.40, 127.17 (Carom); 159.52.
2. Karamysheva, L.A., Torgova, S.I., Agafonova, I.F., and
Petrov, V.F., Liq. Cryst., 2000, vol. 27, p. 393.
3. Landolt-Börnstein. New Series, Madelung, O., Ed.,
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ni, I.M., Mol. Cryst. Liq. Cryst., 2005, vol. 432, p. 1.
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Chem., 2006, vol. 42, p. 243.
3-(4-Octyloxyphenyl)-1H-pyrazol-5(4H)-one
(VIIc). Yield 85%, mp 208°C (from propan-2-ol). UV
spectrum: λmax 265 nm. IR spectrum, ν, cm–1: 3600–
3300, 2800–2000 br (N–H); 3123 (C–Harom); 2924,
2855 (C–Haliph); 1619 (C=O); 1553, 1496 (C=Carom);
9. Kovganko, V.N. and Kovganko, N.N., Russ. J. Org.
Chem., 2006, vol. 42, p. 696.
10. Belmar, J., Alderete, J., Parra, M., and Zusiga, C., Bol.
Soc. Chil. Quım., 1999, vol. 44, p. 367.
11. Aret, E., Meekes, H., Vlieg, E., and Deroover, G., Dyes
Pigm., 2007, vol. 72, p. 339.
1
1248, 1181 (C–O). H NMR spectrum (C5D5N), δ,
12. Marchetti, F., Pettinari, C., and Pettinari, R., Coord.
Chem. Rev., 2005, vol. 249, p. 2909.
13. Arichi, J., Goetz-Grandmont, G., and Brunette, J.P.,
ppm: 0.76 t (3H, CH3, J = 7 Hz), 1.04–1.20 m (8H,
CH2), 1.30 quint (2H, CH2, J = 7 Hz), 1.64 quint (2H,
CH2, J = 7 Hz), 3.85 t (2H, OCH2, J = 7 Hz), 6.32 s
(1H, 4-H), 7.04 d (2H, Harom, J = 9 Hz), 7.88 d (2H,
Hydrometallurgy, 2006, vol. 82, p. 100.
H
arom, J = 9 Hz). 13C NMR spectrum (C5D5N), δC,
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and Huang, C.-H., Inorg. Chem. Commun., 2006, vol. 9,
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16. Laughlin, S.K., Clark, M.P., Djung, J.F., Golebiow-
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sweiler, M.J., VanRens, J.C., Townes, J.A., De, B.,
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ppm: 14.31 (CH3); 22.93, 26.36, 29.52, 29.58, 29.63,
68.28 (CH2); 87.28 (C4); 115.38, 127.17 (Carom);
159.53.
3-(4′-Pentylbiphenyl-4-yl)-1H-pyrazol-5(4H)-one
(VIId). Yield 66%. Phase transition temperatures:
Cr→SmA (270°C)→I (292°C). IR spectrum, ν, cm–1:
3600–3250, 2800–2000 br (N–H); 3151, 3022
(C–Harom); 2955, 2926, 2855 (C–Haliph); 1616 (C=O);
1
1551, 1508 (C=Carom). H NMR spectrum (C5D5N), δ,
ppm: 0.74 t (3H, CH3, J = 7 Hz), 1.12–1.19 m (4H,
CH2), 1.49 quint (2H, CH2, J = 7 Hz), 2.50 t (2H,
C6H4CH2, J = 7 Hz), 6.43 s (1H, 4-H), 7.24 d (2H,
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H
arom, J = 8 Hz), 7.61 d (2H, Harom, J = 8 Hz), 7.71 d
18. Demus, D. and Richter, L., The Texture of Liquid
Crystals, Leipzig: Grandstoffindustie, 1978, p. 219.
(2H, Harom, J = 8 Hz), 8.02 d (2H, Harom, J = 8 Hz).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 12 2010