Valizadeh, Shomali & Gholipour
FULL PAPER
[4] Misslitz, U.; Meyer, N.; Kast, J. DE 418623, 1991.
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1H, PhH), 7.75—7.78 (m, 2H, PhH), 13.08 (s, 1H, OH);
13C NMR (DMSO-d6, 150 MHz) δ: 36.78, 71.41, 113.63,
117.87, 119.56, 122.36, 149.79, 160.52, 163.53; IR
(KBr) νmax: 3331 (br, OH), 1746, 1698, 1627, 1498,
1379 cm . Anal. calcd for C11H11NO4: C 59.73, H 5.01,
N 6.33; found C 60.23, H 4.99, N 6.32.
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1
1-(2-Hydroxyphenyl)-1,2-ethanedione-2-oxime
(2g) 1H NMR (DMSO-d6, 400 MHz) δ: 6.35 (br, 1H,
OH), 7.41—7.45 (m, 2H, PhH), 7.60—7.65 (m, 1H,
PhH), 7.75—7.78 (m, 2H, PhH), 12.82 (s, 1H, OH); 13C
NMR (DMSO-d6, 150 MHz) δ: 114.32, 117.56, 119.75,
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1985, 3, 300.
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John Wiley and Sons Ltd, New York, 1996, p. 509 and references
cited therein.
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2001, 66, 381.
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London and New York, 1986,
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C. The Systematic Identification of Organic Compounds, 6th ed.,
John Wiley and Sons, New York, 1980, p. 220.
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Advanced Student, John Wiley & Sons Inc, New York, 1962, p. 535.
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Wiley & Sons Inc, New York, 1953, pp. 739—745.
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747.
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Soc., Perkin Trans. 2 1998, 157.
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Commun. 1983, 301.
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mun. 1987, 955.
[22] Kim, Y. H.; Park, Y. J.; Kim, K. Tetrahedron Lett. 1989, 30, 2833.
[23] Lardy, C.; Tournier, L.; Prunier, M.; Valeur, E. Tetrahedron Lett.
2010, 51, 2277.
[24] Zyk, N. V.; Nesterov, E. E.; Khiobystov, A. N.; Zefirov, N. S. Russ.
Chem. Bull. 1999, 48, 506.
[25] Zolfigol, M. A.; Zebarjadian, M. H.; Chehardoli, G.; Keypour, H.;
Salehzadeh, S.; Shamsipur, M. J. Org. Chem. 2001, 66, 3619.
[26] Marsh, K. N.; Boxall, J. A.; Lichtenthaler, R. Fluid Phase Equilibria
2004, 219, 93.
121.32, 122.52, 122.98, 149.96, 165.85; IR (KBr) νmax
:
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1
3449 (br, OH), 1684, 1531, 1384 cm . Anal. Calcd for
C8H7NO3: C 58.18, H 4.27, N 8.48; found C 59.08, H
4.26, N 8.46.
Methyl 2,3-dione-2-oxime hexanoate (2h) 1H
NMR (DMSO-d6, 400 MHz) δ: 1.05 (t, J=8.24 Hz, 3H,
CH3), 1.15—1.17 (m, 2H, CH2), 2.64 (t, J=8.24 Hz, 2H,
CH2), 3.65 (s, 3H, OCH3), 12.89 (s, 1H, OH); 13C NMR
(DMSO-d6, 150 MHz) δ: 15.52, 18.45, 23.36, 62.52,
145.56, 158.89, 164.75; IR (KBr) νmax: 3354 (br, OH),
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1
1726, 1694, 1627, 1458, 1374 cm . Anal. calcd for
C7H11NO4 C 48.55, H 6.40, N 8.09; found C 48.74, H
6.43, N 8.08.
Methyl 2,3-dione-2-oxime butanoate (2i) 1H
NMR (DMSO-d6, 400 MHz) δ: 2.35 (s, 3H, CH3), 3.78
(s, 3H, OCH3), 13.34 (s, 1H, OH); 13C NMR (DMSO-d6,
150 MHz) δ: 31.25, 62.53, 147.69, 161.53, 165.82; IR
(KBr) νmax: 3448 (br, OH), 1751, 1654, 1452, 1373
-
1
cm . Anal. calcd for C5H7NO4: C 41.38, H 4.86, N
9.65; found C 41.42, H 4.88, N 9.63.
2,4-Dione-3-oxime pentane 1H NMR (DMSO-d6,
400 MHz) δ: 2.15 (s, 3H, CH3), 13.04 (s, 1H, OH); 13C
NMR (DMSO-d6, 150 MHz) δ: 31.25, 137.79, 159.51,
161.72; IR (KBr) νmax: 3437 (br, OH), 1747, 1634, 1425,
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1
1351 cm . Anal. calcd for C5H7NO3: C 46.51, H 5.46,
N 10.85; found C 46.53, H 5.47, N 10.83.
3,5-Dione-4-oxime heptane 1H NMR (DMSO-d6,
400 MHz) δ: 2.24 (s, 3H, CH3), 13.02 (s, 1H, OH); 13C
NMR (DMSO-d6, 150 MHz) δ: 30.16, 32.42, 136.70,
159.43, 160.63; IR (KBr) νmax: 3435 (br, OH), 1748,
[27] Keskin, S.; Kayrak-Talay, D.; Akman, U.; Hortacsu, Ö. Supercriti-
cal Fluids 2007, 43, 150.
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1
1641, 1430, 1356 cm . Anal. calcd for C5H11NO3: C
[28] Zhao, H.; Yu, N.; Ding, Y.; Tan, R.; Liu, C.; Yin, D.; Qiu, H.; Yin,
D. Microporous Mesoporous Mater. 2010, 136, 10.
[29] Wang, L.; Li, H. P. Tetrahedron 2009, 65, 364.Bi, W.; Tian, M.;
Zhou, J.; Row, K. H. J. Chromatogr. B 2010, 878, 2243.
[30] Bi, W.; Tian, M.; Zhou, J.; Row, K. H. J. Chromatogr. B 2010, 878,
2243.
[31] Yadav, L. D. S.; Patel, R.; Rai, V. K.; Srivastava, V. P. Tetrahedron
Lett. 2007, 48, 7793.
[32] Sun, J.; Cheng, W.; Fan, W.; Wang, Y.; Meng, Z.; Zhang, S. Catal.
Today 2009, 148, 361.
53.49, H 7.05, N 8.91; found C 53.50, H 7.06, N 8.89.
Acknowledgments
The partial financial assistance from the Research
Vice Chancellor of Azarbaijan University of Tarbiat
Moallem is gratefully acknowledged.
References
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Chin. J. Chem. 2012, 30, 163—166