966
H. Valizadeh, H. Gholipour / C. R. Chimie 14 (2011) 963–966
Table 2
Acknowledgement
Comparison of the times and yields of the present method with reported
methods.
The partial financial assistance from the Research Vice
Chancellor of Azarbaijan University of Tarbiat Moallem is
gratefully acknowledged.
Product
number
Time (min)
Yield (%)
Found
Found
Reported [Ref.]
Reported [Ref.]
2a
2b
2c
2d
2e
2f
1.5
2.5
2
–
94
94
91
72
92
92
96
58
63
87 [2]
60–75 [22]
99 [22]
85–90 [28]
99.4 [24]
96 [2]
References
30 [28]
2.5
1.5
1.5
1.75
1.5
3.5
–
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–
–
81 [2]
2g
2j
–
50 [23]
80 [26]
88 [27]
85 [26]
20 [27]
2k
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H3BO3, general procedure
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¨
[9] S. Keskin, D. Kayrak-Talay, U. Akman, O. Hortacsu, J. Supercritical Fluids
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(16.5 mmol) and H3BO3 (18.75 mmol) were mixed thor-
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60 W for a few minutes (depending on the reactants, Table
1). The completion of reaction was monitored by TLC using
(EtOAc/petroleum 1:6) as eluent and the product was
isolated via flash chromatography from EtOAc/petroleum
ether as eluent.
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4. Selected spectroscopic data
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108;
2-Nitrosonaphthalen-2-ol (2b): IR (KBr) (
3405 (OH), 1625 (N=O), 1600 (C=C); 1H NMR (400 MHz,
CDCl3) :14.08(s, 1H,OH), 7.65(d,1H,J = 7.50 Hz),7.49–7.61
n
max/cmÀ1):
d
(m, 4H), 6.39 (d, 1H, J = 7.50 Hz).
(b) H. Valizadeh, A. Shockravi, Synth. Commun. 39 (2009) 4341;
(c) H. Valizadeh, A. Fakhari, J. Heterocycl. Chem. 46 (2009) 1392;
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(f) H. Valizadeh, A. Shomali. (2010) online available. doi:10.1016/
2-Nitrosonaphthalen-1-ol (2d): IR (KBr) (n
max/cmÀ1):
3201 (OH), 1669 (N=O), 1627 (C=C); 1H NMR (400 MHz,
DMSO-d6) d: 13.89 (s, 1H, OH), 7.61–7.81 (m, 4H), 7.01 (d,
1H, J = 7.35 Hz), 7.13 (d, 1H, J = 7.35 Hz).
2-Nitrosobenzene-1,4-diol (2i): IR (KBr) (
3221 (OH), 1631 (N=O), 1600 (C=C); 1H NMR (400 MHz,
(g) H. Valizadeh, A. Fakhari, Mulecules 15 (2010) 2972;
(h) H. Valizadeh, A.A. Azimi, J. Iran. Chem. Soc 8 (2010) 123.
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183l.
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n
max/cmÀ1):
DMSO-d6) d: 11.63 (s, 1H, OH), 6.88 (s, 2H, OH, Harom), 6.80
(d, 1H, J = 7.41 Hz), 6.74 (d, 1H, J = 7.41 Hz).
5-Methyl-2-nitrosophenol (2j): IR (KBr) (
3120 (OH), 1633 (N=O), 1594 (C=C); 1H NMR (400 MHz,
DMSO-d6) d: 13.5 (s, 1H, OH), 7.61 (d, 1H, J = 9.89 Hz), 6.37
(dd, 1H, J = 2.41 and 9.89 Hz), 6.32 (d, 1H, J = 2.41 Hz), 2.09
n
max/cmÀ1):
(s, 3H, CH3).