NJC
TOF) of the catalyst in comparison to previously reported
catalysts are some of the important advantages demonstrated
in this work.
Paper
(
6 B. Pegot, G. Vo-Thanh, D. Gori and A. Loupy, Tetrahedron
Lett., 2004, 45, 6425.
7 A. Zare, A. R. Moosavi-Zare, A. Hasaninejad, A. Parhami,
A. Khalafi-Nezhad and M. H. Beyzavi, Synth. Commun., 2009,
3
9, 3156.
4
. Experimental
8
9
A. Zare, A. Parhami, A. R. Moosavi-Zare, A. Hasaninejad,
A. Khalafi-Nezhad and M. H. Beyzavi, Can. J. Chem., 2009,
8
A. Hasaninejad, A. Zare, M. Shekouhy and J. Ameri Rad,
J. Comb. Chem., 2010, 12, 844.
All chemicals were purchased from Merck or Fluka Chemical
Companies. The known products were identified by comparison
of their melting points and spectral data with those reported in
the literature. The acetic acid functionalized ionic liquids were
prepared according to the literature.
the reactions was monitored by TLC using silica gel SIL G/UV
7, 416.
3
7,38
10 M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare and A. Zare,
Org. Prep. Proced. Int., 2010, 42, 95.
11 M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare and A. Zare,
J. Iran. Chem. Soc., 2010, 7, 646.
2 A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare and A. Zare,
Sci. Iran., Trans. C, 2010, 17, 31.
3 M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare,
H. G. Kruger, Z. Asgari, V. Khakyzadeh and M. Kazem-
Rostami, J. Org. Chem., 2012, 77, 3640.
The progress of
1
13
254 plates. The H NMR (400) and C NMR (100 MHz) were run
on a Bruker Avance DPX-250 FT-NMR spectrometer (d in ppm).
Melting points were recorded on B u¨ chi B-545 apparatus in open
capillary tubes.
1
1
4.1. General procedure for the synthesis of
tetrahydrobenzo[b]pyrans
1
1
4 M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare and
V. Khakyzadeh, Appl. Catal., A, 2011, 400, 70.
5 A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, A. Zare,
E. Ghaemi, V. Khakyzadeh, Z. Asgari and A. Hasaninejad,
Sci. Iran., Trans. C, 2011, 18, 1365.
A mixture of dimedone (1 mmol), malononitrile (1 mmol),
aldehyde (1 mmol) and catalyst ([cmmim]Br or [cmmim][BF
4
])
(0.1 mmol, 10 mol%) was added to a 10 mL round-bottomed
flask connected to a reflux condenser and stirred in an oil-bath
at 110 1C. After completion of the reaction, as monitored by
1
6 M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Zare,
S. B. Azimi, Z. Asgari and A. Hasaninejad, C. R. Chim., 2012,
TLC, H
then stirred and refluxed for 3 min. Then the reaction mixture
was filtered and the solvent of the filtrate (H O) removed under
2
O (2 mL) was added to the reaction mixture, which was
1
5, 719.
7 A. Zare, T. Yousofi and A. R. Moosavi-Zare, RSC Adv., 2012,
, 7988.
2
1
1
reduced pressure to separate the catalyst from the crude
product. The solid residue (crude product) was recrystallized
from hot EtOH (95%) to give the pure product. The recovered
catalyst was washed with ethyl acetate, dried under reduced
pressure and reused for the next run. The catalyst was recovered
and reused four times without any significant changes
observed in the yields and reaction times.
2
8 A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, Z. Asgari,
M. Shekouhy, A. Zare and A. Hasaninejad, RSC Adv., 2012,
2, 8010.
1
9 M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, G. Chehardoli,
F. Derakhshan-Panah, A. Zare and O. Khaledian, Sci. Iran., Trans.
C, 2012, 19, 1584.
2
0 A. Zare, A. R. Moosavi-Zare, M. Merajoddin, M. A. Zolfigol,
T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi,
V. Khakyzadeh, F. Derakhshan-Panah, M. H. Beyzavi,
E. Rostami, A. Arghoon and R. Roohandeh, J. Mol. Liq.,
Acknowledgements
The authors gratefully acknowledge the support of this work
by the Research Affairs Office of Bu-Ali Sina University
2
012, 167, 69.
(Grant number 32-1716 entitled development of chemical
2
1 A. Zare, T. Hekmat-Zadeh, S. Mirzaei-Monfared, M. Merajoddin,
H. Torabi-Monfared, M. A. Zolfigol, A. R. Moosavi-Zare,
E. Rostami, M. Mokhlesi, F. Derakhshan-Panah, S. Porbahi
and S. Balandeh, S. Afr. J. Chem., 2012, 65, 63.
methods, reagent and molecules), the University of Sayyed
Jamaleddin Asadabadi and the University of KwaZulu-Natal,
Durban, South Africa.
22 A. Zare, F. Abi, A. R. Moosavi-Zare, M. H. Beyzavi and
M. A. Zolfigol, J. Mol. Liq., 2013, 178, 113.
Notes and references
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