Solvent-free synthesis of 1,2,4,5-tetrasubstituted imidazoles using nano Fe3O4@SiO2-OSO3H as a stable and magnetically recyclable heterogeneous catalyst

Article abstract of DOI:10.13005/ojc/310173

Nano-Fe₃O₄ encapsulated-silica particles bearing sulfonic acid groups (Fe₃O₄@SiO₂-OSO₃H) has been used as an efficient and magnetically separable heterogeneous catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles by one-pot, four-component reaction of benzil, aromatic aldehydes, primary amines, and ammonium acetate under neat conditions. The effect of various reaction parameters, such as reaction temperature, catalyst loading and solvent effect, were studied. The desired products are obtained in relatively short reaction times with high yields. Importantly, the catalyst could be easily separated from the reaction mixture by a permanent magnet and reused for several times without the significant loss of its activity.

Full text of DOI:10.13005/ojc/310173

ISSN: 0970-020 X
CODEN: OJCHEG
015, Vol. 31, No. (1):
Pg. 573-579
ORIENTAL JOURNAL OF CHEMISTRY
An International Open Free Access, Peer Reviewed Research Journal
2
www.orientjchem.org
Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted
Imidazoles Using Nano Fe O @SiO -OSO H as a Stable
3
4
2
3
and Magnetically Recyclable Heterogeneous Catalyst
SEPIDEHYADEGARIAN,ABOLGHASEM DAVOODNIA* and AHMAD NAKHAEI
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran.
*
Corresponding author E-mail: adavoodnia@yahoo.com, adavoodnia@mshdiau.ac.ir
http://dx.doi.org/10.13005/ojc/310173
(Received: November 12, 2014; Accepted: December 04, 2014)
ABSTRACT
Nano-Fe O encapsulated-silica particles bearing sulfonic acid groups (Fe O @SiO -
3
4
3
4
2
OSO H) has been used as an efficient and magnetically separable heterogeneous catalyst for the
3
synthesis of 1,2,4,5-tetrasubstituted imidazoles by one-pot, four-component reaction of benzil,
aromatic aldehydes, primary amines, and ammonium acetate under neat conditions. The effect of
various reaction parameters, such as reaction temperature, catalyst loading and solvent effect,
were studied. The desired products are obtained in relatively short reaction times with high yields.
Importantly, the catalyst could be easily separated from the reaction mixture by a permanent
magnet and reused for several times without the significant loss of its activity.
Key words: Fe O @SiO -OSO H, Magnetically separable,
3
4
2
3
Solvent-free conditions, 1,2,4,5-Tetrasubstituted imidazoles.
INTRODUCTION
materials; ii) avoiding a lengthy separation of the
intermediates; iii) saving time and resources; iv)
1
-3
In synthetic organic chemistry, the one-pot
multicomponent reaction (MCR) strategy has
become a powerful tool to improve the efficiency of
a reaction wherein a reactant is subjected to
successive chemical reactions in one vessel. This
process consists of two or more synthesis steps
which are carried out without isolation of any
intermediate.The overall advantages of this strategy
involve: i) use of commercially available starting
achieving increase in the chemical yield . The
development of new MCRs and improvement of
known MCRs are therefore areas of considerable
current interest. One such reaction is the synthesis
of 1,2,4,5-tetrasubstituted imidazoles. The
imidazole ring system is one of the most important
substructure found in a large number of natural
products and pharmacologically active
4
,5
compounds . Different substituted imidazoles

5
74
YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
show variable biological activities such as inexpensive. In recent years, the use of
antibacterial, anti-allergic, anti-inflammatory, heterogeneous nanocatalysts have been receiving
antitumor analgesic, glucagon receptor antagonism growing attention, because they have high catalytic
6
-9
37,38
therapeutic agents, and pesticides . Also, some of activities due to their large specific surface area
.
10
them are known as inhibitors of P38 MAP kinase Recently, nano-Fe O encapsulated-silica particles
and B Raf kinase . Recent advances in green bearing sulfonic acid groups (Fe O @SiO -OSO H)
3
4
1
1
3
4
2
3
chemistry and organometallic catalysis has have been prepared and used as an efficient acid
3
9-42
extended the application of imidazoles as ionic catalyst in some organic reactions . They can be
1
2-14
15
liquids
and N-heterocyclic carbenes .
readily separated from the reaction mixture by a
permanent magnet and reused several times. The
Numerous methods for the synthesis of process is more effective than filtration and
,2,4,5-tetrasubstituted imidazoles have been centrifugation in preventing loss of the solid catalyst.
reported.They can be accessed by cyclization of - However, there are no reports on the use of
N-acyl-N-alkylamino--ketoamides in refluxing Fe O @SiO -OSO H as an acidic heterogeneous
1
(
3
4
2
3
1
6
17
AcOH ,
hetero-Cope
rearrangement , catalyst for the synthesis of 1,2,4,5-tetrasubstituted
condensation of a 1,2-diketone with an aryl nitrile imidazoles.
18
and primary amine under microwave irradiation ,
1
9
and N-alkylation of trisubstituted imidazoles .
As a consequence of our interest in
Another direct method involves a four-component developing new efficient synthetic methodologies
4
3-47
condensation of 1,2-diketones or  hydroxyketones
for the synthesis of bioactive molecules and
with aldehydes, primary amines, and ammonium owing to the biological significance of 1,2,4,5-
acetate in the presence of a catalyst such as TFA in tetrasubstituted imidazoles, we wish to report herein
2
0
ionic liquid [Bpy]BF , montmorillonite K10 a solvent-free synthesis of 1,2,4,5-tetrasubstituted
4
2
1
22
23
supported titanium , L-proline , InCl .3H O , BF - imidazoles catalyzed by Fe O @SiO -OSO H, as a
3
2
3
3
4
2
3
24
25
SiO2 , Brønsted acidic ionic liquid , carbon-based green and effective magnetically recyclable
26
27
solid acid , K CoW O .3H O , p-dodecylbenzene heterogeneous catalyst (Scheme 1).
5
12 40
2
2
8
sulfonic acid , FeCl /montmorillonite K10 under
microwave irradiation , NH H PO /Al O
NaHSO /SiO , and H P W O .24H O/SiO
3
2
9
30
,
.
EXPERIMENTAL
4
2
4
2
3
3
1
32
4
2
6
2
18 62
2
2
Each of these methods has its own merit, however,
All chemicals were available commercially
all of the reported methods (except for the reaction and used without additional purification.The melting
catalyzed by FeCl /montmorillonite K10 under points were recorded using a Stuart SMP3 melting
3
microwave irradiation) require relatively prolonged point apparatus.The IR spectra of the productswere
reaction time. Also, some of these catalysts are obtained with KBr disks, using a Tensor 27 Bruker
1
expensive or having other problems like spectrophotometer. The H NMR (400 & 500 MHz)
requirement of solvents for synthesis, and low yields spectra were recorded using Bruker 400 & 500
of the products. Furthermore, the synthesis using spectrometers.
homogeneous catalysts have major problem of
catalyst recovery and reuse. To avoid these General Procedure for the Synthesis of 1,2,4,5-
limitations, the discovery of a new and efficient Tetrasubstituted Imidazoles 5a-m Using
catalyst with high catalytic activity, short reaction Fe O @SiO -OSO H as Catalyst
3
4
2
3
time, recyclability, and simple reaction work-up for
the synthesis of 1,2,4,5-tetrasubstituted imidazoles aldehyde 2 (1 mmol), a primary amine 3 (1 mmol),
is of prime interest. ammonium acetate 4 (1 mmol), and Fe O @SiO -
A mixture of benzil 1 (1 mmol), an aromatic
3
4
2
OSO H (0.10 g) was heated in the oil bath at 130 °C
3
In recent years economic and for 15-60 min. The reaction was monitored by thin-
environmental concerns encourage the application layer chromatography (TLC). Upon completion, hot
of heterogeneous catalysts to carry out various ethanol was added to the reaction mixture and the
3
3-36
organic transformations . These catalysts make catalyst was separated using an external magnet
the processes clean, safe, high-yielding and (Fig 1.).The catalyst was washed with a small portion

YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
575
of hot ethanol (10 mL). The combined filtrate was
concentrated by half and allowed to stand at r.t..
The precipitated solid was collected by filtration,
and recrystallized from ethanol 96% to give
compounds 5a-m in high yields.
attributed to stretching vibration of the adsorbed
4
0,41
water
. The density of the SO H groups was
3
-
1
measured using KOH (0.01 mol L ) as titrant by
acid-base potentiometric titration. The amount of
SO H in the catalyst was 1.5 mmol/g.
3
RESULTSAND DISCUSSION
In the effort to develop an efficient and
environmentally benign method for synthesis of
1,2,4,5-tetrasubstituted imidazoles we initiated our
For our investigations, the catalyst
Fe O @SiO -OSO H was prepared according to the
literature procedure . The FT-IR spectrum of the
studies by adding
a catalytic amount of
3
4
2
3
3
9,40
Fe O @SiO -OSO H to a mixture of benzil (1 mmol),
3
4
2
3
3
9,40
catalyst (Fig. 2a) exhibits the Fe-O vibration
at
benzaldehyde (1 mmol), aniline (1 mmol), and
ammonium acetate (1 mmol), as model reaction, in
different solvents and under solvent-free conditions
(Table 1). We were pleased to see that the reaction
was efficiently catalyzed by Fe O @SiO -OSO H
-
1
-1
-1
5
87 cm .The bands at 1091 cm , 797 cm and 463
cm were attributed to the Si-O-Si asymmetric and
symmetric stretching vibrations as well as bending
-
1
40
vibration, respectively . The spectrum also shows
3
4
2
3
the SO symmetric and asymmetric stretching
modes in 1100-1250 cm that were covered by a
under solvent-free conditions at elevated
temperature leading to a high yield of product 5a.
The reaction conditions were then optimized by
conducting the reaction at different temperatures
and using different amounts of catalyst. The results
2
-
1
4
0,43
-1
stronger absorption of Si-O bond
Also, the absorption band at 1637 cm and the
at 1091 cm .
-
1
-
1
broad band at around 3000-3700 cm were
Table 1: Synthesis of compound 5a in the presence of the
Fe O @SiO -OSO H catalyst under different reaction conditions
3
4
2
3
Entry
Catalyst (g)
Solvent
T (°C)
Time (min)
Isolated yield (%)
1
2
3
4
5
6
7
8
9
1
1
1
1
1
1
1
1
1
1
2
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
130
110
130
110
130
110
130
150
110
130
150
110
130
150
130
120
80
70
80
70
80
60
60
70
60
60
60
50
60
50
22
56
59
61
67
73
83
84
78
88
88
89
94
93
93
30
22
16
15
18
12
0.02
0.02
0.04
0.04
0.06
0.06
0.06
0.08
0.08
0.08
0.10
0.10
0.10
0.12
0.10
0.10
0.10
0.10
0.10
0.10
0
1
2
3
4
5
6
7
8
9
0
1
CH CH OH
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
180
180
180
180
180
180
3
2
CH OH
3
H O
2
CH CN
3
CHCl3
CH CO Et
3
2
Reaction conditions: benzil (1 mmol), benzaldehyde (1 mmol), aniline (1 mmol), ammonium acetate (1 mmol).

5
76
YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
are summarized in Table 1. Low yield of the product obtained when the reaction was run at 130 °C in
was obtained in the absence of the catalyst at 130 the presence of 0.10 g Fe O @SiO -OSO H under
3
4
2
3
°C after 120 min (entry 1) indicating that the catalyst solvent-free conditions (entry 13).
is necessary for the reaction. The best result was
Table 2: Fe O @SiO -OSO H catalyzed synthesis 1,2,4,5-tetra
3
4
2
3
substituted imidazoles 5a-m under the optimized conditions
Entry
R
Ar
Product
Time
Isolated
yield (%)
Melting point (ºC)
Found Reported
(min)
2
2
3
2
2
3
2
2
3
2
2
3
2
4
4
0
8
9
0
4
2
0
7
7
0
2
1
2
3
4
5
6
7
8
9
1
1
1
1
C H
C H
4-ClC H
4-MeC H
6 4
5a
5b
5c
5d
5e
5f
5g
5h
5i
50
25
50
20
15
60
60
45
60
40
55
60
60
94
95
89
97
95
87
88
92
87
92
91
87
88
217-219
150-152
189-191
190-192
240-242
174-176
161-162
166-168
160-162
190-193
190-192
203-205
223-225
216-218
149-151
189-190
192-194
248-250
172-175
162-165
167-168
161-162
187-189
188-191
202-203
222-223
6
5
5
5
5
5
6
5
C H
6
6 4
C H
6
C H
4-O NC H
6
2 6 4
C H
2-thienyl
4-BrC H
4-ClC H
4-MeC H
4-MeOC H
4-ClC H
4-MeC H
4-BrC H
4-MeC H
6
C H CH
6
5
2
2
2
2
6
4
C H CH
6
5
6
4
C H CH
6
5
6 4
C H CH
6
5
6
4
0
1
2
3
4-ClC H
4-MeC H
Me
Me
5j
5k
5l
6
4
6
4
6
4
6
4
4
6
4
5m
6
Reaction conditions: benzil 1 (1 mmol), aromatic aldehyde 2 (1 mmol), primary amine 3 (1 mmol), ammonium acetate
4
(1 mmol), Fe O @SiO -OSO H (0.10 g), 130 ºC, solvent-free.
3 4 2 3
Table 3: Comparison of the efficiencies of various catalysts
for the synthesis of 1,2,4,5-tetrasubstituted imidazoles
Catalyst
Conditions
T/ºC
Time
(min)
Yield
(%)
Ref.
Solvent
Other
TFA
[Bpy]BF4
-
MeOH
MeOH
-
-
-
-
80
-
-
-
-
-
-
-
-
90-180
120-240
510-600
360-540
120
120-150
60-120
120-150
240
3-4
90-180
120
120
15-60
56-90
68-84
76-88
49-84
80-93
85-95
86-94
80-95
73-86
78-89
80-91
85-92
82-91
87-97
20
21
22
23
24
25
26
27
28
29
30
31
32
this
work
Montmorillonite K10 supported titanium
L-Proline
InCl .3H O
120
reflux
r.t.
140
140
130
140
reflux
80
130
140
140
130
3
2
BF -SiO2
3
Brønsted acidic ionic liquid
Carbon-based solid acid
K CoW O .3H O
5
12 40
2
p-Dodecylbenzenesulfonic acid
FeCl /montmorillonite K10
H O
-
2
-
-
-
-
-
MW
3
NH H PO /Al O
-
-
-
-
4
2
4
2
3
NaHSO /SiO
4
2
H P W O .24H O/SiO
6
2
18 62
2
2
Fe O @SiO -OSO H
3
4
2
3

YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
577
Using these optimized reaction conditions,
and in order to evaluate the generality of this model
reaction, we extended the reaction of benzil and
ammonium acetate with a range of other aromatic
aldehydes and primary amines (Table 2).As shown,
in all cases, the expected products were obtained
in high yields over relatively short reaction times.
Easy separation of obtained products from the
catalyst makes this method useful for the synthesis
of 1,2,4,5-tetrasubstituted imidazoles.
reaction time than all the other conditions (except
for the reaction catalyzed by FeCl /montmorillonite
3
K10 under microwave irradiation) and gave high
yields of the desired products with very simple work-
up procedure.
In view of environmental friendly
methodologies, recovery and reuse of the catalyst
is highly preferable. Upon completion of the
reaction, hot ethanol was added and the catalyst
was recovered from the reaction mixture simply by
applying an external permanent magnet. The
recovered catalyst was washed with hot ethanol
and then dried under vacuum at 50 °C for 1 h before
being reused in the same reaction. The catalyst
could be used at least five times with only slight
reduction in the catalytic activity. The yields
In order to know the catalytic efficiency of
Fe O @SiO -OSO H, the data reported in the
3
4
2
3
literature for the synthesis of 1,2,4,5-tetrasubstituted
imidazoles using different type of the catalysts was
compared with Fe O @SiO -OSO H. As shown in
3
4
2
3
Table 3, our reaction conditions gave a shorter
O
Fe O @SiO -OSO H
3
4
2
3
N
N
+
ArCHO
+
RNH2
+
CH COONH
Ar
3
4
O
Solvent-free
30 °C
R
1
1
2
3
4
5a-m
Scheme 1: Fe O @SiO -OSO H catalyzed synthesis of 1,2,4,5-tetrasubstituted imidazoles
3
4
2
3
Fig. 1: The reaction mixture in the
synthesis of 5a after adding hot ethanol
in the presence of a magnetic field
Fig. 2: FT-IR spectra of fresh catalyst Fe O @SiO -
3 4 2
OSO H (a, first run), and recovered catalysts
3
(b-e, second to fifth run, respectively)
for synthesis of compound 5a in model reaction

5
78
YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
obtained were from 94, 93, 93, 91 and 90% in the reported. The catalyst could be readily recovered
first, second, third, fourth and fifth run respectively. using a simple external magnet and reused several
Furthermore, retention of the structure of the catalyst times without any significant loss in activity. Other
was confirmed by comparing the FT-IR spectra of attractive features of this protocol are high yields,
the recovered catalysts (Fig. 2b-e) with that of the relatively short reaction times, avoiding the use of
fresh catalyst (Fig. 2a), for model reaction. As shown, harmful organic solvents in the reaction and
these spectra are almost identical.
reusability of the catalyst. The catalyst can be used
at least five times without substantial reduction in
its catalytic activity.
CONCLUSION
In summary, in this paper a highly efficient,
ACKNOWLEDGEMENTS
neat and green method with a simple work-up
procedure for the synthesis of 1,2,4,5-
The authors express their gratitude to the
tetrasubstituted imidazoles via one-pot, four- Islamic Azad University, Mashhad Branch for its
component reaction of benzil, aromatic aldehydes, financial support.
primary amines, and ammonium acetate has been
REFERENCES
1.
2.
3.
Bagley, M. C.; Lubinu M. C. Top. Heterocycl.
Chem. 2006, 31.
Chebanov, V. A.; Desenko, S. M. Chem. 12.
Heterocycl. Compd. 2012, 48, 566.
Zeinali-Dastmalbaf, M.; Davoodnia, A.; 13.
Heravi, M. M.; Tavakoli-Hoseini, N.;
Khojastehnezhad, A.; Zamani, H. A. Bull.
Steadman, J. G.; Wilson, D. M. Bioorg. Med.
Chem. Lett. 2006, 16, 378.
Dupont, J.; de Souza, R. F.; Suarez, P. A. Z.
Chem. Rev. 2002, 102, 3667.
Davoodnia, A.; Khojastehnezhad, A.;
Bakavoli, M.; Tavakoli Hoseini, N. Chin. J.
Chem. 2011, 29, 978.
Korean Chem. Soc. 2011, 32, 656.
Heers, J.;Backx, L. J.J.;Mostmans, J.H.;Van
Cutsem, J. J. Med. Chem. 1979, 22, 1003.
14.
Davoodnia, A.; Heravi, M. M.; Rezaei
Daghigh, L.; Tavakoli Hoseini, N. Monatsh.
Chem. 2009, 140, 1499.
4
.
.
5
Hunkeler, W.; Mohler, H.; Pieri, L.; Polc, P.; 15.
Bonetti, E.P.;Cumin, R.;Schaffner, R.;Haefely,
Bourissou, D.; Guerret, O.; Gabbai, F. P.;
Bertrand, G. Chem. Rev. 2000, 100, 39.
Zhang, C.;Moran, E. J.;Woiwode, T. F.;Short,
K. M.; Mjalli A. M. M. Tetrahedron Lett. 1996,
37, 751.
W. Nature 1981, 290, 514.
16.
6
7
8
9
.
.
.
.
Ghosh, R.;De, B.Int. J. Pharm. Sci. Rev. Res.
2
013, 23, 237.
Rani, N.;Sharma, A.;Singh, R.Mini-Rev. Med. 17.
Chem. 2013, 13, 1812.
Lantos, I.;Zhang, W.Y.;Shui, X.;Eggleston, D.
S. J. Org. Chem. 1993, 58, 7092.
Balalaie, S.; Hashemi, M. M.; Akhbari, M.
Tetrahedron Lett. 2003, 44, 1709.
Davidson, D.; Weiss, M.; Jelling, M. J. Org.
Chem. 1937, 2, 319.
Wan, Y.; Liu, G. X.; Zhao, L. L.; Wang, H. Y.;
Huang, S.Y.;Chen, L.F.;Wu, H.J. Heterocyclic
Chem. 2014, 51, 713.
Kannan, V.; Sreekumar, K. J. Mol. Catal. A:
Chem. 2013, 376, 34.
Ahsan, I.; Sharma, K. K.; Sharma, A.; Khan, S. 18.
A.; Khan, U. Pharm. Chema. 2014, 6, 320.
Chang, L. L.; Sidler, K. L.; Cascieri, M. A.; de 19.
Laszlo, S.; Koch, G.; Li, B.; Mac Coss, M.;
Mantlo, N.; O’Keefe, S.; Pang, M.; Rolando, 20.
A.; Hagmann, W. K. Bioorg. Med. Chem. Lett.
2
001, 11, 2549.
Murry, J. A. Curr. Opin. Drug. Discov. Dev. 21.
003, 6, 945.
1
1
0.
1.
2
Takle, A.K.;Brown, M.J.B.; Davies, S.;Dean, 22.
D.K.;Francis, G.;Gaiba, A.;Hird, A.W.;King, F.
D.; Lovell, P. J.; Naylor, A.; Reith, A. D.; 23.
Samai, S.;Nandi, G.C.;Singh, P.;Singh, M.S.
Tetrahedron 2009, 65, 10155.
Sharma, S. D.; Hazarika, P.; Konwar, D.

YADEGARIAN et al., Orient. J. Chem., Vol. 31(1), 573-579 (2015)
Tetrahedron Lett. 2008, 49, 2216. Chem. 2011, 41, 1063.
579
2
2
4.
5.
Sadeghi, B.; Mirjalili, B. B. F.; Hashemi, M. M.
Tetrahedron Lett. 2008, 49, 2575.
Davoodnia, A.; Heravi, M. M.; Safavi-Rad, Z.;
Tavakoli-Hoseini, N. Synth. Commun. 2010,
36.
Davoodnia, A.; Tavakoli-Nishaburi, A.;
Tavakoli-Hoseini, N.Bull. Korean Chem. Soc.
2011, 32, 635.
Rayati, S.; Abdolalian, P. Appl. Catal. A: Gen.
2013, 456, 240.
Mirzaei, H.; Davoodnia, A. Chin. J. Catal.
2012, 33, 1502.
Nemati, F.;Heravi, M.M.; Saeedirad, R.Chin.
J. Catal. 2012, 33, 1825.
Kiasat, A. R.; Davarpanah, J. J. Mol. Catal. A:
Chem. 2013, 373, 46.
Xiong, Y.; Zhang, Z.; Wang, X.; Liu, B.; Lin, J.
Chem. Eng. J. 2014, 235, 349.
Nemati, F.; Saeedirad, R. Chin. Chem. Lett.
2013, 24, 370.
Ashrafi, M.; Davoodnia, A.; Tavakoli-Hoseini,
N. Bull. Korean Chem. Soc. 2013, 34, 1508.
Davoodnia, A.Bull. Korean Chem. Soc. 2011,
32, 4286.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
40, 2588.
2
2
2
2
3
3
6.
7.
8.
9.
0.
1.
Tavakoli-Hoseini, N.; Davoodnia, A. Chin. J.
Chem. 2011, 29, 203.
Nagarapu, L.; Apuri, S.; Kantevari, S. J. Mol.
Catal. A: Chem. 2007, 266, 104.
Das, B.; Kashanna, J.; Kumar, R. A.; Jangili,
P. Monatsh. Chem. 2013, 144, 223.
Raghuvanshi, D. S.; Singh, K. N. Indian J.
Chem. 2010, 49B, 1394.
Emrani, A.; Davoodnia, A.; Tavakoli-Hoseini,
N. Bull. Korean Chem. Soc. 2011, 32, 2385.
Karimi, A. R.; Alimohammadi, Z.; Azizian, J.;
Mohammadi, A. A.; Mohammadizadeh, M. R.
Catal. Commun. 2006, 7, 728.
3
3
3
3
2.
3.
4.
5.
Karimi, A. R.; Alimohammadi, Z.; Amini, M. M.
Mol. Divers. 2010, 14, 635.
Agirrezabal-Telleria, I.; Gandarias, I.; Arias,
P. L . Catal. Today 2014, 234, 42.
Davoodnia, A.; Zare-Bidaki, A.; Behmadi, H.
Chin. J. Catal. 2012, 33, 1797.
Davoodnia, A.; Khashi, M.; Tavakoli-Hoseini,
N. Chin. J. Catal. 2013, 34, 1173.
Davoodnia, A, Khashi, M, Tavakoli-Hoseini,
N. Chin. J. Catal. 2014, 35, 1054.
Aoyama, T.; Takido, T.; Kodomari, M. Synlett,
2
004, 13, 2307.
Saburi, E.; Davoodnia, A.; Tavakoli-Hoseini,
N. Synth. React. Inorg. Met-Org. Nano-Met.