Synthesis, characterization and application of 3-methyl-1-sulfonic acid imidazolium tetrachloroferrate as nanostructured catalyst for the tandem reaction of β-naphthol with aromatic aldehydes and amide derivatives

Article abstract of DOI:10.1002/aoc.4058

3-methyl-1-sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl₄} was prepared and fully characterized by fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gra

Full text of DOI:10.1002/aoc.4058

Received: 29 May 2017
DOI: 10.1002/aoc.4058
Revised: 21 July 2017
Accepted: 23 July 2017
F U L L P A P E R
Synthesis, characterization and application of 3‐methyl‐1‐
sulfonic acid imidazolium tetrachloroferrate as
nanostructured catalyst for the tandem reaction of
β‐naphthol with aromatic aldehydes and amide derivatives
Ardeshir Khazaei1
| Ahmad Reza Moosavi‐Zare2
| Saeed Firoozmand1 |
Mohammad Reza Khodadadian1
1 Faculty of Chemistry, Bu‐Ali Sina
University, Hamedan 6517838683, Iran
2 Sayyed Jamaleddin Asadabadi University,
Asadabad 6541835583, I.R., Iran
3‐methyl‐1‐sulfonic acid imidazolium tetrachloroferrate {[Msim]FeCl4} was pre-
pared and fully characterized by fourier transform infrared spectroscopy (FT‐
IR), X‐ray diffraction (XRD), thermal gravimetric analysis (TGA), differential
thermal gravimetric (DTG), field emission scanning electron microscopy
(FESEM), energy dispersive X‐ray analysis (EDX) and vibrating sample magnetom-
eter (VSM) and used, as an efficient catalyst, for the tandem reaction of β‐naphthol
with aromatic aldehydes and benzamide at 110 °C under solvent‐free conditions
to give 1‐amidoalkyl‐2‐naphthols in high yields and very short reaction times.
Correspondence
Ardeshir Khazaei, Faculty of Chemistry,
Bu‐Ali Sina University, Hamedan,
6517838683, Iran.
Email: khazaei_1326@yahoo.com
Ahmad Reza Moosavi‐Zare, Sayyed
Jamaleddin Asadabadi University,
Asadabad, 6541835583, I.R. Iran.
Email: moosavizare@yahoo.com
KEYWORDS
1‐Amidoalkyl‐2‐naphthol, 3‐methyl‐1‐sulfonic acid imidazolium tetrachloroferrate, sulfonic acid
functionalized imidazolium salt, β‐naphthol
Funding information
Bu Ali Sina University
1 | INTRODUCTION
chloride,[20] Ce(SO4)2,[21] Fe(HSO4)3,[22] sulfamic acid/
ultrasound,[23a] multi‐wall carbon nanotube supported
1‐Amidoalkyl‐2‐naphthol derivatives are of importance as
they can be easily converted to biologically active com-
pounds, 1‐aminoalkyl‐2‐naphthols, by amide hydrolysis
reaction. 1‐Amidoalkyl‐2‐naphthols can be also converted
to 1,3‐oxazine derivatives.[1] 1,3‐Oxazines have potentially
different biological activities including antibiotic,[2] anti-
tumor,[3] analgesic,[4] anticonvulsant,[5] antipsychotic,[6]
antimalarial,[7] antianginal,[8] antihypertensive,[9] and
antirheumatic properties.[10] Several catalysts have been
reported to catalyze the synthesis of 1‐Amidoalkyl‐2‐
naphthols, including trityl chloride,[11] [Msim]Cl,[12] Ionic
liquid triethylamine‐bonded sulfonic acid,[13] 1,3‐disul-
fonic acid imidazolium hydrogen sulfate,[14] Saccharin
sulfonic acid,[15] pyrazine‐1,4‐diium trinitromethanide,[16]
silica gel supported dual acidic ionic liquid,[17] 1‐
hexanesulphonic acid sodium salt,[18] hafnium (IV)
bis(perfluorooctanesulfonyl)imide complex,[19] silica
Co (II) Schiff base complex,[23b] poly(bis‐imidazolium‐p‐
phenylenesulfonic acid),[23c] and graphene oxide.[23d]
Thus, search for finding an efficient, general and nonpol-
luting protocol for the synthesis of 1‐aminoalkyl‐2‐naph-
thols is still of practical importance.
Ionic liquids (ILs) have received considerable interest
as eco‐friendly solvents, catalysts and reagents in organic
synthesis, due to their unique properties such as low
volatility, non‐flammability, high thermal stability,
negligible vapor pressure and ability to dissolve a wide
range of materials.[24,25] Considering the high significance
of acidic ILs, recently, sulfonic acid functionalized
imidazolium salts (SAFIS) were prepared as new category
of ionic liquids and solid salts, and applied them as
efficient catalysts in some organic transformations.[26–36]
In continuous of studies on the synthesis of
acidic ionic liquids and acidic salts, we have used 3‐
Appl Organometal Chem. 2017;e4058.
wileyonlinelibrary.com/journal/aoc
Copyright © 2017 John Wiley & Sons, Ltd.
1 of 8
https://doi.org/10.1002/aoc.4058

2 of 8
KHAZAEI ET AL.
methyl‐1‐sulfonic acid imidazolium tetrachloroferrate
{[Msim]FeCl4} (Figure 1) as an efficient catalyst on the
synthesis of 1‐amidoalkyl‐2‐naphthol derivatives (Scheme 1).
5 mmol), and then dry FeCl3 (0.8042 g, 5 mmol) was added
over a period of 5 minutes at 70 °C. Afterward, the reaction
mixture was stirred for 60 minutes at 70 °C to give
[Msim]FeCl4 as a dark green soiled salt in 98% yield.
2 | EXPERIMENTAL
2.1 | General
2.3 | General procedure for the synthesis
of 1‐amidoalkyl‐2‐naphthols
All chemicals were purchased from Merck or Fluka
Chemical Companies. The known products were identi-
fied by comparison of their melting points and spectral
data with those reported in the literature.
To a well‐ground mixture of β‐naphthol (0.288 g, 2 mmol),
aldehyde (2 mmol) and amide derivative (2.4 mmol) in a
10 ml round‐bottomed flask connected to a reflux con-
denser, was added the catalyst (5 mol%), and the resulting
mixture was stirred in an oil‐bath (110 °C). After comple-
tion of the reaction, as monitored by TLC, the reaction
mixture was cooled to room temperature. The crude
product was purified by recrystallization from ethanol
(95%). The spectra of compounds was given in supporting
information.
2.2 | Procedure for the preparation of
[Msim]FeCl4
A round‐bottomed flask (50 ml) was charged with 3‐
methyl‐1‐sulfonic acid imidazolium chloride (0.9931 g,
FIGURE 1 Structures of 3‐methyl‐1‐
sulfonic acid imidazolium
tetrachloroferrate {[Msim]FeCl4}
O
[Msim]FeCl4 (5 mol%)
OH
Ph NH2
OH
°C
R
NH
O
Ph
O
SCHEME 1 The preparation of 1‐
amidoalkyl‐2‐naphthols
R
H
ClSO3H (neat)
CH2Cl2, r.t.
60 min
+
+
N
N
N
N
N
Cl
N
FeCl4
SO3H
SO3H
70 °C
SCHEME 2 The preparation of [Msim]
[Msim]FeCl4
[Msim]Cl
FeCl4
FIGURE 2 IR spectrum of 3‐methyl‐1‐
sulfonic acid imidazolium
tetrachloroferrate {[Msim]FeCl4}

KHAZAEI ET AL.
3 of 8
dry FeCl3 at 70 °C (Scheme 2).[36b] The structure of
[Msim]FeCl4 was studied by FT‐IR, XRD, TGA, DTG,
FESEM, EDX and VSM analysis.
3 | RESULTS AND DISCUSSION
At first, 1‐methylimidazole in dry CH2Cl2 was
reacted with chlorosulfonic acid at room temperature to
give 3‐methyl‐1‐sulfonic acid imidazolium chloride
{[Msim]Cl} as a viscous colorless oil.[12] Then [Msim]
FeCl4 was prepared by the reaction of [Msim]Cl with
In the IR spectrum of new catalyst, the O‐H stretching
of SO3H group was appeared at 2650–3550 cm−1. Also, the
two peaks observed at 1062 cm−1 and 1179 cm−1 related to
vibrational modes of N‐SO2 and O‐SO2 bonds (Figure 2).[37]
The morphology of [Msim]FeCl4 was investigated by
field emission scanning electron microscopy (FESEM).
FESEM analysis of the catalyst is depicted in Figure 3.
As SEM image of the catalyst, indicates that the particles
were prepared in nano size.
XRD pattern of [Msim]FeCl4 was also studied
(Figure 4). Diffraction peaks at various 2θ values includ-
ing 9.1°, 15.5°, 20.1°, 24.1°, 29.2° and 34.7° are shown in
Figure 4. Crystallite size was obtained for the highest peak
(2θ = 29.2°) by Debye–Scherrer's formula given by equa-
tion: D = Kλ/ (βcosθ). The obtained crystallite size for
[Msim]FeCl4 using this formula, was at about 13.7 nm.
Also, inter planer distance was calculated at about
0.3058 nm (for the same highest diffraction line at 29.2°)
by the Bragg equation: dhkl = λ/(2 sin ), (λ: Cu radiation
(0.154178 nm).
FIGURE
(FESEM) of [Msim]FeCl4
3
Field emission scanning electron microscopy
FIGURE 4 XRD diagram of [Msim]
FeCl4
FIGURE 5 The energy‐dispersive X‐ray
spectroscopy (EDX) of [Msim]FeCl4

4 of 8
KHAZAEI ET AL.
Energy dispersive spectroscopy (EDS) spectrum of
Thermal gravimetry (TG) and differential thermal
gravimetric (DTG) of the catalyst was investigated in a
range of temperature between 25 to 600 °C. The TG of
the catalyst showed three weight losses (Figures 6
and 7). The strong loss weight observed after 291 °C and
the other strong weight losses appeared after 494 °C.
Therefore, the molecular decomposition of the catalyst
was occurred after 300 °C.
[Msim]FeCl4 was displayed in Figure 5. As it is shown in
Figure 5, indicates that the existence of carbon, nitrogen,
sulfur, chlorine, iron and oxygen in [Msim]FeCl4.
TABLE 1 Effect of the catalyst amount and temperature on the
reaction between benzaldehyde, β‐naphthol and benzamide.
Catalyst
Entry amount (g) Temp. (C
̊
)
Time (min) Yielda (%)
1
2
3
4
5
6
7
8
9
1
5
110
110
110
110
110
80
10
3
90
95
95
95
95
88
90
92
95
10
15
20
5
3
3
3
FIGURE 6 Thermal gravimetric (TG) analysis of [Msim]FeCl4 at
range of 25–600 °C, with a temperature increase rate of 10 °C
8
5
90
6
5
100
120
5
5
3
aIsolated yield.
TABLE 2 Effect of various solvents on the reaction of benzalde-
hyde, β‐naphthol and benzamide, in the persence of [Msim]FeCl4
Entry Solvent
Temp. (°C) Time (min) Yielda (%)
1
2
3
4
5
6
CHCl3
EtOAc
EtOH
Reflux
Reflux
Reflux
Reflux
15
15
15
15
15
3
40
20
35
30
40
95
CH2Cl2
n‐hexane Reflux
110
FIGURE 7 Differential thermogravimetric (DTG) analysis of
[Msim]FeCl4 at range of 25–600 °C, with a temperature increase
rate of 10 °C
‐
aIsolated yield.
FIGURE 8 Magnetization curve of the
prepared catalyst

KHAZAEI ET AL.
5 of 8
TABLE 3 The solvent‐free synthesis of 1‐aminoalkyl‐2‐naphthols from 2‐naphthol, aromatic aldehydes and benzamide using {[Msim]
FeCl4} at 110 °C
Time
(Min)
Yielda
(%)
TOFb(min−1)/
TONc
Mp °C
(Lit.)
Entry
Aldehyde
Product
1
3
95
6.3/19
244–246
(237–239)
[38]
2
3
4
90
4.5/18
215–217
(217–218)
[39]
4
91
4.5/22.75
252–254
‐
4
5
6
4
5
4
87
88
90
4.3/17.4
3.5/17.6
4.5/18
242–245
(238–239)
[20]
[40]
[39]
233–235
(228–229)
226–228
(225–226)
7
8
4
6
93
95
4.6/18.6
3.1/19
197–199
(182–184)
[41]
245–247
‐
(Continues)

6 of 8
KHAZAEI ET AL.
TABLE 3 (Continued)
Time
(Min)
Yielda
(%)
TOFb(min−1)/
TONc
Mp °C
(Lit.)
Entry
Aldehyde
Product
9
3
2
4
4
85
90
92
94
5.6/17
213–216
(213–215)
[11a]
10
11
12
9.0/18
225–227
(220–221)
[39]
4.6/18.4
4.7/18.8
264–167
(264–266)
[20]
243–245
(240–242)
[20]
13
14
4
3
89
82
4.4/17.8
5.4/16.4
256–259
‐
219–221
(218–219)
[40]
aIsolated yield,
bTurn‐over frequency,
cTurn‐over number.
The magnetization curve that is shown in Figure 8
determined the values of magnetic moment of [Msim]
FeCl4.
To optimize the reaction conditions, the reaction of
benzaldehyde, β‐naphthol and benzamide was studied
using different quantities of [Msim]FeCl4, at range of
80–120 °C under solvent‐free conditions. The results are
depicted in Table 1. As it is shown in Table 1, indicates
that 5 mol% of catalyst was sufficient to give the product
in excellent yields and in very short reaction times at
110 °C (Table 1, entry 3). No improvement in the reaction
results was observed by increasing the amount of the
catalysts and the temperature.
The model reaction was also tested in the persence of
several solvents using 5 mol% of catalyst in comparision
with solvent free‐condition. The results were shown that

KHAZAEI ET AL.
7 of 8
solvent‐free condition was the best condition in this
reaction (Table 2, entry 6).
After optimization of the reaction conditions, the
reaction of β‐naphthol with various aryl aldehydes and
benzamide was tested in the presence of [Msim]FeCl4 at
110 °C in the absence of solvent, in order to assess the
scope and the generality of the catalysts. The results are
depicted in Table 3. As it is shown in Table 3, aryl
aldehydes possessing electron‐releasing substituents,
electron‐withdrawing substituents and halogens on their
aromatic rings were utilized successfully in the reaction,
and gave the expected products in high yields and in short
reaction times.
In a plausible mechanism (Scheme 3) which is sup-
ported by the literature,[12] at first, aromatic aldehyde is
activated by acidic group of [Msim]FeCl4 to give I. Then,
β‐naphthol attacks to the carbonyl group of the activated
aldehyde, and affords intermediate II. Next, by removing
H2O from II, orthoquinone methide (o‐QM, III) is
prepared. [Msim]FeCl4 again activates intermediate III
to give IV as a Michael acceptor. Afterward, Michael
addition of amide to intermediate IV affords the expected
1‐amidoalkyl‐2‐naphthol.
FIGURE 9 The reaction of benzaldehyde (1 mmol), β‐naphthol
(1 mmol) and benzamide (1 mmol) in the presence of the reused
[Msim]FeCl4
4 | CONCLUSIONS
In this work, we have introduced 3‐methyl‐1‐sulfonic acid
imidazolium tetrachloroferrate {[Msim]FeCl4}, as an
efficient catalyst for the synthesis of 1‐amidoalkyl‐2‐naph-
thols, by the condensation reaction of β‐naphthol with
various aryl aldehydes and amides at 110 °C under solvent
free conditions.
Reusability of the catalyst was also studied upon the
reaction of benzaldehyde (1 mmol), β‐naphthol (1 mmol)
and benzamide (1 mmol). The reaction mixture was
extracted by warm acetone to separate from the catalyst.
We observed that the catalytic activity of the catalyst
was restored within the limits of the experimental errors
for four successive runs (Figure 9).
ACKNOWLEDGEMENTS
We sincerely acknowledge the financial supports from
Bu‐Ali Sina University Research Councils and Center of
Excellence in Development of Chemistry Methods
(CEDCM).
FeCl
N
4
FeCl
N
O
S
4
N
O
S
N
O
O
O
ORCID
H
O
FeCl
N
4
H
O
Ardeshir Khazaei http://orcid.org/0000-0001-7990-2266
OH
H
O
H
OH
O
S
H
N
Ahmad Reza Moosavi‐Zare
http://orcid.org/0000-0003-
O
O
O
H
0321-9326
II
I
O
REFERENCES
H N
FeCl
2
4
O
[1] M. Damodiran, N. P. Selvam, P. T. Perumal, Tetrahedron Lett.
2009, 50, 5474.
OH
H
S
N
N
O
S
O
O
-H2O
O
O
N
[2] Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose,
N
O
III
S. Shirato, J. Antibiot. 1972, 25, 44.
IV
[3] S. Remillard, L. I. Rebhun, G. A. Howie, S. M. Kupchan, Science
1975, 189, 1002.
O
O
O
H
H
FeCl
N
4
NH
N
[4] G. Y. Lesher, A. R. Surrey, J. Am. Chem. Soc. 1955, 77, 636.
O
S
OH
+
OH
N
[5] H. S. Mosher, M. B. Frankel, M. Gregory, J. Am. Chem. Soc.
1953, 75, 5326.
O
SCHEME 3 The proposed mechanism for the synthesis of 1‐
amidoalkyl‐2‐naphthols
[6] J. L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot, M.
Millan, Bioorg. Med. Chem. Lett. 1997, 7, 881.

8 of 8
KHAZAEI ET AL.
[7] H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna, S. Croft,
H. Kendrick, V. Yardley, G. Moyna, Bioorg. Med. Chem. Lett.
2001, 11, 1851.
[28] A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, A. Zare, Sci.
Iran., Trans. C 2010, 17, 31.
[29] M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare, H. G.
Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem‐Rostami, J. Org.
Chem. 2012, 77, 3640.
[8] F. Benedini, G. Bertolini, R. Cereda, G. Doná, G. Gromo, S.
Levi, J. Mizrahi, A. Sala, J. Med. Chem. 1995, 38, 130.
[9] R. D. Clark, J. M. Caroon, A. F. Kluge, D. B. Repke, A. P.
Roszkowski, A. M. Strosberg, S. Baker, S. M. Bitter, M. D.
Okada, J. Med. Chem. 1983, 26, 657.
[30] A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, A. Zare, E.
Ghaemi, V. Khakyzadeh, Z. Asgari, A. Hasaninejad, Sci. Iran.,
Trans. C. 2011, 18, 1365.
[10] H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto, N.
Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda, K. Yano,
T. Kuroki, J. Med. Chem. 1997, 40, 105.
[31] M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi‐Zare, A. Zare,
S. B. Azimi, Z. Asgari, A. Hasaninejad, C. R. Chimia 2012,
15, 719.
[11] a) A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, A. Zare, A.
Parhami, A. Khalafi‐Nezhad, Appl. Catal. A: Gen. 2010, 386,
179. b) A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, F. Abi,
A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem‐Rostami, A.
Parhami, H. Torabi‐Monfared, Tetrahedron 2013, 69, 212. c)
A. R. Moosavi‐Zare, M. A. Zolfigol, F. Derakhshan‐Panah, M.
Daraei, Can. J. Chem. 2015, 93, 1245.
[32] A. Khazaei, M. A. Zolfigol, A. R. Moosavi‐Zare, Z. Asgari, M.
Shekouhy, A. Zare, A. Hasaninejad, RSC Adv. 2012, 2, 8010.
[33] M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi‐Zare, G.
Chehardoli, F. Derakhshan‐Panah, A. Zare, O. Khaledian, Sci.
Iran., Trans. C. 2012, 19, 1584.
[34] 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, R. Roohandeh, J. Mol. Liq. 2012, 167, 69.
[12] a) M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare, V.
Khakyzadeh, Appl. Catal. A: Gen. 2011, 400, 70. b) A. R.
Moosavi‐Zare, M. A. Zolfigol, M. Daraei, Synlett 2014, 25,
1173.
[35] 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, S. Balandeh, S. Afr. J. Sci. 2012, 65, 63.
[13] A. Zare, S. Akbarzadeh, E. Foroozani, H. Kaveh, A. R. Moosavi‐
Zare, A. Hasaninejad, M. Mokhlesi, M. H. Beyzavi, M. A.
Zolfigol, J. Sulfur Chem. 2012, 33, 259.
[36] a) A. Zare, F. Abi, A. R. Moosavi‐Zare, M. H. Beyzavi, M. A.
Zolfigol, J. Mol. Liq. 2013, 178, 113. b) P. Gogoi, A. K. Dutta,
P. Sarma, R. Borah, Appl. Catal. A: Gen. 2015, 492, 133.
[14] A. Zare, T. Yousofi, A. R. Moosavi‐Zare, RSC Adv. 2012, 2, 7988.
[15] A. Zare, H. Kaveh, M. Merajoddin, A. R. Moosavi‐Zare, A.
Hasaninejad, M. A. Zolfigol, Phosphorus, Sulfur, Silicon 2013,
188, 573.
[37] A. R. Moosavi‐Zare, M. A. Zolfigol, M. Zarei, A. Zare, V.
Khakyzadeh, A. Hasaninejad, Appl. Catal. A: Gen. 2013, 467,
[16] M. A. Zolfigol, S. Baghery, A. R. Moosavi‐Zare, S. M. Vahdat,
J. Mol. Catal. A: Chem. 2015, 409, 216.
61.
[38] A. P. de los Rios, F. J. Hernandez‐Fernandez, F. Tomas‐Alonso,
J. M. Palacios, D. Gomez, M. Rubio, G. Villora, J. Membr. Sci.
2007, 300, 88.
[17] Q. Zhang, J. Luo, Y. Wei, Green Chem. 2010, 12, 2246.
[18] K. S. Niralwad, B. B. Shingate, M. S. Shingare, Chin. Chem. Lett.
2011, 22, 551.
[39] C. Wang, Y. Wan, H.‐Y. Wang, L.‐L. Zhao, J.‐J. Shi, X.‐X.
Zhang, H. Wu, J. Heterocyclic Chem. 2013, 50, 496.
[19] M. Hong, C. Cai, W. B. Yi, Chin. Chem. Lett. 2011, 22, 322.
[20] B. Datta, M. A. Pasha, Ultrason. Sonochem. 2011, 18, 624.
[21] N. P. Selvam, P. T. Perumal, Tetrahedron Lett. 2006, 47, 7481.
[40] M. Zandi, A. Sardarian, C. R. Chimie. 2012, 15, 365.
[41] B. Adrom, N. Hazeri, M. T. Maghsoodlou, M.
Mollamohammadi, Res. Chem. Intermed. 2015, 41, 4741.
[22] H. R. Shaterian, H. Yarahmadi, M. Ghashang, Bioorg. Med.
Chem. Lett. 2008, 18, 788.
[23] a) S. B. Patil, P. R. Singh, M. P. Surpur, S. D. Samant, Ultrason.
Sonochem. 2007, 14, 515. b) J. Rakhtshah, S. Salehzadeh, Appl.
Organometal. Chem. 2017, 31, https://doi.org/10.1002/
aoc.3560. c) A. S. Amarasekara, J. Nguyen, A. Razzaq,
J. Polym. Res. 2017, 24, 52. d) A. Gupta, D. Kour, V. K. Gupta,
K. K. Kapoor, Tetrahedron Lett. 2016, 57, 4869.
SUPPORTING INFORMATION
Additional Supporting Information may be found online
in the supporting information tab for this article.
[24] P. Wasserscheid, T. Welton, Ionic liquids in synthesis, Wiley‐
VCH, Weinheim 2008.
How to cite this article: Khazaei A,
Moosavi‐Zare AR, Firoozmand S, Khodadadian
MR. Synthesis, characterization and application of
3‐methyl‐1‐sulfonic acid imidazolium
[25] A. R. Moosavi‐Zare, M. A. Zolfigol, M. Zarei, A. Zare, V.
Khakyzadeh, J. Mol. Liq. 2013, 186, 63.
[26] M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare,
Organic Preparations and Procedures International, Vol. 42
2010 95.
tetrachloroferrate as nanostructured catalyst for the
tandem reaction of β‐naphthol with aromatic
aldehydes and amide derivatives. Appl Organometal
Chem. 2017;e4058. https://doi.org/10.1002/aoc.4058
[27] M. A. Zolfigol, A. Khazaei, A. R. Moosavi‐Zare, A. Zare, J. Iran.
Chem. Soc. 2010, 7, 646.