Ionic liquid immobilized on FeNi3 as catalysts for efficient, green, and one-pot synthesis of 1,3-thiazolidin-4-one

Article abstract of DOI:10.1016/j.molliq.2014.07.039

A magnetically ionic liquid (ILs) supported on FeNi₃ nanocatalyst was synthesized and evaluated as a recoverable catalyst for the synthesis of 1,3-thiazolidin-4-one. The main targets are solvent-free conditions, rapid (immediately) and easy immobilization technique, and low cost precursors for the preparation of highly active and stable MPs with high densities of functional groups. The inorganic, magnetic, solid base catalyst was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM). The catalyst is active for the synthesis of 1,3-thiazolidin-4-ones and the products are isolated in high to excellent yields. Supporting this base catalyst on magnetic particles offers a simple and non-energy-intensive method for recovery and reuse of the catalyst by applying an external magnet. Isolated catalysts were reused for new rounds of reactions without significant loss of their catalytic activity.

Full text of DOI:10.1016/j.molliq.2014.07.039

MOLLIQ-04374; No of Pages 5
Journal of Molecular Liquids xxx (2014) xxx–xxx
Contents lists available at ScienceDirect
Journal of Molecular Liquids
journal homepage: www.elsevier.com/locate/molliq
Ionic liquid immobilized on FeNi3 as catalysts for efficient, green,
and one-pot synthesis of 1,3-thiazolidin-4-one
b
Seyed Mohsen Sadeghzadeh a, , Faeze Daneshfar
⁎
a
Department of Chemistry, College of Sciences, Birjand University, P.O. Box 97175-615, Birjand, Iran
Department of Physics, College of Sciences, Birjand University, P.O. Box 97175-614, Birjand, Iran
b
a r t i c l e i n f o
a b s t r a c t
Article history:
A magnetically ionic liquid (ILs) supported on FeNi3 nanocatalyst was synthesized and evaluated as a recoverable
catalyst for the synthesis of 1,3-thiazolidin-4-one. The main targets are solvent-free conditions, rapid (immediately)
and easy immobilization technique, and low cost precursors for the preparation of highly active and stable MPs with
high densities of functional groups. The inorganic, magnetic, solid base catalyst was characterized via Fourier
transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission
electron microscopy (TEM) and vibrating sample magnetometer (VSM). The catalyst is active for the synthesis of
1,3-thiazolidin-4-ones and the products are isolated in high to excellent yields. Supporting this base catalyst on
magnetic particles offers a simple and non-energy-intensive method for recovery and reuse of the catalyst by
applying an external magnet. Isolated catalysts were reused for new rounds of reactions without significant loss
of their catalytic activity.
Received 28 May 2014
Received in revised form 13 July 2014
Accepted 23 July 2014
Available online xxxx
Keywords:
Multi-component cyclization
Magnetic nanoparticles (MNPs)
Solvent-free
Green chemistry
One-pot synthesis
Ionic liquid
© 2014 Elsevier B.V. All rights reserved.
1. Introduction
In recent years, core–shell multi-components have attracted intense
attention because of their potential applications in catalysis [17]. Differ-
The thiazolidin-4-one ring system is a core structure found in various
synthetic pharmaceutical compounds, displaying a broad spectrum of
biological activities [1–6]. Consequently, several synthetic methods
have been developed for the synthesis of 4-thiazolidinones. The main
synthetic routes to thiazolidin-4-ones involve cyclo-condensation of
azomethines (Schiff's base) with mercaptoacetic acid [7]. There are
also reports using chemical agents, such as N-methylpyridinium tosylate
[8] as desiccant, to assist the formation of thiazolidinone derivatives. The
use of [BmIm]OH [9], Hunig's base [10], and Baker's yeast [11] has also
been reported to expedite the cyclo-condensation of the azomethines
and thioglycolic acid.
Ionic liquids (ILs) have emerged as promising homogeneous cata-
lysts [12] because of their unique physicochemical properties including
negligible vapor pressure, wide liquid range, high ionic conductivity and
excellent solubility [13]. Although ILs possess some advantages but their
practical applications have been restricted by some difficulties in its
recovery which lead to economical and environmental problems. On
the other hand, their high viscosity not only limits their mass transfer
during catalytic reactions but also makes their handling difficult. More-
over, the use of relatively large amounts of ILs is costly and may cause
toxicological concerns. These problems can be overcome by immobiliza-
tion of ILs onto solid supports to obtain heterogeneous catalysts [14–16].
ent from single-component that can only supply people with one
function, the core–shell multi-components can integrate multiple func-
tions into one system for specific applications [18–22]. Moreover, the
interactions between different components can greatly improve the
performance of the multi-components system and even generate new
synergetic properties. Among the core–shell structured composites,
the composites with magnetic core and functional shell structures
have received especial attention because of their potential applications
in catalysis, drug storage/release, selective separation, chromatography,
and chemical or biologic sensors [23–32]. The magnetic core has good
magnetic responsibility, and can be easily magnetized. Therefore, the
composites with magnetic core can be conveniently collected, separated
or fixed by external magnet. Engaged in the development of greener
and sustainable pathways for organic transformations, nanomaterial,
and nano-catalysis [33–36], herein, we report a simple and efficient
synthesis of a nano-ferrite-supported, magnetically recyclable, and
inexpensive ionic liquids catalyst and its application for the synthesis
1,3-thiazolidin-4-ones (Scheme 1).
2. Experimental
2.1. Materials and methods
Chemical materials were purchased from Fluka and Merck in high
purity. Melting points were determined in open capillaries using an
⁎
Corresponding author. Tel./fax: +98 561 2502065.
E-mail address: sadeghzadeh_sm@yahoo.com (S.M. Sadeghzadeh).
http://dx.doi.org/10.1016/j.molliq.2014.07.039
0167-7322/© 2014 Elsevier B.V. All rights reserved.
Please cite this article as: S.M. Sadeghzadeh, F. Daneshfar, J. Mol. Liq. (2014), http://dx.doi.org/10.1016/j.molliq.2014.07.039

2
S.M. Sadeghzadeh, F. Daneshfar / Journal of Molecular Liquids xxx (2014) xxx–xxx
S
O
O
FeNi3-ILs
solvent free
N
R1
CHO
OH
+
NH2
R2
+
R1
SH
R2
Scheme 1. Synthesis of thiazolidinon-4-ones in the presence of FeNi3-ionic liquids MNPs.
Electrothermal 9100 apparatus are uncorrected. FTIR spectra were
recorded on a VERTEX 70 spectrometer (Bruker) in the transmission
mode in spectroscopic grade KBr pellets for all the powders. The particle
size and structure were observed by using a Philips CM10 transmission
electron microscope operating at 100 KV. Powder X-ray diffraction data
was obtained using Bruker D8 Advance model with Cu ka radition.
The thermogravimetric analysis (TGA) was carried out on a NETZSCH
STA449F3 at a heating rate of 10 °C min−1 under nitrogen. The magnet-
ic measurement was carried out in a vibrating sample magnetometer
(VSM) (4 inch, Daghigh Meghnatis Kashan Co., Kashan, Iran) at room
temperature. NMR spectra were recorded in DMSO on a Bruker Avance
DRX-400 MHz instrument spectrometer using TMS as internal standard.
The purity determination of the products and reaction monitoring were
accomplished by TLC on silica gel polygram SILG/UV 254 plates.
solid was separated by an external magnet and washed 3 times with
CH2Cl2, ethanol and H2O. After drying at room temperature in vacuum,
FeNi3-ILs were obtained as reddish-brown powder.
2.6. General procedures for preparation of 1,3-thiazolidin-4-ones
A mixture of aldehyde (1 mmol), amine (1 mmol), thioglycolic acid
(1 mmol), and FeNi3-ILs MNPs (0.001 g) was stirred at 50 °C. Upon
completion, the progress of the reaction was monitored by TLC when
the reaction was completed, EtOH was added to the reaction mixture
and the FeNi3-ILs MNPs was separated by external magnet. Then the
solvent was removed from solution under reduced pressure and the
resulting product purified by recrystallization using n-hexane/ethyl
acetate.
2.2. General procedure for the preparation of FeNi3 nanoparticles
2.7. Selected spectral data of the products 2-(2-nitrophenyl)-3-p-
tolylthiazolidin-4-one (4c)
FeCl2·4H2O (1.72 g) and NiCl2·6H2O (4.72 g) were dissolved in 80 mL
of deaerated highly purified water contained in a three neck flask with
vigorous stirring (800 rpm) under nitrogen. As the temperature was
elevated to 80 °C, 10 mL of ammonium hydroxide was added drop by
drop, and the reaction was maintained for 30 min. hydrazine hydrate
(20 mL, 80% concentration) was added to the above suspension. The
black product was separated by putting the vessel on a permanent
magnet and the supernatant was decanted. The black precipitate was
washed for six times with highly purified water to remove the unreacted
chemicals, then the black product FeNi3 was dried in the vacuum.
IR (KBr): υ = 3036, 2930, 1723, 1548, 1529, 1352 cm−1 1H NMR
;
(400 MHz, DMSO-d6): υ = 8.01 (d, J = 8.1 Hz, 1H.), 7.70–7.73 (m,
2H), 7.47–7.52 (m, 1H), 7.36 (d, J = 8.3 Hz, 2H), 7.13 (d, J = 8.2 Hz,
2H), 6.72 (s, 1H), 3.98 (d, J = 15.7 Hz, 1H), 3.78 (d, J = 15.8 Hz, 1H),
2.18 (s, 3H) ppm.
3. Results and discussion
We report the synthesis of a magnetic particle-based solid base with
a high density of ionic liquids groups and discuss its performance as a
novel strong and stable magnetic ionic liquid. We were intrigued by
2.3. General procedure for the preparation of FeNi3/SiO2 nanoparticles
Firstly, a mixture of ethanol (100 mL) and distilled water (20 mL)
was added to magnetic nanoparticles (1 g), and the resulting dispersion
was sonicated for 10 min. After adding ammonia water (2.5 mL),
tetraethyl orthosilicate (TEOS, 2 mL) was added to the reaction solution.
The resulting dispersion was under mechanically stirred continuously
for 20 h at room temperature. The magnetic FeNi3/SiO2 nanoparticles
were collected by magnetic separation and washed with ethanol and
deionized water in sequence.
2.4. General procedure for the preparation of FeNi3/SiO2/SO3H nanoparticles
To a round-bottomed flask (100 mL) FeNi3/SiO2 MNPs (0.40 g) in
CH2Cl2 (50 mL), was added chlorosulfonic acid (12 mmol) dropwise
over a period of 20 min at room temperature (Fig. 1). After vigorous
stirring for 24 h, the magnetic FeNi3/SiO2/SO3H nanoparticles were
collected by magnetic separation and washed with ethanol and deionized
water in sequence.
2.5. General procedure for the preparation of FeNi3-ILs nanoparticles
Ethanolamine (5 mmol) was dispersed in dry CH2Cl2 (20 mL) and
FeNi3/SiO2/SO3H (0.1 g) nanoparticles were added. Then the mixture
was heated to 60 °C for 12 h under nitrogen atmosphere. The resulting
Fig. 1. (a) TEM images of FeNi3-ILs MNPs.
Please cite this article as: S.M. Sadeghzadeh, F. Daneshfar, J. Mol. Liq. (2014), http://dx.doi.org/10.1016/j.molliq.2014.07.039

S.M. Sadeghzadeh, F. Daneshfar / Journal of Molecular Liquids xxx (2014) xxx–xxx
3
Ethanolamine
Tetraethyoxysilane
ClSO3H
FeNi3
OH
FeNi3
O
FeNi3
O
FeNi3
O
O
O
O
Si
OH
-
+H3N
SO3H
SO3
Scheme 2. Schematic illustration of the synthesis for FeNi3-ILs MNPs.
the possibility of applying ionic liquid and nanotechnology for the
design of a novel, active, recyclable, and magnetically recoverable
ionic liquid base derivative (Scheme 2).
The size and structure of the FeNi3-ILs MNPs were also evaluated
using transmission electron microscopy (TEM) (Fig. 1). After being
coated with a SiO2 and organic layer, the typical core–shell structure of
the FeNi3-ILs MNPs can be observed. The dispersity of FeNi3-ILs MNPs
is also improved, and the average size increases to about 20–30 nm.
The structural properties of synthesized FeNi3-ILs MNPs were ana-
lyzed by X-ray power diffraction (XRD). As shown in Fig. 2, XRD patterns
of the synthesized FeNi3-ILs MNPs display several relatively strong
reflection peaks in the 2θ region of 20–80°, which is quite similar to
those of FeNi3 nanoparticles reported by other group. It can be seen
that three characteristic peaks for (FCC)-FeNi3 (2θ = 44.3°, 51.5°,
75.9°) from (111), (200), and (220) planes, are obtained. The sharp
and strong diffraction peaks confirm the good crystallization of the
products (Fig. 2a). The broad band at 2θ = 15.0°–30.0° can be assigned
to the amorphous SiO2 shell (Fig. 2b) (JCPDS card No. 29-0085).
This structure was further supported by the FT-IR spectra. The FT-IR
spectrum of FeNi3-ILs MNPs showed the typical bands at 2921 and
2866 cm−1 attributed to C\H stretching vibrations of alkyl chains.
Moreover, the broad peak at 1033 cm−1 belonged to S_O stretching
vibrations in the sulphonate functional groups. Bands at 1624 and
1502 cm−1 were related to N\H bending vibrations in the ammonium
groups. These results indicated that IL was successfully immobilized on
FeNi3 MNPs (Fig. 2c).
The thermal behavior of FeNi3-ILs MNPs is shown in Fig. 2d. A signif-
icant decrease in the weight percentage of the FeNi3-ILs MNPs at about
130 °C is related to desorption of water molecules from the catalyst
surface. This was evaluated to be 1–3% according to the TG analysis. In
addition, the analysis showed two other decreasing peaks. The first
peak appears at temperature around 250–280 °C due to the decomposi-
tion of SO3H. This is followed by a second peak at 420–460 °C, corre-
sponding to the loss of the organic spacer group. According to the
TGA, the amount of IL supported on FeNi3/SiO2 was evaluated to
be 0.15 mmol g−1. The loading amount of IL on FeNi3/SiO2 was also
quantified via elemental analysis and it was 0.15 mmol g−1 based on
nitrogen and sulfur determination (0.21% and 0.48%, respectively).
The magnetic properties of the nanoparticles were characterized
using a vibrating sample magnetometer (VSM). The magnetization
curves of the obtained nanocomposite registered at 300 K show that
nearly no residual magnetism is detected (Fig. 3), which means that
the nanocomposite exhibited the paramagnetic characteristics. Magnetic
Fig. 2. XRD analysis of (a) FeNi3 MNPs and (b) FeNi3-ILs MNPs, (c) FTIR spectra of FeNi3-ILs
MNPs, and (d) TGA diagram of FeNi3-ILs MNPs.
Fig. 3. Room-temperature magnetization curves of the nano catalysis.
Please cite this article as: S.M. Sadeghzadeh, F. Daneshfar, J. Mol. Liq. (2014), http://dx.doi.org/10.1016/j.molliq.2014.07.039

4
S.M. Sadeghzadeh, F. Daneshfar / Journal of Molecular Liquids xxx (2014) xxx–xxx
a
Table 1
100
90
80
70
60
50
40
30
20
10
0
Comparative of the catalytic activity of FeNi3-ILs MNPs with ILs.a
Entry
Reaction time (min)
Yield (%)b
FeNi3-ILs
ILs
1
2
3
4
5
20
40
60
80
100
64
70
93
93
93
61
68
88
92
94
a
Reaction condition: aldehyde (1 mmol), amine (1 mmol), thioglycolic acid (1 mmol),
and FeNi3-ILs MNPs or ILs (1 mol.%) at 50 °C.
0
0.0002 0.0004 0.0006 0.0008
0.001
0.0012
b
Isolated yields.
Catalyst (g)
b
100
80
60
40
20
0
MNPs is fixed in 93% but ILs showed 94% preparation of product. The
nano-sized particles increase the exposed surface area of the active
component of the catalyst, thereby enhancing the contact between
reactants and catalyst dramatically and mimicking the homogeneous
catalysts. Also, the activity and selectivity of nano-catalyst can be manip-
ulated by tailoring chemical and physical properties like size, shape,
composition and morphology.
After optimization of the reaction conditions, to delineate this ap-
proach, particularly in regard to library construction, this methodology
was evaluated by using different amines, variety of different substituted
aldehyde and of thioglycolic acid in the presence of FeNi3-ILs MNPs
under similar conditions. As can be seen from (Table 2), electronic effects
and the nature of substituents on the amines and aldehyde did not show
strongly obvious effects in terms of yields under the reaction conditions.
The three-component cyclocondensation reaction proceeded smoothly.
A mechanism for the reaction is outlined in Scheme 4. The reaction
occurs via initial formation of the imine intermediate [A] from the
condensation of aldehyde and amine, which reacts with thioglycolic
acid to give the intermediate which subsequently cyclises to afford the
desired 1,3-thiazolidin-4-one. The nano-PbS has Lewis acid (NH+3 ) and
Lewis basic (OH−) sites.
0
10
20
30
40
50
60
70
T (°C)
Fig. 4. (a) Effect of increasing amount of FeNi3-ILs MNPs on the preparation of 1,3-
thiazolidin-4-one in the presence of FeNi3-ILs MNPs at 100 (°C); (b) reaction progress
monitored by GC.
measurement shows that pure FeNi3, and FeNi3-ILs have saturation mag-
netization values of 55.2, and 30.4 emu/g respectively. These nanocom-
posites with paramagnetic characteristics and high magnetization
values can quickly respond to the external magnetic field and quickly
redisperse once the external magnetic field is removed. The result reveals
that the nanocomposite exhibits good magnetic responsible, which
suggests a potential application for targeting and separation.
4. Conclusion
Under the optimal conditions, the same reaction was carried out in
various solvents under similar conditions. In this study, it was found
that a solvent-free condition is more efficient over other solvents with
respect to reaction time and yield of the desired 1,3-thiazolidin-4-one.
Then the reaction progress in the presence of 0.001 g of FeNi3-ILs
MNPs was monitored by GC (Fig. 4a). Using this catalyst system, excel-
lent yields of 1,3-thiazolidin-4-one can be achieved in 1 h at 50 °C. No
apparent by-products were observed by GC in all the experiments and
the cyclic carbonate was obtained cleanly in 93% yield (Fig. 4b).
The catalytic activity of the FeNi3-ILs MNPs was compared with
the ILs (Scheme 3). For this purpose, the reactions were carried out
separately at 50 °C with both the catalysts for the appropriate time
(Table 1). The aliquots of the reaction mixture were collected periodical-
ly at an interval of 20 min. Table 1 shows the variation of the percentage
preparation of 1,3-thiazolidin-4-one with time, when FeNi3-ILs MNPs
and ILs were employed as catalysts. It is evident that, the catalytic activity
of the FeNi3-ILs MNPs is similar with the ILs. After 60 min FeNi3-ILs MNPs
showed 93% preparation of 1,3-thiazolidin-4-one as compared to 88%
with ILs. After 100 min yield of the product in the presence of FeNi3-ILs
In summary, FeNi3-ILs MNP as a new magnetic nanoparticle catalyst
was synthesized directly through reaction of chlorosulfonic acid and
ethanolamine supported on FeNi3/SiO2 MNPs. The synthesized FeNi3-IL
MNP was used as a magnetically recyclable heterogeneous catalyst for
the efficient one-pot synthesis of 1,3-thiazolidin-4-one from the reac-
tion of aldehyde, amine, and thioglycolic acid with high product yields.
The catalytic research on novel approaches toward nanomaterials
should be improved to enhance organic synthesis. For that purpose,
nanoparticle catalyst provides a new way for continuous processes,
because of its simple recyclability. From a scientific point, our results
Table 2
Synthesis of 1,3-thiazolidin-4-one derivatives catalyzed by FeNi3-ILs MNPs.a
Entry
R1
R2
Product
Yield (%)b
Mp
1
2
3
4
5
6
7
8
9
Me
H
NO2
H
Me
Me
Me
H
H
H
H
Cl
NO2
4a
4b
4c
4d
4e
4f
4g
4h
4i
93
90
89
91
94
86
92
90
90
121–123 [37]
105–107 [37]
157–159
129–131 [37]
122–124 [37]
116–118 [37]
105–107 [37]
121–123 [37]
160–162 [37]
O
Cl
Me
NO2
H
OH
HO
O
H3N
S
H
O
a
Reaction condition: aldehyde (1 mmol), amine (1 mmol), thioglycolic acid (1 mmol),
and FeNi3-ILs MNPs (0.001 g) at 50 °C.
b
Scheme 3. Image of ILs.
Yield refers to isolated product.
Please cite this article as: S.M. Sadeghzadeh, F. Daneshfar, J. Mol. Liq. (2014), http://dx.doi.org/10.1016/j.molliq.2014.07.039

S.M. Sadeghzadeh, F. Daneshfar / Journal of Molecular Liquids xxx (2014) xxx–xxx
5
FeNi3
O
-
SO3
+
H3
FeNi3
O
N
O
OH
-
+
NH3
O3S
HO
HO
O
O
S
N
S
H
H
N
N
+
H
H
H
[A]
Scheme 4. A possible mechanism for the one-pot reaction for the synthesis 1,3-thiazolidin-4-one.
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Please cite this article as: S.M. Sadeghzadeh, F. Daneshfar, J. Mol. Liq. (2014), http://dx.doi.org/10.1016/j.molliq.2014.07.039