A Br?nsted Acid Ionic Liquid Immobilized on Fe3O4?SiO2 Nanoparticles as an Efficient and Reusable Solid Acid Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1134/S1070428020020207

Abstract: In the present study, an efficient and magnetically recoverable Br?nsted acid ionic liquid, 1-methyl-3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe₃O₄?SiO₂ magnetic nanoparticles (Fe₃O₄?SiO₂–ImHSO₄) has been used for a high-yield synthesis of 2,3-dihydroquinazolin-4(1H)-ones through the condensation of anthranilamide with aldehydes and ketones in EtOH at room temperature or under reflux. The significant features of the present protocol are short reaction times, high yields of products, ecofriendly reaction conditions, simple work-up, and reusability of the catalyst. The catalyst can be simply magnetically recovered and reused at least five times without considerable loss of its catalytic activity.

Full text of DOI:10.1134/S1070428020020207

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 2, pp. 298–306. © Pleiades Publishing, Ltd., 2020.
A Brønsted Acid Ionic Liquid Immobilized on Fe3O4@SiO2
Nanoparticles as an Efficient and Reusable Solid Acid
Catalyst for the Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
M. Fallah-Mehrjardia,b,* and S. Kalantaria
a Department of Chemistry, Payame Noor University, Tehran, 11369 Iran
b Research Center of Environmental Chemistry, Payame Noor University, Ardakan, Yazd, 97514 Iran
*e-mail: fallah.mehrjerdi@pnu.ac.ir
Received August 07, 2019; revised October 07, 2019; accepted December 20, 2019
Abstract—In the present study, an efficient and magnetically recoverable Brønsted acid ionic liquid, 1-methyl-
3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe3O4@SiO2
magnetic nanoparticles (Fe3O4@SiO2–ImHSO4) has been used for a high-yield synthesis of 2,3-dihydroquinazolin-
4(1H)-ones through the condensation of anthranilamide with aldehydes and ketones in EtOH at room temperature
or under reflux. The significant features of the present protocol are short reaction times, high yields of products,
ecofriendly reaction conditions, simple work-up, and reusability of the catalyst. The catalyst can be simply mag-
netically recovered and reused at least five times without considerable loss of its catalytic activity.
Keywords: magnetic nanoparticles, supported ionic liquids, 2,3-dihydroquinazolin-4(1H)-ones, anthranilamide,
cyclocondensation
DOI: 10.1134/S1070428020020207
Ionic liquids (ILs) are considered as one of the most
important alternatives to organic solvents in the develop-
ment of green chemistry. They offer such advantages as
low melting points and vapor pressures, low coordinating
ability, and excellent thermal and chemical stability and
can replace usual organic solvents in a wide range of
chemical processes [1, 2]. Imidazolium-based ILs showed
a high catalytic activity and received significant interest
as an eco-friendly catalyst in organic transformations [3,
4]. However, these ILs suffer from high viscosity and, as
a result, mass transfer of molecules in the ILs is limited;
furthermore, because of their homogeneous nature, ILs
are more difficult to separate from the final reaction
product [5, 6]. One of the main ways to overcome these
disadvantages is to immobilize ILs on solid supports such
as polymers [7], amorphous silica [8], mesoporous silica
[9], carbon nanotubes [10], or magnetic nanoparticles
(MNPs) [11].
years, magnetic nanoparticles and especially ferrite
ones have found wide application for immobilization of
homogenous ionic liquids. Nanomagnetic-supported ILs
combine the benefits of ILs and heterogeneous catalysts,
such as high designability, high “solubility” of catalytic
site, ease of handling, separation, and recycling [13–15].
Quinazolinones are an important class of nitrogenous
heterocycles, which exhibit potential biological and
pharmaceutical activities [16, 17]. 2,3-Dihydroquina-
zolin-4(1H)-ones are quinazolinone derivatives that
have attracted much attention due to their antibacterial,
antitumor, antifungal, and monoamine oxidaze inhibitory
activity [18–20]. Furthermore, these compounds can be
easily oxidized to quinazolin-4(3H)-ones [21], which, too,
are biologically active compounds and exist in a variety
of natural products, pharmaceutical candidates, and agro-
chemicals [22]. Several methods have been reported for
the synthesis of 2,3-dihydroquinazolin-4(1H)-ones, in-
cluding desulfurization of 2-thioxoquinazolin-4(3H)-ones
[23], reductive cyclization of o-nitrobenzamides or o-azi-
dobenzamides [24], condensation of o-aminobenzamides
with benzil [25], reduction of quinazolin-4(3H)-ones [26],
and cyclocondensation of anthranilamide (2-aminoben-
At present, MNPs have attracted special attention
as prominent catalyst supports due to their vast surface
area-to-volume ratio, low cost, facile synthesis, easy
functionalization, and simple separation be means of an
external magnet [12]. Due to these advantages, in recent
298

A BRØNSTED ACID IONIC LIQUID IMMOBILIZED ON Fe3O4@SiO2 NANOPARTICLES
299
Scheme 1.
.
FeCl3 6H2O
EtO
EtO Si
EtO
Me
NH4OH, H2O
80oC, 1 h
N
N
Cl +
+
.
FeCl2 4H2O
Fe3O4
80oC, 72 h
EtO
EtO Si
EtO
TEOS, NH4OH
EtOH/H2O, rt, 12 h
Me
N
N
_
Cl
IL
Fe3O4@SiO2
CHCl3, reflux, 48 h
O
O
Me
_
Cl
Si
N
N
O
MNP-IL-Cl
1) CH2Cl2, rt
2) H2SO4, 0oC
3) reflux
O
O
Me
Si
N
N
_
O
HSO4
Fe3O4@SiO2–ImHSO4
zamide) with aldehydes or ketones in the presence of
various catalysts [27–45]. However, most of the reported
procedures feature one or more disadvantages, such as
low product yields, prolonged reaction time, difficult
work-up, use of hazardous solvents, and lack of catalyst
reusability. Therefore, search for effective, simple, and
mild synthetic approaches to 2,3-dihydroquinazolin-
4(1H)-ones remains a relevant task.
The Brønsted acid ionic liquid immobilized on Fe3O4@
SiO2 MNPs was prepared as shown in the Scheme 1.
Magnetite nanoparticles were easily prepared by the co-
precipitation of FeCl2 with FeCl3 in an ammonia solution.
The surface of Fe3O4 MNPs was successfully coated with
silica by the ammonia-catalyzed hydrolysis of tetraethyl
orthosilicate (TEOS) to obtain core-shell Fe3O4@SiO2
MNPs. The reaction between 1-methylimidazole and
3-(chloropropyl)triethoxysilane at 80°C gave a 1-methyl-
3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium chloride
ionic liquid, which was immobilized on the surface of
Fe3O4@SiO2 MNPs by the reaction of surface OH groups
in the latter and the organosilyl group in the ionic liquid.
Finally, ion exchange of the Cl– anions for HSO4– was
performed by treatment with conc. H2SO4.
Herein, we report a versatile procedure for the syn-
thesis of 2,3-dihydroquinazolin-4(1H)-ones through the
cyclocondensation of various aldehydes and ketones
with anthranilamide, catalyzed by 1-methyl-3-(3-
triethoxysilylpropyl)-1H-imidazol-3-ium hydrogen sul-
fate immobilized on the surface of Fe3O4@SiO2 MNPs
(Fe3O4@SiO2–ImHSO4) as an efficient and magnetically
recyclable Brønsted acid ionic liquid (Table 1).
The catalyst was characterized by scanning electron
microscopy (SEM), energy dispersive X-ray (EDAX)
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 2 2020

300
FALLAH-MEHRJARDI, KALANTARI
Fig. 2. EDAX spectra of Fe3O4@SiO2–ImHSO4 MNPs.
spectrum is consistent with our expectations and confirms
the presence of carbon, nitrogen, oxygen, iron, silica, and
sulfur in Fe3O4@SiO2–ImHSO4 (Fig. 2).
The FTIR spectra of Fe3O4, Fe3O4@SiO2, and
Fe3O4@SiO2–ImHSO4 are shown in Fig. 3. The FTIR
spectrum of Fe3O4 (Fig. 3) displays a strong band at low
frequencies (578 cm–1) due to Fe–O vibrations and a
broad band at 3200–3600 cm-1, which can be attributed to
surface –OH groups. The FTIR spectrum of Fe3O4@SiO2
(Fig. 3) shows three additional bands around 460, 980,
and 1080 cm–1, which are assignable Si–O–Si bending,
symmetric stretching and asymmetric stretching vibra-
tions, respectively. These peaks confirm the presence of
the silica shell on Fe3O4 MNPs. The introduction of the
linker is confirmed by the observation in the FTIR spec-
trum of Fe3O4@SiO2–ImHSO4 of bands at 1400–1500
and 2850–2950 cm–1 assignable to C–H bending and
stretching vibrations, respectively. The band around
Fig. 1. SEM image of Fe3O4@SiO2–ImHSO4 MNPs.
spectroscopy, Fourier-transform infrared (FTIR) spec-
troscopy, X-ray diffraction (XRD) analysis, vibrating
sample magnetometry (VSM), and thermogravimetric
analysis (TGA).
The particle size distribution was measured and mor-
phological characterization of Fe3O4@SiO2–ImHSO4 was
performed by SEM on a Philips XL30 scanning electron
microscope. As shown in Fig. 1, Fe3O4@SiO2–ImHSO4
MNPs have a spherical shape, and their dimensions range
from 20 to 30 nm.
The components of Fe3O4@SiO2–ImHSO4 MNPs
were analyzed using EDAX spectroscopy. The EDAX
1
2
1
2
3
10
20
30
40 50
60
70
2ș, deg
4000
3000
2000
1000
500
cm–1
Fig. 3. FTIR spectra of (1) Fe3O4, (2) Fe3O4@SiO2, and (3)
Fig. 4. XRD patterns of (1) Fe3O4 and (2) Fe3O4@SiO2–
Fe3O4@SiO2–ImHSO4 MNPs.
ImHSO4 MNPs.
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A BRØNSTED ACID IONIC LIQUID IMMOBILIZED ON Fe3O4@SiO2 NANOPARTICLES
301
Fig. 5. VSM magnetization curves of (a) Fe3O4@SiO2 and (b) Fe3O4@SiO2–ImHSO4 MNPs.
1600 cm–1 is due to imidazole C=N bending and imidaz-
ole ring stretching vibrations (Fig. 3).
temperature, as well as under reflux conditions gave the
desired product with an excellent yield in a short reaction
time (Table 1, entries 9 and 10). In the absence of cata-
lyst, the reaction was not complete after 2 h in refluxing
ethanol (Table 1, entry 11). According to the results, the
highest yields of 2,3-dihydro-2-phenylquinazolin-4(1H)-
one were obtained in the presence of 0.05 g of Fe3O4@
SiO2–ImHSO4 in ethanol and at room temperature or
under reflux (93% or 91%, respectively; Table 1, entries
9 and 10).
The crystal structure of Fe3O4@SiO2–ImHSO4 MNPs
was studied in the 2θ range 0–80°. The XRD pattern dis-
plays peaks at 30.26° (30.31°), 35.63° (35.69°), 43.39°
(43.32°), 53.72° (53.81°), 57.33° (57.26°) and 62.85°
(62.92°) and is quite similar to the XRD pattern of Fe3O4
(the respective peak positions are given in parentheses)
(Fig. 4).
The magnetic properties of the catalyst were studied
by the VSM method (Fig. 5). As seen, the saturation
magnetization value decreased from 42 emu/g in Fe3O4@
SiO2 to about 27 emu/g in Fe3O4@SiO2–ImHSO4. This
decrease is explained by that in the latter case magnetic
nanoparticles have a nonmagnetic ionic liquid coating.
To explore the universality of the developed proce-
dure, a variety of aldehydes and cyclic ketones were
reacted with anthranilamide in the presence of Fe3O4@
SiO2–ImHSO4 under the optimal conditions (Table 2).
Arylaldehydes with both electron-donor and electron-
acceptor substituents reacted with anthranilamide to
give the corresponding 2-aryl-2,3-dihydroquinazolin-
4(1H)-ones in excellent yields (Table 2, entries 2–12).
The reactions with cinnamaldehyde and 2-furaldehyde
under same reaction conditions, too, produced the de-
sired products in high yields (Table 2, entries 13 and
The TGA analysis of Fe3O4@SiO2–ImHSO4 was
performed by heating the sample to 600°C at a rate of
10°C min–1 in air (Fig. 6). Three main weight loss stages
were observed. The first, small (~2%) weight loss at be-
low 130°C was assigned to a loss of physically adsorbed
water, as well as dehydration of the surface OH groups.
The main weight losses at 130–250°C (~8%) and 250–
430°C (~7%) are probably associated with the breakdown
and decomposition of 1-methyl-3-propylimidazolium
groups grafted on the Fe3O4@SiO2 surface.
The catalytic activity of Fe3O4@SiO2–ImHSO4
MNPs was studied in the condensation reaction of
benzaldehyde with anthranilamide under various reac-
tion conditions (Table 1). Among the screened solvents,
including ethanol, water, acetonitrile, dichloromethane,
chloroform, diethyl ether, toluene, acetone, ethyl acetate
and polyethylene glycol, the best results were obtained
in ethanol (Table 1, entries 1–10). The reaction at room
Fig. 6. TGA curve of Fe3O4@SiO2–ImHSO4 MNPs.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 2 2020

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FALLAH-MEHRJARDI, KALANTARI
Table 1. Optimization of conditions of the cyclocondensation of anthranilamide with benzaldehyde in the presence of the
Fe3O4@SiO2–ImHSO4 nanocatalyst
Experiment no.
Catalyst amount, g
Solvent
H2O
Thermal conditions
Reaction time, min
Yield, %
80
1
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
None
0.04
rt
120
120
120
120
120
120
120
120
15
2
MeCN
CH2Cl2
CHCl3
Et2O
rt
traces
traces
traces
traces
traces
60
3
rt
4
rt
5
rt
6
PhMe
EtOAc
PEG-400
EtOH
rt
7
rt
8
rt
traces
93
9
rt
10
11
12
EtOH
reflux
reflux
rt
10
91
EtOH
120
60
traces
89
EtOH
14). Cyclic ketones and diketones were also condensed
with anthranilamide successfully, and the corresponding
spiroquinazolinones were obtained in good yields and
short reaction times (Table 2, entries 15–19). Notewor-
thy is the formation a dispiro compound in the reaction
of cyclohexane-1,4-dione with anthranilamide in a 1 : 2
ratio (Table 2, entry 20).
ves using an efficient and magnetically recyclable
Brønsted acid ionic liquid, Fe3O4@SiO2–ImHSO4. This
developed catalytic synthesis offers several advantages,
including environmental friendliness, high yield, short
reaction time, mild reaction conditions, simple work-up
procedure, ease of separation, and recyclability of the
catalyst and can be considered as a new and suitable
addition to the present methodologies in this area.
The recyclability and reusability of the Fe3O4@SiO2–
ImHSO4 nanocatalyst was tested in the cyclocondensa-
tion of benzaldehyde with anthranilamide in EtOH at
room temperature. After the reaction had been complete
(15 min), Fe3O4@SiO2–ImHSO4 was separated by means
of an external magnet, washed thoroughly with water and
ethanol, dried in a vacuum oven at 60°C, and then reused
in another catalytic cycle. We found that the catalyst could
be magnetically recovered and reused without any appre-
ciable loss of activity in five consecutive catalytic cycles:
yield, % (cycle no.): 93 (1), 91 (2), 90 (3), 87 (4), 83 (5).
EXPERIMENTAL
All of the commercially available chemicals were
purchased from Merck, Fluka, and Aldrich and used
with no further purification. Fe3O4, Fe3O4@SiO2, and
Fe3O4@SiO2–ImHSO4 were prepared pursuant to the
reported procedures [45–47]. All of the products were
characterized by their physical properties and comparison
with authentic samples. The reactions were monitored
by TLC on Polygram SIL G/UV 254 plates. The melting
points were measured in open capillary tubes and on an
Electrothermal 9200 apparatus. The IR spectra were run
on a Shimadzu IRPresting-21 spectrophotometer in the
range of 4000–400 cm–1 in KBr pellets. The 1H and 13C
NMR spectra were recorded in DMSO-d6 solutions on
a Bruker Advanced DPX 400 MHz spectrometer using
TMS as internal reference.
Comparison of the efficacy of the Fe3O4@SiO2–
ImHSO4 nanocatalyst and some of those reported in the
literature in the synthesis of 2-phenyl-2,3-dihydroquinaz-
olin-4(1H)-one (3a) is presented in Table 3. As seen, the
best results, both in terms of reaction time and product
yield, were obtained with Fe3O4@SiO2–ImHSO4.
In conclusion, the present paper described the
synthesis of 2,3-dihydroquinazolin-4(1H)-one derivati-
Synthesisof1-methyl-3-(3-triethoxysilylpropyl)-1H-
imidazol-3-ium chloride. A mixture of 1-methylimid-
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Table 2. Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in EtOHa
Room temperature
Reflux
mp, °C
published
Entry
no.
R1
R2
time,
min
yield,
%
yield,
%
time, min
measured
a
a
1
2
C6H6
H
H
H
H
H
H
H
H
H
H
H
H
H
15
20
25
15
35
75
90
100
35
45
100
70
35
93
90
92
87
95
85
80
82
87
84
89
89
91
10
10
20
10
30
40
60
60
25
40
80
30
30
91
87
88
88
87
87
83
81
89
81
88
87
90
220–222
231–233
187–189
270–272
207–209
185–187
205–207
202–204
189–191
183–184
209–210
189–189
240–243
220–222 [44]
231–233 [44]
191–193 [44]
275–277 [36]
207–209 [44]
185–187 [44]
205–207 [44]
198–200 [36]
190–193 [36]
183–184 [44]
209–210 [44]
–
4-CH3C6H4
3
4-OCH3C6H4
4-OHC6H4
4
5
2-ClC6H4
6
3-ClC6H4
7
4-ClC6H4
8
4-BrC6H4
9
2-NO2C6H4
3-NO2C6H4
4-N(CH3)2C6H4
2,5-(OCH3)2C6H3
C6H5CH=CH
10
11
12
13
240–243 [44]
14
90
90
50
84
166–168
165–167 [44]
15
16
17
125
20
88
91
88
75
10
90
85
92
85
260–262
217–219
197–200
260–262 [44]
217–219 [44]
197–200 [44]
–(CH2)4–
–(CH2)5–
–(CH2)6–
150
18
19
125
80
88
87
80
55
83
86
215–217
> 300
215–217 [44]
> 300 [44]
O
O
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 2 2020

304
Table 2. (Contd.)
FALLAH-MEHRJARDI, KALANTARI
Room temperature
Reflux
mp, °C
measured
Entry
no.
R1
R2
time,
min
yield,
%
yield,
%
time, min
published
a
a
O
20b
30
84
20
84
> 300
> 300 [44]
O
a Isolated yield.
b Anthranilamide–ketone, 2 : 1.
azole (0.82 g, 10 mmol) and (3-chloropropyl)triethoxysi-
lane (2.41 g, 10 mmol) was stirred at 80°C for 72 h under
nitrogen. The resulting viscous yellow liquid was washed
with diethyl ether (3 × 5 mL) to remove unreacted mate-
rial and was dried under high vacuum to obtain the target
product.
Cl– anion, the dry product (1 g) was suspended in dry
CH2Cl2 (20 mL), the suspension was cooled to 0°C, and
and conc. H2SO4 (0.07 mL, 1.3 mmol) was added to it
dropwise with vigorous stirring. The mixture was then let
to warm up to room temperature and refluxed for 48 h,
cooled, filtered, and dried to give the target product.
Synthesis of the Fe3O4@SiO2–ImHSO4 nano-
catalyst. A suspension of Fe3O4@SiO2 nanoparticles
(1 g) in CHCl3 (30 mL) was dispersed under ultrasonic
irradiation for 1 h, after which 1-methyl-3-(3-triethoxy-
silylpropyl)-1H-imidazol-3-ium chloride (0.28 g, 1 mmol)
was added, and the reaction mixture was stirred under
reflux for 48 h under nitrogen. The product was mag-
netically collected, washed with 3 portions of CHCl3,
and dried at 60°C in a vacuum oven. To exchange the
General procedure for the synthesis of 2,3-dihy-
droquinazolin-4(1H)-ones. The Fe3O4@SiO2–ImHSO4
nanocatalyst (0.05 g) was added to a solution of anthra-
nilamide (1 mmol) and aldehyde or ketone (1 mmol)
in ethanol (5 mL), and the reaction mixture was stirred
at room temperature or under reflux conditions during
the time shown in Table 2. After the reaction had been
completion (by TLC in hexane–EtOAc, 3 : 1), the catalyst
was removed with a magnet, the solution was filtered, and
Тable 3. Comparison of the efficiencies of different catalysts in the synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one
Entry no.
Catalyst
[bmim]PF6
Conditions
Solvent-free, 75°C
EtOH, 70°C
EtOH, rt
Time, min
Yield, %
89
References
[27]
1
35
25
15
25
10
6
2
Sc(OTf)3
92
[28]
3
NH4Cl
92
[29]
4
ZrCl4
EtOH/H2O, MWI
Solvent-free, 60°C
EtOH, USI
95
[33]
5
H[Gly2B]
90
[35]
6
Poly(VPyPS)-PW
Y(OTf)3
95
[38]
7
EtOH, rt
90
20
20
15
10
93
[41]
8
α-Chymotrypsin
Fe3O4@ SiO2–SO3H
Fe3O4@SiO2–ImHSO4
Fe3O4@SiO2–ImHSO4
EtOH, 60°C
EtOH, rt
91
[43]
9
92
[44]
10
11
EtOH, rt
93
This work
This work
EtOH, reflux
91
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11. Ayashi, N., Fallah-Mehrjardi, M., and Kiasat, A.R., Russ.
J. Org. Chem., 2017, vol. 53, p. 846.
the filtrate was washed with cold ethanol to obtain the
target product, which was purified by recrystallization
from ethanol. All products are known compounds, and
they were identified by comparing their physicochemi-
cal characteristics and IR and NMR spectra with those
of authentic samples.
https://doi.org/10.1134/S1070428017060069
12. Polshettiwar, V., Luque, R., Fihri, A., Zhu, H., Bouhrara, M.,
and Basset, J.-M., Chem. Rev., 2011, vol. 111, p. 3036.
https://doi.org/10.1021/cr100230z
ACKNOWLEDGMENTS
13. Sun, N., Swatloski, R.P., Maxim, M.L., Rahman, M.,
Harland, A.G., Haque, A., Spear, S.K., Daly, D.T., and
Rogers, R.D., J. Mater. Chem., 2008, vol. 18, p. 283.
https://doi.org/10.1039/B713194A
This study was performed under financial support of the
Research Council of Payame Noor University.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
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