The use of SrFe12O19 magnetic nanoparticles as an efficient catalyst in the modified Niementowski reaction

Article abstract of DOI:10.1002/aoc.3830

Nanomagnetic SrFe₁₂O₁₉ was synthesized through a simple sol–gel auto-combustion and then characterized by FT-IR, XRD, EDXA, VSM, BET and SEM image. Moreover, it was used as catalyst for the first time in the modified Niementowski rea

Full text of DOI:10.1002/aoc.3830

Received: 22 January 2017
DOI: 10.1002/aoc.3830
Revised: 2 March 2017
Accepted: 8 March 2017
F U L L PA P E R
The use of SrFe O magnetic nanoparticles as an efficient
1
2 19
catalyst in the modified Niementowski reaction
1
1
1
Ghodsi Mohammadi Ziarani
| Zhila Kazemi Asl | Parisa Gholamzadeh |
2
2
Alireza Badiei
| Morteza Afshar
1
Department of Chemistry, Alzahra
University, Vanak Square, P.O. Box
Nanomagnetic SrFe O was synthesized through a simple sol–gel auto‐combus-
12 19
1
993893973, Tehran, Iran
tion and then characterized by FT‐IR, XRD, EDXA, VSM, BET and SEM image.
Moreover, it was used as catalyst for the first time in the modified Niementowski
reaction to investigate its catalytic activity. According to the high yield of
quinazolinone products obtained within short reaction times, it was found that
SrFe O can be used as an effective and green nanocatalyst in organic reactions.
2
School of Chemistry, College of Science,
University of Tehran, Tehran, 14155‐6455,
Iran
Correspondence
1
2 19
Ghodsi Mohammadi Ziarani, Department of
Chemistry, Alzahra University, Vanak
Square, P.O. Box 1993893973, Tehran, Iran.
Email: gmziarani@hotmail.com
The nanomagnetic catalyst can be easily separated from the reaction mixture using
an external magnet.
KEYWORDS
magnetic nanoparticles, nanocatalyst, Niementowski reaction, Quinazolinone, SrFe12O
19
1
| INTRODUCTION
combustion of an aqueous solution containing the desired
metal salts and organic complexant, which produces a volu-
minous and fluffy product with high specific surface area.
In 1894, Niementowski published a synthetic procedure
for the preparation of quinazoline derivatives through the
Ferromagnetic ceramics or ferrites are a composition of iron
III) oxide (α‐Fe O ) and another element(s) including Mn,
(
2
3
Ni, Si, Zn, Cu, Co, Ba, Mg and Sr. According to some
advantages of ferrites such as inexpensive cost, simple
preparation procedure, high corrosion and heat resistance,
they are used more than ferromagnetic alloys, whereas the
saturation magnetization of ferrite compounds is very lower
than that of ferromagnetic alloys. Strontium hexaferrite or
SrFe O is a type of magnetic ceramics which was discov-
ered by Went and coworkers in 1952. SrFe O was the
[
8]
reaction of anthranilic acid and ketones. According to the
importance of quinazoline and quinazolinone compounds in
[
9–11]
medicinal chemistry,
Niementowski reaction conditions
were developed and modified to gain a diverse library of such
[
1]
[12–16]
compounds.
According to our previous research in the
[
17–24]
field of catalysis,
and also due to the importance of
12 19
[2]
[25–35]
nanomagnetic catalysts in organic syntheses,
herein,
1
2 19
first ferrite prepared for commercial production around
980s since its anisotropic constant, remanence, and Curie
we want to introduce the first application of prepared
SrFe12 19 MNPs as catalyst in the modified Niementowski
reaction.
1
O
[1]
temperature is relatively high. Thus, up to now, various
preparation approaches have been reported for the synthesis
of SrFe O magnetic nanoparticles (MNPs) including
1
2 19
2
2
| EXPERIMENTAL
[
3]
[4]
[5]
hydrothermal, chemical co‐precipitation, sol–gel, salt
[
6]
[7]
melt methods, and ball milling. The sol–gel auto‐com-
bustion procedure is the best choice for this aim due to its
relatively simple procedure, low reaction temperature which
leads to reducing energy consumption, and short reaction
time. This approach involves gelling and subsequent
.1 | Materials and methods
The chemical substances employed in this work were
obtained from Merck Company and used with no purifica-
tion. Melting points were determined by capillary tube
Appl Organometal Chem. 2017;e3830.
wileyonlinelibrary.com/journal/aoc
Copyright © 2017 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.3830

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MOHAMMADI ZIARANI ET AL.
method with an Electrothermal 9200 apparatus. Infrared (IR)
was analyzed through the mentioned techniques in addition
to the H and C NMR spectra.
1
3
spectra were recorded on KBr disks using a Fourier‐
1
transform (FT)‐IR Bruker Tensor 27 instrument. H NMR
13
(
250 MHz) and C NMR (62.5 MHz) spectra were run on
2
2
.3.1 | 2‐(4‐chlorophenyl)‐3‐(phenylamino)‐
,3‐dihydroquinazolin‐4(1H)‐one 4 g
a Bruker DPX using tetramethylsilane (TMS) as an internal
standard in DMSO‐d . Elemental analyses were performed
6
−
1
on a ThermoFinigan Flash EA 1112 series elemental
analyzer. The X‐ray powder diffraction (XRD) pattern of
the prepared SrFe O nanoparticles was collected by a
FT‐IR (KBr, ν, cm ) = 3299 (NH stretching), 3048 (aro-
matic =C‐H stretching), 2929 and 2835 (asymmetric and
symmetric stretching of aliphatic C‐H, respectively), 1653
(amide C = O stretching), 1607, 1493 and 1435 (aromatic
C = C Stretching), 1304 (NH bending vibration), 750 (C‐Cl
12 19
Philips X'pert MPD diffractometer using Cu Kα radiation
(
λ = 0.15478 nm). The scanning electron microscopy
1
(SEM) image was taken with SEM (MV2300). Surface area
stretching). H NMR (250 MHz, DMSO‐d , δ , ppm) = 4.75
6
H
and pore size distribution of the magnetic nanospheres were
determined by N2 adsorption–desorption at 77 K with
Brunauer–Emmett–Teller (BET) and Barret‐Joyner Halenda
(s, 1H, NH), 5.93 (s, 1H, CH), 6.45–7.92 (m, 13H, ArH and
13
NH), and 7.95 (d, 1H, ArH). C NMR (62.5 MHz, DMSO‐
d , δ , ppm) = 74.29, 113.97, 114.38, 119.54, 121.73,
6
C
(BJH) methods using a BELSORP analysis software. The
127.95, 128.83, 129.00, 134.40, 135.18, 137.81, 145.40,
magnetic measurement of sample was carried out in a vibrat-
ing sample magnetometer (VSM) (Meghnatis Daghigh Kavir
Co.; Kashan Kavir; Iran) at room temperature.
146.34, and 163.54. Anal. Calcd. for C H N OCl
(349.10): C, 68.67; H, 4.61; N, 12.01. Found: C, 67.88; H,
4.89, N, 11.84.
20 16 3
2
.2 | Preparation of SrFe O nanoparticles
2.3.2 | 2‐(2,3‐dichlorophenyl)‐3‐(phenylamino)‐
12
19
2
,3‐dihydroquinazolin‐4(1H)‐one 4 h
The synthetic procedure was directed using the method
published before.
powders (Fe/Sr = 10) were dissolved in deionized water
[
36]
−1
Briefly, Fe(NO ) .9H O and Sr(NO )
3 3
FT‐IR (KBr, ν, cm ) = 3350 (NH stretching), 3059 (aro-
matic =C‐H stretching), 2986 and 2955 (asymmetric and
symmetric stretching of aliphatic C‐H, respectively), 1649
(amide C = O stretching), 1609, 1511 and 1419 (aromatic
C = C Stretching), 1321 (NH bending vibration), 755 (C‐Cl
3
3
2
3
+
(100 ml for 0.1 mole of Fe ) and stirred at 60 °C. After
mixing the solutions together (at 60 °C), citric acid was
added to it in a proper molar ratio with metal nitrates and
stirred vigorously. Then, the solution was cooled down to
room temperature. Subsequently, ammonium hydroxide
1
stretching). H NMR (250 MHz, DMSO‐d , δ , ppm) = 6.32
6
H
(s, 1H, NH), 6.58 (s, 1H, CH), 6.61–7.92 (m, 12H, ArH), and
13
(NH OH) was added dropwise till the pH was adjusted at 7.
7.95 (s, 1H, NH). C NMR (62.5 MHz, DMSO‐d , δ ,
4
6
C
Then, a cationic surfactant (surfactant/strontium =0.4) was
added to the solution. After evaporation of the solvent, upon
ignition, a fluffy powder was obtained which then, ground
and calcined at 900 °C for 1 h.
ppm) = 71.96, 113.77, 114.33, 114.97, 119.38, 121.63,
125.07, 127.70, 128.51, 129.33, 130.71, 134.41, 138.57,
144.93, 146.33, and 164.20. Anal. Calcd. for C H N OCl
2
20
15
3
(349.10): C, 62.51; H, 3.93; N, 10.94. Found: C, 62.69; H,
.01, N, 10.86.
4
2
.3 | General procedure of modified
Niementowski reaction
3 | RESULTS AND DISCUSSION
SrFe O nanoparticles (0.02 g) was activated under
2 19
reduced pressure at 100 °C for removal of the adsorbed water
and then cooled to room temperature. Then, isatoic anhydride
1
3
.1 | Application of SrFe O magnetic
12 19
nanoparticles in the modified Niementowski
reaction
(1 mmol, 0.16 g) and phenyl hydrazine (1 mmol, 0.1 ml) was
added to the catalyst and heated at 120 °C under stirring for
about 5 min. Afterward, benzaldehyde derivative (1 mmol)
was added to the mixture and the reaction was continued at
In order to study the catalytic activity of the SrFe O
2 19
1
nanoparticles in the modified Niementowski reaction, ini-
tially, the reaction of isatoic anhydride 1, phenyl hydrazine
2 and 2‐nitrobenzaldehyde 3a was selected and optimized
as the model reaction. As shown by the results in
Table 1, the use of solvents for this reaction was not effec-
tive as well as a solvent free system. Therefore, among the
tested conditions, solvent‐free system at 120 °C provided
the best results in the presence of SrFe O , with the
120 °C for appropriate time as shown in Table 2. The reaction
completion was monitored by TLC. The resulting crude
product was dissolved in hot EtOH and then, SrFe O
2 19
1
nanoparticles were easily separated from the solution using
an external magnet. The solution was cooled to gain the pure
crystalline product. The products were characterized using
melting point and FT‐IR spectra and also new compound
12 19
shortest reaction time (15 min) in high yield of the

MOHAMMADI ZIARANI ET AL.
3 of 7
TABLE 1 The optimization of reaction condition for the synthesis of dihydroquinazolinone 4a
Entry
Solvent
Catalyst*
Conditions
Time (min)
Yield (%)
1
2
3
4
5
H
2
O
SrFe12
O
O
O
O
19 MNPs
Reflux
Reflux
Reflux
120 °C
120 °C
120
60
80
15
60
N.R.
80
EtOH
SrFe12
SrFe12
SrFe12
19 MNPs
19 MNPs
19 MNPs
‐
H
‐
2
O/EtOH
Trace
91
‐
N.R.
*
0.02 g
SCHEME 1 The modified Niementowski
reaction in the presence of SrFe12
O
19
nanoparticles
TABLE 2 Synthesis of dihydroquinazolinone products 4a–h in the presence of SrFe12O19 MNPs
Entry
No.
R
Time (min)
Yield (%)
m.p.
m.p. [ref.]
[
[
[
[
[
[
37]
38]
37]
38]
37]
37]
1
2
3
4
5
6
7
8
4a
4b
4c
2‐NO
2
15
30
91
88
70
87
85
88
85
90
217–219
220–223
180–184
195–197
224–227
210–214
211–214
185–186
180–182
216–218
177–179
179–180
220–222
205–207
New
4‐OMe
3‐NO
H
2
105
15
4d
4e
4‐NO
4‐F
2
30
4f
15
4 g
4 h
4‐cl
30
2,3‐Cl
2
15
New
SCHEME 2 The proposed mechanism for
the modified Niementowski reaction in the
presence of the SrFe12O19 MNPs

4
of 7
MOHAMMADI ZIARANI ET AL.
TABLE 3 Comparison of different conditions in the Niementowski reaction to obtain derivative 4b
Entry
Catalyst
Bentonite
KAl(SO
CeO
Citric acid/Al
SrFe12 19 MNPs
Solvent
Condition
Time (min)
Yield (%)
Ref.
[
[
[
[
38]
1
2
3
4
5
H
2
O
)))*/60 °C
Reflux
30
420
300
10
75
91
73
90
91
37]
44]
45]
4
)
2
.12H
2
O
EtOH
2
EtOH
Reflux
2
O
3
‐
‐
Grinding
120 °C
O
15
This work
*
))) = ultrasonic radiation
Likewise, to assess the generality and versatility of this
reaction, different dihydroquinazolinone products 4a–h were
prepared successfully under solvent‐free condition in the
presence of SrFe O MNPs (Scheme 1). The obtained
12 19
results (Table 2) were good in terms of the reaction times
and yields. The new products were characterized by FT‐IR,
CHN and NMR spectroscopy data.
According to the previous organic reactions catalyzed by
[
3,39–42]
different types of Strontium,
it was found that
Strontium as an alkaline earth metal can active carbonyl
[
39]
groups through the formation of Sr‐O bond.
Accordingly,
the probable mechanism for this reaction is proposed in
[
43]
Scheme 2. Initially, Sr atoms of SrFe O MNPs
activate
1
2 19
FIGURE 1 Separated SrFe12
external magnet
O19 from the reaction mixture using an
both carbonyl group of the isatoic anhydride 1. Then, NH2
group of phenyl hydrazine 2 attacks to the activated carbonyl
group followed by decarboxylation to give intermediate 6.
product. Moreover, since the reaction was not progressed in
the absence of the catalyst (Entry 5, Table 1), the importance
of SrFe O nanoparticles as the catalyst in this reaction was
Afterwards, the NH groups of the latter is added to the
2
activated carbonyl group of aldehyde 3 to produce imine 7.
Furthermore, an intramolecular Michael addition is occurred
to afford the desired product 4.
12 19
proved.
FIGURE 2 XRD pattern of SrFe12O19 nanoparticles

MOHAMMADI ZIARANI ET AL.
5 of 7
3
.2 | Characterization of the SrFe O
12 19
nanoparticles
The XRD pattern of the prepared SrFe O MNPs is
12 19
displayed in Figure 2. The XRD pattern of SrFe O crystal
12 19
with a magnetoplumbite structure showed twelve characteris-
tic peaks including 2θ = 30.55°, 32.53°, 34.39°, 35.47°,
3
7.33°, 40.63°, 42.67°, 55.51°, 57.01°, 63.37°, 67.87° and
7
2.85° which can be indexed to the (110), (107), (114),
(
(
201), (203), (205), (206), (217), (304), (220), (204) and
317) lattice planes, respectively. The results firmly prove
the successful formation of SrFe O MNPs.
12 19
Furthermore, as shown in the SEM image (Figure 3) the
SrFe O MNPs are spherical particles with average size
12 19
of 70 nm. The FT‐IR spectrum of the SrFe O MNPs is
12 19
FIGURE 3 SEM image of SrFe12O19 nanoparticles
shown in Figure 4 in which the sharp bands at 441, 551,
1
[46]
6
01 cm− are related to the SrFe O .
12 19
To study the hysteresis loops and magnetic properties,
SrFe O nanoparticles was characterized by VSM at room
Moreover, the modified Niementowski reaction (accord-
ing to the Scheme 1) has been considered in several condi-
tions in literature as shown in Table 3. In comparison with
the mentioned methods, the present methodology has several
advantages such as the use of inexpensive magnetic catalyst,
simple procedure, shorter reaction time and excellent yields
with high purity of the products. For the main advantage of
the present technique, we can mentioned that the
nanomagnetic catalyst is separable from the reaction mixture
by the use of an external magnet (Figure 1).
12 19
temperature. As shown in Figure 5 the magnetic saturation
of the compound mentioned above is about 79 emu/g.
According to the hysteresis loops in the magnetization curves
of SrFe O nanoparticles, it is a typical feature of ferromag-
12 19
netic compound.
Figure 6 shows the N adsorption–desorption isotherm of
2
the SrFe O nanoparticles. The observed isotherm is classi-
12 19
fied as III‐type by IUPAC; accordingly, SrFe O nanoparti-
12 19
cles are non‐porous materials which only have external
FIGURE 4 FT‐IR spectrum of the SrFe12O19 nanoparticles

6
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MOHAMMADI ZIARANI ET AL.
TABLE 4 Reuse of SrFe12O19 MNPs for the synthesis of 1a
Entry
Time (min)
Yield (%)
1
2
15
15
91
84
TABLE 5 The results of EDXA for catalyst
Elements (weight%)
Sample
Fe
Sr
O
C
N
Fresh SrFe12
O
19
62
7
31
9.42
‐
‐
FIGURE 5 The room temperature hysteresis loops of SrFe12O
19
nanoparticles
Recycled SrFe12
O
19
0.47
0.07
18.32
71.72
catalyst is for the remained organic compounds which
were not removed during simple washing process.
4
| CONCLUSION
As a conclusion, nanomagnetic SrFe O was prepared
12 19
through a simple sol–gel auto‐combustion method. Charac-
terization of SrFe O MNPs was performed using XRD,
12 19
BET, VSM, EDXA, SEM and FT‐IR analyses. SEM image
showed their average particle size of 70 nm. Afterward, the
catalytic activity of such MNPs was studied in the modified
Niementowski reaction; the quinazolinone products were
obtained in high yields within shorter reaction time compared
to the results reported in literature. Therefore, SrFe O
12 19
MNPs can be used as the green and eco‐friendly efficient cat-
alyst which are easily separated from the reaction mixture by
the use of an external magnet.
FIGURE 6
distributions of the SrFe12
N
2
adsorption/desorption isotherms and BJH pore size
19 nanoparticles
O
ACKNOWLEDGEMENT
We gratefully acknowledge the financial support from the
Research Council of Alzahra University and the University
of Tehran.
surface. The BET surface area of SrFe O nanoparticles
was calculated as 10.4 m /g.
1
2 19
2
The catalyst recyclability was also examined under the
optimized conditions for the model reaction. In this regard,
synthesis of compound 4a was performed in the first run
for four times to recover about 0.07 gr SrFe O . Subse-
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How to cite this article: Mohammadi Ziarani G,
Kazemi Asl Z, Gholamzadeh P, Badiei A, Afshar M.
The use of SrFe O magnetic nanoparticles as an
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