Supramolecular Fe3O4@PEG/?diaza crown ether@Ni: a novel magnetically reusable nano catalyst for the clean synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1002/aoc.4878

Ni@diaza crown ether complex supported on magnetic nanoparticle was provided by grafting technique. The catalytic activity of Fe₃O₄@diaza crown ether@Ni was explored through one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones and it was used as an efficient and recoverably constant nanocatalyst. FT-IR, SEM, TEM, XRD, BET, ICP, EDS, and TGA techniques were employed to specify the nanocatalyst. This heterogeneous catalyst demonstrated acceptable recyclability and could be used again several times with no considerable loss of its catalytic activity.

Full text of DOI:10.1002/aoc.4878

Received: 15 October 2018
DOI: 10.1002/aoc.4878
Revised: 26 November 2018
Accepted: 3 December 2018
F U L L P A P E R
Supramolecular Fe3O4@PEG/−diaza crown ether@Ni: a
novel magnetically reusable nano catalyst for the clean
synthesis of 2‐aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones
Michael Aalinejad1 | Nader Noroozi Pesyan1
Aria Danandeh Asl1
| Nosrat Heidari2 | Hana Batmani1 |
1 Department of Organic Chemistry,
Ni@diaza crown ether complex supported on magnetic nanoparticle was pro-
vided by grafting technique. The catalytic activity of Fe3O4@diaza crown
ether@Ni was explored through one‐pot synthesis of 2,3‐dihydroquinazolin‐
4(1H)‐ones and it was used as an efficient and recoverably constant
nanocatalyst. FT‐IR, SEM, TEM, XRD, BET, ICP, EDS, and TGA techniques
were employed to specify the nanocatalyst. This heterogeneous catalyst demon-
strated acceptable recyclability and could be used again several times with no
considerable loss of its catalytic activity.
Faculty of Chemistry, Urmia University,
57159 Urmia, Iran
2 Department of Physical Chemistry,
Faculty of Chemistry, Urmia University,
57159 Urmia, Iran
Correspondence
Nader Noroozi Pesyan, Department of
Organic Chemistry, Faculty of Chemistry,
Urmia University, 57159, Urmia, Iran.
Email: n.noroozi@urmia.ac.ir;
nnp403@gmail.com
KEYWORDS
2‐Aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones, core‐shell, diaza crown ether, magnetic nanoparticles
1 | INTRODUCTION
media.[6–14] Nanoparticles have gotten considerable atten-
tion in previous two decades due to the fascinating prop-
Shallow functionalization of nano‐magnetic nanoparti-
cles (MNPs) can be used as a well‐organized system to
join the hole among homogeneous and heterogeneous
catalysis. Magnetite is a good‐identified material which
is known as ferrite and/or Fe3O4. It is worth to mention
that this material is utilized to gain stable and magneti-
cally recyclable heterogeneous catalysts for some
homogeneous catalytically active metals like Cu, Ni, Co,
and so on.[1] Nowadays, magnetic nanoparticles have
attracted important consideration because of their various
applications in catalysis and synthesis.[2,3] The superficial
of MNPs could be functionalized basically through fitting
surface adjustments to enable the loading of a diversity of
desirable functionalities.[4] Fe3O4 magnetic nanoparticles
with extensive particular high adsorption ability and
surface area can be parted from fluid under external mag-
netic field.[5] Recently, nanocomposites of organic mate-
rials and inorganic nanoparticles have been of great
concern because of their applications in rapid and high‐
capacity optical and magnetic information storage
erties related to their size.[15] In scientific investigation,
magnetite (Fe3O4) particles have been study extensively,
because their synthesis is comfortable and good
known.[16]
Fe3O4 particles with coated using various ligands have
also been studied such as; Fe3O4–Adenine‐Ni nanocatalyst
for the one‐pot synthesis of polyhydroquinoline
derivatives, oxidation of sulfides to sulfoxides and
oxidation of thiols to disulfides,[17] Immobilized
Fe3O4@AMPD@Ni,[18]
Fe3O4@AMPD@Cu[19]
and
Fe3O4‐Adenin‐Zn nanoparticles[20] as a green and recycla-
ble catalyst for synthesis of 5‐substituted 1H‐tetrazoles and
oxidation reactions.
Quinazolinones are a set of attached heterocycles that
have received much consideration due to their possible
pharmaceutical and biological activities. In all the deriva-
tives, quinazolinones have attracted much more consider-
ation owing to their activities for example
antibacterial,[21] diuretic[22] and anticancer.[23] There are
numerous approaches to prepare this stage of
Appl Organometal Chem. 2019;e4878.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4878

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AALINEJAD ET AL.
compounds.[24–29] Among them, the use of MCM‐41‐
techniques. Firstly, Fourier transform infrared (FT‐IR)
spectra were entered discretely at different steps of cata-
lyst preparation; see the curves (a‐c) (Figure 1). From
these curves, it can be said that the peaks between 583
and 625 cm−1 were attributed to Fe–O bond vibration of
Fe3O4. In addition, the absorption bands at 1350, 1244,
1108 cm−1 are determinable to the symmetric and asym-
metric stretching vibrations of the mesoporous structure
(Si‐O). Peaks at 2871.42 and 2921.52 cm−1 were the
C–H stretching vibration absorption peak of crown ether,
n‐propyl chain and PEG. The band at 3428 cm−1 is
assigned to the stretching vibration of the O‐H groups.
The peaks at around 1736–1636 cm−1 shown in (b) and
(c) demonstrated that crown ether was linked to the
nPr‐MNPs. The absorption bands at 1106 and 1109 cm−1
can be both specified to ether bond.
Biurea‐Ni,[28] Fe3O4‐Serin‐Pd(0)[30] as
a
reusable
nanocatalysts and straightest approach includes conden-
sation of alkyl, aryl aldehydes with anthranilamide in
the attendance of p‐toluenesulfonic acid as a cata-
lyst.[29,31] It should be mentioned that the usage of
heterogeneous and recyclable catalysts presents one of
the strongest and greenways in chemical technology.
Naturally, benignant solid catalysts for example clays
and zeolites rather than mineral acids are utilized for
acid‐catalyzed organic reactions.[32]
In this research, we introduced an interesting magnet-
ically nanocatalyst Fe3O4@diaza crown ether@Ni, a
novel magnetically reusable nanocatalyst for the clean
synthesis of 2‐aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones.
SEM images of the synthesized MNPs@diaza crown
ether@Ni are depicted in Figure 2 (a‐c). The SEM
micrographs corroborate that samples have tidy and
globular morphology. The morphological changes were
checked by this technique that is shown in Figure 2 (b
and c), the catalysts no remarkable changes in the plane
morphology happened during plane modification. In
addition, the morphology of the solid was saved. The
SEM image demonstrate that the catalyst is as nano
particles with the size distribution ranged from 19 to
25 nm.
2 | RESULT AND DISCUSSION
Our research on utilization of new heterogeneous and
retrievable catalysts in organic transformations encour-
aged us to provide a new heterogeneous catalyst
(Fe3O4@diaza crown ether@Ni) and to study its utiliza-
tion in the synthesis of 2‐aryl‐2,3‐dihydroquinazolin‐
4(1H)‐ones. Scheme 1 represents the details of the
catalyst preparation process.
To show the supporting nickel metal on MNPs surface,
the EDS analysis of Fe3O4 –diaza crown ether‐Ni was
accomplished (Figure 3). The results show the existence
of Fe, Si, Ni, O, N, and C in functionalized MNPs and also
2.1 | Catalyst characterization
Ni complex supported on nanoporous MNPs, is entirely
specified by SEM, EDS, FT‐IR, XRD, BET, ICP and TGA
SCHEME 1 Synthesis of MNPs@diaza
crown ether@Ni

AALINEJAD ET AL.
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FIGURE 3 EDS spectrum of Fe3O4@diaza crown ether@Ni
nanocatalyst
FIGURE 1 FT‐IR spectra of Fe3O4 (a), Fe3O4@nPr‐Cl (b),
Fe3O4@ nPr‐aza crown ether@Ni (c)
Figure 5 demonstrates the low angle X‐ray powder
refraction pattern of samples Fe3O4, Fe3O4@diaza crown
ether@Ni. For the XRD pattern of Fe3O4, the peaks at
30.2°, 35.5°, 40.1°, 57.3°, and 62.9° were respectively
equivalent to the (220), (311), (400), (511), and (440) crys-
tal planes of a pure Fe3O4 with a cubic spinal struc-
ture.[33,34] According the XRD pattern of Fe3O4@diaza
crown ether@Ni, all the peaks of Fe3O4 have been
observed. It should be noted that the peaks at 16.5°, 34°,
demonstrated that the mass percents are 76.07%, 3.70%,
1.24%, 9.87%, 2.86% and 6.26%, respectively.
TEM micrograph has been a suitable tool for deter-
mining the particle shape and size distribution. As it
can be seen in Figure 4, the magnetic cores of the nano-
particles were uniform in both shape and in size. It
should be mentioned that the size of the MNPs@diaza
crown ether@Ni nanocatalyst is around 20–30 nm.
FIGURE 2 SEM images of a) Fe3O4 and
b,c) Fe3O4@diaza crown ether@Ni

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AALINEJAD ET AL.
FIGURE
4
TEM image of Fe3O4@diaza crown ether@Ni
nanocatalyst
39.6°, 56.1°, 62.9°, 63.5°, 67.3° and 72.6° correspond to
orthorhombic aza crown ether‐Ni.
Figure 6 is indicative of the thermal gravimetric analy-
sis (TGA) curves of (a) MNPs@diaza crown ether@Ni
and (b) TGA/DTA analysis of MNPs@diaza crown
ether@Ni which shows a weight loss due to the decompo-
sition upon heating the small amount of weight loss
below 200 °C is attributed removal of solvent molecules.
The weight loss within range of 200–800 °C is associated
with the decomposition of organic functional groups
located inside framework. The TGA diagrams confirmed
the formation of Ni complex.
The magnetization curves of MNPs@diaza crown
ether@Ni gained from the vibration sample magnetome-
ter (VSM), is shown in Figure 7 and determined that the
severity of the saturation magnetization (Ms) of
MNPs@diaza crown ether@Ni were 15.00 emu g−1. More-
over, the magnetic particles has super paramagnetism due
to the zero forcible energy and since it is free of hysteresis.
FIGURE 6 (A) TGA thermograms, (B) TGA/DTA analysis of
MNPs@diaza crown ether@Ni nanocatalyst
The hole properties of the made microspheres have
been specified by nitrogen absorption. The specific plane
areas computed using the Brunauer–Emmett–Teller
(BET) technique for the synthesized MNPs@diaza crown
ether@Ni catalyst and it was 7.573 m2.g−1. The hole
FIGURE 5 The XRD patterns of a) Fe3O4 nanoparticles b)
FIGURE
7
VSM curve of MNPs@diaza crown ether@Ni
Fe3O4@diaza crown ether@Ni
nanocatalyst

AALINEJAD ET AL.
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volume was 4.838 cm3.g−1 (Figure 8). It should be men-
tioned that the corresponding hole size distributions of
the catalyst was specified as 2.555 nm which has been
done using the Barrett–Joyner–Halenda (BJH) technique.
Note that MNPs@diaza crown ether@Ni catalyst is meso-
porous (2 < Dv < 50 nm).
TABLE 1 Effects of various parameters on the synthesis of 2‐
phenyl‐2,3‐dihydroquinazolin‐4(1H)‐one
Cat.
(mg)
Temp
(°C)
Time
(min)
Yield
(%)
Entry
Solvent
PEG
2.2 | Synthesis of quinazolines
compounds by catalytic amounts of
MNPs@diaza crown ether@Ni
1
2
3
4
5
6
7
0
8
6
8
8
8
8
rt
200
Trace
PEG
rt
50
95
90
87
91
80
85
PEG
rt
60
We checked catalytic activity of Fe3O4@diaza crown
ether@Ni as a new heterogeneous catalyst in the one‐
pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones.
Towards this end, the reaction of 2‐aminobenzamide
and benzaldehyde was explored to establish the ideal con-
ditions. Optimization of the catalyst for the synthesis of
the desired quinazoline in attendance various catalytic
amount of Fe3O4@diaza crown ether@Ni is shown in
Table 1. The best results were gained with benzaldehyde
(1.0 mmol) and 2‐aminobenzamide (1.0 mmol) in the
presence of MNPs@diaza crown ether@Ni (8 mg) and
PEG (2 ml) at room temperature (Table 1, entry 2). It
should be noted that the use of lower amounts of catalyst
(6 mg) does not have any improvement on the outcome
(Table 2, entry 3). The reaction of different aldehydes
with 2‐aminobenzamide were done just after successfully
synthesizing of 2,3‐dihydroquinazolin‐4(1H)‐ones. The
obtained results have been reported in Table 2. From this
Table, it can be concluded that a broad limit of aldehydes
can react with 2‐aminobenzamide and as a result, com-
pounds 3 are obtained (For more information, see
Supporting information).
PEG
60
70
70
30
30
EtOH
EtOAC
CH2Cl2
40
100
120
Reaction conditions: Aldehyde (1.0 mmol), 2‐aminobenzamide (1.0 mmol).
The productivity and capability of MNPs@diaza crown
ether@Ni system in synthesis of quinazolines were high‐
lighted by comparison of the gained result with other
reported systems (Table 3). As shown in this table, The
MNPs@diaza crown ether@Ni is the best catalyst for
the synthesis of 2,3‐dihydroquinazolin‐4(1H)‐one deriva-
tives in green solvent under gentle reaction conditions.
This catalyst has important characteristics such as eco‐
friendly, commercially available, cheap and chemically
stable materials and also the low cost.
2.3 | Recyclability of the catalyst
From a practical point of view, the reusability of catalysts
is a significant privilege. To consider the optimal reaction
situation (Table 2, entry 1), we checked the recycling of
the catalyst. When the reaction was done, the catalyst
was trapped by an external magnet, washed with Et2O,
and used again 6 runs with no remarkable reduction in
activity (Figure 9). The mediocre isolated yield for 6 runs
was 93%, which shows the applied reusability of this cat-
alyst. Reproducible catalytic activity and remarkably low
leaching of Ni from MNPs functionalized with diaza
crown ether were seen. Based on ICP‐OES measurement,
the measured Ni has been specified for unreacted catalyst
(2.5%) and after sixth run (2%).
To test the leaching of nickel in the reaction mixture
and the heterogeneity of the catalyst, we accomplished
hot filtration for the synthesis of 2,3‐dihydroquinazolin‐
4(1H)‐ones with 2‐aminobenzamide and various deriva-
tives of aldehydes. In this test, we got the yield of product
in first twenty minutes of the reaction of 32%. Then, the
FIGURE
8
Nitrogen adsorption–desorption isotherm of
MNPs@diaza crown ether@Ni nanocatalyst

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AALINEJAD ET AL.
TABLE 2 MNPs@diaza crown ether@Ni catalyzed the one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones in PEG
Entry
Product (3)
a
Time (min)
Yield(%)
MP (°C) [ref]
1
25
92
222–225[30,35]
2
3
25
10
88
73
200–202[30,36]
b
230–231[30,37]
c
4
15
92
185–187[30,38]
d
5
6
15
10
95
87
197–199[30,35]
e
190–192[30,37]
f
7
8
5
92
77
179–182[37]
168–170[38]
g
50
h
9
35
40
30
91
80
95
209–211[38]
i
j
10
11
189–191[30,35]
225–226[30,35]
k
(Continues)

AALINEJAD ET AL.
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TABLE 2 (Continued)
Entry
Product (3)
Time (min)
Yield(%)
MP (°C) [ref]
12
50
93
241–243[38]
l
The products were specified by comparing their spectral and physical data with the valid samples.
catalyst was separated and the filtrate permitted to react
further. After this hot filtration, it was concluded that
no further reaction was seen. The yield of reaction in this
stage was 32%, corroborating the leaching of nickel was
insignificant (Figure 10).
(University of Kurdistan, Sanandaj, Iran). The particle
morphology was checked by SEM using FESEM‐TESCAN
MIRA3 (University of Kurdistan, Sanandaj, Iran). Bruker
1
Avance spectrometers, 300 for H and 75 MHz for 13C
was employed in order to obtain the 1H, 13CNMR spectra
(Urmia University, Urmia, Iran). The Barrett–Joyner‐
Halanda (BJH) method was utilized and the pore volume
and pore measure distribution were resulted from the
desorption profiles of the isotherms. TGA curves were
entered using a Shimadzu DTG‐ 60 instrument (Univer-
sity of Kurdistan, Sanandaj, Iran). In addition, the
Brunauer–Emmett–Teller (BET) technique was used to
measure the specific surface area of instance.
3 | EXPERIMENTAL
3.1 | Materials and instruments
All substrates and reagents were obtained from Merck
and Aldrich chemical companies in high purity and used
with no further purification. As it has been mentioned
earlier, all the products were characterized by valuation
their spectral data and physical with valid samples. KBr
pellets using a Nexus 670 FT‐IR spectrometer (Urmia
University, Urmia, Iran) was employed to perform FT‐
IR spectra. TLC was also used to monitor the reaction
over silica gel 60 F254 aluminum sheet. The X‐ray diffrac-
tion (XRD) measurements were collected by a X'PertPro
with wavelength 1.54 Å while some diffraction patterns
were entered in the 2θ range (10–80°). The EDX of the
MNPs were done utilizing a FESEM TESCAN MIRA3
3.2 | Preparation of nanoparticle
Fe3O4@PEG (MNPs)
In a typical procedure, in a two‐neck flask, Fe3O4 nano-
particles were synthesized by FeCl3.6H2O and
FeCl2.4H2O according to the reported method.[45] Under
ultrasonic irradiation, Fe3O4@PEG magnetic nanoparti-
cles were prepared. In a 250 ml, three‐necked flask
Fe3O4 nanoparticles (1.0 g), deionized water (50 ml) and
a solution of 25 ml sodium dodecyl sulfate (20 mol%)
TABLE 3 Comparison of the synthesis of 2‐phenyl‐2,3‐
dihydroquinazolin‐4(1H)‐one with MNPs@diaza crown ether@Ni
and other reported systems
Time Yield
Temp C (min) (%)
°
Entry
Catalyst
Lit.
This
1
MNPs–diaza
rt
50
95
crown ether‐Ni
work
[39]
2
3
4
5
6
7
Sc (OTf)3
PPA‐SiO2
Ga (OTf)3
TFE
70
70
70
78
100
70
25
90
55
90
90
30
92
91
87
90
82
94
[40]
[41]
[42]
[43]
[44]
TABA
FIGURE 9 Recycling of MNPs@diaza crown ether@Ni in the
synthesis of 2‐phenyl‐2,3 dihydroquinazolin 4(1H)‐one
NaHSO4

8 of 9
AALINEJAD ET AL.
and stirring under reflux for 20 hrs. Then, the resulting
solid was collected by an external magnet. Next, in order
to remove any unanchored metal ion, it was washed for
many times with EtOH and dried in vacuum at 70 °C
for 12 hrs. Finally, the catalyst gained is designated as
MNPs@diaza crown ether@Ni.
3.6 | General procedure for the
preparation of 2,3‐dihydroquinazolin‐4
(1H)‐ones compounds
In a 25 ml round bottom flask equipped by a magnetically
stirrer, dissolved aldehydes (1 mmol), 2‐aminobenzamide
(1 mmol), MNPs@diaza crown ether@Ni (5 mg) in 2 ml
PEG. The blend was mixed at the room temperature for a
suitable reaction period of time (Table 2). TLC was
employed to check the advance of the reaction. After the
termination of the reaction, the catalyst was separated by
an external magnet and washed with ethanol, vacuum
dried and stockpiled for other runs. The combination was
extracted with H2O and Ethyl acetate. Finally, the solid
residue was recrystallized in minimum hot EtOH, afforded
2,3‐dihydroquinazolin‐4(1H)‐ones in good yields. Then, by
FT‐IR, 1H and 13C NMR spectroscopy data reaction prod-
ucts 3 were specified (See Supporting Information).
FIGURE 10 Hot filtration diagram for the synthesis of 2,3‐
dihydroquinazolin‐4(1H)‐ones
were mixed under nitrogen climate. For half an hour, the
obtained mixture was kept under ultrasonic vibration
with 95 W. Next, for an hour, the PEG‐400 solution
(25 ml) was added to the suspension again under ultra-
sonic vibration. Then, the obtained products were puri-
fied by magnetic field separation. Finally, for nine hrs,
the products were dried under vacuum at 50 °C.[46]
3.3 | Preparation of MNPs@(CH2)3Cl
4 | CONCLUSION
The obtained MNPs powder (4.8 g) with of 3‐
chloropropyltrimethoxysilane (CPTMS) (5.0 g) was added
to n‐hexane (90 ml) and the combination under refluxing
and nitrogen atmosphere was stirred for 24 hrs. An exter-
nal magnet was employed to collect the resulting solid
where it was washed with n‐hexane. At the last step,
the solid was dried under vacuum in order to obtain
MNPs@(CH2)3‐Cl.
In closing, Fe3O4@diaza crown ether@Ni nanocomposite
was synthesized by means of core‐shell method. The cat-
alytic activity of Fe3O4@diaza crown ether@Ni was
explored
through
one‐pot
synthesis
of
2,3‐
dihydroquinazolin‐4(1H)‐ones. This catalyst had high
conversion amount and could be easily regained and
reused many times with no considerable loss of its cata-
lytic activity. To sum up, the proposed catalyst is useful
and adsorbent for synthesis of these series of compounds
for economic accessibility and more selectivity.
3.4 | Preparation of Fe3O4@PEG ‐diaza
crown ether
ORCID
In
a 100 ml round bottom flask a mixture of
MNPs@(CH2)3Cl (1 g), aza crown ether (1 g) and Et3N
(2 ml) in EtOH (50 ml) under reflux was stirred for
20 hrs. Subsequently, the product was washed for many
times with EtOH. Finally, for 12 hrs, it was dried in vac-
uum oven at 70 °C.
Nader Noroozi Pesyan
434X
https://orcid.org/0000-0002-4257-
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