A novel magnetic nanocatalyst Fe3O4@PEG–Ni for the green synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1002/aoc.5710

Ni-PEG (polyethylene glycol) complex supported on magnetic nanoparticle was created by grafting. The catalytic activity of Fe₃O₄@PEG–Ni was explored through one-pot green synthesis of 2,3-dihydroquinazolin-4(1H)-ones and used as an efficient and recoverable nanocatalyst. FT-IR, XRD, EDS, BET, TGA, VSM and SEM techniques were employed to specify the nanocatalyst. This heterogeneous nanocatalyst demonstrated acceptable recyclability and could be reused several times with no considerable loss of its catalytic activity.

Full text of DOI:10.1002/aoc.5710

Received: 14 December 2019
DOI: 10.1002/aoc.5710
Revised: 19 February 2020
Accepted: 15 March 2020
F U L L P A P E R
A novel magnetic nanocatalyst Fe3O4@PEG–Ni for the
green synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Nader Noroozi Pesyan
| Aria Danandeh Asl | Shadi Namdar
Department of Organic Chemistry,
Faculty of Chemistry, Urmia University,
Urmia, 57159, Iran
Ni-PEG (polyethylene glycol) complex supported on magnetic nanoparticle
was created by grafting. The catalytic activity of Fe3O4@PEG–Ni was explored
through one-pot green synthesis of 2,3-dihydroquinazolin-4(1H)-ones and used
as an efficient and recoverable nanocatalyst. FT-IR, XRD, EDS, BET, TGA,
VSM and SEM techniques were employed to specify the nanocatalyst. This het-
erogeneous nanocatalyst demonstrated acceptable recyclability and could be
reused several times with no considerable loss of its catalytic activity.
Correspondence
Nader Noroozi Pesyan, Department of
Organic Chemistry, Faculty of Chemistry,
Urmia University, 57159, Urmia, Iran.
Email: nnp403@gmail.com; n.noroozi@
urmia.ac.ir
K E Y W O R D S
2,3-dihydroquinazolin-4(1H)-ones, magnetic nanoparticle, nano catalyst, polyethylene glycol
1 | INTRODUCTION
of the nanocatalyst from the reaction mixture using an
external magnet.[26]
The
superficial
functionalization
of
magnetic
Usually, 2,3-dihydroquinazolin-4(1H)-ones are pre-
pared using the reductive cyclization of aldehydes or
ketones with 2-aminobenzamide in the presence of acid
catalysts.[27,28] These heterocyclic compounds are also
synthesized by various metal nanocatalysts.[29–31]
2,3-Dihydroquinazolin-4(1H)-one derivatives exist that
included six-membered heterocyclic ring molecules that
have been reported to retain a wide range of biological
properties, such as antihistaminic, pharmaceutical, anti-
biotic, analgesic, antitumor and antibacterial activi-
ties.[27,32,33] However, most of these processes suffer from
longer reaction time, tedious workup, harsh reaction con-
ditions, unsatisfactory yields, the use of large quantities
of environmentally toxic catalysts. Thus, the development
of simple, efficient, high-yielding and environmentally
friendly approaches using new catalysts for the synthesis
of these compounds is an important task.
Nickel complexion has been complexed with PEG
functionalized nanostructured Fe3O4 and applied as an
excellent nanocatalyst for the green synthesis of
2,3-dihydroquinazolin-4(1H)-ones by cyclocondensation
of 2-aminobenzamide with aromatic aldehydes under
mild reaction conditions in ethylene glycol as a green
solvent.
nanoparticles can be used as a well-organized system
between homogeneous and heterogeneous catalysis. Mag-
netite (Fe3O4) is a well-described material that is
employed to obtain stable and magnetically recyclable
heterogeneous catalysts for some homogeneous catalyti-
cally active metals like Cu, Ni and Co.[1]
Magnetic nanoparticles have attracted attention
because of their broad applications in catalysis and syn-
thesis.[2,3] The surface of magnetic nanoparticles (MNPs)
could be utilized to enable the loading of the range of
desirable functionalities.[4] Recently, nanocomposites of
organic materials and inorganic nanoparticles have
drawn interest because of their applications in rapid and
high-capacity optical and magnetic information storage
media.[5–12] Nanoparticles have received much attention
in the last two decades owing to their fascinating proper-
ties related to their size.[13] In scientific research, magne-
tite nanoparticles have been studied comprehensively,
because their synthesis is easy and well known.[14]
In addition, magnetic nanocatalysts are studied for
the synthesis of various organic compounds[15–22] and the
degradation of organic pollutant dyes.[23–25] The magnetic
properties make them useful to facilitate the separation
Appl Organomet Chem. 2020;e5710.
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2 | RESULTS AND DISCUSSION
This paper describes the synthesis and characterization of
a new recoverable magnetic nanocatalyst and its use for
the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. A ver-
satile and concise route for the synthesis of the new mag-
netic nanoparticle is outlined in Scheme 1. Polyethylene
glycol was used as a widely available and green com-
pound as a ligand for capturing Ni ions.
2.1 | Catalyst characterization
FT-IR, X-ray diffraction (XRD), energy dispersive X-ray
spectroscopy (EDS), Brunauer–Emmett–Teller(BET),
TGA and scanning electron microscopy (SEM) tech-
niques were used to characterize the structure of
Fe3O4@PEG–Ni magnetic nanocatalyst. Figure 1 shows
the FT-IR spectra obtained for MNPs, MNP–(CH2)3Cl
and MNP–(CH2)3PEG–Ni, in curves a, b and c, respec-
tively. In the FT-IR spectrum of the nanocatalyst the
bands appeared at 3397, 2956 and 2924 cm−1 related to
stretching vibrations of OH and CH aliphatic absorption
bands, respectively. The bands appearing at 1626,
997–1383, 576 and 450 cm−1 correspond to the symmetric
and asymmetric stretching vibrations of Si–O, Fe–O and
Ni–O bond vibrations in the catalyst, respectively.
Figure 2 shows morphological changes in MNPs and
MNP–(CH2)3PEG–Ni by SEM images. These images con-
firm that the catalyst was formed in uniform nanometer-
sized particles. In addition, it can be concluded that the
morphology of MNP–(CH2)3PEG–Ni (Figure 2b) is the
same as the particle form of MNP–(CH2)3PEG
(Figure 2a).
FIGURE 1 FT-IR spectra of: (a) MNPs; (b) MNP–(CH2)3Cl;
and (c) MNP–(CH2)3PEG–Ni
42.50 and 0.45% were respectively detected in MNP–
(CH2)3PEG–Ni.
Figure 4 shows the dark-brown colored powder of the
sample and SEM–EDS mapping of MNP–(CH2)3PEG–Ni
(distribution of C, O, Si, Cl, Fe, Ni elements). Elemental
mapping is one of the best tools to analyze a single spot
to give a spectrum that provides information about the
presence of elements and can show the quantity of each
element as a map. In the present nanocatalyst, SEM–EDS
mapping assigned each element and confirmed the for-
mation of the nanocatalyst (Figure 4).
The EDX data indicate the existence of Fe, Si, C, O,
Cl and Ni in MNP–(CH2)3PEG–Ni (Figure 3a). The EDS
results of the MNP–(CH2)3PEG–Ni are provided in
Figure 3b. As can be seen from curve a, Fe, Si, C, O and
Ni elements with mass percentages 39.36, 1.74, 14.23,
Figure 5 shows the measurement of the magnetic
characteristics of MNP–(CH2)3PEG–Ni, which was done
by vibrating sample magnetometry (VSM) at room tem-
perature. The value of magnetization saturation of MNP–
(CH2)3PEG–Ni was nearly 40 emu g−1. The saturation
SCHEME 1 Synthesis of
Fe3O4@PEG–Ni magnetic nanocatalyst

NOROOZI PESYAN ET AL.
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FIGURE 2 Scanning electron microscopy (SEM) images of MNP–(CH2)3PEG–Ni
FIGURE 3 EDS of MNP–(CH2)3PEG–Ni
magnetization of the Fe3O4@SiO2-DMG–Ni (II) catalyst
was about 35 emu g−1 [34]
The amount was decreased
compared with the saturation magnetization of the Fe3O4
MNPs (about 60 emu g−1 [35]
owing to the anchoring of
the SiO2 and Ni–PEG complex onto the surface of the
Fe3O4 MNPs. In comparison, the saturation magnetiza-
tion of MNP–(CH2)3PEG–Ni was more than the reported
MNP–DMG–Ni (II) nanocatalyst.
The XRD patterns of magnetic nanocatalyst showed
five distinct peaks at 2θ = 2, 11, 51, 58 and 86ꢀ,
.
)

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NOROOZI PESYAN ET AL.
FIGURE 4 The dark-brown colored powder and SEM–EDS mapping of MNP–(CH2)3PEG–Ni (distribution of C, O, Si, Cl, Fe and Ni
elements)
the decomposition of organic functional groups located
inside the framework. The TGA diagrams confirmed the
formation of Ni complex.
Figure 8 shows the nitrogen adsorption and desorp-
tion isotherms of the MNP–(CH2)3PEG–Ni nanocatalyst.
The hole properties of the made microspheres were speci-
fied by nitrogen absorption–desorption. The specific
plane area was computed using the BET technique for
the synthesized MNP–(CH2)3PEG–Ni nanocatalyst and it
was 38.487 m2.g−1. The hole volume was 8.8427 cm3.g−1
(Figure 8). The corresponding hole size distribution of
the nanocatalyst was specified as 10.859 nm, which was
done using the Barrett–Joyner–Halenda technique (for
more information see the Supplementary Material).
These results indicated that the MNP–(CH2)3PEG–Ni
nanocatalyst was obtained as mesoporous type
(2 < Dv < 50 nm, Dv is the particle diameter of the vol-
ume distribution).
FIGURE 5 Vibrating sample magnetometry (VSM) analysis of
the MNP–(CH2)3PEG–Ni
respectively. Two broad and single diffraction peaks at
2θ = 2ꢀ and 11ꢀ observed in XRD patterns of MNP–
(CH2)3PEG–Ni confirmed the presence and preservation
of the mesoporous framework of the nano-structures.
Two peaks at 2θ = 51 and 58ꢀ confirmed the existence of
Fe3O4 nanoparticles (Figure 6).
2.2 | Synthesis of 2,3-dihydroquinazolin-
4(1H)-ones by catalytic amounts of Fe3O4 @
PEG–Ni
The thermogravimetric analysis - differential scanning
calorimetry (TGA-DSC) analysis of MNP–(CH2)3PEG–Ni
is shown in Figure 7. TGA/DSC analysis of MNP–
(CH2)3PEG–Ni showed weight loss owing to decomposi-
tion upon heating. The 10.13% weight loss below 350ꢀC
was attributed removal of solvent molecules and PEG. The
weight loss between 350 and 800ꢀC was associated with
After provision and characterization of the magnetic
nanocatalyst structure, we concentrated our attention on
the synthesis of 2,3-dihydroquinazolin-4(1H)-ones (3a–l)
in the reaction of various aldehydes (1a–l) with
2-aminobenzamide (2). In finding a simple, proficient
and eco-friendly method for the synthesis of 3a–l in the
presence of Fe3O4@PEG–Ni as an efficient, stable and

NOROOZI PESYAN ET AL.
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FIGURE 6 XRD patterns of MNP–(CH2)3PEG–Ni
FIGURE 7 TGA–DSC analysis of
MNP–(CH2)3PEG–Ni
recyclable
nanocatalyst,
the
reaction
of
bis[2,3-dihydroquinazolin-4(1H)-one], 3l, was obtained in
excellent yield (Table 2, entry 12).
2-aminobenzamide 2 and benzaldehyde 1a was studied
to create optimal conditions. Optimization of the catalyst
for the synthesis of the preferred 3 in the presence of dif-
ferent catalytic amount of Fe3O4@PEG–Ni is shown in
Table 1. The best results were obtained with benzalde-
hyde 1a (1.0 mmol) and 2-aminobenzamide 2 (1.0 mmol)
in the presence of Fe3O4@PEG–Ni (5.0 mg) and Ethylene
glycol (EG) (5.0 ml) at room temperature (Table 1, entry
3). The use of lower and higher amounts of catalyst
(3.0 and 8.0 mg) did not affect the outcome (Table 2,
entries 2 and 4, respectively). The reaction of various
aldehydes 1 with 2-aminobenzamide 2 was done only
after successfully synthesizing 3. The results are reported
in Table 2. In this table, it can be established that a broad
range of aldehydes can react with 2-aminobenzamide,
and as a result, compounds 3 are obtained. We performed
the reaction of terphthalaldehyde as a dialdehyde under
the same reaction and the product 2,20-(1,4-phenylene)
The productivity and capability of MNPs@PEG–Ni
system in synthesis of quinazolines were highlighted by
comparison of the gained result with other reported
systems (Table 3). As shown in this table, MNPs@PEG–
Ni is the best catalyst for the synthesis of
2,3-dihydroquinazolin-4(1H)-one derivatives in green
solvent under gentle reaction conditions. This catalyst
has important characteristics such as biocompatibility,
low cost, commercial availability and also chemically
stable materials. A plausible reaction mechanism for the
formation of 2,3-dihydroquinazolin-4(1H)-ones is shown
in Scheme 2.
2.3 | Recyclability of the catalyst
Reuse of catalysts is an important advantage for commer-
cial applications. To investigate this issue, catalyst

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NOROOZI PESYAN ET AL.
catalytic cleaning to be detectable or significantly altered
(Figure 9). Reproducible catalytic activity and remarkably
low leaching of MNPs with PEG were seen.
2.4 | Hot filtration
In testing for the leaching of nickel in the reaction
mixture and the heterogeneity of the catalyst, hot
filtration was performed for the synthesis of 2,3-
dihydroquinazolin-4(1H)-ones with 2-aminobenzamide
and various derivatives of aldehydes. Also in this test, we
obtained a 35% yield of product in the first 20 min of the
reaction. Then, the 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
the reaction at this stage was 35%, confirming that the
leaching of nickel was insignificant (Figure 10).
3 | EXPERIMENTAL
FIGURE 8 The nitrogen adsorption and desorption isotherm
of the MNP–(CH2)3PEG–Ni
3.1 | Material and methods
recovery was investigated for the one-pot cyclization
All solvents, substrates and reagents were purchased
from Merck and Aldrich Chemical Companies in high
purity and used without further purification. FT-IR spec-
trometer measurements were recorded on Nexus
670 apparatus using KBr pellets (Urmia University,
Urmia, Iran). Nanostructures were characterized using
XRD measurements collected using X’pertpro with wave-
length 1.54 Å while some diffraction patterns were
entered in the 2θ range (10–80ꢀ) (Lorestan University,
reaction
between
benzaldehyde
1a
and
2-aminobenzamide 2 under optimized reaction condi-
tions in ethylene glycol (Table 1, entry 3). After comple-
tion of the reaction, the catalyst was removed quickly
and easily from the reaction mixture and washed several
times with water and ethanol. After drying the catalyst,
we used it directly for the next run. The catalyst was
found to be reusable at least six times, without causing
TABLE 1
Effects of different parameters on the synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a)
Entry
Catalyst (mg)
Solvent
Temperature (ꢀC)
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
0
3
5
8
5
5
5
5
PEG
EG
rt
200
55
27
25
20
30
90
90
Trace
78
rt
EG
rt
93
EG
rt
88
EG
60
70
70
30
89
EtOH
EtOAC
CH2Cl2
85
82
80
Reaction conditions: aldehyde (1.0 mmol), 2-aminobenzamide (1.0 mmol) with different solvents.

NOROOZI PESYAN ET AL.
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TABLE 2
Fe3O4 catalyzing the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones (3a–l) in EG
Entry
1
Product (3)
Time (min)
Yield (%)
M.p. (ꢀC)a [reference]
20
94
224–226[27,29,30]
201–203[29,30,36]
229–231[29,30,37]
186–188[26,29,30]
a
2
3
4
20
7
90
78
92
b
c
10
d
5
6
10
5
95
95
196–198[27,29,30]
e
191–193[29,30,37]
f
7
5
95
179–181[29,30,37]
g
8
45
30
35
80
93
83
167–169[26,29,30]
208–210[26,29,30]
188–190[27,29,30]
h
9
i
10
j
(Continues)

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NOROOZI PESYAN ET AL.
TABLE 2 (Continued)
Entry
11
Product (3)
Time (min)
Yield (%)
M.p. (ꢀC)a [reference]
25
95
224–225[27,29,30]
k
12
40
93
241–242[26,29,30]
l
aThe products were assigned by comparing their spectral and physical data with reliable samples and the literature.
TABLE 3
Comparison of the performance of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one with magnetic nanoparticles (MNPs)@PEG–
Ni and other reported systems
Entry
Catalyst
Temperature (ꢀC)
Time (min)
Yield (%)
Reference
1
2
3
4
5
6
7
MNPs@PEG–Ni
NaHSO4
Sc (OTf)3
PPA-SiO2
TFE
rt
45
30
25
90
90
55
90
95
94
92
91
90
87
82
_
[38]
70
70
70
78
70
100
[39]
[40]
[41]
[42]
[43]
Ga (OTf)3
TBAB
TBAB, Tetra-n-butylammonium bromide.
Khorramabad, Iran). The Barrett–Joyner–Halenda
method was utilized and the pore volume and pore mea-
sure distribution were deduced from the desorption pro-
files of the isotherms. The BET technique was used to
measure the specific surface area (Beam Gostar Taban
lab, Tehran, Iran). TGA curves were entered using a
Shimadzu DTG-60 instrument (Beam Gostar Taban lab,
Tehran, Iran). Also, the magnetic properties of
nanoparticles were measured using a VSM (PPMS-9 T) at
300 K (University of Mohaghegh Ardabili, Ardabil, Iran).
Different solutions of ferrous chloride hexahydrate
(FeCl3.6H2O) and ferric chloride tetra hydrate
(FeCl2 4H2O) were prepared with a molar value of Fe3+
/
.
Fe2+. In the typical method, 1.2 g of FeCl2 4H2O and
2.4 g of FeCl3 6H2O were dissolved in 40 ml of deionized
.
.
water. Then, 10 ml of 25% ammonium hydroxide
(NH4OH) solution was slowly added to the above mixture
and it was vigorously stirred (60 min, 700 rpm, 70ꢀC).
The result of the reaction was a black precipitate that was
subsequently isolated with the aid of an external magnet.
The separated nanoparticles were rinsed with ethanol
and water and finally dried in a vacuum 50ꢀC for 20 h.
3.2 | Synthesis of Fe3O4 nanoparticles
(MNPs)
3.3 | Preparation of MNP–(CH2)3Cl
One of the best ways to separate nanoparticles from a
solution is by magnetizing the particles. Magnetic parti-
cles were synthesized by the following reaction:
The
MNP
powder
(1.3
g)
with
of
3-chloropropyltrimethoxysilane (1.5 g) was added to

NOROOZI PESYAN ET AL.
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SCHEME 2 Proposed mechanism for synthesis of
2,3-dihydroquinazolin-4(1H)-ones in the presence of MNP–
(CH2)3PEG–Ni
FIGURE 9 Recycling of MNP–(CH2)3PEG–
Ni in the construction of 2,3-dihydroquinazolin-
4(1H)-ones
ethanol (25 ml) and the combination was stirred under
reflux for 24 h. Then the resulting solid was washed with
EtOH and then, as the last step, the solid was dried under
vacuum in order to obtain MNP–(CH2)3–Cl.
repeatedly with EtOH. Finally, it was dried for 12 h in a
vacuum oven at 60ꢀC.
3.5 | Preparation support PEG–Ni
3.4 | Preparation of support PEG
The functionalized support PEG (1.6 g) was blended with
Ni (NO3).6H2O (0.8 g) in EtOH (30 ml) and stirred under
reflux for 20 h. The resulting solid was collected using an
external magnet. Then, in order to remove any unan-
chored metal ions, it was washed repeatedly with EtOH
In a 50 ml round-bottom flask a mixture of MNP–
(CH2)3–Cl (1 g), PEG-600 (1 g) and EtOH (35 ml) under
reflux was stirred for 20 h. Then the product was washed

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NOROOZI PESYAN ET AL.
ORCID
Nader Noroozi Pesyan https://orcid.org/0000-0002-
4257-434X
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Firstly, to a one-necked flask were added aldehydes
(1 mmol), 2-aminobenzamide (1 mmol), nanocatalyst
(5 mg) and ethylene glycol (5 ml). The mixture was
stirred at room temperature for a suitable reaction time
(Tables 1 and 2). Then the reaction's progress was
checked using thin layer chromatography (TLC). At the
end of the reaction, the catalyst was separated using an
external magnet and washed with ethanol and water, and
vacuum dried until used for the next reaction. The reac-
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the product was recrystallized from ethanol for additional
purification, obtaining 2,3-dihydroquinazolin-4(1H)-ones
in good yields. Then, the data reaction products 3 were
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1
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4 | CONCLUSION
In summary, the Fe3O4@PEG–Ni nanocomposite was
synthesized by means of grafting. The catalytic activity of
Fe3O4@PEG–Ni was explored through one-pot green syn-
thesis of 2,3-dihydroquinazolin-4(1H)-ones. This catalyst
had a high conversion value and could be easily recov-
ered and reused many times with no considerable loss of
its catalytic activity. Briefly, the proposed catalyst was
useful as well as nontoxic and adsorbent for the synthesis
of these series of compounds economically and with
more selectivity.

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How to cite this article: Noroozi Pesyan N,
Danandeh Asl A, Namdar S. A novel magnetic
nanocatalyst Fe3O4@PEG–Ni for the green
synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
Appl Organomet Chem. 2020;e5710. https://doi.org/
10.1002/aoc.5710