Synthesis and characterization of copper(II) Schiff base complex supported on Fe3O4 magnetic nanoparticles: A recyclable catalyst for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1002/aoc.3354

Fe₃O₄-Schiff base of Cu(II) is found to be a recyclable and heterogeneous catalyst for the rapid and efficient synthesis of various 2,3-dihydroquinazolin-4(1H)-one derivatives from the two-component condensation of 2-aminobenzamide and an aldehyde. This reaction is simple, green and cost-effective. Separation and recycling can also be easily done by magnetic decantation of the Fe₃O₄ nanoparticles with an external magnet. The prepared catalyst was characterized using thermogravimetry, Fourier transform infrared spectroscopy, vibrating sample magnetometry, inductively coupled plasma analysis, X-ray diffraction and scanning electron microscopy.

Full text of DOI:10.1002/aoc.3354

Full paper
Received: 22 February 2015
Revised: 22 May 2015
Accepted: 16 June 2015
Published online in Wiley Online Library: 6 August 2015
(wileyonlinelibrary.com) DOI 10.1002/aoc.3354
Synthesis and characterization of copper(II)
Schiff base complex supported on Fe3O4
magnetic nanoparticles: a recyclable catalyst for
the one-pot synthesis of 2,3-dihydroquinazolin-
4(1H)-ones
Arash Ghorbani-Choghamarani*, Zahra Darvishnejad and Masoomeh Norouzi
Fe3O4–Schiff base of Cu(II) is found to be a recyclable and heterogeneous catalyst for the rapid and efficient synthesis of various
2,3-dihydroquinazolin-4(1H)-one derivatives from the two-component condensation of 2-aminobenzamide and an aldehyde. This
reaction is simple, green and cost-effective. Separation and recycling can also be easily done by magnetic decantation of the Fe3O4
nanoparticles with an external magnet. The prepared catalyst was characterized using thermogravimetry, Fourier transform infra-
red spectroscopy, vibrating sample magnetometry, inductively coupled plasma analysis, X-ray diffraction and scanning electron
microscopy. Copyright © 2015 John Wiley & Sons, Ltd.
Keywords: magnetic nanoparticle; 2,3-dihydroquinazolin-4(1H)-one; 2-aminobenzamide, Schiff base; copper(II)
catalysts facilitates easy catalyst recovery and recycling, as well as
Introduction
product separation, and is a longstanding pursuit of catalysis
science.[19] When the size of the support material is decreased to
Nitrogen heterocyclic compounds are produced by the chemical in-
dustry and academia for a variety of applications, including those
related to biological activities, such as antitumor, antibiotic,
antidefibrillatory, antipyretic, analgesic, antihypertonic, diuretic,
antihistamine, antidepressant and vasodilating behaviour.[1] In
particular, 2,3-dihydroquinazolin-4(1H)-one derivatives are used as
reagents in manufacturing and industry.[2] Furthermore, the
quinazolinone skeleton is frequently found in various natural
products. Some examples include the anticancer compound
trimetrexate, the sedative methaqualone, the α-adrenergic receptor
antagonist doxazosin and the antihypertensive agent ketanserin.[3]
Several strategies for their synthesis have been developed: conden-
sation of anthranilamide with an aldehyde or ketone using
p-toluenesulfonic acid as a catalyst;[4] desulfurization of 2-thioxo-
4(3H)-quinazolinones;[5] reaction of isatoic anhydride with Schiff
bases;[6] and one-step conversion of 2-nitrobenzamides to 2,3-
dihydro-4(1H)-quinazolinones.[7]
Recently, magnetic nanoparticles have attracted much attention
among the academic and industrial scientific community.[8–13] Be-
cause of the advantages of a larger surface area to volume ratio
as well as homogeneity in aqueous solution, biomolecule-coated
nanoparticles have shown promising applications in complicated
biosystems.[14,15] Through a combination of the unique optical, elec-
tronic or magnetic properties of nanoparticles with various probes,
functionalized nanoparticles have become an exploitable field for
biosensing and diagnostic applications.[16] Nanoparticles have
attracted significant interest as efficient supports for homogeneous
catalyst immobilization.[17,18] The immobilization of homogeneous
the nanometre scale, the activity of nanoparticle-supported cata-
lysts can be significantly improved, compared to homogeneous
catalysts immobilized on conventional support matrices.[20]
Experimental
Materials
Chemicals and solvents used in this work were obtained from
Sigma-Aldrich, Fluka or Merck and were used without further
purification.
Instrumentation
The particle size and morphology were investigated using a JEOL
JEM-2010 scanning electron microscopy (SEM) instrument at an ac-
celerating voltage of 200 kV. Fourier transform infrared (FT-IR) spec-
tra were recorded as KBr pellets with a Bruker VRTEX 70 FT-IR
spectrophotometer. Thermogravimetric analysis (TGA) curves were
recorded using a PL-STA 1500 device (Thermal Sciences). 1H NMR
and 13C NMR spectra were recorded with a Bruker FX 400Q NMR
*
Correspondence to: Arash Ghorbani-Choghamarani, Department of Chemistry,
Faculty of Science, Ilam University, PO Box 69315516, Ilam, Iran.
E-mail: arashghch58@yahoo.com; a.ghorbani@mail.ilam.ac.ir
Department of Chemistry, Faculty of Science, Ilam University, PO Box 69315516,
Ilam, Iran
Appl. Organometal. Chem. 2015, 29, 707–711
Copyright © 2015 John Wiley & Sons, Ltd.

A. Ghorbani-Choghamarani et al.
spectrometer. The amount of Cu in the catalyst was measured using
an inductively coupled plasma (ICP) atomic emission spectrometer
(Sare Kelasam, PerkinElmer, Optima 8000). Vibrating sample mag-
netometry (VSM) measurements were performed using an MDKFD
VSM instrument. Magnetization measurements were carried out in
an external field of up to 15 kOe at several temperatures. X-ray
diffraction (XRD) was conducted using a PW3050/60 goniometer.
The generator settings were 40 mA/40 kV with Cu Kα radiation of
λ = 1.5406 Å. Continuous scanning was carried out from 10.01° as
2θ start position to 79.95° as 2θ end position, with a step size of
0.02° and step time of 48.19 s.
ethanol (5 ml) under reflux conditions for the appropriate time, as
given in Table 1. After completion of the reaction (TLC monitoring),
the reaction mixture was cooled to room temperature. After reac-
tion completion, catalyst was separated using an external magnet
and the reaction mixture washed with ethanol. The filtrate was con-
centrated to dryness, and the crude solid product washed with
diethyl ether to afford pure 2,3-dihydroquinazolin-4(1H)-ones in
95–98% yields (Table 1).
Results and discussion
Characterization of Cu(II)–Schiff base complex-functionalized
magnetic Fe3O4 nanoparticles
Preparation of magnetic Fe3O4 nanoparticles
A mixture of FeCl3ꢀ6H2O (5.838 g, 0.022 mol) and FeCl2ꢀ4H2O (2.147 g,
0.011 mol) was dissolved in 100 ml of deionized water in a three-
necked flask (250 ml) at 80°C under nitrogen atmosphere. Subse-
quently, 10 ml of aqueous NH3 solution (32%) was added into the
mixture within 30 min with vigorous mechanical stirring. The resulting
black precipitate was isolated by magnetic decantation, washed with
double-distilled water until neutral, further washed twice with ethanol
and dried at 80°C in vacuum to afford Fe3O4 (2.90 g).
The process for the preparation of the Fe3O4–Schiff base of Cu(II)
catalyst is depicted in Scheme 1, showing the most probable
modes for coordination of Cu to imine-modified magnetic nanopar-
ticles. First, imine is typically prepared by the condensation of pri-
mary amine and aldehyde. Then, copper(II) nitrate is added to the
resulting imine. Subsequently, the Schiff base complex is reacted
with magnetic nanoparticles to obtain Cu(II)–Schiff base complex-
functionalized magnetic Fe3O4 nanoparticles. The prepared catalyst
was characterized using FT-IR spectroscopy, TGA, SEM, VSM, ICP
analysis and XRD.
Preparation of Schiff base complex of Cu(II)
Figure 1(a)–(d) shows the FT-IR spectra obtained for Schiff base li-
gand, Schiff base complex of Cu(II), Fe3O4 nanoparticles and Fe3O4–
Schiff base of Cu(II), respectively. Figure 1(a), showing the spectrum
of the free ligand, exhibits a C¼N stretch band at 1633 cmꢁ1, while
in the spectrum of the complex, this band shifts to lower frequency
and appears at 1624 cmꢁ1 due to coordination of the nitrogen with
the metal (Fig. 1(b)). A strong absorption at 580 cmꢁ1 is characteristic
of the Fe–O stretching vibration, but, for Fe3O4 nanoparticles, this ap-
pears blue-shifted at 572 cmꢁ1 due to the size reduction. The broad
feature at 3000–3500 cmꢁ1 for magnetic nanoparticles corresponds
to the –OH stretching of hydroxyl groups. In the spectrum of
Fe3O4–Schiff base of Cu(II) (Fig. 1(d)), a band appears at 1620 cmꢁ1
due to imine bond (mainly ascribed to C¼N stretching). The absorp-
tions around 1111 and 1001 cmꢁ1 correspond to Si–O stretching vi-
bration. The band observed at about 2854–2922 cmꢁ1 can be
assigned to the aliphatic C–H group.
The Schiff base was prepared as follows. 3-Aminopropyl(triethoxy)silane
(1 mmol, 0.176 g) in ethanol (25 ml) was added to a solution of
salicylaldehyde (1 mmol, 0.122 g) in ethanol (5 ml) at room temper-
ature. The colour of the reaction solution changed to yellowish, due
to imine formation (conversion was up to 95%, measured using
TLC). The resulting Schiff base ligand, as a bright yellow precipitate,
was separated by filtration. This yellow-coloured precipitate was
collected and washed with ethanol. The precipitate was dried un-
der vacuum at room temperature. The crude product was recrystal-
lized from ethanol to afford the pure product.
The Schiff base complex with metal ions was prepared as fol-
lows. A solution of the corresponding Schiff base (2 mmol) in
ethanol and anhydrous Cu(NO3)2 (0.178 g, 1 mmol) were mixed
at room temperature and left to stand for 4 h under stirring. A
colour change from yellow to light green was observed. Then
the complex was filtered and was washed with a large excess
of ethanol. The greenish blue-coloured precipitate was collected
and dried under vacuum at room temperature. Then the product
was purified by recrystallization from ethanol, affording the
resulting pure Schiff base complex.
Table 1. Synthesis of 2,3-dihydroquinazolin-4(1H)-one derivativesa
Preparation of Fe3O4–schiff base of Cu(II)
Entry
Aldehyde
4-ClC6H4CHO
Time (min) Yield (%)b
M.p. (°C)
199–200[3]
225–230[21]
197–200[22]
186–189[21]
211–216[3]
219–223[3]
161–165[24]
189–192[22]
184–185[23]
160–164[24]
The supported copper(II) complexes were prepared by adding a
suspension of magnetic nanoparticles (2 g) in ethanol (5 ml) to a
vigorously stirred Schiff complex of metal ions (1 mmol). The
resulting mixture was refluxed for 4 h. The solvent was removed
and the resulting solid was dried at 80°C overnight to afford
Fe3O4–Schiff base complex of Cu(II) (21% was loaded on magnetic
nanoparticles, as was determined using TGA). The FT-IR spectrum of
the catalyst showed the expected bands, including a distinctive
band due to C¼N stretching.
1
2
3
4
5
6
7
8
9
10
210
105
165
135
60
95
99
97
99
99
99
95
98
99
94
4-CH3C6H4CHO
4-BrC6H4CHO
4-CH3OC6H4CHO
3,4-(CH3O)2C6H4CHO
C6H5CHO
60
4-C2H3OC6H4CHO
4-FC6H4CHO
180
165
150
30
3-BrC6H4CHO
C3H7CHO
General procedure for preparation of 2,3-dihydroquinazolin-4
(1H)-ones
aReaction conditions: aldehyde (1 mmol), 2-aminobenzamide (1
mmol), catalyst (1.5 mol%) and ethanol solvent (10 ml) at reflux
temperature. DHQ, 2,3-dihydroquinazolin-4(1H)-one derivative.
bIsolated yield.
A mixture of 2-aminobenzamide (1 mmol), aldehydes (1 mmol) and
Fe3O4–Schiff base complex of Cu(II) (1.5 mol%) was stirred in
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Cu(II)–salen–Fe3O4 nanoparticles as catalyst for the synthesis of DHQs
Scheme 1. Synthesis of Fe3O4–Schiff base of Cu(II).
Figure 1. FT-IR spectra of (a) Schiff base ligands [(OH)-salen], (b) Schiff base
complex of Cu(II), (c) Fe3O4 nanoparticles and (d) Fe3O4–Schiff base of Cu(II).
TGA was also performed. The profiles obtained are presented in
the supporting information.
SEM images of Fe3O4–Cu)II) Schiff base complex at different mag-
nifications are shown in Fig. 2. The Fe3O4–Schiff base of Cu)II) ex-
hibits a cluster of aggregated spherical particles with an average
size of between 70 and 80 nm in diameter. The surface morphology
of the supported Schiff base of Cu)II) is practically identical to that of
molecular sieve supports and is composed of relatively well-
formed, spherical particles having rather uniform coating of organic
layers.[25]
Figure 2. SEM images of Fe3O4–Schiff base of Cu(II) at different
magnifications.
Furthermore, ICP optical emission spectral analyses show
that Cu(II) is supported on the Fe3O4 nanoparticles. The Cu
concentration is found to be 5.075% in Fe3O4–Schiff base
of Cu(II).
The XRD pattern of Fe3O4–Schiff base of Cu(II) is consistent with
the patterns of spinel ferrites described in the literature (Fig. 4). The
XRD pattern of the synthesized nanoparticles shows six characteris-
tic peaks at 2θ = 30.4°, 35.7°, 43.3°, 53.7°, 57.3° and 62.9° related to
the corresponding indices (220), (311), (400), (422), (511) and
(440), respectively.[27]
The magnetic properties of Fe3O4–Cu)II) Schiff base complex
were characterized using VSM (Fig. 3). The saturation magnetization
is 47.0 emu gꢁ1. A slight decrease of the saturation magnetization
of Fe3O4–Schiff base of Cu(II) is due to the successful grafting of
the Schiff base of Cu on the surface of the Fe3O4 nanoparticles. It
is reported that the saturation magnetization of bare Fe3O4 nano-
particles is 69.23 emu gꢁ1 [26]
.
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A. Ghorbani-Choghamarani et al.
Table 2. Optimization of amount of Fe3O4–Schiff base of Cu(II)a nitriles.
Entry
Catalyst
Time
(min)
Yield
(%)b
1
2
3
4
5
6
7
8
No catalyst
600
165
165
165
165
165
360
300
Tracec
46
Fe3O4–Schiff base of Cu(II) (0.39 mol%)
Fe3O4–Schiff base of Cu(II) (0.79 mol%)
Fe3O4–Schiff base of Cu(II) (1.18 mol%)
Fe3O4–Schiff base of Cu(II) (1.5 mol%)
Fe3O4–Schiff base of Cu(II) (2.37 mol%)
Fe3O4 nanoparticles (20 mg)
57
74
97
97
Trace
97
Homogeneous Schiff base of Cu(II) (20 mg)
aReaction conditions: 4-boromobenzaldehyde (1 mmol), 2-
aminobenzamide (1 mmol) and ethanol solvent (10 ml) under
reflux conditions.
bIsolated yield.
cReaction proceeds in the absence of catalyst.
Figure 3. Magnetization curve for Fe3O4–Schiff base of Cu(II).
increase in the quantity of Fe3O4–Schiff base complex of Cu(II) from
0.39 to 1.5 mol% enhances the product yield from 46 to 97%
(Table 2, entries 2–5). It is evident that the best result is obtained
when using of 1.5 mol% of Fe3O4–Schiff base complex of Cu(II)
(Table 2, entry 5). A greater amount of catalyst has substantially less
effect on the yield and time of the reaction (Table 2, entry 6). Most
significantly, reactions with unfunctionalized magnetic nanoparti-
cles afford trace amounts of the expected product (Table 2, entry 7),
which confirms the role of the Schiff base complex of Cu(II) in the
catalysis (Table 2, entry 8).
With this optimized result in hand, we further investigated
the best reaction conditions. The reaction conditions were opti-
mized by conducting the reaction at various temperatures,
namely room temperature (25°C), 45, 60 and 80°C. It is ob-
served that the yield increases as the reaction temperature
increases (Table 3).
Figure 4. XRD pattern Fe3O4–Schiff base of Cu(II).
The optimized reaction conditions were subsequently applied to
the reaction between various aldehydes and 2-aminobenzamide
(Table 1). In most cases, the desired 2,3-dihydroquinazolin-4(1H)-
ones are obtained in high yields. Aromatic aldehydes with electron-
rich and electron-deficient substituents work well. In a typical
procedure, 1 mmol of aldehyde and 1 mmol of 2-aminobenzamide
were mixed in ethanol in the presence of 1.5 mol% of Fe3O4–Schiff
base complex of Cu(II) and the reaction mixture was stirred for
60–210 min. After work-up, the corresponding 2,3-dihydroquinazolin-
4(1H)-one is obtained in good yield.
Catalytic studies
In connection with our ongoing work on multi-component
condensations,[21–23,25,28,29,31] we now report a facile, rapid and
one-pot two-component combination for the preparation of 2,3-
dihydroquinazolin-4(1H)-one derivatives in the presence of Schiff
base complex of Cu(II) immobilized on Fe3O4 as a heterogeneous,
non-toxic,[30] reusable, inexpensive and easily available catalyst
(Scheme 2).
In an initial endeavour, 4-bromobenzaldehyde (1 mmol) and
2-aminobenzamide (1 mmol) were stirred at room temperature in
the absence of catalyst under reflux conditions in ethanol. After
24 h, the resulting yield is very poor (Table 2, entry 1). In order to
find an appropriate amount of catalyst and optimal temperature,
various amounts of catalyst were screened at different
temperatures.
Table 3. Optimization of reaction temperaturea
Entry
Temperature (°C)
Yield (%)b
1
2
3
4
25
45
60
80
Tracec
Tracec
20
In this connection, we investigated the outcome of the reaction
with various amounts of Fe3O4–Schiff base complex of Cu(II). An
96
aReaction conditions: 4-boromobenzaldehyde (1 mmol), 2-
aminobenzamide (1 mmol) and ethanol solvent (10 ml) at reflux
temperature.
bIsolated yield.
cReaction proceeds in the absence of catalyst.
Scheme 2. Synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
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Cu(II)–salen–Fe3O4 nanoparticles as catalyst for the synthesis of DHQs
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Reusability of Fe3O4–schiff base of Cu(II)
Reusability of Fe3O4–Schiff base complex of Cu(II) was confirmed by
performing a series of consecutive experiments. After completion
of the reaction, nanoparticles were magnetically separated. The
deposited catalyst was washed three to four times with ethanol
to ensure the complete removal of any organic residuals. The
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extraction. The results shown in Fig. 5 clearly indicate that no loss of
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Conclusions
We have described a successful strategy, an efficient and convenient
green synthesis, for the preparation of 2,3-dihydroquinazolin-4(1H)-
ones, which involves a valuable two-component cyclo condensation
reaction of aldehydes and 2-aminobenzamide using an inexpensive,
non-toxic and easily available Fe3O4–Schiff base of Cu(II) catalyst.
The method offers several advantages including high yield of
products, a recyclable catalyst and easy experimental work-up.
The catalyst can be recovered from the reaction by decantation
of the reaction mixture in the presence of an external magnet
and can be used in up to seven runs with little loss of activity.
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Supporting information
Acknowledgements
The authors thank the research facilities of Ilam University, Ilam,
Iran, for financial support of this research project.
Additional supporting information may be found in the online ver-
sion of this article at the publisher’s web site.
Appl. Organometal. Chem. 2015, 29, 707–711
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