Preparation of core/shell/shell CoFe2O4/OCMC/Cu (BDC) nanostructure as a magnetically heterogeneous catalyst for the synthesis of substituted xanthenes, quinazolines and acridines under ultrasonic irradiation

Article abstract of DOI:10.1002/aoc.5580

Highly efficient synthesized magnetic cobalt ferrite nanoparticles supported on OCMC?Cu (BDC) was utilized in the preparation of biologically active heterocyclic compounds through one-pot three-component reactions between of aldehydes, dimedone, aryl amin

Full text of DOI:10.1002/aoc.5580

Received: 14 October 2019
DOI: 10.1002/aoc.5580
Revised: 14 January 2020
Accepted: 25 January 2020
F U L L P A P E R
Preparation of core/shell/shell CoFe2O4/OCMC/Cu (BDC)
nanostructure as a magnetically heterogeneous catalyst for
the synthesis of substituted xanthenes, quinazolines and
acridines under ultrasonic irradiation
Mohammad Ali Ghasemzadeh
| Fatemeh Ghaffarian
Department of Chemistry, Qom Branch,
Islamic Azad University, Qom, Islamic
Republic of Iran
Highly efficient synthesized magnetic cobalt ferrite nanoparticles supported on
OCMC@Cu (BDC) was utilized in the preparation of biologically active hetero-
cyclic compounds through one-pot three-component reactions between of
aldehydes, dimedone, aryl amines/2-naphthol/urea under ultrasonic irradia-
tion. This method has various advantages including excellent yields, little cata-
lyst loading, simple procedure, facile catalyst separation, short reaction times,
eco-friendly approach and simple purification. The catalyst was characterized
by various spectroscopy methods such as fourier-transform infrared (FT-IR),
energy-dispersive X-ray (EDX), scanning electron microscope (SEM), X-ray dif-
fraction (XRD) and N2 adsorption–desorption isotherm (BET). Furthermore,
the heterocyclic compounds were characterized by spectral techniques. The
nanocomposite was simply separated byusing an external magnet, and it can
be recycled several times without significant loss of activity.
Correspondence
Mohammad Ali Ghasemzadeh,
Department of Chemistry, Qom Branch,
Islamic Azad University, Qom, I. R. Iran.
Email: ghasemzadeh@qom-iau.ac.ir
Funding information
Islamic Azad University, Qom Branch,
Qom, I. R. Iran, Grant/Award Number:
2016-13929
K E Y W O R D S
Acridines, CoFe2O4@OCMC@cu (BDC), metal–organic framework, Quinazolins, Xanthenes
1 | INTRODUCTION
widespread interest in the preparation of the quinazoline
compounds has been engendered using their broad
Multi-component reactions (MCRs) are main synthetic
methods for preparation of numerous complex molecules
under one-pot conditions from three or more simple raw
materials.[1,2] In recent years, MCRs have been consid-
ered as fast, inexpensive, and environmentally friendly
methods.
biological properties such as anti-microbial, anti-
diabetic, hypnotic, anti-inflammatory, and antitumoral
activity.[5,6]
Xanthenes have many important biological activities
including anti-tumoral, gastric secretion inhibitor, and
opiaceous or cytotoxic activities.[7]
Heterocyclic rings have a rich chemistry in a wide
range of medicinal, pharmaceutical and industrial
fields.[3] These versatile molecules extensively present in
numerous natural products such as vitamins, hormones,
dyes, and drugs.[4] In recent years, synthesis of heterocy-
clic compounds via MCRs has attracted a lot of attention
due to their extensive biological effects. Among them,
In addition, acridine derivatives have attracted con-
siderable attention over the past few years due to their
biological effects such as antimalarial, fungicidal, anti-
inflammatory, anti-viral, anti-microbial, anti-cancer,
anti-parasitic, and anti-tubercular activities.[8–12]
Metal ferrite nanoparticles or bimetal oxide magnetic
nanoparticles (MNPs)are a class of MNPs which have
Appl Organometal Chem. 2020;e5580.
wileyonlinelibrary.com/journal/aoc
© 2020 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.5580

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GHASEMZADEH AND GHAFFARIAN
various applications in several fields. Among these metal
ferrite MNPs, cobalt ferrite (CoFe2O4) MNPs are more
attractive owing to their mechanical hardness, chemical
stability, high thermal, and high magnetization.[13]
Metal–organic frameworks (MOFs), which are con-
structed via coordinating polytopic organic ligands with
clusters or metal ions, have aroused tremendous attention
in the fields of catalysis,[14] gas adsorption and desorp
tion,[15–17]drug delivery[18–20] and sensing,[21,22] due to
their unique features such as various functionalities, exte
nsive surface areas, adjustable internal surface properties,
and high regular pores.[23–30]
Moreover, MOFs can be applied as precursors to take
tailorable functional materials including metal oxide and
carbon composites through thermal/chemical treatments.
Metal–organic frameworks have been used as an effi-
cient catalyst in the catalytic hydrogenation of 2,3,5-trime
thylbenzoquinone,[31] Mizoroki-Heck cross-coupling
reaction,[32] preparation of spiro oxindole derivatives,[33]
pyrano[2,3-d]pyrimidines,[34] propargylamines,[35] indoli
zines,[36] quinoxaline,[37] and pyrano[2,3-c]-pyrazoles.[38]
In the present work, we synthesized some quina
zoline, xanthene and acridine derivatives via three-
component reactions of aldehydes, dimedone and urea/
anilines/2-naphthol in the presence of CoFe2O4@OCMC
@Cu (BDC) as an effective, recyclable and robust catalyst
(Scheme 1).
commercial reagent grade and were used without further
purification. All melting points are uncorrected and were
determined in capillary tube on Boetius melting point
microscope.1H NMR and 13CNMR spectra were obtained
on Bruker 400 MHz spectrometer with DMSO-d6 as sol-
vent using TMS as an internal standard. Fourier-
transform infrared (FTIR) spectrum was recorded on
Magna-IR, spectrometer 550. The elemental analyses
(C, H, andN) were obtained from a Carlo ERBA Model
EA 1108 analyzer. Powder X-ray diffraction (XRD) was
carried out on a Philips diffractometer of X'pert Company
with mono chromatized Cu Kα radiation (λ = 1.5406 Å).
Microscopic morphology of products was visualized by
scanning electron microscope (SEM) (LEO 1455VP). The
mass spectra were recorded on a Joel D-30 instrument at
an ionization potential of 70 eV. The compositional anal-
ysis was done by Energy-dispersive X-ray (EDX, Kevex,
Delta Class I). Nitrogen adsorption–desorption isotherms
ꢀ
were measured at 196 C using a Belsorp mini automatic
adsorption instrument after degassing the samples at
150 ꢀC for 5 hr.
2.2 | Preparation ofCoFe2O4/OCMC/cu
(BDC)
CoFe2O4/OCMC/Cu (BDC)nanocomposite were synthe-
sized according to a previously reported method by
ghasemzadeh and co-workers.[39] Firstly, poly-
vinylpyrrolidone (PVP) (0.12 g) was dissolved in a mix-
ture of water and ethanol (30 ml). Then, CoFe2O4/
OCMC (0.06 g) was added and the reaction mixture was
dispersed by ultrasonic bath for 15 min. Subsequently, a
mixture of copper (II) nitrate (0.022 g) and terephthalic
2 | EXPERIMENTAL
2.1 | Materials and instrumentation
Chemicals were purchased from the Sigma-Aldrich and
Merck in high purity. All of the materials were of
SCHEME 1 Synthesis of xanthenes, quinazolines
and acridines in the presence of CoFe2O4@OCMC/Cu
(BDC) under ultrasonic irradiation

COFE2O4/OCMC/CU (BDC) CATALYZED SYNTHESIS OF XANTHENES, QUINAZOLINS AND ACRIDINES
3 of 10
acid (0.053 g) dissolved in dimethylformamide (DMF)
(2 ml) was added and the reaction mixture was dispersed
for 10 min. The slurry was placed in an autoclave and
heated at 100 ꢀC for 4 hr. Finally, the resulted nanostruc-
ture was collected by an external magnet and washꢀed
with water/DMF mixture and dried in an oven at 80 C
for 24 hr (Scheme 2).
progress was monitored by TLC using hexane/ethyl
acetate (8:2). After completion of the reaction, the
reaction mixture was dissolved in dichloromethane and
the catalyst was separated by an external magnet.
Finally, the solvent was evaporated under reduced
pressure and the residue was recrystallized from etha-
nol to afford the pure product.
2.3 | General procedure for the synthesis
oftetrahydrobenzo[a]xanthen-11-ones (4a-l)
using CoFe2O4/OCMC/cu (BDC)
2.4 | General procedure for the synthesis
of octahydroquinazolinones (5a-l) using
CoFe2O4/OCMC/cu (BDC)
A mixture of aldehyde (1 mmol), 2-naphthol (1 mmol),
dimedone (1 mmol), was added to a flask containing
ethanol (2.5 ml) and water (2.5 ml). The reaction mix-
ture was sonicated in the presence of CoFe2O4/
OCMC/Cu (BDC) nanocomposites (0.002 g) under
30 kHz frequency at room temperature. The reaction
CoFe2O4/OCMC/Cu (BDC)nanocomposite (0.005)was
added to a mixture of dimedone (1 mmol), aldehyde
(1 mmol) and urea (1 mmol) in ethanol/water
(1:1,10 ml). The reaction mixture was sonicated at
30 kHz frequency for 10–20 min at room temperature.
The progress of the reaction was continuously monitored
SCHEME 2 The preparation steps of
OCMC/Cu (BDC)-functionalized magnetic
CoFe2O4 nanoparticles
FIGURE 1 The SEM images of
CoFe2O4@OCMC@Cu (BDC)

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GHASEMZADEH AND GHAFFARIAN
by TLC. After completion of the reaction, the reaction
mixture was dissolved in dichloromethane and the cata-
lyst was separated by an external magnet. The product
was obtained after evaporation of the solvent and recrys-
tallization from ethanol.
3 | RESULTS AND DISCUSSION
3.1 | Investigation of catalytic activity of
cu (BDC)-MOF fanctionalized
CoFe2O4@OCMC in the synthesis of
1,8-dioxo-decahydroacridines,
2.5 | General procedure for the synthesis
of 1,8-dioxo-decahydroacridines(6a-6 l)
using CoFe2O4/OCMC/cu (BDC)
octahydroquinazolinones and
tetrahydrobenzo[a]xanthen-11-ones
CoFe2O4/OCMC/Cu (BDC) nanostructure was initially
synthesized and evaluated by FE-SEM, EDX, FT-IR, XRD
and BET analysis.
The surface morphology of the synthesized CoFe2O4/
OCMC/Cu (BDC)-MOF was investigated by FE-SEM
analysis (Figure 1). It is clear that the magnetic CoFe2O4/
OCMC/Cu (BDC) nanocomposite has a flower shape
with diameter about 20–40 nm.
A mixture of anilines (1 mmol), dimedone (2 mmol),
aldehyde (1 mmol) and nanocatalyst (0.002 g) was
added to a flask containing ethanol (2.5 ml) and water
(2.5 ml). The reaction progress was continuously moni-
tored by TLC. Upon completion, the reaction mixture
was dissolved in dichloromethane and the catalyst was
separated by an external magnet. The product was
afforded by evaporation of the solvent without any
purification.
The structure and crystalline phase of the catalyst
was analyzed by XRD spectroscopy (Figure 2). In the
Spectral data of some products are given in Supple-
mentary Information.
XRD
pattern
of
CoFe2O4@OCMC@Cu
(BDC)
(Figure 3B), the diffraction peaks at 2θvalues of 18.29ꢀ,
30ꢀ, 35.44ꢀ, 37.06ꢀ, 42ꢀ, 53ꢀ, 56.98ꢀ and 62.59ꢀ were
observed indicating the maintenance of the crystalline
structure of CoFe2O4 during the functionalization.
The chemical purity of the CoFe2O4/OCMC/Cu
(BDC) nanocatalyst was investigated by energy-dispersive
X-ray spectroscopy (EDX), which is given in Figure 3.
The EDX spectrum shows the presence of Co, Cu, Fe, C,
O and N as the elements of the nanocomposites.
Fourier transform infrared (FT-IR) spectroscopy was
utilized to confirm the catalyst structure (Figure 4). For
the pure magnetic nanoparticles (Figure 4a), the strong
peak at 579 cm−1is related to the Fe-O vibration of the
nanocatalyst. The other significant peaks at 3410 cm−1
,
1628 cm−1attribute to O − H stretching and bending
FIGURE 2 XRD patterns of CoFe2O4 (a) and
CoFe2O4@OCMC@Cu (BDC) (b)
vibrations of the absorbed water molecules on the surface
FIGURE 3 The EDX spectrum of
CoFe2O4@OCMC@Cu (BDC)

COFE2O4/OCMC/CU (BDC) CATALYZED SYNTHESIS OF XANTHENES, QUINAZOLINS AND ACRIDINES
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FIGURE 4 FT-IR spectra of CoFe2O4 NPs
(a), CoFe2O4@OCMC(b), CoFe2O4
@OCMC@Cu (BDC) (c)
of cobalt ferrite nanoparticles. In the case of
CoFe2O4@OCMCnanocomposite, the broad peak at
3429 cm−1 corresponds to stretching vibrations of amine
and hydroxyl groups of chitosan (Figure 4b). The peaks
at 1657 cm−1and 1379 cm−1are also related to the
stretching vibrations of carbonyl group and N-H bending
vibration
of
chitosan.
In
terms
of
the
CoFe2O4@OCMC@Cu (BDC) (Figure 4c), the band
at2925cm−1attributes to aliphatic C-H asymmetric
stretching vibrations of DMF, and the characteristic peak
at 1504 cm−1 is related to C=C vibrations of aromatic
ring moiety.
The strong peaks at 1390 and 1577 cm−1 are due to
symmetric and asymmetric vibrations of carboxylate
anions in the MOF structure. It is important to say that
the bond observed at 1666 cm−1 corresponds to C=O
vibration of DMF.
The surface area, total pore volumes and average pore
diameter of the catalyst were investigated by N2
FIGURE 5 N2 adsorption/desorption isotherms of
CoFe2O4@OCMC@Cu (BDC)
adsorption–desorption
isotherm
spectrum
(BET)
(Figure 5).[39] It is clear that the specific surface area, the
average pore diameter, and the average pore diameter of
CoFe2O4@OCMC@Cu (BDC) are 64.933 m2/g, 11.46 nm,
and 0.186 cm3/g, respectively. It is also important to men-
tion that the surface area of CoFe2O4@OCMC@Cu
(BDC) decreases gradually due to the presence of the
OCMC polymer and the heavy atoms of Cu (BDC) clus-
ters in the catalyst framework.
Afterwards, the catalytic influence of OCMC/Cu
(BDC) coated CoFe2O4 NP was evaluated for the synthe-
sis of acridine, quinazolinone and xanthene derivatives
through the reaction of dimedone, 4-chlorobenzaldehyde,
urea/2-naphthol/aniline as model reactions (Table 1).
The reaction was optimized under various conditions
such as temperature, catalyst, and solvent.
Initially, the preparation of 4a, 5a, 6a (as examples of
three types of the prepared xanthenes, quinazolines and
acridines) was studied using different solvents such as
ethanol, dichloromethane, water, and acetonitrile under
catalyst-free conditions. The results showed that no prod-
uct was formed under ultrasonic irradiations. Subse-
quently, the reaction was carried out for the preparation
of 4a, 5a, 6a compounds in the presence of various sol-
vents and CoFe2O4/OCMC/Cu (BDC) (0.01 g) as catalyst.

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GHASEMZADEH AND GHAFFARIAN
TABLE 1 The effect of different solvents and catalysts in the synthesis of 4a, 5a, 6a derivatives
Entry
1
Compound
Solvent
CH3CN
H2O
Catalyst
T (ꢀC)
u.s.
u.s.
u.s.
u.s.
u.s
Time (min)
Yield%
56
4a
4a
4a
4a
5a
5a
5a
5a
6a
6a
6a
6a
4a
4a
4a
5a
5a
5a
6a
6a
6a
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
CoFe2O4/OCMC/Cu (BDC)
ZnO NPs
25
20
10
60
48
10
45
32
10
30
18
15
40
35
25
32
25
30
35
25
22
2
60
3
C2H5OH
CH2Cl2
H2O
96
4
56
5
64
6
C2H5OH
CH3CN
CH2Cl2
C2H5OH
CH2Cl2
H2O
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
u.s.
94
7
61
8
79
9
97
10
11
12
13
14
15
16
17
18
19
20
21
84
90
CH3CN
C2H5OH
C2H5OH
C2H5OH
C2H5OH
C2H5OH
C2H5OH
C2H5OH
C2H5OH
C2H5OH
83
82
Fe3O4NPs
80
CoFe2O4NPs
85
ZnONPs
78
Fe3O4 NPs
84
CoFe2O4NPs
81
ZnO NPs
85
Fe3O4NPs
80
CoFe2O4NPs
95
The results are summarized in Table 1. As shown in this
Table, the best results were obtained using the ethanol as
solvent (entries 3, 6, and 9).
In order to investigate the catalytic activity, we also
carried out the model reactions in the presence of several
catalysts in ethanol. The best results were observed when
the CoFe2O4/OCMC/Cu (BDC) nanostructure was used
as catalyst.
The amounts of catalyst loading was examined by
using the various amounts of CoFe2O4@OCMC@Cu
(BDC)
for
the
preparation
of
xanthene(4a),
quinazolinone (5a) and acridine (6a) (Table 2). 0.005 g

COFE2O4/OCMC/CU (BDC) CATALYZED SYNTHESIS OF XANTHENES, QUINAZOLINS AND ACRIDINES
7 of 10
TABLE 2 The optimization of model reaction by using various amounts of the catalyst
Entry
Compound
Catalyst (g)
0.001
Time (min)
Yield%
1
2
3
4
5
6
7
8
7
8
9
4a
4a
4a
5a
5a
5a
5a
5a
6a
6a
6a
25
10
10
25
18
15
10
10
30
10
10
82
96
96
82
95
90
94
94
80
97
96
0.002
0.005
0.001
0.002
0.003
0.005
0.007
0.001
0.002
0.003
TABLE 3 Preparation of acridine, quinazolinone and xanthene derivatives using CoFe2O4/OCMC/Cu (BDC) as the catalysta
Product 4 (a-l)
Product 5 (a-l)
Product 6 (a-l)
Entry
R
Time (min)
Yield%b
96
Time (min)
Yield%
94
R'
Time (min)
Yield%b
98
1
p-Cl
10
10
10
10
15
15
10
10
15
10
15
10
10
10
10
10
10
20
10
10
20
10
20
10
4-F
10
10
10
10
13
13
10
10
13
10
13
10
2
H
94
92
H
97
3
3,4-Cl2
p-Me
2-F
90
91
p-CH3O
p-OMe
p-Cl-2-F
p-CH3O
p-OMe
H
93
4
92
89
91
5
87
85
86
6
p-OH
p-CN
3-NO2
2-Me
p-Br
2-Me
p-OMe
84
84
90
7
91
90
93
8
93
88
91
9
86
83
H
92
10
11
12
91
93
3-Cl-p-CH3
H
94
83
86
91
92
90
H
92
aIsolated yield.
bReaction conditions: dimedone (1 mmol), aryl amines/2-naphthol/urea(1 mmol) and aldehydes (1 mmol) in the.
Presence of CoFe2O4@OCMC/Cu (BDC) in ethanol under ultrasonic irradiation

8 of 10
GHASEMZADEH AND GHAFFARIAN
and 0.002 g were chosen as the optimal amounts of
the catalyst for the preparation of 5a, 4a and 6a
respectively.
With the optimized reaction conditions in our hand,
evaluation of the catalyst efficiency was investigated for
the reaction of a variety of aryl aldehydes, dimedone and
urea/2-naphthol/amines to produce of acridine, xanthene
and quinazolinone derivatives with good to excellent
yields (Table 3). Table 3 shows that the aldehydes bearing
electron withdrawing groups lead to products with higher
yields with shorter reaction time. On the other hand, the
aldehydes with electron donating groups exhibit lower
efficiency with longer reaction time.
FIGURE 6 The reusability of CoFe2O4/OCMC/Cu (BDC) as a
catalyst in the synthesis of xanthene (4a), quinazolinone (5a),
acridine (6a) in model reaction
SCHEME 3 The reasonable
mechanism for the synthesis of
xanthenes (4), quinazolinones (5), and
acridines (6) in the presence of
CoFe2O4/OCMC/Cu (BDC) catalyst

COFE2O4/OCMC/CU (BDC) CATALYZED SYNTHESIS OF XANTHENES, QUINAZOLINS AND ACRIDINES
9 of 10
3.2 | Recyclability of catalyst
ORCID
Mohammad Ali Ghasemzadeh https://orcid.org/0000-
Eventually, the reusability of theCoFe2O4/OCMC/Cu
(BDC)-MOF was studied under the optimized reaction
conditions. After completion of the reaction, the catalyst
was easily separated from the reaction mixture by an
external magnet and was reused in the three model reac-
tions shown in Figure 6. It is clear that the catalyst can
be used six times without a significant loss in activity per-
formance (Figure 6).
A plausible mechanism for the preparation of
octahydroquinazolinones, 1,8-dioxo decahydroacridines,
and tetrahydrobenzo[a]xanthen-11-ones using CoFe2O4/
OCMC/Cu (BDC) is shown in Scheme 3. It is presumed
that CoFe2O4 and Cu (BDC) acts as Lewis acids which
increase the electrophilicity of the carbonyl groups of the
dimedone and aldehyde through a strong coordination
bond.[40,41] The first step is assumed to be a Knoevenagel
condensation between the aldehyde and dimedone to
generate the adduct A, which can act as a Michael accep-
tor. Then urea/amine and 2-naphthol attack to interme-
diate A in a Michael-type reaction to produce an open
chain intermediate B,C,D. Finally, the intermediates
undergo intramolecular cyclization using the nucleo-
philic attack followed by dehydration to form the
products.
0002-8309-6727
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In conclusion, we have demonstrated that CoFe2O4/
OCMC/Cu (BDC) nanocatalyst is an effective catalyst for
the MCRs of xanthenes, quinazolines and acridines using
aromatic aldehydes, dimedone, aryl amines/2-naph
thol/urea at room temperature under ultrasonic irradia-
tion conditions. The heterocyclic compounds including
tetrahydrobenzo[a]xanthen-11-ones,
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ACKNOWLEDGMENTS
The author gratefully acknowledges the financial support
of this work by the Research Affairs Office of the Islamic
Azad University, Qom Branch, Qom, I. R. Iran [grant
number 2016-13929].

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SUPPORTING INFORMATION
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How to cite this article: Ghasemzadeh MA,
Ghaffarian F. Preparation of core/shell/shell
CoFe2O4/OCMC/Cu (BDC) nanostructure as a
magnetically heterogeneous catalyst for the
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