Anchoring of Cu–dimethylglyoxime complex in MCM-41 matrix: a new, recyclable, and highly efficient nanocatalyst for the green preparation of 2,3-dihydroquinazolin-4(1H)-ones

Article abstract of DOI:10.1007/s00706-021-02793-9

A new heterogeneous nanocatalyst containing Cu–dimethylglyoxime complex grafted to an MCM-41 matrix was synthesized. This recoverable nanocomposite was applied as a highly effective, green, thermally stable catalyst in the one-pot reductive cyclization of aromatic aldehydes with 2-aminobenzamide. 2,3-Dihydroquinazolin-4(1H)-ones were obtained in 80–98% yield. The MCM-41-silylcyclopropyl-dimethylglyoxime-Cu heterogeneous nanocomposite was well identified using X‐ray diffraction, field emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy‐dispersive X‐ray spectroscopy, Brunauer–Emmett–Teller technique, and thermogravimetric analysis. The eco-friendly nanocatalyst demonstrated excellent recyclability: it could be reused for at least six successive cycles without any notable decrease in its catalytic function. Graphic abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s00706-021-02793-9

Monatshefte für Chemie - Chemical Monthly (2021) 152:833–844
https://doi.org/10.1007/s00706-021-02793-9
ORIGINAL PAPER
Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new,
recyclable, and highly efcient nanocatalyst for the green preparation
of 2,3‑dihydroquinazolin‑4(1H)‑ones
Nishtman Hassanloie1 · Nader Noroozi Pesyan1 · Golaleh Sheykhaghaei2 · Khadijeh Ojaghi Aghbash1
Received: 11 June 2020 / Accepted: 31 May 2021 / Published online: 14 July 2021
© Springer-Verlag GmbH Austria, part of Springer Nature 2021
Abstract
A new heterogeneous nanocatalyst containing Cu–dimethylglyoxime complex grafted to an MCM-41 matrix was synthesized.
This recoverable nanocomposite was applied as a highly efective, green, thermally stable catalyst in the one-pot reductive
cyclization of aromatic aldehydes with 2-aminobenzamide. 2,3-Dihydroquinazolin-4(1H)-ones were obtained in 80–98%
yield. The MCM-41-silylcyclopropyl-dimethylglyoxime-Cu heterogeneous nanocomposite was well identifed using X‐ray
difraction, feld emission scanning electron microscopy, Fourier transform infrared spectroscopy, energy‐dispersive X‐ray
spectroscopy, Brunauer–Emmett–Teller technique, and thermogravimetric analysis. The eco-friendly nanocatalyst demon-
strated excellent recyclability: it could be reused for at least six successive cycles without any notable decrease in its catalytic
function.
Graphic abstract
Keywords MCM-41 · Cu–dimethylglyoxime complex · 2,3-Dihydroquinazolin-4(1H)-one · Nanocatalyst
Introduction
has attracted much attention because of their several unique
properties including large pore volume (normally over 0.8
cm3/g), unique channel structure, well thermal stability,
large surface area (∼1000 m2/g), and good biocompatibil-
ity as well as ready surface functionalization [3, 4]. Due to
unique properties these mesoporous creating suitable prop-
erties such as controllable, morphologies, narrow pore size
distribution, structural simplicity, and ease synthesis with
insignifcant pore obstruction and pore networking [5–8].
These properties have made MCM-41 frequent support for
heteropoly acids [9], immobilizing acids [10], complexes
[11, 12], metal oxides [13], etc. Also, these mesoporous have
been used for several applications such as adsorption [14],
support of various catalysts [15], environmental science
[16], sensors [17], drug delivery [18], etc. Finally, there is
also the possibility of presentation transition metals includ-
ing Cr [19], Pd [20], Mn [21], Cu [22], VO [23], Ni [15,
Recently, nanoporous materials have a superior role in green
chemistry and have received a lot of attention amongst the
industrial and academic scientifc society, owing to facile
recovery, high surface area, and their fundamental infuence
on the human life quality and economic advance [1, 2]. Also,
these nanostructures have versatile applications in materials
science owing to shape and size-selective diferent usages.
Among them, mesoporous silica materials like MCM‐41
as the typical representative of the M41S material family
* Nader Noroozi Pesyan
n.noroozi@urmia.ac.ir; nnp403@gmail.com
1
2
Department of Organic Chemistry, Faculty of Chemistry,
Urmia University, 57159 Urmia, Iran
Department of Chemistry, Science and Research Branch,
Islamic Azad University, 1477893800 Tehran, Iran
Vol.:(0123456789)
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N. Hassanloie et al.
24], Mo [25], V [26], Co [27], and Fe [28] in the MCM-41
matrix to preparing diferent redox heterogeneous catalysts.
From a long time ago, copper-dimethylglyoxime com-
plexes have been examined due to their possible utilization
in organic and catalysis reactions [29]. Its catalytic property
increases by grafting of the copper-dimethylglyoxime com-
plex onto the MCM-41 matrix. 2,3-Dihydroquinazolinones,
six-membered heterocyclic compounds, are of interest to
many chemists owing to extensive range of diferent biologi-
cal and pharmacological activities, anticancer, antifertility,
antihistaminic, antibiotic, cytotoxicity, antibacterial, antitu-
mor, painkiller, angiotensin II AT1 receptor antagonists, and
mono amine oxidase inhibition [30–32]. Generally, various
methods have been presented for the synthesis of 2,3-dihyd-
roquinazolinones [33–36]. Among them, 2,3-dihydroquina-
zolin-4(1H)-one derivatives were synthesized via reductive
cyclization of 2-aminobenzamide with various ketones
or aldehydes in the presence of acid catalysts [32, 37]. In
this synthetic process, many methods have been developed
using diferent catalytic systems under diferent conditions
[38–41]. Nevertheless, most of these catalytic processes
have unfavorable reaction conditions such as harsh reaction
conditions, longer reaction time, use of a major amount of
poisonous and costly catalysts, unpleasant yields, and frus-
trating workup. So one of the goals of organic chemists is to
develop better reaction conditions for the synthesis of these
compounds using novel catalysts.
solvent with excellent yields, low reaction time, and easy
workup.
Results and discussion
In our examinations on the use of heterogeneous nano-
catalysts in organic reactions [42], herein, we synthesized
a novel copper-dimethylglyoxime complex supported on
MCM-41. We also checked its function as an efective het-
erogeneous and recoverable nanocatalyst in the preparation
of 2,3-dihydroquinazolin-4(1H)-one derivatives. The details
of the nanocatalyst preparation method were presented in
Scheme 1.
Catalyst characterization
The nanocatalyst was fully characterized by XRD (X‐ray
diffraction), FESEM (field emission scanning electron
microscopy), FT-IR (Fourier transform infrared spectros-
copy), EDS (energy‐dispersive X‐ray spectroscopy), BET
(Brunauer–Emmett–Teller technique), and TGA (thermo-
gravimetric analysis). The FT-IR spectra of MCM-41-di-
methylglyoxime-Cu were shown in Fig. 1. As is depicted
in Fig. 1, for the MCM-41, the absorption peaks at 1652,
1085, 805, and 459 cm−1 are related to stretching vibrations
(symmetric and asymmetric) of Si–O-Si. Also, the peak at
3409 cm−1 indicates the presence of O─H groups stretch-
ing vibration. Stretching vibrations at 2953 and 3305 cm−1
attributed to the C─H of the chloropropylsilyl group. The
existence of the grafted complex of Cu–dimethylglyoxime to
functionalized MCM-41 can be confrmed by the presence of
Herein, we synthesized a complex of copper-dimethylg-
lyoxime based on MCM-41 nanoparticles and utilized it for
the preparation of 2,3-dihydroquinazolin-4(1H)-one deriva-
tives using cyclocondensation of aromatic aldehydes with
2-aminobenzamide under conditions of refux in ethanol
Scheme 1
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Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new, recyclable, and highly…
835
Fig. 1 FT-IR spectra of a MCM-41 b Cu(II)-dimethylglyoxime‐MCM-41
peaks at 1395 and 579 cm−1 that are allocated to stretching
vibrations of C─N and Cu─N (Fig. 1) [43, 44].
complex and framework of silicate, or may be because of the
alterations in the thickness of the wall. Thus, it can be found
out that the preparation of the nanocatalyst has been accom-
plished on the internal pore channels of the MCM-41/Si.
Thermal stability of Cu(II)-dimethylglyoxime/MCM-41
mesoporous was determined using the TGA and TGA/DTA
analysis. TGA (Fig. 5, top) and TGA/DTA (Fig. 5, bottom)
curves showed primary weight decrease at temperatures
under 200 °C owing to desorption of organic solvent and
water molecules. Furthermore, raising the temperature from
200 to 800 °C, the major weight decrease was observed due
to the thermal decomposition of organic functional groups
located inside the framework.
The spherical morphology of MCM-41 and Cu(II)‐
dimethylglyoxime‐MCM‐41 was studied using FESEM
images (Fig. 2). The FESEM images confrm that MCM‐41
has almost spherical and regular morphology. The size dis-
tribution histogram for MCM‐41 and Cu(II)‐dimethylgly-
oxime‐MCM‐41 nanoparticles (Fig. 2) was shown a mean of
89.8 2.4 nm and 86.8 2.0 nm, respectively. It confrmed
that these structures maintain their high monodispersity pro-
fle even after immobilization on the support.
As shown in Fig. 3, the EDX has confrmed the presence
of every anticipated element in the produced Cu(II)‐dimeth-
ylglyoxime‐MCM‐41, including O, C, Si, N, and Cu with
the relative weight percents 30.0, 20.5, 39.30, 1.3, and 8.9%,
respectively. Moreover, the presence of the element of nitro-
gen in elemental analysis demonstrates dimethylglyoxime
ligand has fully bonded onto MCM-41, and the metal of Cu
has coordinated successfully to the ligand of dimethylgly-
oxime. These results indicate that the new nanocatalyst was
constructed successfully.
The N2 adsorption–desorption isotherm of the Cu(II)-
dimethylglyoxime/MCM-41 nanocomposite was shown in
Fig. 6. The pore features of the prepared nanocomposite
were investigated using the Brunauer–Emmett–Teller (BET)
technique. The BET entire cavity capacity and surface areas
for the nano composites were 0.1819 m3 g−1 and 1.400
m2 g−1, respectively. By using the technique of Barrett-
Joyner-Halenda (BJH), the corresponding pores diameter
distributions of Cu(II)-dimethylglyoxime/MCM-41 were
specifed as 1.21 nm (Fig. 7). The structure of the porous
medium contains pores more than 2 nm (Dv >2 nm) which
demonstrates a mesoporous structure.
Figure 4 demonstrates the low-angle powder XRD pat-
terns of Cu(II)-dimethylglyoxime/MCM-41 and MCM-41
samples. The XRD pattern of MCM-41 illustrates the pres-
ence of three refection peaks corresponding to (200), (110),
(100) and planes at 2θ=4.33°, 3.87°, and 2.41°, respectively.
These patterns confrm the presence of ordered hexagonal
mesoporous structure of MCM-41 (Fig. 4a). As shown in
Fig. 4b, during the functionalization steps, a remarkable
decline in the severity of XRD peaks was seen. It is due to
decrease of dispersion contrast between the channel wall of
Catalytic activity of the Cu(II)‑dimethylglyoxime/
MCM‑41
We examined the catalytic activity of Cu(II)-dimethyl-
glyoxime/MCM-41 as a novel, stable, and recyclable
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N. Hassanloie et al.
Fig. 2 SEM micrographs and size distribution histograms of a MCM-41 and b Cu(II)-dimethylglyoxime‐MCM‐41
The various parameters such as the reaction tempera-
ture, the amount of catalyst, time, and various solvents were
studied, and the results were summarized in Table 1. The
best results were obtained with 1.0 mmol benzaldehyde and
1.0 mmol 2-aminobenzamide in the presence of 5 mg Cu(II)
dimethylglyoxime/MCM-41 and 5 cm3 ethanol as solvent at
80 ºC (Table 1, entry 12). Furthermore, with the utilization
of further quantities of 8 mg catalyst and fewer quantities of
4 mg catalyst, the favored results and desired yields did not
obtain (Table 1, entries 13 and 2, respectively).
After optimization experiments, the optimized conditions
(ethanol solvent, 5 mg catalyst, and refux conditions) were
applied for the preparation of 2,3-dihydroquinazolin-4(1H)-
ones (Table 2). The reaction of 2-aminobenzamide (1) with
various aromatic aldehydes derivatives was carried out. It
can be observed that a broad range of aldehyde derivatives
2 react with 2-aminobenzamide readily and give compounds
3 in suitable yields. It is also notable that only small conden-
sation rate diferences occur between aldehydes substituted
with electron-donating and electron-attracting groups.
The proposed mechanism for the preparation of quina-
zolines derivatives was presented in Scheme 3. According
Fig. 3 The EDX spectrum of Cu(II)-dimethylglyoxime/MCM-41
heterogeneous nanocatalyst in preparation of 2,3-dihydro-
quinazolin-4(1H)-one derivative (Scheme 2). In this regard,
the one-pot reaction of benzaldehyde and 2-aminobenza-
mide was performed to fnd the optimal conditions. The opti-
mized conditions were shown in Table 1 for preparing the
quinazoline in the presence of diferent catalytic quantities
of Cu(II)-dimethylglyoxime/MCM-41.
1 3

Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new, recyclable, and highly…
837
Fig. 4 XRD patterns of MCM-41 a and Cu(II)-dimethylglyoxime/MCM-41 (b)
Fig. 5 TGA thermogram of Cu(II)-dimethylglyoxime/MCM-41 (top) and TGA/DTA analysis of Cu(II)-dimethylglyoxime/MCM-41 (bottom)
to this mechanism, Cu(II)-dimethylglyoxime/MCM-41 is
an active catalyst for the production of 2,3-dihydroquina-
zoline-4(1H) ones. First, the proposed catalyst coordinated
to aldehyde oxygen to produce intermediate a, then imine
b generated by nucleophilic attack of primary amine to
intermediate a with loss of water. Afterward, under an
intramolecular cyclization by the attack of amide nitro-
gen on the activated imine carbon, the desired 2,3-dihy-
droquinazoline-4(1H) one 3 is formed. It is noteworthy
that the mechanism for the reaction has not been studied.
We suggest the following possibility. We have not deter-
mined whether or not the catalyst functions in both steps
as shown.
Further, the efciency of the prepared catalyst was com-
pared with other nanoparticle-based metal catalysts for the
synthesis of the model product. To have a more precise
comparison, the reaction condition, time, temperature, and
solvent for each protocol were considered in Table 3. As
obvious, our procedure is comparable with those of previ-
ously reported catalytic systems in terms of yields of the
products, reaction temperature, and time. In addition to
this, the present catalyst is more efective than the others
due to some important benefts such as its eco-friendly,
stability, recyclability, etc.
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838
N. Hassanloie et al.
Scheme 2
Recyclability of the catalyst
Finally, the stability and reusability of the catalyst were sig-
nifcant parameters in the potential application of organic
transformation. To survey this trait, the reusability of the
Cu(II)-DMG@MCM-41 was examined in the reaction of
aromatic aldehydes with 2-aminobenzamide as a model
reaction according to optimal conditions (Fig. 8).
At the end of each reaction cycle, the catalyst was sepa-
rated using centrifugation and dried after washing with dis-
tilled water and ethanol. Then the catalyst is utilized for the
next run. The results in Fig. 8 indicate that the proposed
catalyst is recycled up to six successive runs. Furthermore,
after six runs, the nature of the recycled nanocomposite was
examined by SEM (Fig. 9). The conclusions of the analyses
showed that the recycled nanocomposite after six periods
had no signifcant decrease in catalytic activity that the struc-
ture of the mesoporous silica did not change signifcantly.
P / P0
Fig. 6 Nitrogen adsorption–desorption isotherm of Cu(II)-dimethylg-
lyoxime/MCM-41
Conclusion
In summary, a new complex of Cu–dimethylglyoxime
anchored to MCM-41 nanostructure was synthesized using
the sol–gel method. It developed as an innovative promise
catalyst and efectively green recyclable catalytic system in
the synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Advan-
tages of the catalytic system are simple preparation, high
reaction speed, green conditions, simple workup, excellent
yields of products, excellent stability, and reusability of the
catalyst.
Experimental
The used solvents and chemicals were obtained from Fluka,
Aldrich, and Merck and used without further purifcation.
The particle morphology and size of nanoparticles were
checked using FESEM (Day Petronic Company, Tehran,
Iran) with a TESCAN MIRA3, also EDS analysis was
accomplished by a TESCAN MIRA3 (Day Petronic Com-
pany, Tehran, Iran). The FT‐IR spectra were taken by KBr
pellets utilizing a Nexus 670 FT‐IR spectrometer (Urmia
University, Urmia, Iran). Thin-layer chromatography was
used for monitoring reaction over silica gel 60 F254 alu-
minum sheet. 1H NMR spectrum (300 MHz) and 13C NMR
spectrum (75 MHz) were recorded by a Bruker NMR
rp / nm
Fig. 7 Pore size distribution curves of Cu(II)-dimethylglyoxime/
MCM-41
1 3

Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new, recyclable, and highly…
839
Table 1 Optimization of reaction parameters for the synthesis of 2-phenyl-2,3-dihydroquinazolin-4(1H)-one (3a)
Entry
Cat./mg
Solvent
Temp /oC
Time/min
Yield/%a, b
1
2
3
4
5
6
7
8
0
4
5
5
5
5
5
5
5
5
3
5
8
5
EtOH
EtOH
Refux
Refux
100
Refux
rt
Refux
Refux
Refux
100
60
60
60
50
50
50
40
45
50
50
40
25
25
60
Trace
90
No reaction
Solvent free
THF
CH2Cl2
CH2Cl2
CH3CN
EtOAC
PEG
EtOH
EtOH
EtOH
EtOH
60
55
75
80
78
45
80
92
97
97
68
9
10
11
12
13
14
rt
Refux
Refux
Refux
Refux
H2O
aReaction conditions: 2-aminobenzamide (1 mmol), aldehyde (1 mmol), 5 mg catalyst
bIsolated yields
spectrometer (Urmia University, Urmia, Iran). The crystal-
line structures were checked by powder XRD measurements
with a wavelength of 1.54 Å and several templates of difrac-
tion were entered in the 2θ confne (1–80°) (Day Petronic
Company, Tehran, Iran). Melting points were recorded using
an IA9200 melting point device. Curves of TGA were col-
lected using an STA 1500 appliance from Scientifc Ameri-
can Rheometric (Day Petronic Company, Tehran, Iran).
Synthesis of MCM‑41‑(CH2)3Cl
The prepared MCM-41 nanoparticles (4.8 g) with 5.0 g
3-chloropropyltrimethoxysilane (CPTMS) was mixed with
96 cm3 of n-hexane and the reaction mixture was stirred
under N2 atmosphere and refux conditions for 24 h. The
outcome sediments were gathered by fltration, after wash-
ing with ethanol. The resulting MCM-41-(CH2)3-Cl was
dried under vacuum.
Synthesis of siliceous MCM‑41
Synthesis of MCM‑41‑(CH2)3Cl functionalized
with dimethylglyoxime (MCM‑41‑CPTMS‑DMG)
Firstly, 1.0 g surfactant cetyltrimethylammonium bromide
(CTAB, 2.74 mmol) was mixed with a solution containing
3.5 cm3 NaOH (2 M) and 480 cm3 deionized water under
stirred at 80 °C. After homogenizing the mixture, 5 cm3
tetraethyl orthosilicate (TEOS) was slowly added dropwise
into the solution, it gives a mixture of white suspension.
The mixture of reaction was refuxed for 2 h at 80 °C. The
product was fltered and dried at 70 °C after being washed
with deionized water, then it was calcined at 550 °C for
5 h to eliminate the surfactants of remain. Eventually, Si-
MCM-41 was prepared.
In a 50 cm3 round-bottomed fask equipped with a mag-
netic stirrer, 0.5 g dimethylglyoxime (DMG), 0.5 g MCM-
41-(CH2)3Cl, 1.0 cm3 triethylamine (TEA), and 25 cm3
ethanol were mixed and refuxed for 24 h under N2 atmos-
phere. After washing with ethanol, it was dried under
vacuum at 60 °C for 12 h.
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N. Hassanloie et al.
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Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new, recyclable, and highly…
841
1 3

842
N. Hassanloie et al.
Scheme 3
Table 3 Comparison of the
activity of diverse catalysts
in the paper to preparation of
2-phenyl-2,3-dihydroquinazolin-
4(1H)-one
Entry Catalyst
Solvent
Temp/ºC Time/min Yield /% Lit
1
2
3
4
Cu(II)-DMG@MCM-41
EtOH
EtOH
EtOH
CH3CN
TFE
Solvent free 70
Solvent free rt
Solvent free 100
80
70
70
rt
25
55
25
10
90
90
10
90
25
30
30
30
40
98
87
92
96
90
91
83
82
92
92
90
97
93
This work
[35]
[47]
[48]
[49]
Ga(OTf)3
Sc(OTf)3
Cyanuric chloride
TFE
5
78
6
7
8
PPA-SiO2
Citric acid
TABA
[50]
[51]
[52]
[53]
9
Fe3O4@MCM-41@EDTA@Ni EtOH
NH2SO3H
MCM41-Biurea-Ni
CuCl2/Fe3O4−TEDETA
Br3‐TBA‐Fe3O4
78
10
11
12
13
H2O
PEG
EtOH
H2O
70
rt
[54]
[15]
Refux
70
[34]
[55]
Synthesis of MCM‑41‑CPTMS‑DMG‑Cu
General synthesis for the preparation
of 2,3‑dihydroquinazolin‑4(1H)‑ones
Finally, a mixture of 0.8 g MCM-41-CPTMS-DMG, 0.4 g
CuCl2·2H2O, and 20 cm3 ethanol was refuxed for 24 h
under N2 atmosphere. The purifed resulting precipitate was
washed with EtOH and dried at 60 °C for 12 h to product
MCM-41-CPTMS-DMG-Cu.
A mixture of 0.136 g 2-aminobenzamide (1 mmol), alde-
hyde (1 mmol), and 5 mg MCM-41-CPTMS-DMG-Cu was
stirred in 5 cm3 ethanol and heated at 80 °C. The reaction
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Anchoring of Cu–dimethylglyoxime complex in MCM‑41 matrix: a new, recyclable, and highly…
843
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