Preparation and characterization of a silica-based magnetic nanocomposite and its application as a recoverable catalyst for the one-pot multicomponent synthesis of quinazolinone derivatives

Article abstract of DOI:10.1002/aoc.3373

An environmentally benign magnetic silica-based nanocomposite (Fe₃O₄/SBA-15) as a heterogeneous nanocatalyst was prepared and characterized using Fourier transform infrared and ultraviolet-visible diffuse reflectance spectroscopies,

Full text of DOI:10.1002/aoc.3373

Full paper
Received: 22 June 2015
Revised: 14 July 2015
Accepted: 31 July 2015
Published online in Wiley Online Library: 13 September 2015
(wileyonlinelibrary.com) DOI 10.1002/aoc.3373
Preparation and characterization of a silica-
based magnetic nanocomposite and its
application as a recoverable catalyst for the
one-pot multicomponent synthesis of
quinazolinone derivatives
Ali Maleki*, Mahboubeh Rabbani and Shirin Shahrokh
An environmentally benign magnetic silica-based nanocomposite (Fe O /SBA-15) as a heterogeneous nanocatalyst was prepared
3
4
and characterized using Fourier transform infrared and ultraviolet–visible diffuse reflectance spectroscopies, scanning electron
microscopy, X-ray diffraction, vibrating sample magnetometry and Brunauer–Emmett–Teller multilayer nitrogen adsorption. Its
catalytic activity was investigated for the one-pot multicomponent synthesis of 2,3-dihydroquinazolin-4(1H)-ones starting from
isatoic anhydride, ammonium acetate and various aldehydes under mild reaction conditions and easy work-up procedure in
refluxing ethanol with good yields. The nanocatalyst can be recovered easily and reused several times without significant loss
of catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd.
Additional supporting information may be found in the online version of this article at the publisher’s web-site.
Keywords: composite nanostructures; magnetic nanocatalyst; Fe O nanoparticles; SBA-15; multicomponent reaction
3
4
Introduction
Magnetic iron oxide nanoparticles are particularly attractive owing to
their unique properties and potential applications in various fields.
isatoic anhydride, aldehydes and amines or ammonium acetate using
[1]
[18]
[19]
[20]
catalysts such as Ga(OTf) , Bi(NO ) ꢀ5H O, KAl(SO ) ꢀ12H O,
4 2
[21] [22] [23] [24]
3
3 3
2
2
In general, the naked nanoparticles tend to aggregate into large clus-
ters. This problem can be overcome by immobilizing the nanoparti-
cles on substrates such as polymers, carbons and mesoporous
PTSA, Fe O , SrCl ꢀ6H O and Cu(C H SO ) ꢀ6H O.
3
4
2
2
6
5
3 2
2
In continuation of our recent researches towards the development
of green, simple and environmentally benign protocols in organic
[2]
[25]
silica. SBA-15, as a highly ordered mesoporous material, is one of
the best substrates for this purpose, due to its large surface area, high
reactions, herein, for the first time, we introduce a magnetite–
silica nanocomposite (Fe O /SBA-15) as an efficient nanocatalyst in
3
4
[3]
chemical and thermal stability and good compatibility. The integra-
tion of mesoporous silica with magnetic nanoparticles to form po-
rous magnetic nanocomposites is undoubtedly of great interest for
practical applications. These types of magnetic nanocomposites
have the advantages of both mesoporous silica and magnetic nano-
particles. In recent years, several studies have been done on the
synthesis and application of these magnetic nanocomposites in or-
multicomponent reactions (MCRs) for the one-pot synthesis of 2,3-
dihydroquinazolin-4(1H)-one derivatives 4a–g using isatoic anhy-
dride (1), ammonium acetate (2) and various aldehydes (3) in
refluxing ethanol in good to excellent yields (Scheme 1). To the best
of our knowledge, this is the first synthesis of dihydroquinazolinones
catalysed by superparamagnetic composite nanoparticles via MCRs.
[4]
ganic manufacturing.
Results and discussion
Quinazoline derivatives are an important class of heterocyclic com-
pounds that have diverse biological and pharmaceutical properties
such as antifertility, antibacterial, antiviral, antitumor and antifungal
Characterization of nanocatalyst
[5]
activities. Quinazolin-4(3H)-one analogues as important pharmaco-
Fourier transform infrared (FT-IR) spectroscopy of Fe
3 4
O /SBA-15
[6]
logically active compounds have been synthesized using several
The FT-IR spectra of neat SBA-15, neat Fe and Fe O
3
O
4
3 4
/SBA-15
[7–24]
methods.
The most common procedure involves the condensa-
samples are shown in Fig. 1. Their comparison confirms the efficient
tion reaction of anthranilamide with aldehydes or ketones using
[
7]
[8]
[9]
[10]
various catalysts such as TiCl –Zn, Sc(OTf) , NH Cl, HCl,
4
3
[13]
4
[14]
[11]
[12]
[15]
p-toluenesulfonic acid (PTSA), SmI2, CuCl2, MnO2, KMnO4,
* Correspondence to: Ali Maleki, Catalysts and Organic Synthesis Research
Laboratory, Department of Chemistry, Iran University of Science and
Technology, Tehran 16846-13114, Iran. E-mail: maleki@iust.ac.ir
[
16]
ionic liquid or 2,2,2-trifluoroethanol without additional catalyst
and copper-catalysed Ullmann N-arylation coupling process.
[
17]
Several strategies for the synthesis of 2,3-dihydroquinazolinone
derivatives involve a one-pot three-component condensation of
Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry,
Iran University of Science and Technology, Tehran 16846-13114, Iran
Appl. Organometal. Chem. 2015, 29, 809–814
Copyright © 2015 John Wiley & Sons, Ltd.

A. Maleki et al.
3 4
Scheme 1. Fe O /SBA-15-catalysed synthesis of 2,3-dihydroquinazolin-
4(1H)-ones 4a–j.
3 4 3 4
Figure 1. FT-IR spectra of neat SBA-15, neat Fe O and Fe O /SBA-15.
loading of Fe O nanoparticles on SBA-15 and the formation of the
3
4
magnetic composite nanocatalyst. For neat Fe O , the bands at 561
3
4
ꢁ
1
and 640 cm are ascribed to Fe–O of iron oxide nanoparticles. In
the FT-IR spectrum of neat SBA-15, the symmetric and asymmetric
stretching vibration bands of Si–O–Si bond are observed at 810
ꢁ
1
ꢁ1
and 1093 cm , respectively. The peak at 452 cm is assigned
to the Si–O–Si bending vibration. A broad band around 3440
ꢁ
1
cm is assigned to stretching vibration of O–H in water mole-
cules adsorbed on the surface and the stretching vibration of sur-
Figure 2. (A) Wide-angle XRD patterns of neat SBA-15, Fe and Fe
SBA-15. (B) Small-angle XRD patterns of neat SBA-15 and Fe O /SBA-15.
3 4
3
O
4
3 4
O /
face silanol groups. After the loading of Fe
3
O
4
nanoparticles on
ꢁ
1
SBA-15, bands at 640 and 1150 cm can be attributed to the
4
c)
Fe–O–Si bond. However, the presence of Fe–O–Si bonds cannot
be seen clearly in the FT-IR spectrum because the band overlaps
with the Si–O vibration of neat SBA-15.
can be observed that both of the synthesized samples show the
same pattern, which indicates that the hexagonally structured
SBA-15 silica with highly ordered mesoporous channels is main-
tained during the preparation of the heterogeneous catalyst,
although the strong peak for Fe O /SBA-15 compared with SBA-15
X-ray diffraction (XRD) analysis of Fe O /SBA-15
3
4
3
4
The structure of the as-synthesized Fe O inside SBA-15 was inves-
3
4
is decreased. This could be due to the presence of Fe O nanoparti-
3 4
tigated using XRD. Figure 2(A) shows wide-angle XRD patterns of
neat SBA-15, Fe O and Fe O /SBA-15 samples.The diffraction
cles in SBA-15 pores meaning the sizes of pores are smaller than in
SBA-15 and the mesostructure of SBA-15 is disordered which leads
to weaker reflections. Therefore these changes reveal that the
Fe O nanoparticles are well immobilized in the SBA-15 nanocages.
3
4
3 4
peaks observed at 30.00°, 35.48°, 43.14°, 53.44°, 57.04° and 62.58°
are well indexed to the cubic spinel structure of pure Fe O (JCPDS
3
4
3
4
file no. 19-0629). No peaks of iron hydroxide, hematite or other
impurities are detected, suggesting the complete formation of
magnetite, and also the strong and sharp peaks reveal that the
Fe O particles are well crystallized. For the neat SBA-15 and
Nitrogen adsorption–desorption isotherms of Fe
3 4
O /SBA-15
The textural properties of neat SBA-15 and Fe O /SBA-15 samples
were determined using nitrogen adsorption–desorption isotherms
3
3
4
4
3 4
Fe
O
/SBA-15, the broad diffraction peak between 20° and 30° is
attributed to the silicon material. In addition, the results reveal the
production of Fe /SBA-15 nanocomposite.
Figure 2(B) shows the small-angle XRD patterns of neat SBA-15
and Fe /SBA-15 nanocomposite. Pure SBA-15 exhibits a strong
10 0) diffraction peak with two small peaks (11 0) and (20 0) asso-
at 77 K. As can be seen in Fig. 3, the isotherms of neat SBA-15 and
Fe O /SBA-15 are type IV (H ) hysteresis loops that are typical for
3 4 2
mesoporous materials with ordered channels. Moreover, in com-
parison with neat SBA-15, Brunauer–Emmett–Teller (BET) surface
O
3 4
O
3 4
(
3 4
area and pore volume of Fe O /SBA-15 are decreased. This indi-
ciated with a two-dimensional hexagonal p6mm mesostructure,
confirming the highly ordered mesostructure of the silica host. It
cates the successful incorporation of Fe
SBA-15.
3 4
O into nanocages of
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Copyright © 2015 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2015, 29, 809–814

Preparation and application of a magnetic composite nanocatalyst
Figure 3. Nitrogen adsorption–desorption isotherms of neat SBA-15 and
Fe O /SBA-15.
3 4
Magnetic properties of Fe O /SBA-15
3
4
The magnetic hysteresis loops for neat SBA-15, Fe O and Fe O /
3
4
3 4
SBA-15 are shown in Fig. 4. The magnetic properties of the samples
were analysed using vibrating sample magnetometry (VSM) with
an applied field ꢁ7.3 ≤ H ≤ 7.3 kOe at room temperature. When
the Fe O is immobilized on SBA-15, the saturation magnetization
3
4
(
0
M ) is decreased (M of neat SBA-15, Fe O and Fe O /SBA-15 is
.0, 15.2 and 5.9 emu g , respectively). According to the curves,
s s 3 4 3 4
ꢁ
1
the remanent magnetization (M ) of Fe O and Fe O /SBA-15 is
r
3
4
3 4
ꢁ
1
1
.2 and 0.4 emu g , respectively. The coercivity field of Fe
and Fe /SBA-15 is 8 Oe. Therefore, it can be concluded from
the hysteresis loops that Fe and Fe /SBA-15 are magnetically
soft at room temperature.
3 4
O
3 4
O
O
3 4
3 4
O
Scanning electron microscopy (SEM) imaging of Fe O /SBA-15
3
4
As seen in Fig. 5, the SEM image of SBA-15 exhibits vermicular-
shaped particles. The SEM image of magnetite in Fig. 5 shows that
the material has a uniform morphology and particle size distribu-
tion. The regular morphology indicates that the particles are well
crystallized. The SEM image of Fe O /SBA-15 in Fig. 5 shows the
3
4
3 4 3 4
Figure 5. SEM images of SBA-15, Fe O and Fe O /SBA-15.
morphology of well-dispersed spherical particles that may be attrib-
uted to the presence of magnetite-coated silica nanoparticles.
These particles are homogeneous and the average size distribution
is about 80 nm. An increased surface roughness is observed in
Fe O /SBA-15, which may be attributed to the presence of iron
3
4
oxide particles on the surface of mesoporous silica.
3 4
Optical properties of Fe O /SBA-15
The ultraviolet (UV)–visible diffuse reflectance spectroscopy (DRS) tech-
3 4 3 4
Figure 4. Magnetic hysteresis loops for neat SBA-15, Fe O and Fe O /
SBA-15.
3 4
nique can be utilized to investigate the photocatalytic activity of Fe O
Appl. Organometal. Chem. 2015, 29, 809–814
Copyright © 2015 John Wiley & Sons, Ltd.
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A. Maleki et al.
nanoparticles encapsulated in mesoporous SBA-15 silica composites.
Figure 6 shows the UV–visible absorption spectra of neat SBA-15 and
from Table 1, the reaction proceeds very efficiently by varying the
structure of the aldehyde, and no undesirable side reactions are ob-
served under these reaction conditions.
It should be mentioned that both electron-withdrawing and
2 3 3
electron-releasing groups, such as NO , COOH, OCH and CH ,
Fe
tion bands in both UV and visible regions (200–800 nm). The band
gap energy (E ) according to the band maxima of the absorption spec-
trum was evaluated using the Tauc equation:
3 4 3 4
O /SBA-15. The spectrum of Fe O /SBA-15 exhibits broad absorp-
g
and also halogens such as Cl suitably react and give the expected
products in reasonable times and in good isolated yields.
The aldehyde derivatives containing electron-acceptor groups
have a better performance in the reaction to synthesize 2,3-
dihydroquinazolin-4(1H)-one. In contrast, the presence of stronger
electron-donor groups in benzaldehyde leads to longer reaction
time. This is because, for aldehyde containing electron-acceptor
groups, the carbon of the carbonyl group is more positive and nu-
cleophilic attack proceeds more easily and the reaction time
becomes shorter. The 2-carboxy group is an electron-acceptor
group and therefore its activity should be higher and the reactions
should occur in shorter times, but due to its steric effect the effi-
ciency of reaction increases.
À
Á
n
ðαhνÞ ¼ B hν ꢁ Eg
where hν is the photon energy, α is the absorption coefficient and B
is a constant value. The value of n is assigned to transitions, taking
different values for allowed and forbidden, direct and indirect transi-
n
tions. By plotting (αhν) versus hν in eV with n = 2 for direct
transitions, and then by obtaining the extrapolation point of this
curve (inset of Fig. 6), the band gap energy of the product is esti-
mated at about 2.2 eV.
These results reveal that the prepared nanocomposite can also
play a suitable role as a photocatalyst under light irradiation. In fact,
the presence of Fe O encapsulated in SBA-15 leads to a suitable
3
4
required energy for electron transfer from valence band to conduc-
tion band and, therefore, this synthesized photocatalyst can be
activated in the visible region.
Table 1. Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence
of Fe O /SBA-15
3 4
Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones in Presence of
3 4
Fe O /SBA-15 Nanocatalyst
To investigate the catalytic activity of the prepared Fe O /SBA-15
3
4
nanocatalyst in MCRs, a model experiment was carried out. First,
to optimize the reaction conditions, the reaction of 1 mmol of each
of isatoic anhydride, ammonium acetate and 3-nitrobenzaldehyde
was performed as a model reaction in the presence of various sol-
Entry
R
Product Time Yield
M.p. (°C)
Reported
a
(
h) (%)
Found
vents (H
The best results are obtained in refluxing EtOH. The results also con-
firm that the best amount of Fe /SBA-15 catalyst is 40
2
O, EtOH and CH
3
CN) and under solvent-free conditions.
[30]
1
2
3
4
5
6
7
8
9
C
6
H
5
4a
4b
4c
4d
4e
4f
3.5 75
2.5 78
217–220
198–200
198–200
201–203
192–193
228–230
270
218–220
190–192
198–200
203–205
192–193
225–227
—
[30]
[31]
[32]
[32]
[12]
3-NO
4-NO
2
C
C
6
H
H
4
3 4
O
2
6
4
3
3
75
75
ꢁ
1
mg mmol of the raw materials.
To compare Fe /SBA-15 catalytic activities, the model reaction
was also carried out in the presence of various solid, liquid and Lewis
acids, such as Amberlyst-21, HOAc and FeCl , respectively, and also
Fe and SiO alone. The best yield is obtained with Fe /SBA-15.
To illustrate the need for the presence of catalyst for these reactions,
an experiment was conducted in the absence of Fe /SBA-15.
The yield in this case is a trace amount after 5 h. As a result,
Fe /SBA-15 is an important component of the reaction.
Due to the success of the reaction described above, we investi-
gated the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives
a–j from MCRs of isatoic anhydride, ammonium acetate and vari-
ous aldehydes under the optimized reaction conditions. As evident
4-ClC
4-OCH
4-CH
2-COOHC
2-ClC
2,4-di-ClC
4-OHC
6 4
H
3 4
O
3
C
6
H
4
4.5 70
4 73
3
C
6
H
4
3
6
H
4
4g
4h
4i
1.5 65
3.5 75
2.5 70
O
4
2
3
O
4
[31]
[33]
[34]
3
6
H
4
205–208
164–165
205–208
203–205
165–167
210–212
6
H
3
3 4
O
10
6
H
4
4j
4
70
a
Isolated yields.
3 4
O
4
3 4
Figure 6. UV–visible DRS curves of SBA-15 and Fe O /SBA-15. The inset
shows a Tauc plot of Fe /SBA-15.
3
O
4
Scheme 2. Proposed mechanism for the formation of 4a–j.
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Appl. Organometal. Chem. 2015, 29, 809–814

Preparation and application of a magnetic composite nanocatalyst
adsorption method in a conventional volumetric technique with
a Micromeritics ASAP 2020 instrument. UV–visible DRS spectra
were obtained with a Shimadzu MPC-2200 spectrophotometer.
Melting points were measured using an Electrothermal 9100 ap-
paratus and are uncorrected. FT-IR spectra were recorded with
a Shimadzu FT-IR-8400S spectrometer using KBr pellets for sam-
1
ple preparation. H NMR spectra were recorded with a Bruker
DRX-250 Avance spectrometer at 250 MHz. Elemental analyses
were performed with an Elementar Analysen systeme GmbH
VarioEL.
All the products were identified by comparison of their spectro-
scopic and analytical data with those of authentic samples (please
see Table 1 and supporting information file).
3 4
Figure 7. Reusability of the Fe O /SBA-15 catalyst in the synthesis of 4b.
Preparation of mesoporous SBA-15
A possible mechanism for the formation of 4a–j in the presence
Mesoporous silica SBA-15 material was prepared using
tetraethyl orthosilicate (TEOS) as silica precursor and Pluronic
P123 (amphiphilic triblock copolymers, EO PO EO ) as tem-
of Fe O /SBA-15 is shown in Scheme 2. The reaction presumably
3
4
proceeds via the reaction of isatoic anhydride (1) and ammonium
acetate (2) to produce 2-aminobenzamide (5) by releasing a CO2
20
70
20
plate using the hydrothermal method according to protocols
molecule. Next, its active NH group could react with aldehyde 3
[26–29]
2
reported previously.
to form compound 6. Then, adduct 6 is cyclized by losing a water
molecule, and then an intramolecular nucleophilic attack of 7
affords compound 8. Finally, a 1,5-hydrogen shift yields the 2,3-
dihydroquinazolin-4(1H)-ones 4a–j.
The ability of the heterogeneous nanocatalyst was determined
by examining its reusability in the model reaction for the synthesis
of 2-(3-nitrophenyl)-2,3-dihydro-4(1H)-quinazolinone. After each re-
action, the catalyst was completely washed with ethanol and then
dried before being used in subsequent runs. The results show that
the catalyst can be reused for four consecutive runs without signif-
icant loss of its catalytic activity (Fig. 7).
In a typical procedure, 4.0 g of P123 was dissolved in 100 ml of
HCl (2.1 M) and the solution was stirred at 40°C for 4 h. After disso-
lution, 6.3 g of TEOS was slowly added to the solution and the
water–P123 mixture kept under static conditions at 40°C for 24 h.
Then, the resulting gel was put into a Teflon autoclave for hydro-
thermal treatment at 100°C for 48 h. After that, the obtained white
solid was filtered and washed with deionized water several times,
air-dried at room temperature and then the as-synthesized SBA-
15 was calcined at 550°C for 5 h to remove the surfactant template.
3 4
Preparation of Fe O /SBA-15 nanocomposite
Conclusions
First, 0.0017 mol of FeCl
3
ꢀ6H O (0.482 g) and 0.0008 mol of
2
FeCl ꢀ4H O (0.1774 g) were dissolved in 40 ml of deoxygenated
2
2
3 4
In summary, Fe O /SBA-15 as an efficient and eco-friendly hetero-
water and stirred for 2 h to make sure that the salts were
completely dissolved. Then, 0.5 g of SBA-15 was suspended into
the above sol solution. Aqueous ammonia solution was added into
the solution under ultrasonication and nitrogen atmosphere, until
the pH of the solution reached 9. The mixture was sonicated for
geneous composite nanocatalyst was prepared and characterized
using FT-IR spectroscopy, DRS, SEM, XRD, VSM and BET analyses.
Then, its catalytic activity was investigated in the one-pot multi-
component synthesis of 2,3-dihydroquinazolin-4(1H)-ones starting
from isatoic anhydride, ammonium acetate and various aldehydes
under mild reaction condition and easy work-up procedure in eth-
anol with good yields. The present nanocatalyst was recovered eas-
ily and reused without any significant loss of catalytic activity.
30 min and then left to stand overnight. Finally, the precipitates
were collected and washed several times with deionized water
and alcohol until the pH decreased to 7. The sample was then
heated under nitrogen atmosphere to 500°C with a heating rate
ꢁ
1
of 5°Cmin and maintained at 500°C for 1 h.
Experimental
General procedure for synthesis of 2,3-dihydroquinazolin-4
General
(1H)-ones 4a–g
All solvents, chemicals and reagents used in this work were of
analytical or synthetic grade and used without further purifica-
tion. XRD measurements were carried out using a JEOL X-ray
diffractometer with Cu Kα radiation. The low-angle XRD patterns
of mesoporous materials were obtained with a diffractometer
A mixture of 1 (1 mmol), 2 (1 mmol) and an aldehyde 3 (1 mmol) in
the presence of Fe O /SBA-15 nanocatalyst (0.04 g) in 5 ml of EtOH
3
4
was refluxed in a round-bottomed flask for the appropriate time as
indicated in Table 1. After completion of the reaction, as indicated
by TLC (ethyl acetate–n-hexane, 2:1), the catalyst was removed
easily by adsorbing onto the magnetic stirring bar when the stirring
was stopped. Then, the reaction solution was filtered off and the
residue was purified by washing further with water, and then crys-
tallized from EtOH to give pure crystalline products 4a–g. The
Fe O /SBA-15 nanocatalyst was then washed with EtOH, air-dried
3 4
and used directly several times in other fresh reactions without loss
of efficiency.
(PANalytical, model X’Pert Pro MPD) with monochromatized
Cu Kα radiation (λ = 1.54060 Å, 40.0 kV, 40.0 mA). Magnetic
properties of the samples were obtained using a vibrating sam-
ple magnetometer (Lakeshore). The particle morphologies of
the as-prepared powders were observed with a Tescan (model
Vega II) SEM instrument at 30 kV. Surface area and pore size
distribution were determined using the BET multilayer nitrogen
Appl. Organometal. Chem. 2015, 29, 809–814
Copyright © 2015 John Wiley & Sons, Ltd.
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A. Maleki et al.
[
[
17] V. L. Truong, M. Morrow, Tetrahedron Lett. 2010, 51, 758–760.
18] J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett.
Acknowledgment
The authors gratefully acknowledge the financial support from the
Iran National Science Foundation (INSF) and partial support from
the Research Council of the Iran University of Science and
Technology.
2008, 49, 3814–3818.
19] I. Mohammadpoor-Baltork, A. R. Khosropour, M. Moghadam,
S. Tangestaninejad, V. Mirkhani, S. Baghersad, A. Mirjafari, C. R. Chim.
[
2
011, 14, 944–952.
[
[
[
20] M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary,
A. A. Mohammadi, Tetrahedron Lett. 2005, 46, 6123–6126.
21] M. Baghbanzadeh, P. Salehi, M. Dabiri, G. Kozehgary, Synthesis 2006,
344–348.
References
22] Z.-H. Zhang, H.-Y. Lu, S.-H. Yang, J.-W. Gao, J. Comb. Chem. 2010, 12,
643–646.
[23] M. Wang, T. T. Zhang, Y. Liang, J. J. Gao, Chin. Chem. Lett. 2011, 22,
1423–1426.
[24] M. Wang, T. T. Zhang, Y. Liang, J. J. Gao, Monatsh. Chem. 2012, 143,
835–839.
[25] a) A. Maleki, Tetrahedron 2012, 68, 7827–7833; b) A. Maleki, Tetrahedron
Lett. 2013, 54, 2055–2059; c) A. Maleki, Helv. Chim. Acta 2014, 97,
587–593; d) A. Maleki, N. Ghamari, M. Kamalzare, RSC Adv. 2014, 4,
9416–9423; e) A. Maleki, M. Kamalzare, Catal. Commun. 2014, 53,
67–71; f) A. Maleki, RSC Adv. 2014, 4, 64169–64173; g) A. Maleki,
M. Aghaei, N. Ghamari, Chem. Lett. 2015, 44, 259–261; h) A. Maleki,
R. Paydar, RSC Adv. 2015, 5, 33177–33184.
[26] Y. J. Li, G. W. Zhou, W. T. Qiao, Y. Y. Wang, Mater. Sci. Eng. B 2009, 162,
120–126.
[27] A. Sayari, B. H. Han, Y. Yang, J. Am. Chem. Soc. 2004, 126, 14348–14349.
[28] K. Kosuge, T. Sato, N. Kikukawa, M. Takemori, Chem. Mater. 2004, 16,
899–905.
[29] Y. Xu, G. Zhou, C. Wu, T. Li, H. Song, Solid State Sci. 2011, 13, 867–874.
[30] P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth.
Commun. 2006, 36, 2287–2292.
[31] a) M. Wang, T. T. Zhang, Z. G. Song, Chin. Chem. Lett. 2011, 22, 427–430;
b) Y. Zong, Y. Zhao, W. Luo, X. H. Yu, J. K. Wang, Y. Pan, Chin. Chem. Lett.
2010, 21, 778–781.
[32] J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett.
2008, 49, 3814–3818.
[33] Z. Song, L. Liu, Y. Wang, X. Sun, Res. Chem. Intermed. 2012, 38, 1091–1099.
[34] M. Wang, J.-J. Gao, Z.-G. Song, L. Wang, Org. Prep. Proc. Int. 2012, 44,
159–163.
[
[
1] S. G. Kwon, T. Hyeon, Acc. Chem. Res. 2008, 41, 1696–1709.
2] B. Julian-Lopez, C. Boissiere, C. Chaneac, D. Grosso, S. Vasseur, S. Miraux,
E. Duguet, C. Sanchez, J. Mater. Chem. 2007, 17, 1563–1569.
[
[
3] Z. Lu, J. Dai, X. Song, G. Wang, W. Yang, Colloids Surf. A 2008, 317,
4
50–456.
4] a) S. Rostamizadeh, N. Shadjou, M. Azad, N. Jalali, Catal. Commun. 2012,
6, 218–224; b) R. Ghahremanzadeh, Z. Rashid, A. H. Zarnani, H. Naeimi,
2
Appl. Catal. A 2013, 467, 270–278; c) H. Aliyan, R. Fazaeli, R. Jalilian, Appl.
Surf. Sci. 2013, 276, 147–153.
[
[
[
[
5] A. M. Alafeefy, A. A. Kadi, O. A. Al-Deeb, K. E. H. El-Tahir, N. A. Al-Jaber,
Eur. J. Med. Chem. 2010, 45, 4947–4952.
6] J.-F. Liu, J. Lee, A. M. Dalton, G. Bi, L. Yu, C. M. Baldino, E. McElory,
M. Brown, Tetrahedron Lett. 2005, 46, 1241–1244.
7] D. Shi, L. Rong, J. Wang, Q. Zhuang, X. Wang, H. Hu, Tetrahedron Lett.
2
003, 44, 3199–3201.
8] a) J. X. Chen, H. Y. Wu, W. K. Su, Chin. Chem. Lett. 2007, 18, 536–538; b)
A. Maleki, S. Shahrokh, in Proceedings of the 1st International Electronic
Conference on Materials, Sciforum Electronic Conference Series, Vol. 1,
2
014, paper b010.
9] A. Shaabani, A. Maleki, H. Mofakham, Synth. Commun. 2008, 38,
751–3759.
[
3
[
[
[
[
[
10] L. H. Klemm, T. J. R. Weakley, R. D. Gilbertson, Y.-H. Song, J. Heterocycl.
Chem. 1998, 35, 1269–1273.
11] M.-J. Hour, L.-J. Huang, S.-C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi,
E. Hamel, K.-H. Lee, J. Med. Chem. 2000, 43, 4479–4487.
12] G. Cai, X. Xu, Z. Li, P. Lu, W. P. Weber, J. Heterocycl. Chem. 2002, 39,
1
271–1272.
13] R. J. Abdel-Jalil, W. Voelter, M. Saeed, Tetrahedron Lett. 2004, 45,
475–3476.
3
14] C. Balakumar, P. Lamba, D. Pran Kishore, B. Lakshmi Narayana,
K. Venkat Rao, K. Rajwinder, A. Raghuram Rao, B. Shireesha,
B. Narsaiah, Eur. J. Med. Chem. 2010, 45, 4904–4913.
Supporting information
[
[
15] T. Hisano, M. Ichikawa, A. Nakagawa, M. Tsuji, Chem. Pharm. Bull. 1975,
Additional supporting information may be found in the online ver-
sion of this article at the publisher’s web-site.
23, 1910–1916.
16] J. Chen, W. Su, H. Wu, M. Liu, C. Jin, Green Chem. 2007, 9, 972–975.
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