Homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles (MSNs-HPZ-SO3H) as an efficient catalyst for one-pot synthesis of 1-amidoalkyl-2-naphthols

Article abstract of DOI:10.1039/c5nj02974k

Mesoporous silica nanoparticles are efficiently functionalized with homopiperazine sulfamic acid. The resulting MSNs-HPZ-SO₃H is employed as a nanocatalyst in one-pot synthesis of 1-amidoalkyl-2-naphthols, through three-component condensation r

Full text of DOI:10.1039/c5nj02974k

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Homopiperazine sulfamic acid functionalized
mesoporous silica nanoparticles (MSNs-HPZ-SO3H)
as an efficient catalyst for one-pot synthesis of
1-amidoalkyl-2-naphthols
Cite this:DOI: 10.1039/c5nj02974k
Zahra Nasresfahani, Mohammad Zaman Kassaee* and Esmaiel Eidi
Mesoporous silica nanoparticles are efficiently functionalized with homopiperazine sulfamic acid. The
resulting MSNs-HPZ-SO3H is employed as a nanocatalyst in one-pot synthesis of 1-amidoalkyl-2-naphthols,
through three-component condensation reaction of aromatic aldehydes, amides/urea and b-naphthol,
under thermal solvent-free conditions. Characterizations of the catalyst are carried out using XRD, SEM,
FT-IR, TGA-DTA and nitrogen adsorption–desorption analysis. This protocol is developed as a safe and
convenient alternative method for the synthesis of 1-amidoalkyl-2-naphthols utilizing an ecofriendly catalyst.
Received (in Montpellier, France)
24th October 2015,
Accepted 18th March 2016
DOI: 10.1039/c5nj02974k
www.rsc.org/njc
HClO4–SiO2,21 zwitterionic salts,22 and Brønsted acidic ionic
liquids.23 However, these procedures have their own drawbacks,
Introduction
Multicomponent reactions (MCRs) are very elegant and efficient such as high reaction temperature, prolonged reaction time, the
methods for accessing complex structures in a single synthetic use of toxic solvents or low yields. Therefore, it is still desirable
operation from the corresponding building blocks. The MCRs to seek novel catalysts that are recyclable and capable of
are often carried out in one-pot and designed to go through performing the reaction under mild conditions. On the other
easy procedures with high atom-economy and great selectivity. hand, recently mesoporous materials have received much attention,
This is mostly due to the generation of carbon–carbon and particularly those that are designed based on functionalized
carbon heteroatom bonds.1 One of these MCRs is the preparation mesoporous silicas because of their high surface area, tunable
of 1-amidoalkyl-2-naphthols. These compounds and their deri- nanoscale pores, ease of the grafting of organic scaffolds to
vatives which bear 1,3-amino oxygenated functional groups balance between the hydrophilic and hydrophobic character
have attracted intense attention. This is due to their ubiquitous of the porous architecture, exciting host–guest chemistry, and
role as essential building blocks for a variety of biologically supramolecular interaction to different extents with the reactant
important natural products, synthetic pharmaceuticals, and molecules.24,25 Organically functionalized mesoporous silicas
potent drugs, including a number of nucleoside antibiotics and have been extensively utilized for the last decade because of
HIV protease inhibitors.2 Also, these compounds can be converted their versatile applications in many frontier areas of science like
into important ‘drug-like’ materials by amide hydrolysis and gas storage,26 proton conduction,27 uranium sequestration,28
formation of aminoalkylnaphthols. The hypertensive and broad energy transfer,29 catalysis,30–32 Here in, we have developed a
cardiac effects of these substrates and their potential biological synthetic strategy for the design of a homopiperazinesulfamic
activities have been evaluated extensively. They include anti- acid functionalized mesoporous silica (MSNs-HPZ-SO3H) and
biotic,3 antitumor,4 analgesic,5 anticonvulsant,6 antipsychotic,7 its use as an efficient nanocatalyst for the one-pot synthesis
antimalarial,8 antihypertensive,9 and antirheumatic properties.10 of 1-amidoalkyl-2-naphthols via three-component reaction of
Various improved methods have been developed for the preparation b-naphthol, aldehydes, and amides/urea, under solvent-free
of 1-amidoalkyl-2-naphthols from aldehydes, b-naphthols, and conditions.
amides or urea, under thermal and sonication conditions. Reported
catalysts include p-TSA,11 montmorillonite K10,12 iodine,13
H4SiW12O40,14 dodecylphosphonic acid,15 cyanuric chloride,16
Results and discussion
Bi(NO3)3Á5H2O,17 ZrO(OTf)2,18 P2O5,19 thiamine hydrochloride,20
In order to reach at MSNs-HPZ-SO3H, we prepared mesoporous
silica nanoparticles (MSNs) via sol–gel method.33 Which it was
Department of Chemistry, Tarbiat Modares University, P.O. Box 14155-4838,
sequentially treated with 3-chloropropyltriethoxysilane (CPTMS)
to give 3-chloropropyl-functionalized (MSNs-Cl). Reaction of the
Tehran, Iran. E-mail: kassaeem@modares.ac.ir, drkassaee@yahoo.com;
Fax: +98-21-88006544; Tel: +98-912-1000392
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Scheme 1 Preparation of the nanocatalyst (MSNs-HPZ-SO3H).
latter with homopiperazine gave MSNs-HPZ. Finally, reaction
with chlorosulfonic acid (ClSO3H) produced novel nanocatalyst
(MSNs-HPZ-SO3H) (Scheme 1).
Characterization of the catalyst
The as-prepared catalyst is also characterized by Fourier transform
infrared spectroscopy (FT-IR), X-ray diffraction (XRD), Scanning
electron microscopy (SEM), thermogravimetric/differential thermal
analyses (TGA-DTA), nitrogen adsorption–desorption analysis.
Reflections in XRD pattern of pure MSNs are assigned to (100),
(110), and (200) planes in the highly ordered 2D hexagonal
arrangement. The values of d-spacing for these XRD peaks
appear at 40.01, 26.97 and 22.46 Å, respectively (Fig. 1a). For
MSNs-HPZ and MSNs-HPZ-SO3H only a reflection associated
with (100) peak are observed. The intensity of this reflection
after functionalizing with HPZ is lower than that of the original
MSNs. After loading of sulfonic chloride, the intensity of XRD
reflections on MSNs-HPA-SO3H is weakened further (Fig. 1b).
Fig. 2 FT-IR spectra of: (a) MSNs, (b) MSNs-Cl, (c) MSNs-HPZ, (d) MSNs-
HPZ-SO3H.
FT-IR spectra of MSNs, MSNs-Cl, MSNs-HPZ, and MSNs- However, these peaks cannot be resolved due to its overlap with
HPZ-SO3H are illustrated in Fig. 2. For the parent MSNs, asym- the absorbance of Si–O–Si stretch in the 960–1350 cmÀ1, broad
metric and symmetric Si–O–Si characteristic stretching vibrations peak around 2500–3600 cmÀ1 for MSNs-HPZ-SO3H is due
at 1086 cmÀ1 and 801 cmÀ1 along with Si–OH at 962 cmÀ1 and to acidic OH vibration signal of SO3H. Also, a new band at
bending Si–O–Si at 461 cmÀ1 are observed. The broad peak around approximately 580 cmÀ1 is due to the presence of a SO2 group in
3450 cmÀ1 is due to the surface silanols and adsorbed water MSNs-HPZ-SO3H (Fig. 2d).
molecules and the peak at 1635 cmÀ1 is assigned to the H–O–H
The morphology of the MSNs-HPZ-SO3H nanocatalyst is inves-
bending vibration of the free or absorbed water molecules. tigated by SEM as shown in (Fig. 3a). This micrograph illustrates
Stretching vibrations of anchored alkyl groups appear as weak that the nanoparticles have a semi-spherical morphology. The
C–H symmetric and asymmetric absorptions at 2930 and obtained histogram confirms that the size distribution is narrow
2960 cmÀ1, respectively. In addition, N–SO2, O–SO2 and SQO bonds with a 23 nm average value and a 17 nm standard deviation
stretching vibrations should be observed around 1000–1300 cmÀ1
.
(Fig. 3b).
Fig. 1 Small-angle XRD patterns of: (a) MSNs, (b) MSNs-HPZ, and MSNs-HPZ-SO3H.
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Fig. 3 SEM image (a), and particle size distribution (b) of the MSNs-HPZ-SO3H.
Fig. 4 TGA/DTA analyses for MSNs-HPZ-SO3H nanocatalyst.
Thermogravimetric/differential thermal analyses (TGA/DTA) nanoparticles. The weight loss between temperature ranges
are presented in Fig. 4. In the TGA curve the weight loss from of 200–670 1C in the TGA curve are mainly associated with
25–120 1C can be assigned to the release of physically adsorbed oxidative decomposition of organic and inorganic functional
water, solvent and organic groups on the external surface of groups.
Fig. 5 N2 adsorption/desorption isotherms: (a) MSNs, (b) MSNs-HPZ.
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Scheme 2 Synthesis of 1-amidoalkyl-2-naphthols.
N2 adsorption/desorption is a common method for charac- Table
2
Solvent effects on reaction of b-naphthol, acetamide and
benzaldehyde, in the presence of 10 mg of the catalyst
terization of mesoporous materials. It provide information
about the specific surface area, average pore diameter and pore
volume, etc. N2 adsorption/desorption isotherms of MSNs and
MSNs-HPZ are shown in Fig. 5. These isotherms exhibit type IV
curve, which are characteristic of uniform mesoporous materials.
The BET surface area, pore volume, and pore diameter of MSNs
Entry
Solventa
Temperature (1C)
Time (min)
Yieldb (%)
1
2
3
4
5
6
7
CH3CN
EtOH
CH2Cl2
DMF
Toluene
n-Hexane
Solvent free
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
120
240
240
240
240
240
240
60
53
75
70
60
30
50
94
are 783 m2
corresponding values for MSNs-HPZ are decreased to 313 m2 gÀ1
0.175 cm3 À1, and 2.2 nm, respectively. These observations
g g
À1, 0.767 cm3 À1, and 3.9 nm, respectively. The
,
g
a
b
2 ml solvent was used. Isolated yields.
indicate that the organic groups have successfully been anchored
at the surface of the mesopores.
and presence of solvents such as EtOH, CH3CN, CH2Cl2, DMF,
toluene, and n-hexane. Almost all the reactions were less efficient
in the presence of solvent than in its absence, considering the
reaction time and yield% (Table 2).
To determine the effect of temperature, condensation of
b-naphthol with acetamide and benzaldehyde was examined in
the presence of MSNs-HPZ-SO3H at different temperatures.
When the reaction temperature was varied from room temperature
to 120 1C, the product yield gradually increased, with the highest
yield being obtained at 120 1C (Fig. 6).
After optimizing the reaction conditions, three-component
condensation of various aldehydes and amides with b-naphthol
over MSNs-HPZ-SO3H was carried out. The results showed a
highly effective performance of the catalyst in the preparation
of 1-aminoalkyl-2-naphthols (Table 3). In all cases, aromatic
Catalytic activity of MSNs-HPZ-SO3H in synthesis of
1-amidoalkyl-2-naphthols
After characterization of MSNs-HPZ-SO3H, its role as a hetero-
geneous catalyst was evaluated in the exclusive synthesis of
1-amidoalkyl-2-naphthol derivatives (Scheme 2).
In order to optimize conditions for synthesis of 1-amidoalkyl-
2-naphthols, reaction of benzaldehyde with b-naphthol and
acetamide was selected as the model reaction. Effects of catalyst
amount, solvent, and temperature was probed. At first, the model
reaction studied with different amounts of catalyst (5, 10, 15,
20 mg) in various times under solvent-free conditions. The best
result was obtained when reaction reached 94% conversion
in 60 minutes with 10 mg catalyst. It is important to note that
in the absence of the catalyst, only trace product detected
(Table 1). To compare the effects of solutions to that of solvent-
free conditions, we carried out the reaction in the absence
Table 1 Effect of the catalyst amount on the reaction of b-naphthol with
acetamide and benzaldehyde at 120 1C
Entry
Catalyst (mg)
Time (min)
Yielda (%)
1
2
3
4
5
6
7
8
9
10
0
5
5
10
10
10
10
10
15
20
480
60
90
15
30
45
60
80
60
60
(Trace)
50
75
35
53
70
94
94
87
80
Fig. 6 Effect of temperature on the model reaction: (condensation of
b-naphthol, benzaldehyde, and acetamide over MSNs-HPZ-SO3H).
a
Isolated yields.
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Table 3 Synthesis of 1-aminoalkyl-2-naphthols in the presence of MSNs-
HPZ-SO3H under solvent-free conditions
aldehydes with substituent carrying either electron-donating or
electron-withdrawing groups gave the products in excellent
yields.
A plausible mechanism is proposed for the synthesis of
1-amidoalkyl-2-naphthols mediated over MSNs-HPZ-SO3H
Time Yielda M.p.
(min) (%) found (1C) reported (1C)
M.p.
Entry Ar
R
1
2
3
4
5
6
7
7
Ph
4-Cl–C6H4
2-Cl–C6H4
4-Me–C6H4 CH3 100
3-NO2–C6H4 CH3 100
4-OMe–C6H4 CH3 110
3-OMe–C6H4 CH3 120
3-OH–C6H4 CH3 105
4-OH–C6H4 CH3 90
Ph
4-Cl–C6H4
2-Cl–C6H4
3-NO2–C6H4 Ph
3-Br–C6H4
4-Me–C6H4 Ph
4-OH–C6H4 Ph 115
Ph NH2 90
3-OMe–C6H4 NH2 100
3-NO2–C6H4 NH2 80
CH3 60
CH3 90
CH3 80
94
92
95
85
93
82
85
90
92
84
91
93
89
86
85
90
82
86
90
80
238–242
229–230
205–207
210–212
239–240
182–184
204–206
225–228
240–242
235–237
180–182
283–285
230–231
228–231
212–215
221–223
176–178
166–169
186–189
171–172
242–244 [ref. 34]
226–228 [ref. 34] (Scheme 3). The reaction proceeded via the formation of an
206–207 [ref. 19]
212–213 [ref. 35]
241–242 [ref. 34]
181–183 [ref. 34] nanocatalyst (complex I) obtain complex (II). The removal of
203–205 [ref. 34]
227–229 [ref. 36]
238–240 [ref. 36]
238–240 [ref. 19] amides via a Michael addition (complex IV) afford the expected
179–181 [ref. 34]
284–285 [ref. 19]
232–234 [ref. 37]
230–232 [ref. 37]
213–215 [ref. 34]
220–223 [ref. 37]
175–177 [ref. 34]
167–169 [ref. 34]
188–190 [ref. 38]
170–172 [ref. 38]
intermediate ortho-quinonemethide (III). At first, nucleophilic
addition of b-naphthol to the activated aldehydes by the
water from complex (II) produces intermediate (III) as an ortho-
quinone methide. The reaction activated intermediate (III) with
8
10
11
12
13
14
15
16
17
18
19
20
Ph
95
Ph 100
amidoalkyl naphthols.
Ph
90
80
Reusability of MSNs-HPZ-SO3H nanocatalyst
Ph 105
90
Reusability of MSNs-HPZ-SO3H was investigated using model
reaction. The catalyst was recovered after each run, washed
thoroughly with ethanol, dried in an oven at 80 1C, for 4 h, and
tested in the subsequent run. The procedure was repeated, and
the results indicated that the catalyst could be recycled five
times with a slight loss of its catalyst activity (Fig. 7).
4-Cl–C6H4
NH2 105
a
Isolated yields.
Scheme 3 Plausible mechanism for the synthesis of 1-aminoalkyl-2-naphthols using MSNs-HPZ-SO3H.
Fig. 7 Reusability of MSNs-HPZ-SO3H nanocatalyst.
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Conclusions
General procedure for the preparation of (MSNs-HPZ)
A solution of 1 g (10 mmol) of homopiperazine, in dry toluene
and propyl amine, was added drop wise to a suspension of
0.5 g of the MSNs-Cl in toluene. The system was kept in reflux,
under nitrogen atmosphere and stirring, for 24 h. At the end,
the solid was filtered and washed in Soxhlet with 10 mL of
n-butyl amine, then with 12 mL of diethyl ether and a dichloro-
methane solution. This procedure help to eliminate HCl, which
otherwise would remain on the catalyst surface, and would
deactivate it. After this treatment, MSNs-HPZ was dried under
vacuum.
MSNs-HPZ-SO3H was fabricated and fully characterized, then
used as a new nanocatalyst in an efficient, one-pot preparation
of 1-aminoalkyl-2-naphthols derivatives, from the three-component
condensation reaction of various aromatic aldehydes, b-naphthol,
and amide/urea, under thermal solvent-free conditions. The one-
pot nature and the use of a heterogeneous solid acid material as
the eco-friendly nanocatalyst make this protocol an interesting
alternative to multi-step approaches. It offers several promising
advantages such as high yield, easy handling, good reaction time,
reusability of the nanocatalyst and compliance with the green
chemistry. These advantages, in general, highlight this protocol
as a useful and attractive methodology among of the methods
reported in the literature, for the rapid synthesis of biologically
active 1-amidoalkyl-2-naphthols.
General procedure for the preparation of (MSNs-HPZ-SO3H)
Finally for synthesis of MSNs-HPZ-SO3H, to a solution of MSNs-
HPZ (0.5 g) in n-hexane (2 mL), Et3N (0. 1 mL) was added. The
mixture was stirred for 5 min. Then, chlorosulfonic acid
(0.1 mL) was added. The mixture was stirred for next 3 h for
completing the reaction. Afterwards, the residue was filtered
and washed with toluene, ethanol, water, and dried under
vacuum.
Experimental
Materials and methods
Chemical reagents in high purity were purchased from Merck
and Aldrich and used without further purification. Melting
points were determined in open capillaries using an Electro-
thermal 9100 apparatus and are uncorrected. Fourier transform
infrared (FT-IR) spectra were recorded using KBr pellets in the
range 400–4000 cmÀ1 on a Nicolet IR-100 infrared spectro-
meter. The NMR spectra were recorded on a Brucker DRX
500-Avance spectrometer operating at 500 MHz for 1H NMR
in DMSO-d6 with TMS as an internal standard. X-ray diffraction
(XRD) was performed on Philips XPert 1710 diffractometer. The
latter appeared with Co Ka (a = 1.79285 Å) voltage: 40 kV.
Thermogravimetric/differential thermal analyses (TGA/DTA)
were done on a thermal analyzer with a heating rate of 10 1C
minÀ1 over a temperature range of 25–800 1C. The particle
morphology was examined by scanning electron microscopy
using SEM (HITACHI S-4160), on gold coated samples.
Acidity of MSNs-HPZ-SO3H
Titrations were utilized to determine the acid loading of the
catalysts. At first, 100 mg of MSNs-HPZ-SO3H was dispersed in
20 ml H2O by sonicating for 40 min at room temperature after
which the pH of solution was acidic, two drops of phenolphthalein
indicator solution was added. The acidic solution was titrated to
neutrality using 0.1 M NaOH solution to determine the loading of
acid sites on the MSNs-HPZ-SO3H catalyst. The results revealed
that the samples of MSNs-HPZ-SO3H possessed 2.1 mmol H+ gÀ1
.
This process was repeated for recovered catalyst after reaction, the
results showed no substantial change in amount of acid loading of
catalyst. Hence, no leaching of the acid occurred during the course
of the reaction.
General procedure for the preparation of substituted 1-
amidoalkyl-2-naphthols
General procedure for the preparation of (MSNs)
MSNs was synthesized according to the sol–gel method.33
Specifically, 0.5 g of CTAB and 0.14 g of NaOH were mixed in
240 mL deionized water. The solution was stirred vigorously at
80 1C for 2 h, then 2.5 mL of tetraethyl orthosilicate (TEOS) was
added, and the reaction was continued for another 2 h. The
as-prepared product (MSNs-CTAB) was washed 3 times with
ethanol and re-dispersed in 200 mL of ethanol containing 2 g of
NH4NO3, at 80 1C. The remaining mixture was refluxed for 6 h.
In this process the CTAB template was removed. The resulting
precipitate was collected by centrifugation and washed with
ethanol repeatedly. Finally, it was dried under vacuum to give
MSNs as a white powder.
A mixture of aldehyde (1 mmol), b-naphthol (1 mmol), amide/
urea (1.2 mmol), and the catalyst (10 mg) were stirred at 120 1C,
in an oil bath for the appropriate time. After completion of the
reaction (monitored by TLC), the mixture was cooled to room
temperature, the resulting solidified blend was diluted with hot
ethanol and stirred for 5 min. The catalyst was filtered off,
and the solution was concentrated under reduced pressure, to
obtain the product which was recrystallized from ethanol.
Products were characterized by spectral data and comparison
of their physical data with the literature. Spectral data for
N-[(3-methoxy phenyl)-(2-hydroxy-napthalen-1-yl)-methyl]-acetamide
(Table 3, entry 7).
FT-IR (KBr, cmÀ1): 3372, 3178, 3062, 1643, 1582, 1514, 1437,
General procedure for the preparation of (MSNs-Cl)
1364, 1305, 1282, 1232, 1153, 1057, 989, 943, 863, 815, 748, 687,
1
MSNs-Cl was prepared by refluxing 0.5 g of MSNs with 0.5 g of 614, 573; H NMR (500 MHz, DMSO-d6): d (ppm) 1.97 (s, 3H,
3-chloropropyltrimethoxysilane (CPTMS) in toluene, under a CH3), 3.65 (s, 3H, OCH3), 6.69–6.7 (m, 3H, ArH), 7.08–7.26
nitrogen atmosphere, for 24 h. The resulting solid was filtered (m, 4H, ArH), 7.35 (t, 1H, ArH), 7.74–7.82 (m, 3H, ArH and
and washed with toluene, then dried under vacuum.
CH), 8.44 (d, J = 10 Hz, 1H, NH), 9.99 (s, 1H, ArOH).
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18 H. Hashemi and A. R. Sardarian, J. Iran. Chem. Soc., 2013,
10, 745–750.
19 G. C. Nandi, S. Samai, R. Kumar and M. Singh, Tetrahedron
Lett., 2009, 50, 7220–7222.
20 M. Lei, L. Ma and L. Hu, Tetrahedron Lett., 2009, 50,
6393–6397.
21 H. R. Shaterian, H. Yarahmadi and M. Ghashang, Tetrahedron,
2008, 64, 1263–1269.
References
1 (a) A. Domling and I. Ugi, Angew. Chem., Int. Ed., 2000, 39,
3168–3210; (b) H. R. Hobbs and N. R. Thomas, Chem. Rev.,
2007, 107, 2786–2820; (c) A. Domling, Chem. Rev., 2006, 106,
17–89; (d) D. Tejedor and F. Garcia-Tellado, Chem. Soc. Rev.,
2007, 36, 484–491; (e) G. Shanthi and P. T. Perumal, Tetra-
hedron Lett., 2009, 50, 3959–3962.
2 S. Knapp, Chem. Rev., 1995, 95, 1859–1876.
3 Y. Kusakabe, J. Nagatsu, M. Shibuya, O. Kawaguchi, C. Hirose
and S. Shirato, J. Antibiot., 1972, 2, 44–47.
4 S. Remillard, L. I. Rebhun, G. A. Howie and S. M. Kupchan,
Science, 1975, 189, 1002–1005.
5 G. Y. Lesher and A. R. Surrey, J. Am. Chem. Soc., 1955, 77,
636–641.
6 H. S. Mosher, M. B. Frankel and M. Gregory, J. Am. Chem.
Soc., 1953, 75, 5326–5328.
7 J. L. Peglion, J. Vian, B. Gourment, N. Despaux, V. Audinot
and M. Millan, Bioorg. Med. Chem. Lett., 1997, 7, 881–886.
8 H. Ren, S. Grady, D. Gamenara, H. Heinzen, P. Moyna,
S. Croft, H. Kendrick, V. Yardley and G. Moyna, Bioorg. Med.
Chem. Lett., 2001, 11, 1851–1854.
9 R. D. Clark, J. M. Caroon, A. F. Kluge, D. B. Repke, A. P.
Roszkowski, A. M. Strosberg, S. Baker, S. M. Bitter and
M. D. Okada, J. Med. Chem., 1983, 26, 657–661.
10 H. Matsuoka, N. Ohi, M. Mihara, H. Suzuki, K. Miyamoto,
N. Maruyama, K. Tsuji, N. Kato, T. Akimoto, Y. Takeda,
K. Yano and T. Kuroki, J. Med. Chem., 1997, 40, 105–111.
11 M. M. Khodaei, A. R. Khosropour and H. Moghanian,
Synlett, 2006, 916–920.
22 D. Kundu, A. Majee and A. Hajra, Catal. Commun., 2010, 11,
1157–1159.
23 A. R. Hajipour, Y. Ghayeb, N. Sheikhan and A. E. Ruoho,
Tetrahedron Lett., 2009, 50, 5649–5651.
24 B. M. Pereza, J. Roeserb, A. Thomasb and P. Hesemanna,
Appl. Organomet. Chem., 2013, 27, 290–299.
25 E. Merino, E. V. Sesto, E. M. Maya, M. Iglesias, F. Sanchez
and A. Corma, Chem. Mater., 2013, 25, 981–988.
26 A. Comotti, S. Bracco, P. Valsesia, L. Ferretti and P. Sozzani,
J. Am. Chem. Soc., 2007, 129, 8566–8576.
27 M. Sharifi, C. Kohler, P. Tolle, T. Frauenheim and M. Wark,
Small, 2011, 7, 1086–1097.
28 P. J. Lebed, J. D. Savoie, J. Florek, F. Bilodeau, D. Lariviere
and F. Kleitz, Chem. Mater., 2012, 24, 4166–4176.
29 N. Mizoshita, K. I. Yamanaka, S. Hiroto, H. Shinokubo,
T. Tani and S. Inagaki, Langmuir, 2012, 28, 3987–3994.
30 N. A. Brunelli, K. Venkatasubbaiah and C. W. Jones, Chem.
Mater., 2012, 24, 2433–2442.
31 K. Liu, R. Jin, T. Cheng, X. Xu, F. Gao, G. Liu and H. Li,
Chem. – Eur. J., 2012, 18, 15546–15553.
32 M. Sasidharan and A. Bhaumik, ACS Appl. Mater. Interfaces,
2013, 5, 2618–2625.
12 S. Kantevari, S. V. Vuppalapati and L. Nagarapu, Catal.
Commun., 2007, 8, 1857–1862.
33 I. I. Slowing, B. G. Trewyn and V. S. Y. Lin, J. Am. Chem. Soc.,
2007, 129, 8845–8849.
13 B. Das, K. Laxminarayana, B. Ravikanth and B. R. Rao,
J. Mol. Catal. A: Chem., 2007, 261, 180–183.
34 Q. Zhang and J. Luo andY. Wei, Green Chem., 2010, 12,
2246–2254.
14 A. R. Supal and G. S. Gokavi, J. Chem. Sci., 2010, 122,
189–192.
15 M. Zandi and A. R. Sardarian, C. R. Chim., 2012, 15,
365–369.
35 H. Moghanian, A. Mobinikhaledi, A. G. Blackmanc and
E. Sarough-Farahanib, RSC Adv., 2014, 4, 28176–28185.
36 A. Ghorbani-Choghamarani and S. Rashidimoghadam,
Chin. J. Catal., 2014, 35, 1024–1029.
16 G. H. Mahdavinia and M. A. Bigdeli, Chin. Chem. Lett., 2009,
20, 383–386.
37 R. Tayebee, M. Amini, M. Akbari and A. Aliakbari, Dalton
Trans., 2015, 44, 9596–9609.
17 M. Wang, Y. Liang, T. T. Zhang and J. J. Gao, Chin. Chem.
Lett., 2012, 23, 65–68.
38 M. Esmaeilpour, J. Javidi and M. Zandi, Mater. Res. Bull.,
2014, 55, 78–87.
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