New, stable and reusable magnetic Fe3O4/PEG@CPTMS-thioaminophenol@Ni nanocatalyst for the synthesis of dispiro-cyclopropanes’s Meldrum’s acid

Article abstract of DOI:10.1007/s13738-019-01775-3

Magnetic Fe₃O₄/PEG@CPTMS-thioaminophenol@Ni nanocatalyst as a heterogeneous, stable and reusable nanocatalyst was formed. This nanocatalyst was characterized by FT-IR, XRD, TGA, ICP, SEM, EDS and VSM techniques and was used for six t

Full text of DOI:10.1007/s13738-019-01775-3

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-019-01775-3
ORIGINAL PAPER
New, stable and reusable magnetic Fe3O4/PEG@
CPTMS‑thioaminophenol@Ni nanocatalyst for the synthesis
of dispiro‑cyclopropanes’s Meldrum’s acid
Nader Noroozi Pesyan1 · Sepideh Bibak1 · Michael Aalinejad1
Received: 4 February 2019 / Accepted: 30 August 2019
© Iranian Chemical Society 2019
Abstract
Magnetic Fe3O4/PEG@CPTMS-thioaminophenol@Ni nanocatalyst as a heterogeneous, stable and reusable nanocatalyst
was formed. This nanocatalyst was characterized by FT-IR, XRD, TGA, ICP, SEM, EDS and VSM techniques and was used
for six times without decreasing activity. This nanocatalyst was used successfully for the synthesis of 3,3,10,10-tetramethyl-
13-aryl(alkyl)-2,4,9,11-tetraoxadispiro[5.0.57.16]tridecane-1,5,8,12-tetraones (dispiro-cyclopropane’s based on Meldrum’s
acid) by the reaction of various aldehydes and Meldrum’s acid in the presence of triethylamine and cyanogen bromide in
excellent yield.
Graphic abstract
R
CHO
O
O
O
O
PE
OH
N
HO
HO
PE
P E G
3
G
One-pot
Et
G
OH
4 PE
BrCN
Fe3O
G
PE
O
G
P E G
PE
OH
P E G
G
O
O
Si
Ni
100%
N
S
O
O
O
O
O
O
O
O
R
Keywords Fe3O4 · Dispiro-cyclopropane · Meldrum’s acid · 2-Amino thiophenol
Introduction
* Nader Noroozi Pesyan
Fe3O4/polyethylene glycol (PEG-400) as a core–shell mag-
n.noroozi@urmia.ac.ir; nnp403@gmail.com
netic nanoparticles was introduced as a greenly nanocatalyst
[1]. Hybrid inorganic–organic magnetized nanoparticles had
1
Department of Organic Chemistry, Faculty of Chemistry,
Urmia University, 57159 Urmia, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
constantly reading case reason to their biomedical utilization,
to protein separation [2], therapeutic transfer of DNA and
drugs [3], inhibition of their aggregation by building a clog
barrier among the prepared biocompatibility, renderer prob-
able for link aim region and avoid the reconnoiter [4]. PEG is
a biotic biocompatible polymer and is utilization as cover for
nanoparticles which is an egregious between the more proper
polymers because of its remarkable attribute for instance,
greatly hydrophilic nature (hydrophilicity), fexibility and
adaptability, safe and nonimmunogenicity [5]. PEG is sorption
to the superfcial of the micelle to form a compound micelle.
The absorption probably outcomes not just of the hydrophilic
sling of polymer moving toward the cations yet additionally
from the coat among the cations and the single-electron couple
from the O2 particle in PEG [6]. PEG sorption per absorbing
can draw out fow time in a blood circulation system. Indeed,
the modifcation magnetite nanoparticles by PEG is able to
sorption contrarily the protein sorption and in this manner
protection a strategic distance from their acknowledgment by
macrophage cells and yet encourage the nanoparticle take-up
to diagnosis malignancy cells in a tumor remedy [7, 8]. The
visualization from nanoparticles by PEG expands the particles
sparsity, biocompatible and material soundness [9].
dispiro-cyclopropanes based on Meldrum’s acid. The
reaction scheme of the magnetically nanocatalyst is
shown in Scheme 1.
Ni-complex supported on magnetic nanoparticle (MNP)
is totally characterized by FT-IR, TGA, VSM, ICP, XRD,
SEM and EDS analyses. The FT-IR spectrum of MNP was
recorded and is shown in Fig. 1 (curve a). According to the
information obtained from the IR and according to curve a,
the peak observed in the nearly 3500 and 571 cm−1 regions
is related to the vibrational stretching frequencies of OH and
Fe–O, respectively. In curve b, due to PEG coupling, the
intensity of the peaks of C–H and C–O stretching frequen-
cies are appeared at nearly 2900 and 1100 cm−1, respec-
tively. The C–H absorption bands of n-propyl linker are also
shown at 2922 cm−1. The Si–O absorption bands are also
observed at 1100, 1200, 1108 cm−1 and corresponded to
the symmetric and asymmetric stretching vibrations of the
mesoporous structure of Si–O. In curve c, the vibration band
at nearly 1450 and 1603 cm−1 corresponded to symmetric
and unsymmetric C=C stretching frequency and confrmed
the linking of 2-aminothiophenol. Apparently, a peak at
2400 cm−1 attributed to S–H stretching frequency in curves
c and d. The chemical analysis of SH group in catalyst indi-
cated that the 2-aminothiophenol is attached to the spacer by
the NH2 group. For these experiments, we used the sodium
plumbite solution for the indication of SH group.
Cyclopropane backbone is one of the most important
organic structures that can be found in natural product and
some organic compounds structures. The cyclopropane is an
essential structure in numerous natural compounds which
included antifungal, antibacterial, antiviral and some chemi-
cal restraint exercises [10–12]. Several routes were reported
for the synthesis of some full-substituted cyclopropanes in the
absence of catalyst [13–16]. Previously, according to one-pot
reaction of Meldrum’s acid, aldehydes and cyanogen bromide
(BrCN) in the presence of Et3N, cyclopropanes were prepared
[17]. Instead, in this reaction, the long reaction time, unsatis-
factory yields of products were insufcient of the reaction.
Meldrum’s acid is a heterocyclic compound and it has
organic and pharmaceutical properties. Likewise, it executes
as a wellspring of geminal dicarboxylic functional groups
which gets a great deal of consideration in the science and
pharmacology [18–22]. Owing to the importance of cyclo-
propanes and dispiro-cyclopropanes, initially, we presented
synthesis of MNP–Ni and characterized the nanocatalyst
structure. The MNP–Ni is used as an efcient heterogeneous
nanocatalyst for the synthesis of dispiro-cyclopropanes from
the one-pot reaction of Meldrum’s acid with various alde-
hydes and BrCN in the presence of Et3N in excellent yield.
Scanning electron microscopy (SEM) images of the
synthesized MNP–Ni are shown in Fig. 2. The size and
morphology of particles was thought out with SEM. These
nanoparticles had a middle size of where about 19–20 nm.
As well ready particles include of small particles with regu-
larly sphere morphology. This observation display that the
PEG surfactant can sorption adoptive on preferred shape
of crystal, which can interdict the loose growth of Fe3O4
nanoparticles.
To indicate the supporting Ni on ligand, energy-disper-
sive spectrum (EDS) analysis of Fe3O4/PEG@CPTMS-
2-aminothiophenol@Ni was carried out (Fig. 3). The results
indicate the presence of C, N, O, Si, S, Fe and Ni elements
in MNP and furthermore demonstrate the rate level of
each individually 14.08%, 4.54%, 26.98%, 6.46%, 19.65%,
27.94% and 0.34%, respectively. The amount of Ni is 1.18%
which was determined by inductively coupled plasma-opti-
cal emission spectrometry (ICP-OES).
Figure 4 shows the TGA curves for MNP–Ni accommo-
dating with TGA bends, the essential weight dwindles to
temperatures less 370 °C is because of the loss of water and
natural solvents such as EtOH and the second weight loss is
increasing the temperature from 370 to 600 °C is extensively
to the decomposition of covalently organic compound (Fig. 4).
The measurement of the magnetization curve of
Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni is pre-
sented in Fig. 5 and is gained from the vibration sample
Results and discussion
This article described the synthesis and characteri-
zation of new heterogeneous and recyclable nano-
catalyst (MNP–Ni) and its using to synthesis of
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Journal of the Iranian Chemical Society
Scheme 1 Synthesis of MNPs@2-aminothiophenol@Ni
Fig. 1 FT-IR spectra of Fe3O4
(a), Fe3O4/PEG@CPTMS (b),
Fe3O4/PEG@CPTMS-2-ami-
nothiophenol (c), Fe3O4/PEG@
CPTMS-2-aminothiophenol@
Ni (d)
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Journal of the Iranian Chemical Society
Fig. 3 EDS spectrum of Fe3O4/PEG@CPTMS-2-aminothiophenol@
Ni
Fig. 4 TGA analysis of Fe3O4/PEG@CPTMS-2-aminothiophenol@
Ni
magnetometer (VSM). It is determined that the severity
of the saturation magnetization (Ms) of Fe3O4/PEG@
Fig. 2 SEM images of Fe3O4 (a), Fe3O4/PEG@CPTMS-2-aminothio-
phenol@Ni (b, c)
CPTMS-2-aminothiophenol@Ni were 7.0 emu g−1
.
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Journal of the Iranian Chemical Society
Fig. 5 VSM curve of Fe3O4/
PEG@CPTMS-2-aminothio-
phenol@Ni
a cubic spinal structure. According to XRD pattern after
having properties of crystalline catalyst maintained and
treated with Fe3O4 courier region are in place [23, 24].
According the XRD pattern of Fe3O4/PEG@CPTMS-
2-aminothiophenol@Ni, all the peaks of Fe3O4 have been
observed. It should be noted that the peaks at 34°, 39.6°,
56.1°, 62.9° and 63.5° correspond to orthorhombic crystal
system of Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni
nanocatalyst (Fig. 6).
Synthesis of 3,3,10,10-tetramethyl-13-aryl(alkyl)-
2,4,9,11-tetraoxadispiro[5.0.57.16]tridecane-1,5,8,12-
tetraone compounds by catalytic amounts of Fe3O4/PEG@
CPTMS-2-aminothiophenol@Ni
We performed the cyclopropanation reaction in the
presence of new heterogeneous catalyst of Fe3O4/PEG@
CPTMS-2-aminothiophenol@Ni. We checked catalytic
activity as a new heterogeneous catalyst in the one-pot syn-
thesis of dispiro-cyclopropanes’s Meldrum’s acid. Optimiza-
tion of the catalyst for the synthesis of the desired cyclopro-
pane scafold in the attendance of various catalytic amount
of Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni is shown
in Table 1. The best results were gained in the presence of
Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni (0.03 mg),
EtOH (3 min) and/or MeOH (10 min) at 0 °C (Table 1,
entries 3 and 5, respectively). It should be noted that the use
of higher amounts of catalyst (0.07 mg) gained 80% product
(Table 1, entries 2 and 4, respectively). The maximum reac-
tion yield in the absence of catalyst was 60% (Table 1, entry
1). We concluded that the 0.03 mg of catalyst was the best
optimum condition. After successful synthesis of cyclopro-
pane scafold in the presence of catalyst with good perfor-
mance of various aldehydes in the reactions with Meldrum’s
acid, the results are reported in Table 2. Results indicated
Fig. 6 XRD patterns of Fe3O4 and Fe3O4/PEG@CPTMS-2-ami-
nothiophenol@Ni
Moreover, the magnetic particles have super paramag-
netism due to the zero forcible energy and since it is free
of hysteresis. One can conclude this kind of nanoparti-
cles is paramagnetism. The magnetization saturation (MS)
8000 estimated to be and copious magnetization pointer
the high-speed reaction the nanocatalysts in the magnetic
part.
According to the analysis of Fe3O4/PEG@CPTMS-
2-aminothiophenol@Ni and its comparison with the XRD
patterns of Fe3O4, the peaks at 30.2°, 35.5°, 40.1°, 57.3°,
and 62.9° were respectively equivalent to the (220), (311),
(400), (511), and (440) crystal planes of a pure Fe3O4 with
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Journal of the Iranian Chemical Society
Table 1 The efect of diferent parametersa on the synthesis of compounds 3
Entry
Cat. (mg)
Solvent
Base
Temp. (°C)
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
0
EtOH
EtOH
EtOH
MeOH
MeOH
EtOH
EtOH
EtOH
Et3N
Et3N
Et3N
Et3N
0
0
0
0
0
0
0
0
400
30
3
30
10
7
60
80
95
80
95
92
72
83
0.07
0.03
0.07
0.03
0.03
0.03
0.03
Et3N
NaOAc
DABCO
N-methylmorpholine
20
15
Bolded cases indicated the best condition
aThe molar ratio of aldehyde 1, Meldrum’s acid 2, BrCN, and Et3N were 1: 2: 1: 1, respectively
that the yields of aldehydes including electron-withdrawing
substituents were higher than that of electron-donating sub-
stituents (Table 2). Comparison of several methods for syn-
thesis of cyclopropane is shown in Table 3. For example, the
yield of 3a in the presence of catalyst was better than to the
absence of catalyst under the same reagents and condition.
The reaction mechanism of the cyanogen bromide (BrCN)
is shown in Scheme 2. In this reaction, the BrCN plays a major
role. The reaction of BrCN with Meldrum’s acid 2 formed
the salt of 4. Previously, the structure of 4 was characterized
(Scheme 2) [25, 27–29]. Similar to the synthesis of dispiro-
cyclopropanes 3 under catalyst-free condition [17], a proposed
reaction mechanism for the formation of 3 in the presence of
nanocatalyst is shown in Scheme 3. There are two possible
pathways for continuation of reaction via an intermediate A.
The product of C-attack was observed (path a). Owing to the
inductive efect of oxygen atom into ring, the O-attack cannot
occur and compounds 5 were not observed (Scheme 3) [17].
Recyclability of the catalyst
Renewable catalysts in commercial use are important after
completion, and the catalyst reaction is discretized by a
magnet and washed with Et2O and for six runs without the
decrease in activity used, as shown in Fig. 8. Ni percentage is
reused six runs specifed by (ICP-OES) Ni percentage before
using in reaction (1.18%) and after 6 runs (1%). According
to the SEM analysis, the particle size before the reaction was
19 nm, and after six times 32 nm was determined.
Experimental
Materials and instruments
All starting materials and solvents used in this work pur-
chased from Merck, Aldrich and Fluka Companies. FT-IR
spectra were done with KBr pellets utilizing a Nexus 670
FT-IR spectrometer (Urmia University, Urmia, IRAN).
Thin-layer chromatography (TLC) was used for the con-
trol of reaction progression was Al sheet-coated G/UV254
plates. The nanocatalyst morphology was investigated
by an examining SEM (Day Petronik Company, Tehran,
IRAN) using FESEM-TESCAN MIRA3. The 1H (300) and
13C NMR (75 MHz) spectra were recorded on BRUKER
NMR-Spectrometer (Urmia University, Urmia, IRAN). The
Hot fltration
To test the saturation of Ni in nanocatalyst for cyclopropana-
tion, we performed the product in this test, and in the middle
of this time, we isolated 45% of the catalyst from the reaction
mixture, resulting from the absence of any advance in the reac-
tion. The yield of reaction in this step was 45%, emphasizing
the leaching of Ni was insignifcant and is outlined in Fig. 7.
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Journal of the Iranian Chemical Society
Table 2 Synthesis of 3 with the reaction of various aldehydes (1) with Meldrum’s acid (2) in the presence of nanocatalyst
Entry
1
Product (3)
Time (min)
4
M.P. (°C)a, Lit.
Yield (%)b
90
216–218
217–218 [17]
a
b
c
2
3
5
5
217–219
88
90
216–218 [17]
212–213
212–214 [17]
4
5
5
2
205–207
92
95
204–205 [17]
d
191–192
192–194 [17]
e
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Journal of the Iranian Chemical Society
Table 2 (continued)
Entry
Product (3)
Time (min)
2
M.P. (°C)a, Lit.
Yield (%)b
96
6
202–204
202–203 [17]
f
7
8
3
3
197–199
94
91
198–199 [17]
g
205–206
204–205 [17]
h
9
4
192–194
80
192–193 [17]
i
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Journal of the Iranian Chemical Society
Table 2 (continued)
Entry
10
Product (3)
Time (min)
3
M.P. (°C)a, Lit.
Yield (%)b
95
177–179
178–180 [17]
j
11
3
179–180
93
178–179 [17]
k
12
13
5
5
177–178
89
91
178–180 [17]
l
127–129
126–128 [17]
m
aAll products are identifed by comparing their physical and spectral data with valid compounds
bYield refers to obtained product
thermogravimetric examination (TGA) bends are recorded
utilizing a Shimadzu DTG60 instrument (Day Petronik Com-
pany, Tehran, IRAN). The EDX (energy-dispersive X-ray) of
the MNPs were recorded using a FESEM-TESCAN MIRA3
(Day Petronik Company, Tehran, IRAN). The percentage
of Ni was measured by inductively coupled plasma-optical
emission spectrometry (ICP-OES) (Tarbiat Modares Univer-
sity, Tehran, IRAN). PEG with molecular weight 400 was
applied in whole reaction. Vibrating sample magnetometer
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Journal of the Iranian Chemical Society
Table 3 Comparison of several
methods for the synthesis of
cyclopropane
Entry
Cat. (mg)
–
Reagent and condition
Yield (%)
References
1
2
Dimedone, BrCN, Et3N
BrCN, Et3N, 0 °C
75
95
[25]
This work
Fe3O4/PEG@CPTMS-
2-aminothiophenol@Ni
3
4
5
–
Meldrum’s acid, BrCN, Et3N
70 °C, 3 h, PhF
BrCN, EtONa
60
94
80
[17]
[26]
[27]
Rh2(Opiv)4
–
nitrogen gas for 24 h under refux, then the sediment was
separated by magnet. It was dried at 67 °C for 6 h.
Preparation of Fe3O4@PEG‑2‑aminothiophenol
In a round-bottom fask, a mixture of MNPs@(CH2)3Cl
(1 g) with 2-aminothiophol (1 g) with Et3N (2 ml) in EtOH
(50 ml) was refuxed and the resulting cooking was separated
from the EtOH by magnet. For 12 h, it was dried at 70 °C.
Preparation of Fe3O4@PEG‑2‑aminothiophol–Ni
The precipitate from the previous step was mixed with the
solution of 20 ml of Ni (NO3)2·6H2O in ethanol and was
refuxed for 20 h and dried at a temperature of 60 °C. The
fnal MNPs–Ni catalyst was synthesized.
Scheme 2 Mechanism of the formation of salt 4 in the presence of
BrCN [17, 25, 27–29, 32]
General procedure for the preparation
of dispiro‑cyclopropane compounds (3)
(VSM)Lbkfb modeh-Meghnatis Daghigh Kavir company
(Azad University of Mahabad, Mahabad, IRAN, X-ray
Powder Difraction (XRD) was measured and accomplished
by a X’PertPro (University of Tabriz, Tabriz, IRAN). The
nomenclature of compounds 3 was done by means of Chem-
Draw Professional version 15.0.
In a 25-ml round-bottom fask equipped with stirrer, 0.05 g
(0.48 mmol) cyanogen bromide (BrCN) was dissolved in
5 ml methanol at 0 °C. Then, 0.288 g (0.96 mmol) Mel-
drum’s acid, 0.106 g (0.48 mmol) aldehyde were dissolved
in 10 ml methanol, added 0.04 g (0.63 mmol) triethylamine
and then, the amount of 0.0003 g of the catalyst Fe3O4@
PEG-2-aminothiophenol was added into a funnel. This
solution was then added dropwise into the BrCN solution
in round-bottom fask at 0 °C to room temperature (Atten-
tion!! The cyanogen bromide is toxic. Reactions should be
carried out in a well-ventilated hood). The reaction control
was monitored by TLC. After completion of the reaction,
the catalyst was separated by an outer magnet and washed
with few ml of methanol. After 5 min, the white precipitate
formed, fltered of, washed by fresh methanol and dried.
Preparation of nanoparticle Fe3O4@PEG (MNPs)
In this method, a Fe3O4 nanoparticle fusion was synthesized
using FeCl3·6H2O and FeCl2·4H2O [30]. The magnetic nano-
particles of Fe3O4 synthesized in combination with solvent
and PEG 400 (1.0 g) were mixed into ultrasonic apparatus
for 30 min, and then the mixture was added to the ultrasonic
apparatus for 1 h and then the magnetic product was sepa-
rated by a magnet and dried for 9 h at 87 °C [23, 31].
Preparation of MNPs@(CH2)3Cl
After formation of magnetic deposition (5.3 g), 3-chloro-
propyl trimethoxysilane (CPTMS) (5.0 g) to 90 ml n-hex-
ane was added and the reaction mixture was combined with
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Journal of the Iranian Chemical Society
Scheme 3 Proposed reaction mechanism for the formation of 3 in the presence of nanocatalyst
Fig. 8 Recycling of Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni
Fig. 7 Hot fltration of Fe3O4/PEG@CPTMS-2-aminothiophenol@Ni
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Journal of the Iranian Chemical Society
13. N. Noroozi Pesyan, M.A. Kimia, M. Jalilzadeh, E. Şhin, J. Chin.
Chem. Soc. 60, 35–44 (2013)
Conclusion
14. M.N. Elinson, A.N. Vereshchagin, N.O. Stepanov, T.A. Zai-
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In summary, we prepared magnetically nanoparticles Fe3O4
by core–shell method in excess PEG as the protective sig-
nifcant advantages of the nanocatalyst consist of the short
reaction time and high yields of products, recyclable catalyst
at minimum six times without decrease in catalyst activ-
ity. This nanocatalyst is an efcient heterogeneous catalyst
for the synthesis of dispiro-cyclopropanes from the one-pot
response of Meldrum’s acid with various aliphatic and aro-
matic aldehydes and BrCN in the presence of triethylamine.
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