Isatin-SO3H coated on amino propyl modified magnetic nanoparticles (Fe3O4@APTES@isatin-SO3H) as a recyclable magnetic nanoparticle for the simple and rapid synthesis of pyrano[2,3-d] pyrimidines derivatives

Article abstract of DOI:10.1002/aoc.4602

Isatin-SO₃H coated on amino propyl modified magnetic nanoparticles (Fe₃O₄@APTES@isatin-SO₃H) is found to be a novel, efficient, and reusable magnetic nanocatalyst, and characterized by FT-IR, SEM, TEM, XRD, EDX,

Full text of DOI:10.1002/aoc.4602

Received: 22 June 2018
DOI: 10.1002/aoc.4602
Revised: 20 August 2018
Accepted: 22 August 2018
F U L L P A P E R
Isatin‐SO3H coated on amino propyl modified magnetic
nanoparticles (Fe3O4@APTES@isatin‐SO3H) as a recyclable
magnetic nanoparticle for the simple and rapid synthesis of
pyrano[2,3‐d] pyrimidines derivatives
Sami Sajjadifar
| Zohreh Gheisarzadeh
Department of Chemistry, Payame Noor
University, POBOX 19395‐4697, Iran,
Tehran
Isatin‐SO3H coated on amino propyl modified magnetic nanoparticles
(Fe3O4@APTES@isatin‐SO3H) is found to be a novel, efficient, and reusable
magnetic nanocatalyst, and characterized by FT‐IR, SEM, TEM, XRD, EDX,
VSM, and TGA analysis. The magnetic nanocatalyst demonstrated outstanding
performance in synthesis of pyrano[2,3‐d] pyrimidines derivatives via one‐pot
three‐component reaction of various aromatic aldehydes 1, malononitrile 2,
and barbituric acid 3 under reflux conditions in mixture of H2O:EtOH (1:1)
as solvent. Easy workup procedure, short reaction time, high yield, simple
preparation and easy recovery of the catalyst, mild reaction conditions are
some advantages of this work.
Correspondence
Sami Sajjadifar, Department of Chemistry,
Payame Noor University, PO BOX 19395‐
4697, Iran, Tehran.
Email: sami.sajjadifar@yahoo.com
KEYWORDS
Fe3O4@APTES@isatin‐SO3H, magnetic nano catalyst, Multicomponent reaction (MCR), Pyrano[2,3‐
d] pyrimidines
1 | INTRODUCTION
combinatorial chemistry, diversity oriented synthesis
(DOS) and simple reaction design.[16] Moreover,
Magnetic nanoparticles (MNPs) can be regarded as an
attractive field in various biological, medical, and
industrial application, such as solar water,[1] solar cells,[2]
semiconductors,[3] data storage,[4] magnetic fluids,[5] mag-
neto‐thermal therapy,[6,7] magnetic resonance imaging,[8]
biomolecular sensors,[9,10] and drug delivery.[11,12] One of
the most applicable capabilities of nanoparticles in the
organic chemistry is the catalyst role with a high surface
to volume ratios and their surface atoms which are very
active and selective.[13] These nanocatalysts can play two
different roles as the sites of catalysis and supports for
catalytic processes.[14] Nowadays, nanomagnetic core shell
catalysts are excellent supports for various catalysts.[15]
It should be mentioned that much attention have
been paid to multicomponent reactions (MCRs) in
various research fields, such as medicinal chemistry,
employing of one‐pot multicomponent reactions by a
recoverable nanomagnetic core shell catalyst can be
considered as a branch of the green chemistry domain.
In this sense, pyrano[2,3‐d] pyrimidines and their
derivatives can be regarded as important compounds in
the field of drugs and pharmaceutical due to their useful
characteristics as anti‐coagulant, diuretic, spasmolytic,
anti‐cancer and anti‐anaphylactic.[17] In recent years,
the synthesis of pyrano[2,3‐d] pyrimidines derivatives
has been reported in the presence of various catalyst,
such as SBA‐Pr‐SO3H,[18] succinimidinium N‐sulfonic
acid hydrogen sulfate,[19] tetrabutylammonium bromide
(TBAB),16b Al‐HMS‐20,16c triethyamine,16d choline
chloride. ZnCl2,[20] diammonium hydrogen phosphate
(DAHP),[21] γ‐Fe2O3@HAp‐Ni2+ [22]
,
[BMIm]BF4,[23]
Zn[(L)proline]2,[24] microwave conditions,[25] DABCO,16b
Appl Organometal Chem. 2018;e4602.
wileyonlinelibrary.com/journal/aoc
© 2018 John Wiley & Sons, Ltd.
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SAJJADIFAR AND GHEISARZADEH
[KAl (SO4)2],[26] and ultrasonic irradiation.[27] However, a
lot of these methods suffer from one or more following
disadvantages: need to high temperatures, usage of toxic
catalysts and solvent, waste creation, long reaction time,
harsh reaction conditions, low yields of products, and for-
mation of side product. Hence, a crucial need to develop-
ment a novel catalyst to the synthesis of pyrano[2,3‐d]
pyrimidines and environmentally friendly procedures
indicating a strong demand for this research.
In continuation of our previously research interest
related to the maturation of the design, construction,
applications and knowledge‐based development of solid
acids,[28] herein we report a simple, rapid, and new proce-
dure for the synthesis of pyrano[2,3‐d] pyrimidines deriv-
atives catalyzed with Isatin‐SO3H coated on amino propyl
modified magnetic nanoparticles Fe3O4@APTES@isatin‐
SO3H as a magnetic nanoparticle (Scheme 1).
2.2 | General procedure for the
preparation of Fe3O4@APTES@isatin‐SO3H
In the first step, magnetite phase Fe3O4 was prepared
according to the literature procedure.[29] In the second
step, Fe3O4 (3 g) was dispersed in 40 ml ethanol and
30 min was sonicated. Then, 3‐aminopropyltrietho-
xysilane (5 ml, 21.36 mmol) was added to the suspended
solid nanoparticles under mechanical stirring, and the
reaction mixture were refluxed under nitrogen for
8 hr.[30] Amino propyl modified magnetic nanoparticles
(Fe3O4@APTES) was filtered, washed twice with EtOH
and dried in vacuum at 50 °C. In the third step, Isatin
(10 mmol, 1.76 g) in 50 ml of ethanol was added to the
Fe3O4@APTES (3 g) and the mixture was refluxed for
8 hr at 80 °C. The resulting solid was filtered, washed
and dried in a same procedure to create the nano‐
Fe3O4@APTES@isatin. In the fourth step, chloro sulfuric
acid (1.16 ml, 10 mmol) was added drop wise to a mixture
of nano‐Fe3O4@APTES@isatin in dry dichloromethane
(10 ml) and the reaction mixture was stirred for 6 hr.
Finally, the nano‐Fe3O4@APTES@isatin‐SO3H as a brown
solid was obtained after filtering, washing and drying
(Scheme 2).
2 | EXPERIMENTAL
2.1 | General
All chemicals were purchased from Merck or Fluka
Chemical Companies. All known compounds were iden-
tified by comparison of their melting points and spectral
data with those reported in the literature. Progress of
the reactions was monitored by thin layer chromatogra-
phy (TLC) using silica gel SIL G/UV 254 plates. Melting
Points were taken on an Electrothermal capillary melting
2.3 | General Procedure for the synthesis
of pyrano[2,3‐d] pyrimidinone derivatives
4a‐r
A mixture of aldehydes (1 mmol), malononitrile (1 mmol),
barbituric acid (1 mmol) and nano‐Fe3O4@APTES@isatin‐
SO3H MNPs (20 mg) in mixture of EtOH:H2O (1:1) (5 ml)
was stirred at reflux conditions for appropriate time
(Table 3). After the reaction completion, monitored by
1
point apparatus and are uncorrected. H and 13C NMR
spectra were recorded using a Bruker instrument (1H at
400 MHz and 13C at 100 MHz) in CDCl3 or DMSO‐d6 sol-
vent with tetramethylsilane (TMS) as internal standard.
SCHEME 1 The reaction of aldehydes,
malononitrile with barbituric acid
catalyzed nano‐Fe3O4@APTES@isatin‐
SO3H

SAJJADIFAR AND GHEISARZADEH
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SCHEME 2 The preparation of nano‐Fe3O4@APTES@isatin@SO3H MNPs
TLC, the reaction mixture was allowed to cool, the catalyst
The FT‐IR spectra of nano‐Fe3O4@APTES‐
was separated by magnetic field, hot ethanol was added,
the solvent was evaporated and, finally, the residue was
dried. Then, the solid residue was recrystallized in hot
ethanol to afford pure crystals of pyrano[2,3‐d]
pyrimidinone derivatives with excellent yields (86–95%). 7‐
amino‐5‐(4‐fluorophenyl)‐2,4‐dioxo‐1,3,4,5‐tetrahydro‐2H‐
pyrano[2,3‐d]pyrimidine‐6‐carbonitrile (Table 3, entry 17):
1HNMR (DMSO‐d6, 400 MHz): δ 4.22 (s, 1H), 7.11 (s, 2H),
7.22 (d, 2H), 7.39 (d, 2H), 11.04 (s, 1H), 12.05 (s, 1H). 13C
NMR (DMSO‐d6, 100 MHz): δ 36.62, 60.36, 89.96, 120.75,
130.89, 133.88,141.92,151.16, 153.88, 159.19,161.73,164.45.
isatin@SO3H MNPs is exhibited in Figure 1. As depicted
in Figure 1, in nano‐Fe3O4@APTES‐isatin@SO3H MNPs,
the adsorption peak at 579 cm−1 can be assigned to
the Fe‐O in Fe3O4 MNPs. Furthermore, the adsorption
peak at 2886 cm−1 is related to the stretching vibration
of C‐H groups in nano‐Fe3O4@APTES. In nano‐
Fe3O4@APTES@isatin, the absorption peaks at 1482, 1507,
and 1618 cm−1 were assigned to the C═C, C═N, and C═O
stretching vibrations, respectively. After the aciditation pro-
cess by chlorosulfonic acid, the adsorption peak at 3365
and 3595 cm−1 are related to OH and NH bond of the
stretching vibration in nano‐Fe3O4@APTES‐isatin@SO3H
MNP. Moreover, the absorption peaks at 1011–1071 cm−1
is related to the O═S═O asymmetric and symmetric
stretching modes, and the absorption peaks at 1174 cm−1
can be assigned to the S‐O stretching vibrations.
3 | RESULTS AND DISCUSSION
3.1 | Catalyst characterization results
To get additional insight into the shapes and particle
Based on our experience in the design, synthesis and appli-
cation of nanostructured catalysts in the past, the recyclable
magnetic nanoparticle (nano‐Fe3O4@APTES@isatin‐SO3H
MNPs) was prepared by the route illustrated in Scheme 2.
In the first step, we prepared magnetic nanoparticles
(Fe3O4) according to the procedure in the literature.[29]
In the second step, then Fe3O4 was coated with
aminopropyltriethoxysilane and give Fe3O4@APTES.[30]
In the third step, Fe3O4@APTES was allowed to react
with Isatin under reflux conditions for 8 hr at 80 °C, and
give nano‐ Fe3O4@APTES‐isatin. Finally, the nano‐
Fe3O4@APTES@isatin which was aciditation using chloro
sulfuric acid gave nano‐Fe3O4@APTES@isatin‐SO3H
MNPs. The prepared magnetic nanocatalyst is characterized
by various techniques, such as FT‐IR, SEM, TEM, XRD,
EDX, VSM, and TGA analysis.
sizes and morphology of the nano‐Fe3O4@APTES@isatin‐
FIGURE 1 FT‐IR spectra of nano‐Fe3O4@APTES@isatin‐SO3H

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SAJJADIFAR AND GHEISARZADEH
SO3H MNPs, scanning electron microscopy (SEM) and
transmission electron microscopy were (TEM) used
(Figure 2). As depicted in Figure 2, particles have nearly
spherical shape with sizes of about 16 nm.
The structure of the nano‐Fe3O4@APTES@isatin‐SO3H
MNPs was depicted by x‐ray diffraction patterns technique.
The XRD pattern of the nano‐Fe3O4@APTES@isatin‐SO3H
MNPs was considered in a range of 20–80° (Figure 3). As
FIGURE 3 XRD patterns of nano‐Fe3O4@APTES@isatin‐SO3H
FIGURE
4
Vibrating sample magnetometry curves nano‐
Fe3O4@APTES@isatin‐SO3H
FIGURE
2
(a) Scanning electron microscopy (SEM), (b)
Transmission electron microscopy (TEM) of nano‐
Fe3O4@APTES@isatin‐SO3H MNPs
FIGURE 5 TGA spectrum of nano‐Fe3O4@APTES@isatin‐SO3H

SAJJADIFAR AND GHEISARZADEH
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The thermo gravimetric analysis of nano‐
Fe3O4@APTES@isatin@SO3H shows the mass loss of
organic materials as they decompose upon heating
(Figure 5). As can be seen in Figure 5, an initial weight
loss near to 90 °C (1–1.5%) which can be due to the
weight losing of water trapped on the surface of them.
The weight loss about in 4% about 156–300 °C is related
to the thermal decomposition of Isatin on the surface of
Fe3O4@APTES@isatin. Furthermore, there is a weight
loss of the nano‐Fe3O4@APTES@isatin‐SO3H about 9%
at 300–500 °C, which is attributed to the thermal decom-
position of the MNPs catalyst.
The EDX spectrum of nano‐Fe3O4@APTES@isatin‐
SO3H is exhibited in Figure 6 in which the synthesized
MNP catalyst contains only carbon (C), nitrogen (N), oxy-
gen (O), silicon (Si), sulfur (S), and iron (Fe) elements.
Therefore, the EDX spectrum does not possess extra‐
peaks addition of catalyst meaning that the MNP catalyst
is pure and composed only of C (7.08), N (1.27), Fe
(24.23), O (53.04), Si (1.69), and S (12.69).
FIGURE 6 EDX spectrum of nano‐Fe3O4@APTES@isatin‐SO3H
depicted in Figure 3, the XRD patterns of the synthesized
particles show nine characteristic peaks at (2θ = 30.5°,
34.7°, 25.1°, 43.1°, 53.6°, 57.8°, 62.5°, and 74.6°. The sample
show very broad peaks indicating the ultra‐fine nature and
small crystallite size of the particles.
The
magnetic
properties
of
the
nano‐
3.2 | Application of nano‐
Fe3O4@APTES@isatin‐SO3H was depicted by vibrating
sample magnetometric technique at room temperature.
The magnetic field associate magnetization curves were
determined in the applied field sweeping range of
−10000 to 10000 Oe at room temperature. As can be seen
in Figure 4, magnetization saturation was found as
26.5 emu/g.
Fe3O4@APTES@isatin‐SO3H catalyst in the
one‐pot three component synthesis of
pyrano[2,3‐d] pyrimidines derivatives
First, the condensation reaction of benzaldehyde 1a
(1 mmol) with malononitrile (2, 1 mmol) and barbituric
acid (3, 1 mmol) under solvent‐free conditions at room
TABLE 1 Effect of the catalyst amount on the reaction between benzaldehyde (1a) with malononitrile (2) and barbituric acid (3)
Entry
Catalyst (mg)
Time (min)
Yield (%)a
Product
1
Catalyst‐free
120
30
2
3
5
75
30
78
81
10
4
15
20
25
30
30
40
86
88
85
5
6
aIsolated yield.

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SAJJADIFAR AND GHEISARZADEH
TABLE 2 Effect of the various solvent and temperature on the reaction between benzaldehyde (1a) with malononitrile (2) and barbituric
acid (3)
Entry
Solvent (5 mL)
Temperature (°C)
Time (min)
Yield (%)a
Product
1
CHCl3
Reflux
20
90
2
3
4
5
6
7
EtOAc
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
30
15
15
15
30
30
40
75
91
92
94
90
77
65
EtOH
H2O
EtOH:H2O
CH2Cl2
CH3CN
n‐Hexane
8
aIsolated yield.
TABLE 3 Scope of one‐pot three‐component synthesis of pyrano[2,3‐d] pyrimidines derivatives
m.p. (°C)
Found Reported
Entry
Product
Time (min)
Yield (%)a
TON TOF
1
15
94
134.2 8.9
205–206 205–207[22]
2
7
92
131.4 18.7
232–234 235–237[22]
(Continues)

SAJJADIFAR AND GHEISARZADEH
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TABLE 3 (Continued)
m.p. (°C)
Found Reported
Entry
Product
Time (min)
Yield (%)a
TON TOF
3
15
93
132.8 8.8
239–241 241–243[22]
4
10
92
131.4 13.1
238–240 238–240[22]
5
6
7
7
89
95
127.1 18.1
135.7 19.3
226–227 225–226[22]
235–237 237–240[22]
7
8
12
10
95
93
135.7 11.3
132.8 13.2
269–271 272–274[22]
226–228 226–228[22]
(Continues)

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SAJJADIFAR AND GHEISARZADEH
TABLE 3 (Continued)
m.p. (°C)
Found Reported
Entry
Product
Time (min)
Yield (%)a
TON TOF
9
12
92
131.4 10.9
223–224 225–227[22]
10
15
91
130 8.6
282–284 280–282[22]
11
12
12
92
88
131.4 10.9
125.7 17.9
222–223 223–225[22]
7
252–253 252–254[22]
13
14
7
90
88
128.5 18.3
237–239 235–236[22]
20
125.7 6.2
159–160 161–163[22]
(Continues)

SAJJADIFAR AND GHEISARZADEH
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TABLE 3 (Continued)
m.p. (°C)
Found Reported
Entry
Product
Time (min)
Yield (%)a
TON TOF
15
12
87
124.2 10.3
270–272 269–271[22]
16
17
18
25
86
92
90
122.8 4.9
131.4 16.4
128.5 6.4
333–334 332–334[22]
265–266 268–270[22]
150–152 ‐
8
20
4r
aIsolated yield.
temperature was examined in the presence of a catalytic
amount of nano‐Fe3O4@APTES@isatin‐SO3H as the
model reaction for the optimization of conditions
(Table 1). As can be seen in Table 1, under catalyst‐free
conditions at room temperature (Table 1, entry 1), the
reaction was slowly and give the product 4a in a low yield
(30%) after 120 min. When 5 mg of catalyst was used, the
reaction carried out in 78% after only 75 min (Table 1,
entry 2), that show add catalyst cause improvement of
yield and time. When 20 mg of catalyst was used, the
product 4a was obtained in excellent yield (88%) after
only 30 min (Table 1, entry 5).
In the next study, to compare the efficiency of solu-
tion conditions, the condensation reaction of benzalde-
hyde (1a, 1 mmol) with malononitrile (2, 1 mmol) and
barbituric acid (3, 1 mmol) in various solvent such as
CHCl3, EtOAc, EtOH, H2O, mixture of EtOH:H2O
(1:1), CH2Cl2, CH3CN, and n‐hexane at reflux
conditions was examined in the presence of nano‐
Fe3O4@APTES@isatin‐SO3H MNPs (20 mg) as the
model reaction for the optimization of conditions
(Table 2). As can be seen in Table 2, when the mixture
of EtOH:H2O (1:1) was used, the excellent yield (94%)
was obtained after only 15 min (Table 2, entry 5).

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SAJJADIFAR AND GHEISARZADEH
Consequently, the condensation reaction of benzalde-
calculated by the determination of its H+ of the catalyst
through titration with NaOH (0.01 mol/L). For this
purpose, nano‐Fe3O4@APTES@isatin‐SO3H (20 mg) was
titrated by 0.7 ml of NaOH (0.01 mol/L) and then mol%
of catalyst was calculated. Turnover frequency (TOF)
and turnover number (TON) values for nano‐
Fe3O4@APTES@isatin‐SO3H were calculated for the all
derivatives in Table 3 and recyclability of the nano‐
hyde 1a with malononitrile 2 and barbituric acid 3 under
mixture of EtOH:H2O (1:1) at reflux conditions in the
presence of nano‐Fe3O4@APTES@isatin‐SO3H (20 mg)
was selected as the optimization of conditions. Therefore,
as the optimized conditions and this reaction was
developed with various aldehydes (including aldehydes
possessing electron‐releasing substituents, electron‐with-
drawing substituents and halogens on their aromatic
ring), and results summarized in Table 3. Use of ethanol,
water, or mixture of ethanol:water as green solvent in the
reaction medium has several advantages, such as lack of
carcinogenic effects, environmental safety, comparatively
low cost to operate, and clean procedure. As can be seen
in Table 3, various aldehydes were reacted with
malononitrile and barbituric acid under optimized condi-
tions and give products 4a‐r in excellent yields (86–95%)
and short reaction time (7–25 min).
Recovery
and
reusability
of
the
nano‐
Fe3O4@APTES@isatin‐SO3H MNPs was investigated
(Figure 7). The reaction of benzaldehyde (1 mmol) with
malononitrile (1 mmol) and barbituric acid (1 mmol)
under mixture of EtOH:H2O (1:1) at reflux conditions in
the presence of nano‐Fe3O4@APTES@isatin‐SO3H MNPs
(20 mg) was selected as model reaction. After completion
of the reaction, the reaction mixture was cooled to room
temperature, hot ethanol was added to the reaction
mixture. Afterwards, the catalyst was recovered by an
external magnet, washed with ethanol, weighted and pre-
served for the following assay. The catalyst was reused for
seven times without any significant changes in the yields
and the reaction times. As can be seen in Figure 7, prod-
uct 4a obtained with 94, 93, 92, 92, 90, 88, and 88% yield.
Also, the SEM image of the used catalyst showed that size
and shape of the catalyst particles remained almost the
same after seven runs (Figure 8).
FIGURE 8 SEM image of nano‐Fe3O4@APTES@isatin‐SO3H
MNPs after 7 runs
TABLE 4 Calculator of TON and TOF for the synthesis of 4a
catalyzed nano‐Fe3O4@APTES@isatin‐SO3H MNPs
Run 1 Run 2 Run 3 Run 4 Run 5 Run 6 Run 7
TON 134.2 132.8 131.4 131.4 128.5 125.7 125.7
In next study, the acidic content of nano‐
Fe3O4@APTES@isatin‐SO3H was characterized and
TOF
8.9
8.8
7.7
7.7
6.4
5.7
5.7
FIGURE 7 Reusability study of catalyst in the reaction between benzaldehyde, barbituric acid and malononitrile

SAJJADIFAR AND GHEISARZADEH
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TABLE 5 Comparison of the results in the synthesis of 4d catalyzed by nano‐Fe3O4@APTES@isatin‐SO3H MNPs and other those reported
catalysts in the literatures
Entry
Catalyst
Condition
Time (min)
Yield (%)a
1
2
3
4
5
6
7
SBA‐Pr‐SO3H
Solvent‐free/140 °C
EtOH/r.t.
10–45
2 h
30–91[18]
71–81[24]
85–95[25]
82–95[26]
80–92[27]
81–88[30]
86–95
DAHP
γ‐Fe2O3@HAp‐Ni2+ NPs
EtOH/r.t.
15–35
3–5 h
0.5–12 h
30–45
7–25
[BMIm]BF4
[BMIm] BF4/90 °C
EtOH/Reflux
H2O/80 °C
Zn[(l)proline]2
[KAl (SO4)2]
nano‐Fe3O4@APTES@isatin‐SO3H MNPs
EtOH:H2O/Reflux
aIsolated yield.
SCHEME 3 Possible mechanism for
the synthesis of pyrano[2,3 d] pyrimidines
derivatives catalyzed by nano‐
Fe3O4@APTES@isatin‐SO3H MNPs
Fe3O4@APTES@isatin‐SO3H in each 7 run. The TOF and
TON values were summarized in Table 3 and 4.
To separate various substituents, we have presented
the results of those reported catalysts to confirm the con-
densation of various benzaldehydes with malononitrile
and barbituric acids in Table 5. Table 5 illustrated that
nano‐Fe3O4@APTES@isatin‐SO3H MNPs has improved
the synthesis of pyrano[2,3‐d] pyrimidinone derivatives.
According other works, we consider that nano‐
Fe3O4@APTES@isatin‐SO3H MNPs catalyst for the syn-
thesis of pyrano[2,3‐d] pyrimidines derivatives. As can
be seen in Scheme 3, we suggest a probable mechanism
for the reaction.
4 | CONCLUSION
To sum up, we have designed, prepared, and character-
ized Isatin‐SO3H coated on amino propyl modified mag-
netic nanoparticles (Fe3O4@APTES@isatin‐SO3H) as an
efficient, novel and reusable heterogeneous magnetic
nanocatalyst. Prepared magnetic nanocatalyst applied
successfully for the pyrano[2,3‐d] pyrimidines derivatives
of different substituted aldehydes, malononitrile and
barbituric acid. The magnetic nanocatalyst was recovered
magnet and reused for seven cycles. Excellent yield, short
reaction time, ease of catalyst separation, and thermal
stability and reducing the leaching of theses nanocatalyst

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SAJJADIFAR AND GHEISARZADEH
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into the bio environment are the important advantages of
this nanocatalyst.
ACKNOWLEDGMENTS
The authors wish to thank the Payame Noor University of
Ilam for financial support to carry out this research.
ORCID
Sami Sajjadifar http://orcid.org/0000-0001-8661-1264
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How to cite this article: Sajjadifar S,
Gheisarzadeh Z. Isatin‐SO3H coated on amino
propyl modified magnetic nanoparticles
(Fe3O4@APTES@isatin‐SO3H) as a recyclable
magnetic nanoparticle for the simple and rapid
synthesis of pyrano[2,3‐d] pyrimidines derivatives.
Appl Organometal Chem. 2018;e4602. https://doi.
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