Design and characterization of Dendrimer of MNPs as a novel, heterogeneous and reusable nanomagnetic organometallic catalyst for one-pot synthesis of hydroxyl naphthalene-1,4-dione derivatives under solvent-free conditions

Article abstract of DOI:10.1002/aoc.4183

A novel super acidic magnetic nanoparticle as catalyst was successfully synthesized. The preparation of this dendrimer sulfonic acid functionalized γ-Fe₂O₃ magnetic core-shell silica nanoparticles as a new recoverable and heterogeneous nanocatalyst was described. The new catalyst was characterized using various techniques such as scanning electron microscopy (SEM), energy dispersive spectrum (EDS), and thermo gravimetric synthesis (TGA). Moreover, we have examined the catalytic activity of the catalyst for one-pot, efficient and facile synthesis of 2-hydroxy-1,4-naphthoquinone derivatives via a three-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and aniline derivatives. High yields of products, short reaction times, waste-free, mild, ambient and solvent-free reaction conditions are advantages of this protocol. Also, the catalyst can be easily recovered by an external magnetic and reused several times without significant loss of its catalytic activity.

Full text of DOI:10.1002/aoc.4183

Received: 5 September 2017
DOI: 10.1002/aoc.4183
Revised: 19 October 2017
Accepted: 19 October 2017
F U L L P A P E R
Design and characterization of Dendrimer of MNPs as a
novel, heterogeneous and reusable nanomagnetic
organometallic catalyst for one‐pot synthesis of hydroxyl
naphthalene‐1,4‐dione derivatives under solvent‐free
conditions
Fouziyeh Mollazehi | Hamid Reza Shaterian
Department of Chemistry, Faculty of
A novel super acidic magnetic nanoparticle as catalyst was successfully synthe-
sized. The preparation of this dendrimer sulfonic acid functionalized γ‐Fe2O3
magnetic core‐shell silica nanoparticles as a new recoverable and heteroge-
neous nanocatalyst was described. The new catalyst was characterized using
various techniques such as scanning electron microscopy (SEM), energy disper-
sive spectrum (EDS), and thermo gravimetric synthesis (TGA). Moreover, we
have examined the catalytic activity of the catalyst for one‐pot, efficient and
facile synthesis of 2‐hydroxy‐1,4‐naphthoquinone derivatives via a three‐
component condensation reaction of 2‐hydroxynaphthalene‐1,4‐dione, aro-
matic aldehydes and aniline derivatives. High yields of products, short reaction
times, waste‐free, mild, ambient and solvent‐free reaction conditions are advan-
tages of this protocol. Also, the catalyst can be easily recovered by an external
magnetic and reused several times without significant loss of its catalytic
activity.
Sciences, University of Sistan and
Baluchestan, P.O. Box 98135‐674,
Zahedan, Iran
Correspondence
Hamid Reza Shaterian, Department of
Chemistry, Faculty of Sciences, University
of Sistan and Baluchestan, P.O. Box 98135‐
674, Zahedan, Iran
Email: hrshaterian@chem.usb.ac.ir
KEYWORDS
2‐Hydroxy‐1,4‐naphthoquinones, dendrimer magnetic nanoparticles, nanomagnetic organometallic
catalyst
1 | INTRODUCTION
immobilized on silica have been investigated inten-
sively and applied for several catalytic organic
A class of macromolecules with specific properties and
functional groups have been utilized as dendrimers.[1,2]
Dendrimers are highly branched and globular macromol-
ecules which show unique properties such as their
high degree of branching, multivalency, globular architec-
ture and well‐defined molecule weight, make them
promising new scaffoleds for drug delivery.[3,4] Research
groups demonstrated that dendronization can signifi-
cantly improve the properties of catalysts immobilized
on polymeric support.[5–8] Among them, dendrimers
transformations.[9]
The use of heterogeneous catalysts has been widely
studied. These catalysts are easily removable from the
reaction media by simple filtration after completion of
the reaction and in many cases, they are reusable.[10–14]
Magnetic core‐shell nanostructures were forecast as mag-
netic strong catalysts in organic reactions. Within the past
few years, magnetic nanoparticles emerged as a new class
of semi‐heterogeneous supports for catalysts.[15] Fe3O4
and γ‐Fe2O3 magnetic silica nanoparticles (MSNPs) have
Appl Organometal Chem. 2017;e4183.
wileyonlinelibrary.com/journal/aoc
Copyright © 2017 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.4183

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MOLLAZEHI AND SHATERIAN
supermagnetic properties, so that these nanoparticles can
be easily recycled in the presents of an external magnetic
field. Other advantages of these catalysts are mentioned to
high surface area, superior stability of thermal and chem-
ically, surface modification ability, low toxicity and cost.
A silica shell does not only protect the magnetic cores,
but can also prevents the direct contact of the magnetic
core with additional agents linked to the silica surface
thus avoiding unwanted interactions. Silica coatings have
several advantages arising from their stability under aque-
ous conditions (at least if the pH value is sufficiently low),
easy surface modification and easy control of inter‐
particle interactions, both in solution and within struc-
tures, through variation of the shell thickness.
MSNPs can be easily synthesized at room temperature
under mild conditions and the functionalization of these
materials with reactive species should be made to facili-
tate incorporation of other molecules on the surface of
the γ‐Fe2O3/SiO2 nanoparticles.[16–19] The existence of
many hydroxyl groups on the γ‐Fe2O3 MNPs surface leads
to a reaction with alkoxysilane reagents such as tetraethyl
orthosilicate (TEOS) to form Si‐O bonds and provide reac-
tion sites for further functionalization of γ‐Fe2O3/SiO2
MSNPs.[20–23] For the modification and functionalization
of the surface of γ‐Fe2O3/SiO2 MSNPs, the (3‐
aminopropyl)triethoxysilane (APTES) and some silane
reagents as potential candidates were used.[10,13,16–19]
An important class of convergent organic reactions
that have an import and role in organic chemistry are
multi‐component reactions (MCRs).[24] In this reaction
three or more starting materials react together to form a
unique product. The ability of the formation of multi‐
bonds in a one‐pot reaction with high atom efficiency
and mild and environmentally benign conditions is due
to special interest. Researches on MCRs have received a
rapidly increasing attention in both academic and indus-
trial researches.[25]
of 2‐hydroxy‐1,4‐naphthoquinone derivatives from 2‐
hydroxynaphthalene‐1,4‐dione, aromatic aldehydes and
hetrocyclic amines under solvent free conditions
(Scheme 2). The condition of Mannich reaction with this
new dendrimer super acidic magnetic nano particles was
very impressive. High yield of products in a few seconds
time with simple work‐up shows this MNPs catalyst is
very suitable in the organic synthesis.
2 | EXPERIMENTAL
All reagents were purchased from Merck and Aldrich and
used without further purification. The NMR spectra were
provided on Brucker Avance 300 MHz instrument in
DMSO‐d6. Infrared (IR) spectra were recorded applying
a JASCO FT‐IR 460 Plus spectrophotometer. Melting
points were determined in open capillaries using a
BUCH510 melting point apparatus. Thin layer chroma-
tography (TLC) was performed on silica‐gel Poly Gram
SIL G/UV 254 plates. Elemental compositions were deter-
mined with a Leo 1450 VP scanning electron microscope
equipped with an SC7620 energy dispersive spectrometer
(SEM‐EDS) presenting a 133 Ev resolution at 20 Kv.
2.1 | Preparation of γ‐Fe2O3 magnetic
nanoparticles (MNPs)
Fe3O4 nanoparticles were synthesized via the co‐precipita-
tion of Fe2+ and Fe3+ ions (molar ratio 1:2) in alkali solu-
tion. FeCl3.6H2O (2 mmol) separately were dissolved in
hydrochloric acid (4 ml) and also FeCl2.4H2O (1 mmol)
were dissolved by hydrochloric acid (1 ml). Then, two
solutions of Fe2+ and Fe3+ added to each other. Resulting
solution was stirred in room temperature and then was
dropped a 25% NH4OH solution to iron solution with pre-
cisely constant rate to obtain small and uniforms parti-
cles. Fe3O4 was collected by a permanent magnet,
followed by washed several times with water and dried
at 100 °C in vacuum for 24 h. In the next step, it converted
to γ‐Fe2O3 at 300 °C for 3 h.[28]
2‐Hydroxy‐1,4‐napthoquinone (HNQ) has been
known for the past 4000 years, is principal natural dye
in the leaves of henna.[26] Today, semipermanents hair
dyes containing henna as well as its pure dye ingredient
HNQ are extensively used and have become increasingly
popular because of their natural origin.[27] Moreover, mol-
ecules containing the hetrocyclic quinone group consti-
tute an important class in organic chemistry because of
their various biological activities (such as antitumor, anti-
bacterial and anti‐inflammatory agents), industrial appli-
cations, and potential as intermediates in the synthesis
of hetrocycles.[26]
2.2 | Preparation of γ‐Fe2O3 magnetic
silica nanoparticles (MSNPs)
The γ‐Fe2O3 was dispersed in 40 ml ethanol stirred for 1 h,
and then tetraethyl orthosilicate (TEOS, 10 mL) was
added to the mixture and stirred at 40 °C for 24 h. The
silica‐coated magnetic nanoparticles were separated by a
permanent magnet, followed it washed several times with
ethanol and diethyl ether and dried at 100 °C in vacuum
for 12 h.
Herein, we described a method for synthesis of a novel
dendrimer super acidic magnetic nanoparticles catalyst
(Scheme 1). We used this dendrimer super acidic mag-
netic nanoparticles as catalyst for the one‐pot synthesis

MOLLAZEHI AND SHATERIAN
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SCHEME 1 Synthesis of a novel
dendrimer super acidic magnetic
nanoparticles as catalyst
SCHEME 2 One‐pot synthesis of
hydroxyl naphthalene‐1,4‐dione
derivatives
washed several times with diethylether and dichloro-
methane and dried at 100 °C in vacuum for 12 h.[9]
2.3 | Preparation of aminopropyl‐modified
silica‐coated γ‐Fe2O3 MNPs (γ‐Fe2O3/SiO2‐
Propyl‐NH2)
The obtained MSNPs was dispersed in 40 ml of dry
toluene by sonication for 45 min, and then slowly
to rise temperature to 105 °C, in this time 1 ml
(3‐aminopropyl)‐triethoxysilane (APTES) was added to
the mixture and let that the mixture was refluxed for
24 h in 105 °C. The solid product was separated with an
external magnet after cooling to room temperature,
2.4 | Preparation of PAMAM dendrons on
the silica‐coated magnetic nanoparticles
(γ‐Fe2O3/SiO2‐Propyl‐NH‐AMAM)
This step is the most important step in this synthesis of
MNPs. Silanated particles was suspended in 50 ml of
dry ethanol, and after sonication for 35 min, 0.2 ml of

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MOLLAZEHI AND SHATERIAN
ethylpropiolate were added and the mixture was heated
at 50 °C for at least 72 h. After cooling to the room tem-
perature, the particles were separated magnetically,
washed 3 times with dry ethanol, and dried at 100 °C
under a vacuum for 24 h. Then, the nanoparticle was
solved in dry ethanol and sonicated for 35 min. After
that, 0.2 ml ethylenediamine dropwise was added to
the mixture at room temperature. The final solution
was heated at 50 °C for 72 h, Then, the magnetic nano-
particles was separated by an external magnet, washed
three times with ethanol and dried at 100 °C in vacuum
for 12 h.
washed with dichloromethane and dried at 100 °C in
vacuum for 12 h.
2.6 | General procedure for synthesis of 2‐
hydroxyl naphthalene‐1,4‐dione derivatives
under ambient and solvent free conditions
The mixture of the aldehydes (1 mmol), anilines (1 mmol),
2‐hydroxynaphthalene‐1,4‐dione (1 mmol), and 0.05 g
super acidic magnetic nanoparticles as catalyst was stirred
under ambient and solvent free conditions for the speci-
fied time. Completion of the reaction was monitored
using TLC. For separation of catalyst, ethanol (5 ml) was
added to the reaction mixture and heated to solve the
desired product. Then, the catalyst was separated with
an external magnet. Ethanolic solution was remained to
cold, the precipitated crude product was filtered. The
obtained crude was dried and recrystallized with EtOH
to produce the pure product. The recovered catalyst was
dried and reused in subsequent runs. All the desired
products were characterized by comparison of their
physical data with those of known compounds.
2.5 | Preparation of PAMAM sulfonic acid
functionalized γ‐Fe2O3 MSNPs (γ‐Fe2O3/
SiO2‐Propyl‐NH‐AMAM‐SO3H)
At finally steps, result powder of nanomagnetic particles
was suspended in dry dichloromethane, then
chlorosolfonic acid (0.2 ml) was added dropwise at room
temperature. Eventually, the mixture was separated and
FIGURE 1 SEM images of MNPs dendrimer (γ‐Fe2O3/SiO2‐Propyl‐NH‐AMAM‐SO3H) as catalyst

MOLLAZEHI AND SHATERIAN
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2.6.1 | Selected spectra for two Known
products are given below
2‐hydeoxy‐3‐[phenyl(phenylamino)methyl]naphthalene‐
1,4‐dione (Table 2, Entry 1): mp 142‐145 °C; IR (KBr)
(νmax/cm‐1): 3431 (OH), 3319 (NH), 1660 (CO), 1639
1
(CO). H NMR (300 MHZ, DMSO‐d6): δ= 6.00 (IH, s,
CH), 7.26‐8.09 (14H, m, Ar and NH), 9.27 (1H, s,OH).
13C NMR (75 MHz, DMSO‐ d6): δ=37.4, 113.5, 123.9,
126.0, 126.6, 128.5, 129.7, 130.4, 132.8, 133.2, 133.7,
135.1, 138.1, 146.2, 156.9, 157.7, 181.9, 184.2.
FIGURE 3 EDS spectrum of MNPs dendrimer (γ‐Fe2O3/SiO2‐
Propyl‐NH‐AMAM‐SO3H) as catalyst
2‐hydroxy‐3‐[(4‐methoxyphenyl)(p‐tolyamino)
methyl)]naphthalene‐1,4‐dione (Table 2, Entry 5): mp
144‐147∘ C; IR (KBr)(νmax/cm‐1): 3452 (OH),3324(NH),
1
1665 (CO), 1631 (CO).; H NMR (300 MHz, DMSO‐d6):
δ=2.31 (3H, s, CH3),3.69 (3H, s, OCH3),6.03 (1H, s,CH),
7.22‐8.06 (12H, m, H‐Ar), 9.19 (1H, s,OH).13C NMR
(75 MHz, DMSO‐d6): δ= 21.2, 37.3, 55.3, 113.4, 123.9,
125.9, 126.4, 128.5, 129.6, 130.3, 132.6, 133.1, 135.0,138.1,
146,156.8,157.6, 181.8,184.
3 | RESULTS AND DISCUSSION
New dendrimer MNPs as a novel catalyst was prepared
based on a chemical co‐precipitating method. The
magnetic nanocatalyst was characterized using different
techniques such as SEM, EDS and TGA. Figure 1 exhibits
SEM images of MNPs dendrimer. As it is shown, the
nanoparticles have uniformity spherical morphology.
The average size of particles was determined using
histogram curve, and it is about 65 nm (Figure 2). The
energy dispersive spectrum (EDS) indicates the presence
of Fe, O, Si, C, N, Cl, S atoms in the catalyst (Figure 3);
which it verified the success of silica‐coating and stabiliza-
tion of NH‐AMAM‐SO3H on chloro‐functionalized
γ‐Fe2O3@SiO2 substrate. TGA analysis of the catalyst was
depicted in Figure 4. As it was observed, γ‐Fe2O3/SiO2‐Pro-
pyl‐NH‐AMAM‐SO3H is stable up to 300 °C and keeps its
FIGURE
4
Thermogravimetric (TGA) and differential
thermogravimetric (DTG) of MNPs dendrimer (γ‐Fe2O3/SiO2‐
Propyl‐NH‐AMAM‐SO3H) as catalyst
thermal stability in reaction. The lost weight at about
100 °C, corresponds to water desorption of surface catalyst.
The second weights loss can be related to the decomposi-
tion of the immobilized organic part. The total weight loss
was calculated to be 12.6% and the amount of organic part
loaded on γ‐Fe2O3/SiO2 was equal to 10.8 mmol/gr.
To optimize reaction conditions, the solvent‐free
reaction of 2‐hydroxynaphthalene‐1,4‐dione, benzalde-
hyde and aniline in the presence of different amount of
TABLE 1 Optimization of the amount of γ‐Fe2O3/SiO2‐Propyl‐
NH‐AMAM‐SO3H as catalyst in three‐component synthesis of 2‐
hydroxy‐1,4‐naphthoquinone from the reaction of benzaldehyde,
aniline and 2‐hydroxynapthalene‐1,4‐dione under solvent free and
ambient conditions
Entry
Catalyst (gr)
Time (min)
Yield (%)
1
0.02
3:30
80
2
3
0.05
0.1
2:45
2:00
93
92
FIGURE
2
Particle size distribution histogram of MNPs
dendrimer (γ‐Fe2O3/SiO2‐Propyl‐NH‐AMAM‐SO3H) as catalyst

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MOLLAZEHI AND SHATERIAN
TABLE 2 Three‐Component synthesis of hydroxyl naphthalene‐1,4‐dione derivatives from the reaction of 2‐hydroxynapthalene‐1,4‐dione,
anilines and aldehydes in presence of dendrimer super magnetic nanoparticles (0.05 gr) as catalysts under solvent‐free and ambient conditions
Entry
X
Y
Product
Time(min)
Yielda
Mp: Obsd (Lit)
Ref.
1
H
H
2:45
93
143‐146 (144‐146)
23
2
3
4
H
4‐CH3
2:45
3:30
3:00
92
92
91
145‐148 (147‐150)
152‐155 (150‐153)
147‐150 (146‐149)
32
29
32
H
4‐F
4‐CH3
4‐CH3
5
6
7
8
4‐OCH3
4‐CH3
4‐OH
4‐CH3
3:15
2:15
2:15
2:30
93
92
90
90
142‐144 (144‐147)
144‐147 (145‐148)
188‐192 (185‐190)
140‐144 (145‐148)
32
29
29
29
H
H
4‐NO2
H
(Continues)

MOLLAZEHI AND SHATERIAN
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TABLE 2 (Continued)
Entry
X
Y
Product
Time(min)
Yielda
Mp: Obsd (Lit)
Ref.
9
4‐Cl
4‐CH3
2:00
93
146‐149(146‐149)
32
10
11
12
4‐Br
4‐CH3
4‐CH3
4‐CH3
3:40
3:10
3:20
88
84
82
146‐147 (147‐150)
150‐151 (149‐152)
142‐143 (141‐144)
32
29
29
4‐OH
4‐NO2
13
14
15
2‐Cl
4‐CH3
4‐CH3
4‐F
3:15
3:40
2:55
80
80
87
147‐149 (149‐152)
144‐143 (144‐147)
148‐150 (149‐152)
29
32
29
3‐NO2
4‐CH3
16
4‐NO2
4‐F
3:10
83
146‐150 (149‐152)
29
(Continues)

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MOLLAZEHI AND SHATERIAN
TABLE 2 (Continued)
Entry
X
Y
Product
Time(min)
Yielda
Mp: Obsd (Lit)
Ref.
17
H
2:30
86
144‐146 (145‐148)
32
18
4‐NO2
2:50
82
146‐149 (148‐151)
32
aYields refer to isolated yields after purifications
SCHEME 3 The suggest mechanism for
preparation of hydroxyl naphthalene‐1,4‐
dione derivatives using MNPs dendrimer
(γ‐Fe2O3/SiO2‐Propyl‐NH‐AMAM‐SO3H)
as catalyst
FIGURE 6 The investigation of the recyclability of the catalyst in
the reaction of 2‐hydroxynapthalene‐1,4‐dione, aniline and
benzaldehyde (model reaction)
acidic dendrimer nanomagnetic particles as catalyst
under ambient and solvent‐free conditions was selected
as a model (Table 1).
FIGURE 5 The recovery of MNPs dendrimer (catalyst) by an
external magnet

MOLLAZEHI AND SHATERIAN
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TABLE 3 Comparison the results of dendrimer super magnetic nanocatalyst with other catalysts in the literature for preparation of 2‐
hydroxy‐3‐(phenyl(phenylamino)methyl)naphthalene‐1,4‐dione
Entry
Catalyst
Conditions
Time
Yield (%)
Ref.
[30]
1
PPA
H2O/ambient temperature
6 h
87
[29]
[33]
[32]
[12]
[23]
[31]
[13]
2
3
4
5
6
7
8
9
InCl3(25 mol%)
ZrOCl
H2O (reflux)
6 h
91
88
91
91
90
90
91
93
H2O (Neat) 100 °C
7 h
MCM‐41
EtOH/Room temperature
Solvent‐free/Room temperature
Solvent‐free/Room temperature
Solvent‐free/Room temperature
Solvent‐free/Room temperature
Solvent‐free/Room temperature
3 h
Nano Copper(II)oxide
SBPPSA
11 min
8 min
8 min
6 min
2:45 min
3‐HPAA
[Et3NH][HSO4]
Dendrimer nanoparticle
Present work
As it was shown in Table 1, the effective amount of the
catalyst was investigated. Generally, the reaction rate
increased with the amount of catalyst. It was found that
0.05 g of the catalyst was the appropriate amount in basis
of time and yield for the preparation of the desired prod-
uct. Hence, the optimal amount of catalyst was chosen
to be 0.05 gr in the subsequent reactions.
literature, we have summarized some of the results for
the preparation of 2‐hydroxy‐3‐[phenyl(phenylamino)
methyl]naphthalene‐1,4‐dione (Table 3, Entry 1). The
results show that dendrimer super magnetic nanoparticle
is the most efficient catalyst with respect to the reaction
time and yields of the product relative to the other
catalysts.
Next, three‐component condensation reaction of
aromatic aldehydes, anilines, and 2‐hydroxynapthalene‐
1,4‐dione under optimized conditions for preparation of
hydroxyl naphthalene‐1,4‐diones was investigated.
Interestingly, a variety of aromatic aldehydes and anilines
including, ortho, meta, para‐substituted were used and
corresponding products were synthesized in excellent
yields at short reaction times (Table 2). In accordance
with Table 2, both aromatic aldehydes and anilines carry-
ing electron‐donating or electron‐withdrawing substitu-
ent act well under these reaction conditions.
4 | CONCLUSIONS
In this research,
a
new synthesized dendrimer
supermagnetic nano catalyst was used for preparation of
2‐hydroxy‐1,4‐naphthoquinone derivatives under solvent‐
free and ambient conditions for the first time. The attrac-
tive features of this protocol are the simple procedure,
cleaner reaction, and use of recyclable nanocatalyst. High
yields of products, shorter reaction time toward other
catalysts and easy separation of the catalyst from the
reaction media without any noticeable loss of its activity
after at least six times makes this green method suitable
for applications in organic synthesis.
We suggest mechanism according to the literature.[29]
At first, aromatic aldehyde was activated by the acidic
group of dendrimer super magnetic nano catalyst. Then,
aniline was condensed with the activated aldehyde to
afford imine. Subsequently, 2‐hydroxynaphthalene‐1,4‐
dione was added to the imine. Tautomerization converts
intermediate to the desired product (Scheme 3).
ACKNOWLEDGMENT
We are thankful to the University of Sistan and
Baluchestan Research Council for the partial support of
this research.
The recyclability of the catalyst in the model reaction
of 2‐hydroxynapthalene‐1,4‐dione, aniline and benzalde-
hyde in the presence of γ‐Fe2O3/SiO2‐Propyl‐NH‐
AMAM‐SO3H nanoparticles was checked (Table 2, Entry
1). The catalyst can be recovered by an external magnet
(Experimental section, Figure 5), washing with hot etha-
nol and drying at 100 °C. The catalyst was recovered in
high yields and the catalyst was used in the mentioned
reaction for six times. It showed the same activity as fresh
catalyst without any loss of significant in its activity
(Figure 6).
ORCID
Hamid Reza Shaterian
http://orcid.org/0000-0002-0118-
1072
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