A simple synthesis of magnetic nanoparticles-supported 4-aminomethylbenzoic acid as a highly efficient and reusable catalyst for synthesis of 2-amino-4H-chromene derivatives

Article abstract of DOI:10.1007/s11164-017-3008-2

A new 4-aminomethylbenzoic acid-functionalized Fe₃O₄ magnetic nanoparticles as a hybrid heterogeneous catalyst was synthesised and characterized by FT-IR, XRD, TGA, TEM, SEM and VSM techniques. The catalytic activity of this nanocata

Full text of DOI:10.1007/s11164-017-3008-2

Res Chem Intermed
DOI 10.1007/s11164-017-3008-2
A simple synthesis of magnetic nanoparticles-supported
4-aminomethylbenzoic acid as a highly efficient
and reusable catalyst for synthesis of 2-amino-4H-
chromene derivatives
Mohammad Mehdi Khodaei1,2 Abdolhamid Alizadeh1,2
•
•
Maryam Haghipour1
Received: 10 April 2017 / Accepted: 10 June 2017
Ó Springer Science+Business Media B.V. 2017
Abstract A new 4-aminomethylbenzoic acid-functionalized Fe3O4 magnetic
nanoparticles as a hybrid heterogeneous catalyst was synthesised and characterized
by FT-IR, XRD, TGA, TEM, SEM and VSM techniques. The catalytic activity of
this nanocatalyst was probed through one-pot synthesis of 2-amino-4H-chromene
derivatives from three component reactions of various aldehydes, malononitrile and
dimedone. The chemically and thermally stable catalyst was easily recovered using
an external magnet and reused for at least five successive runs without significant
loss of its activity. The simplicity of the method, high yields of the products, mild
reaction conditions and low reaction times are the other advantages of this
procedure.
Keywords Nanoparticle Á Heterogeneous catalyst Á 4-Aminomethylbenzoic
acid Á 2-Amino-4H-chromene Á Aldehydes Á Dimedone
Introduction
Synthesis of new magnetic nanoparticles-supported catalyst has attracted consid-
erable attention due to their facile separation from the reaction mixture using an
external magnet and providing improved reusability of the catalyst by sustaining
their catalytic efficiency after several repeated reactions [1]. This type of catalyst
support is now growing and finds a powerful position in catalytic reactions. The gap
between homogeneous and heterogeneous catalysis is bridged by surface
&
Mohammad Mehdi Khodaei
mmkhoda@razi.ac.ir
1
2
Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran
Nanoscience and Nanotechnology Research Center (NNRC), Razi University,
Kermanshah 67149-67346, Iran
123

M. M. Khodaei et al.
functionalization of magnetic nanoparticles. These catalysts are widely used in
biotechnology since they have good biocompatibility and biodegradability charac-
teristics which could be important for functional organic materials grafted to Fe3O4
nanoparticles [2, 3]. The use of magnetic nanoparticles without surface function-
alization as catalysts is not promising, since their surface is highly active and leads
to the agglomeration of the catalyst particles; coating the catalyst surface with shell
as prevents this deficiency [4–8]. It is important to note that organic catalyst-
functionalized magnetic nanoparticles indicate not only a high degree of chemical
and thermal stability but also high catalytic activity [9–11].
Compounds containing 2-amino-4H-chromene are found in a number of natural
products such as tannins and polyphenols which are commonly found in a variety of
fruits, vegetables, teas and red wines [12]. The interest in these compounds is
increasing because of their reported benefit to health. In addition, the 2-amino-4H-
chromene moiety is present in a variety of naturally occurring compounds that have
anticoagulant, anticancer, anti-ancaphylactia, antibacterial and fungicidal activities
[13–18].
In the present study, we present our results on the preparation and character-
ization of 4-aminomethylbenzoic acid (AMBA)-functionalized Fe3O4 magnetic
nanoparticles (AMBA–Fe3O4) as an active and stable magnetically separable basic
nanocatalyst and its catalytic application for the one-pot synthesis of 2-amino-4H-
chromene derivatives from dimedone, various arylaldehydes and malononitrile in
ethanol under mild conditions (Scheme 1).
R
CHO
R
O
O
AMBA-Fe3O4 (Catalyst)
Ethanol, 60 oC
CN
CN
CN
NH2
Me
Me
+
+
O
O
H2N
H2N
O
O
O
O
O
O
NH2
Fe3O4
=
AMBA-Fe3O4
O
O
O
O
H2N
H2N
Scheme 1 Synthesis of 2-amino-4H-chromene derivatives using 4-aminomethylbenzoic acid-
functionalized Fe3O4 magnetic nanoparticles as a nanomagnetic catalyst
123

A simple synthesis of magnetic nanoparticles supported…
Experimental
Physical measurements
Melting points were measured on an Electrothermal 9100 apparatus. The X-ray
powder diffraction (XRD) of the catalyst was carried out on a Philips PW 1830
˚
X-ray diffractometer using a CuKa source (k = 1.542 A) in a range of Bragg’s
angle (10°–80°) at room temperature. Scanning electron microscopy (SEM)
analyses were taken using VEGA//TESCAN KYKY-EM 3200 microscope (accel-
eration voltage 26 kV). Transmission electron microscopy (TEM) experiments were
conducted on a Philips EM 208 electron microscope. Thermogravimetric analysis
(TGA) was recorded on a Stanton Red craft STA-780 (London, UK). NMR spectra
were recorded on a Bruker DRX-400 AVANCE instrument (300 MHz for 1H,
75 MHz for 13C). The spectra were measured in DMSO-d6 as the solvent. FT-IR
spectra were recorded on an FT-IR Bruker vector 22 spectrophotometer. Magnetic
measurements were performed using a vibration sample magnetometer (VSM,
MDK, and Model 7400) analysis.
General procedure
Preparation of 4-aminomethylbenzoic acid functionalized Fe3O4 nanoparticles
FeCl3Á6H2O (2.43 g, 0.09 mol) and FeCl2Á4H2O (0.89 g, 0.0045 mol) were
dispersed in 100 mL distilled water by sonication until the salts dissolved
completely. Then, 0.3 g of AMBA in 10 ml NH4OH solution was added to the
above mixture under constant nitrogen flow, and, as a result, a black suspension was
formed. This suspension was refluxed at 100 °C for 12 h. AMBA–Fe3O4
nanoparticles were separated from the aqueous solution by a magnetic field,
washed with distilled water four times and then dried in an oven overnight
(Scheme 2).
Scheme 2 Preparation of AMBA–Fe3O4 nanoparticles
123

M. M. Khodaei et al.
General procedure for the synthesis of 2-amino-4H-chromene derivatives
To a 3 mL mixture of ethanol, aldehyde (1 mmol), malononitrile (1 mmol,
0.066 g), dimedone (1 mmol, 0.141 g) and AMBA–Fe3O4 magnetic nanoparticles
(0.05 g) as a catalyst were added and the mixture was stirred at 60 °C for a specific
time. When the reaction was complete (monitored by TLC), the solvent was
evaporated. Then, the reaction mixture was dissolved in CH2Cl2 (15 mL), and
subsequently AMBA–Fe3O4 was separated by a magnetic field and washed with dry
CH2Cl2 three times and checked for its reusability. The solvent of the solution
containing the product was evaporated, the solid residue was recrystallized using
ethanol and the product obtained as a white powder. All of the desired products
were characterized by comparison of their physical data with those reported in the
literature.
Selected spectra of the products
2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran
(Table 2, entry 1; see later): white solid; mp = 231–232 °C; IR (KBr): mmax = 3452
1
and 3426 (NH2), 2199 (CN), 1668 (C=O), 1222 (C–O) cm-1; H NMR (300 MHz,
DMSO-d6): d = 0.99 (2s, 6H, 2CH3), 2.09 and 2.25 (d, 2H, J = 15.9 Hz, 16.2 Hz
CH2), 3.29 (d, 2H, J = 6.6 Hz CH2), 4.16 (s, 1H, CH), 7.00 (s, 2H, NH2), 7.17 (dd,
3H, J = 9.0 Hz, 3CHarom), 7.27 (d, 2H, J = 9.0 Hz, 2CHarom) ppm; 13C NMR
(75 MHz, DMSO-d6): d = 28.9, 32.3, 36.0, 50.4, 58.8, 113.2, 120.2, 127.0, 127.6,
128.1, 128.8, 145.2, 158.9, 162.9, 196.1 ppm.
2-Amino-4-(2-chlorophenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahy-
drobenzo[b]pyran (Table 2, entry 8; see later): white solid; mp = 192–194 °C; IR
(KBr): mmax = 3426 and 3229 (NH2), 2192 (CN), 1678 (C=O), 1220 (C–O) cm-1
;
1H NMR (300 MHz, DMSO-d6): d = 1.04 (2s, 6H, 2CH3), 2.07 and 2.25 (AB
quartet, 2H, J = 15.9 Hz, CH2), 2.46 (m, 2H, CH2), 4.69 (s, 1H, CH), 7.00 (s, 2H,
NH2), 7.17 (d, 2H, J = 4.2 Hz, 2CHarom), 7.35 (d, 2H, J = 4.2 Hz, 2CHarom) ppm;
13C NMR (75 MHz, DMSO-d6): d = 27.3, 28.9, 32.2, 33.3, 40.0, 50.4, 27.3, 112.2,
119.7, 127.9, 128.6, 129.9, 130.4, 132.6, 142.0, 159.1, 163.6, 196.0 ppm.
2-Amino-4-(4-methylphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahy-
drobenzo[b]pyran (Table 2, entry 9; see later): white solid; mp = 214–215 °C; IR
(KBr): mmax = 3420 and 3282 (NH2), 2195 (CN), 1679 (C=O), 1216 (C–O) cm-1
;
1H NMR (300 MHz, DMSO-d6): d = 0.97 (2s, 6H, 2CH3), 2.24 (3H, CH3), 2.46
(d, 4H, CH2), 4.12 (s, 1H, CH), 6.99 (m, 6H, 4 CHarom and NH2); 13C NMR
(75 MHz, DMSO-d6) ppm: d = 21.0, 28.9, 32.4, 39.4, 39.7, 50.4, 58.9, 113.3,
120.2, 127.5, 129.3, 136.1, 142.3, 158.9, 162.7, 196.1 ppm.
2-Amino-4-(4-hydroxy-3-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-
tetrahydrobenzo[b]pyran (Table 2, entry 12; see later): white solid;
mp = 241–242 °C. IR (KBr): mmax = 3496 (OH), 3402 and 3255 (NH2), 2192
(CN), 1654 (C=O), 1208 (C–O) cm-1; 1H NMR (300 MHz, DMSO-d6): d = 1.03 (2s,
6H, 2CH3), 2.09 and 2.25 (AB quartet, 2H, J = 15.9 Hz, CH2), 2.49 (m, 2H, CH2),
3.70 (s, 1H, OCH3), 4.07 (s, 1H, CH), 6.51 (d, 1H, J = 6.9 Hz, CHarom), 6.66 (d, 2H,
J = 10.8 Hz, 2CHarom), 6.90 (s, 2H, 2CHarom), 8.80 (s, 1H, OH) ppm; 13C NMR
123

A simple synthesis of magnetic nanoparticles supported…
(75 MHz, DMSO-d6): d = 21.1, 28.1, 30.3, 37.4, 39.8, 58.2, 59.9, 111.9, 113.5, 115.8,
119.9, 120.3, 136.3, 145.7, 147.7, 158.2, 162.6, 196.1 ppm.
Results and discussion
Characterization of the prepared AMBA–Fe3O4 magnetic nanoparticles
X-ray diffraction (XRD) analysis
X-ray diffraction was used to identify phases of the synthesized AMBA-Fe3O4
magnetic nanoparticles. The result shown in Fig. 1 was fitted for the observed six
peaks with the following Miller indices: (2 2 0), (3 1 1), (4 0 0), (4 2 2), (5 1 1) and
(4 4 0) that identified them as Fe3O4 nanoparticles. The XRD peaks are broad
indicating the small nanoparticles. Applying the Scherrer equation [19, 20], the
calculated size was estimated to be about 15 nm which is in a good agreement with
the TEM observations.
Fourier transform infrared (FT-IR) analysis
The peak around 3428 cm-1 is referred to the N–H stretching vibration. The peaks
around 2923 and 2854 cm-1 are ascribed to the asymmetric and symmetric
vibrations of C–H stretching. The adsorption peaks at 1632, 1398 and 1028 cm-1
correspond to the asymmetric and symmetric stretching vibrations of the carboxy-
late group of the 4-aminomethylbenzoic acid moiety. The characteristic absorbing
peak of Fe3O4 appeared at 584 cm-1, which can be ascribed to the vibration of the
Fe–O group. Therefore, the obtained data from FT-IR spectroscopy can confirm the
existence of the magnetic nanoparticles and aromatic ligand moiety in the structure
of the AMBA–Fe3O4 nanoparticles (Fig. 2).
Fig. 1 XRD powder pattern of AMBA–Fe3O4 nanoparticles
123

M. M. Khodaei et al.
Fig. 2 FT-IR spectra for Fe3O4 nanoparticles and AMBA–Fe3O4 nanoparticles
Thermogravimetric analysis (TGA)
Thermal gravimetric analysis (TGA) was implemented at the range of 25–900 °C
under N2 atmosphere in order to define the loading of organic groups coated on the
Fe3O4 magnetic nanoparticles (Fig. 3). The TGA curve of the AMBA–Fe3O4
nanoparticles shows the mass loss of the organic functional group as it decomposes
upon heating (volatile components disappeared before a temperature of about
100 °C were ignored). The curve shows a weight loss of about 9.37% between 100
Fig. 3 TGA thermograms of AMBA–Fe3O4 nanoparticles
123

A simple synthesis of magnetic nanoparticles supported…
and 800 °C, resulting from the decomposition of the functional group grafting to the
Fe3O4 surface.
Morphological characteristic
Surface morphology, particle shape, fundamental physical properties and size
details of the prepared AMBA–Fe3O4 magnetic nanoparticles were investigated
through SEM and TEM microscopies (Fig. 4a, b). As can be seen from the TEM and
SEM images, the average particle size is estimated to be 15–30 nm while AMBA–
Fe3O4 showed a sphere-like structure. As shown in Fig. 4b, a basically core–shell
structure (dark-colored core for Fe3O4 magnetic nanoparticles and light-colored
shell for AMBA) was obtained.
Vibrating sample magnetometer (VSM)
The VSM data for the Fe3O4 nanoparticles and 4-aminomethylbenzoic acid-
functionalized Fe3O4 nanoparticles samples, recorded at room temperature, are
shown in Fig. 5. The sigmoidal shape of the M (H) curves with nearly zero
hysteresis confirms the superparamagnetic nature of these nanoparticles at room
temperature. The saturation magnetization of the Fe3O4 nanoparticles was 68 emu/
g, whereas that of 4-aminomethylbenzoic acid-functionalized Fe3O4 nanoparticles
was reduced to 55 emu/g. The saturation magnetization of the AMBA–Fe3O4
nanoparticles clearly decreased because the diamagnetic contribution of the organic
group resulted in a low mass fraction of the Fe3O4 nanoparticles.
Catalytic activity of AMBA–Fe3O4 nanoparticles
First, to find the optimization conditions, the reaction of 4-chlorobenzaldehyde,
malononitrile and dimedone in the presence of the AMBA–Fe3O4 magnetic
nanocatalyst was selected as a model reaction. The reaction was carried out with
different amounts of nanocatalyst (0.02, 0.05 and 0.10 g) at different temperatures
Fig. 4 a SEM images of AMBA–Fe3O4 nanoparticles and b TEM micrographs of AMBA–Fe3O4
nanoparticles
123

M. M. Khodaei et al.
Fig. 5 Room-temperature magnetization curves of Fe3O4 nanoparticles and AMBA–Fe3O4 nanoparticles
(25, 40 and 60 °C) in an ethanol solvent. The obtained results in Table 1 show that
an optimal condition was 20 mol% of AMBA–Fe3O4 magnetic nanocatalyst at
60 °C (Table 1, entry 8).
Next, various aldehydes were used in the reactions that led to the corresponding
products in high to excellent yields (Table 2). As shown in Table 2, the reactions
with arylaldehydes, including electron-donating groups or electron-withdrawing
groups substituents, afforded the desired products in high to excellent yields.
Natural aldehydes such as vanillin and cinnamaldehyde also gave the corresponding
products in high yields. Isonicotincarboxaldehyde as a hetero-aromatic aldehyde
Table 1 Optimization conditions for preparation of 2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-
5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile from 4-chlorobenzaldehyde, malononitrile and dimedone
in the presence of different amounts of AMBA–Fe3O4 as magnetic nanocatalyst at different temperatures
Entry
Amount of
catalyst (g)
Temperature
(°C)
Time (min)
Yield (%)a
1
2
3
4
5
6
7
8
9
a
0.02
0.05
0.10
0.02
0.05
0.10
0.02
0.05
0.10
25
25
25
40
40
40
60
60
60
100
100
100
75
–
Trace
35
49
60
74
85
93
93
75
75
25
20
20
Yields refer to isolated product
123

A simple synthesis of magnetic nanoparticles supported…
Table 2 One-pot synthesis of 2-amino-4H-chromene derivatives using AMBA–Fe3O4 as nanocatalyst
Melting point (oC)
Time
Entry
Aldehyde
C6H5CHO
Product
Yield (%)
(min)
Reported
[Refs.]
Found
O
CN
1
21
92
231–232
228–231 [21]
Me
O
NH2
Me
CN
O
4-CNC6H4CHO
4-HOC6H4CHO
2
3
4
5
6
7
21
22
20
20
23
20
94
91
93
92
92
92
226
225–226 [22]
212–214 [21]
209-211 [23]
181–182 [24]
199–201 [24]
181–184 [22]
CN
NH2
Me
O
Me
OH
O
215–217
209–210
CN
Me
Me
Me
O
NH2
Me
Cl
O
4-ClC6H4CHO
CN
O
NH2
Me
NO2
O
3-NO2C6H4CHO
CN
180–182
201–203
O
NH2
Me
Br
O
4-BrC6H4CHO
2-NO2C6H4CHO
2-ClC6H4CHO
4-MeC6H4CHO
CN
Me
Me
Me
O
NH2
Me
O
NO2
CN
180–182
192–194
O
NH2
Me
O
Cl
CN
8
9
21
22
93
91
194–195 [21]
210–213 [23]
O
NH2
Me
Me
O
CN
214–215
Me
O
NH2
Me
123

M. M. Khodaei et al.
Table 2 continued
Melting point (oC)
Reported
Time
(min)
Entry
10
Aldehyde
Product
Yield (%)
Found
[Refs.]
O
1-Naphthaldehyde
Cinnamaldehyde
Vanilline
CN
25
25
88
216–217
180–181
241–242
210–212
–
215–218 [24]
Me
O
NH2
Me
O
11
12
13
14
85
91
90
0
182–184 [25]
138–240 [26]
214–216 [27]
–
CN
Me
NH2
Me
OH
OMe
O
CN
23
Me
O
N
NH2
Me
O
Isonicotinaldehyde
Butyraldehyde
CN
21
Me
NH2
Me
O
CN
24 h
O
NH2
Me
Me
a
Yields refer to isolated product
afforded a satisfactory result. However, butyraldehyde as an aliphatic aldehydes did
not proceed further this reaction.
The mechanism of the formation of 2-amino-4H-chromene derivatives in the
presence of AMBA–Fe3O4 as a catalyst via a three-component coupling strategy is
proposed to begin with a Knoevenagel condensation between malononitile and the
aromatic aldehyde, followed by the Michael addition of dimedone to the
Knoevenagel product, and finally an intramolecular ring closure (Scheme 3) [28].
We also investigated the recyclability of the AMBA–Fe3O4 as a magnetic
nanocatalyst using the model reaction of benzaldehyde, malononitrile and dimedone
(Table 2, entry 1). The results showed that AMBA–Fe3O4 is a stable catalyst in
reaction media and can be reused five times without any significant loss of its
activity (Fig. 6).
123

A simple synthesis of magnetic nanoparticles supported…
O
Fe3O4
NH2
O
O
H
O
O
O
Ar
H
+
NH2
Ar
O
H
NC
CN
O
- H2O
Fe3O4
O
O
Fe3O4
NC
CN
O
Knoevenagel condensation
Michael additian
O
Ar
O
CN
NH2
NH2
H
O
Ar
H
CN
tautomerization
CN
O
O
Ar
O
H
Protonation
CN
NH
O
Ar
O
H
O
Fe3O4
NH2
CN
O
Cyclization
N
Scheme 3 The suggested mechanism for the formation of the 2-amino-4H-chromene derivatives
Fig. 6 The recycling of the AMBA–Fe3O4 nanoparticles as a catalyst
To show the efficiency of this method, the results of the synthesis of 2-amino-4H-
chromene derivatives by our method was compared with those reported in the
literature. The results show that this nanocatalyst is very efficient with respect to the
reaction times and yields (Table 3).
123

M. M. Khodaei et al.
Table 3 Comparison of the results of the AMBA–Fe3O4 magnetic nanocatalyst with other catalysts in
the synthesis of 2-amino-4H-chromene derivatives
Entry
Catalyst
Conditions
Time
(min)
Yield (%)a [refs.]
1
2
SO42-/MCM-41 (25 mg)
EtOH, reflux
50
80
86 [29]
90 [30]
Pentafluoropropionic acid
(PFPA) (0.054%)
EtOH:H2O (1: 1), r.t
3
4
Starch solution (4 ml)
50 °C
EtOH:H2O (1:1), reflux
30
45
92 [23]
90 [31]
Silica bonded S-sulfonic acid
(0.1 g)
5
AMBA–Fe3O4 nanoparticle
(0.05 gr)
60 °C, EtOH
20
93 (Present work)
a
Yields refer to isolated products
Conclusions
We have developed a new 4-aminomethylbenzoic acid functionalized Fe3O4
magnetic nanoparticles as an active and reusable base hybrid heterogeneous
catalyst. This basic nanocatalyst was characterized by different methods and its
applicability for the preparation of 2-amino-4H-chromene derivatives from
arylaldehyde, malonitrile and dimedone was investigated. This heterogeneous
catalyst is highly active and has a very high surface area, and its thermal stability
was confirmed by different characteristic techniques. The recoverability and
reusability of this inexpensive catalyst are other advantages of the protocol.
Acknowledgements This research was supported by the Research Council of the Razi University in Iran.
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