Magnetic nickel ferrite nanoparticles as an efficient catalyst for the preparation of polyhydroquinoline derivatives under microwave irradiation in solvent-free conditions

Article abstract of DOI:10.1007/s11164-015-2163-6

An easy and convenient method is reported for the synthesis of polyhydroquinoline derivatives in solvent-free conditions under microwave irradiation in the presence of magnetic nickel ferrite nanoparticles (NiFe₂O₄ MNPs) as a catalys

Full text of DOI:10.1007/s11164-015-2163-6

Res Chem Intermed
DOI 10.1007/s11164-015-2163-6
Magnetic nickel ferrite nanoparticles as an efficient
catalyst for the preparation of polyhydroquinoline
derivatives under microwave irradiation in solvent-free
conditions
Hamideh Ahankar1 Ali Ramazani1
•
•
Sang Woo Joo2
Received: 27 January 2015 / Accepted: 1 July 2015
Ó Springer Science+Business Media Dordrecht 2015
Abstract An easy and convenient method is reported for the synthesis of polyhydro-
quinoline derivatives in solvent-free conditions under microwave irradiation in the presence
of magnetic nickel ferrite nanoparticles (NiFe2O4 MNPs) as a catalyst. Excellent yields
(82–94 %), facile work-up, achieving high purity of products via simple recrystallization,
and short reaction times (2–5 min) are some advantages of this procedure. It is worth noting,
the catalyst is magnetically removed without significant loss of activity for reuse a few times.
Graphical Abstract
Ar
H
O
Ar
O
O
1a-r
O
2
O
t
E
O
OEt
+
NiFe2O4 MNPs(10 mol %)
MW, Solvent-free
N
H
O O
5a-r
4
NH4OAc
3
&
&
Ali Ramazani
aliramazani@gmail.com
Sang Woo Joo
swjoo@yu.ac.kr
1
2
Department of Chemistry, University of Zanjan, P O Box 45195-313, Zanjan, Iran
School of Mechanical Engineering, Yeungnam University, Gyeongsan 712-749,
Republic of Korea
123

H. Ahankar et al.
Keywords Nickel ferrite Á Magnetic nanoparticles Á Polyhydroquinoline Á
Microwave irradiation Á Solvent-free
Introduction
Polyhydroquinolines derivatives, 4-substituted 1,4-dihydropyridines (1,4-DHPs)
compounds (Fig. 1), are an essential framework of a great category of biologically
active heterocycles [1]. They are well-known compounds as an important class of
drugs and analogues of NADH co-enzymes [2]. The therapeutic usages of 1,4-DHPs
include significant biological activity [3, 4], various drugs such as nifedipine,
nicardipine, benidipine, amolodipine, lacidipine, (Fig. 2) and other related deriva-
tives for treatment of hypertension as an effective cardiovascular agent [5, 6], and
having a variety of biological properties such as vasodilator, antitumour, antidi-
abetic, anti-atherosclerotic, bronchodilator, anti-oxidant, geroprotective and hep-
taprotective agents [7, 8].
Quinoline derivatives with 1,4-dihydropyridine scaffolding have pharmacolog-
ical properties. Some compounds of this family are antimalarial, anti-asthmatic,
anti-inflammatory, antibacterial, and tyrosine kinase inhibiting agents [9, 10]. Other
researches indicate that 1,4-DHPs express different medical functions as neuropro-
tectants, having platelet anti-aggregatory activity, cerebral anti-ischemic agents, and
chemosensitizers [11, 12]. Also, numerous synthetic methods by MCRs have been
reported for the preparation of 1,4-dihydropyridine derivatives under different
conditions [13–18].
In view of the importance of polyhydroquinolines derivatives, numerous and
various methods by MCRs have been reported for synthesis of these compounds,
which include the use of grinding [19], solar thermal energy [20], microwave
irradiation by Ni nanoparticles [21], ZnO-Beta Zeolite [22], PEG 4000-bound
acetoacetate [23], composite-A (ZnFe0.2Al1.8O4) [24], and silica sulfuric acid [25];
and also using different catalysts such as L-proline [26], montmorillonite K-10 clay
[27], molecular iodine [28], Scolecite (CaAl2Si3O10Á3H2O) [29], ZnO nanoparticles
[30], HClO4–SiO2 [31], nanocrystalline copper(II) oxide [32], ionic liquids [33],
and metal triflates such as Yb(OTf)3 [34]. In addition, these MCRs have been
performed by use of BINOL-phosphoric acid [35], Carbon-based Solid acid (CBSA)
Fig. 1 General molecular
structure of 1,4-DHPs
R
R2
R1
R2
R1
N
H
123

Magnetic nickel ferrite nanoparticles as an efficient…
NO2
CO2
N
Ph
NO2
MeO2C
MeO2C
CO2Me
N
H
N
H
Nicardipine
Nifedipine
NO2
CO2
MeO2C
N
N
H
Ph
Benidipine
CO2
Cl
MeO2C
CO2Me
MeO2C
CO2Me
O
N
H
NH2
N
H
Lacidipine
Amlodipine
Fig. 2 Molecular structures of dihydropyridine drugs
[36], DBH or DCH [37], and SO3H-functionalized ILs under ultrasound irradiation
[38].
However, in past reports, the existence of some drawbacks such as long reaction
times, harsh conditions, toxic organic solvents, high temperatures, high costs, low
123

H. Ahankar et al.
product yields, being expensive, having difficulty to reuse, and unecofriendly
catalysts limit the use of these methods.
In recent years, magnetic nanoparticles (MNPs) have emerged as an attracting
class of catalysts, because of the increasing need to develop low-cost, green,
efficient, and reusable catalysts. Their nano-size property maximizes the contact
between reactants and the catalyst, thus mimicking a heterogeneous catalyst. Use of
magnetically separable catalysts is one of the most promising strategies. These
systems combine the advantages of nanosized catalysts and magnetic properties,
thus, providing the opportunity for quantitative recovery of the catalyst by the use of
an external magnet, making it cost-effective and potentially applicable for industrial
application [39, 40].
In this regard, iron-based materials, which benefit their terrestrial abundance and
low toxicity, have been extensively exploited as catalysts in many organic
transformations. Nickel ferrite MNPs are inexpensive, air-stable, magnetically
separable, and economical catalysts [41–44]. There are very limited and there are
less references about catalytic properties of nickel ferrite MNPs [45–47]. These
spinel-type bimetal oxides, have shown great potential in the field of use for
catalysis, although they have so far been less investigated.
In recent years, the organic reactions on solid supports in the absence of a solvent
and in solvent-free conditions have received considerable attention of synthetic
chemists because of their high efficiency, environmentally benign conditions,
convenient workup procedures, enhanced selectivity, milder reaction conditions,
much improved reaction rates and formation of cleaner products [48]. Aiming to use
these advantages, we planned to develop a solvent-free protocol for synthesis of
polyhydroquinoline derivatives in solvent-free conditions.
As part of our ongoing program to develop efficient and robust methods for
the synthesis of heteroatom-containing organic compounds [49–52], we report an
easy and convenient method for synthesis of polyhydroquinoline derivatives in
solvent-free conditions under microwave irradiation in the presence of magnetic
nickel ferrite nanoparticles (NiFe2O4 MNPs) as a catalyst. According to the best
of our knowledge, there is no report on the use of NiFe2O4 MNPs as a magnetic
Ar
H
O
O
2
O
Ar
O
O
1(a-r)
NiFe2O4 MNPs (10 mol %)
MW, Solvent-free
OEt
OEt
+
O O
N
H
4
5(a-r)
NH4OAc
3
Scheme 1 Synthesis of polyhydroquinoline derivatives in the presence of NiFe2O4 MNPs
123

Magnetic nickel ferrite nanoparticles as an efficient…
nanocatalyst. Therefore, this fact has caused us to apply the new catalyst for the
synthesis of polyhydroquinoline derivatives with a facile and appropriate method
under eco-friendly conditions, as shown in Scheme 1.
Experimental
Materials and methods
Starting materials were obtained from Merck, Fluka, and Aldrich and were used
without further purification. The methods used to follow the reactions are TLC. The
microwave-assisted procedures were carried out in a Milestone Microwave Oven
operating at 1600 W. Melting points were measured on an Electrothermal 9100
1
apparatus (LABEQUIP LTD., Markham, Ontario, Canada) and are uncorrected. H
(DMSO-d6) and 13C NMR (DMSO-d6) spectra were recorded on a Bruker DRX-250
Avance spectrometer at 250.13 and 62.90 MHz, respectively. IR spectra were
measured on a Jasco 6300 FTIR spectrometer. Elemental analysis was performed
using inductively coupled plasma optical emission spectroscopy (ICP-OES, Model:
VISTA-PRO).
The structural properties of NiFe2O4 MNPs were analyzed by X-ray powder
diffraction (XRD) with a X’Pert-PRO advanced diffractometer using Cu (Ka)
˚
radiation (wavelength: 1.5406 A), operated at 40 kV and 40 mA at room
temperature in the range of 2h from 20° to 80°. The particle size and morphology
of the surfaces of the sample were analyzed by a scanning electron microscopy)
KYKY Co., China, Model: EM 3200). The disc was coated with gold in an
ionization chamber. Transmission electron microscopy was studied using a Zeiss-
EM10C TEM instrument with an accelerating voltage of 80 kV.
Preparation of catalyst (NiFe2O4 MNPs)
Nickel ferrite nanoparticles were prepared via the auto-combustion assisted sol–gel
method of Fe(III) and Ni(II) ions (molar ratio 2:1) in ammonia solution [53, 54].
Briefly, Fe(NO3)3Á9H2O (2 mol), Ni(NO3)2Á6H2O (1 mol) and citric acid as
chelating agent (3 mol) were dissolved in deionized water. The pH value was
controlled at 7 by dropwise adding ammonia solution (28 %) to the reaction mixture
under fixed stirring. Then, the solution was vaporized in a water bath (60 °C) to
form a sticky gel. The temperature was increased to 80 °C in order to obtain a thick
gel. The thick gel was held on a hot plate for auto combustion and the temperature
was increased to ca. 200 °C. A large amount of gases such as CO2, H2O, and N2
were released and auto combustion occurred, giving rise to a dark brown ferrite
powder. The powder was washed with deionized water and acetone three times and
separated by using a strong external magnet.
123

H. Ahankar et al.
General experimental procedure for the synthesis of polyhydroquinoline
derivatives
A mixture of aldehyde 1a–r (1 mmol), dimedone 2 (1 mmol), ammonium acetate 3
(1.5 mmol), ethylacetoacetate 4 (1 mmol), and 23.4 mg of NiFe2O4 nanoparticles
(10 mol%) were taken in a glass rod and irradiated in a microwave oven (500 W;
when the reaction mixtures were placed under microwave irradiation, MW heating
causes melting reactants that led to the partially liquefied reaction mixture and
achieved fairly good mixing of the reactants with the catalyst). The progress of the
reaction was checked by TLC (n-Hexane: EtOAc, 10:4). After completion, the
resulting product was heated in ethanol. The catalyst was magnetically removed
from the mixture and washed several times with ethanol for reuse. Then, the residue
was poured into crushed ice and stirred for several minutes. The solid product was
filtered and the pure product was obtained by recrystallization from hot ethanol–
water.
Physical and spectral data of ethyl 4-(4-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-
1,4,5,5,7,8-hexahydroquinoline-3-carboxylate (5m, Table 3, Entry 13): Yield:
94 %; M.P. 233–235 °C (Ref. [42] 232–234 °C). IR (KBr): 3488, 3277, 3073,
2958, 2930, 1683, 1491, 1590, 1480, 1194 cm-1
.
1H NMR (DMSO-d6,
250.13 MHz) d 0.83 (3H, s, CH3), 0.98 (3H, s, CH3), 1.12 (3H, t, CH3,
J = 6.5 Hz), 1.91–2.42 (4H, m, 2 9 CH2), 2.38 (3H, s, CH3), 3.94 (2H, q, CH2,
J = 6.2 Hz), 4.71 (1H, s, CH), 6.54 (2H, d, J = 6.8 Hz, Arom.), 6.91 (2H, d,
J = 7.0 Hz, Arom.), 8.96 (1H, s, OH), 9.04 (1H, s, NH). 13C NMR (DMSO-d6,
62.90 MHz) d 14.60, 18.68, 26.89, 29.61, 32.56, 35.21, 50.73, 59.39, 104.56,
110.76, 114.87, 128.77, 138.86, 144.82, 149.59, 155.67, 167.45, 194.76.
20
30
40
50
60
70
2θ
Fig. 3 XRD pattern of NiFe2O4 MNPs
123

Magnetic nickel ferrite nanoparticles as an efficient…
Results and discussion
Catalyst characterization
Magnetic nickel ferrite nanoparticles were synthesized by the auto-combustion
assisted sol–gel method [43, 44]. The structural properties of the NiFe2O4 MNPs
were investigated by X-ray diffraction (XRD), scanning electron microscopy
(SEM), transmission electron microscopy (TEM), inductively coupled plasma
(ICP), and IR. The X-ray diffraction (XRD) pattern of catalyst powder presented the
average diameter of that was determined to be 59.2 nm by the Debye–Scherrer
equation (Fig. 3). The diffraction peaks at 30.45°, 35.76°, 37.30°, 43.43°, 53.84°,
57.34°, and 63.01° corresponded with Miller indices observed in (2 2 0), (3 1 1), (2
2 2), (4 0 0), (4 2 2), (5 1 1), and (4 4 0) planes, respectively. These results show the
cubic spinel structure of nickel ferrite (JCPDS: 01-074-2081).
The grain size and morphology of the NiFe2O4 MNPs powder were determined
by scanning electron microscopy (SEM) (Fig. 4). SEM images show the average
size of the grains with spherical morphology is 59 nm and that has good agreement
with the XRD pattern.
Also, the grain and size morphology of the NiFe2O4 MNPs were investigated by
transmission electron microscopy (TEM) (Fig. 5). They had spherical morphology
Fig. 4 SEM images of NiFe2O4 MNPs
123

H. Ahankar et al.
Fig. 5 TEM images of NiFe2O4 MNPs with magnification of 63KX
with a size distribution from 20 to 84 nm and a mean grain size of 46 nm. The
presence of some larger particles could be attributed to aggregating (it may be a
result of a long time (ca. 20 months) holding the NiFe2O4 MNPs in their pure form
at the laboratory conditions) or overlapping of smaller particles.
Inductively coupled plasma (ICP) analysis of nickel ferrite presented the atomic
ratio of Ni–Fe at about 0.53, which is close to NiFe2O4 and 24.8 % of its weight
contains the nickel element.
123

Magnetic nickel ferrite nanoparticles as an efficient…
100
80
60
40
4000
350
3000
2500
2000
1500
1000
500
0
Wavenumber(cm-1)
Fig. 6 FTIR spectrum of NiFe2O4 MNPs
Table 1 Effect of the catalyst amount on the synthesis of polyhydroquinoline derivatives
Entry
Catalyst (mol%)
Time (min)
Yield (%)a
1
2
3
4
None
5
20
12
4
75
85
94
92
10
15
4
Reactions were carried out with 4-hydroxybenzaldehyde 1m (1 mmol), dimedone 2 (1 mmol), ammo-
nium acetate 3 (1.5 mmol), and ethyl acetoacetate 4 (1 mmol), under microwave irradiation at 500 W in
solvent-free conditions
a
Isolated yield
Table 2 Effect of microwave power on the synthesis of polyhydroquinoline derivatives
Entry
Catalyst (mol%)
Microwave power (W)
Time (min)
Temperature (°C)
Yield (%)a
1
2
3
4
5
6
10
10
10
10
10
–
400
450
500
600
–
4
4
–
78
89
94
72
81
79
–
4
–
4
–
30
45
110
110
–
Reactions were carried out with 4-hydroxybenzaldehyde 1m (1 mmol), dimedone 2 (1 mmol), ammo-
nium acetate 3 (1.5 mmol), and ethyl acetoacetate 4 (1 mmol), with 23.4 mg of NiFe2O4 MNPs
(10 mol%) in solvent-free conditions
a
Isolated yield
123

H. Ahankar et al.
Table 3 NiFe2O4 MNPs catalyzed the synthesis of polyhydroqunoline derivatives via a four-component
Hantzsch condensation
Entry
Ar
Product
Time (min)
Yield (%)a
M.P. (°C)
References
1
Ph
5a
5b
5c
5d
5e
5f
3
2
3
3
3
4
4
3
4
4
4
4
4
4
4
3
3
5
90
92
90
85
90
93
89
85
90
87
82
91
94
87
87
87
85
90
201–204
240–242
176–178
207–209
244–247
231–234
207–209
254–256
233–235
259–261
256–258
239–241
233–235
182–184
228–231
247–249
237–240
198–200
202–204 [34]
241–243 [26]
176–179 [26]
206–207 [37]
245–246 [30]
231–233 [30]
208–210 [30]
253–255 [34]
234–235 [38]
260–261 [34]
257–259 [34]
241–243 [32]
232–234 [42]
181–183 [33]
229–231 [34]
246–248 [34]
238–240 [37]
197–199 [38]
2
4-NO2–C6H4
3-NO2–C6H4
2-NO2–C6H4
4-Cl–C6H4
3-Cl–C6H4
2-Cl–C6H4
4-Br–C6H4
3-Br–C6H4
4-Me–C6H4
4-MeO–C6H4
4-MeS–C6H4
4-OH–C6H4
4-(Me)2CH–C6H4
4-(Me)2N–C6H4
2-Furyl
3
4
5
6
7
5g
5h
5i
8
9
10
11
12
13
14
15
16
17
18
5j
5k
5l
5m
5n
5o
5p
5q
5r
2-Thienyl
2-Naphthal
Reaction conditions: aldehyde 1a–r (1 mmol), dimedone 2 (1 mmol), ammonium acetate 3 (1.5 mmol),
ethyl acetoacetate 4 (1 mmol), and 23.4 mg of catalyst (10 mol%) under microwave irradiation (500 W)
in solvent-free conditions
a
Isolated yield
Also, the FT-IR spectrum of the NiFe2O4 MNPs is demonstrated in Fig. 6. Two
principle absorption bands in the range of 400–600 cm-1 are seen. The first band is
around 469 cm-1 and the second one is around 580 cm-1, attributed to the long
bond length of oxygen metal ions in the octahedral sites and the shorter bond length
of oxygen–metal ions in the tetrahedral sites in the spinel structure, respectively. A
large number of OH groups are presented on the surface of the MNPs that show a
broad absorption band at about 3439 cm-1 for the stretching mode of H2O
molecules.
The role of prepared catalyst in the synthesis of polyhydroquinoline derivatives
was investigated under microwave irradiation in solvent-free conditions. We
optimized the reaction conditions such as catalyst amount, microwave power, and
reaction times. First, the efficiency and amount of the NiFe2O4 MNPs catalyst were
investigated in a model reaction of 4-hydroxy benzaldehyde 1m (1 mmol),
dimedone 2 (1 mmol), ammonium acetate 3 (1.5 mmol), and ethylacetoacetate 4
(1 mmol) for the synthesis of compound 5m (Table 3, entry 13). As shown in
Table 1, the optimum yield of the product was obtained when 23.4 mg of catalyst
(10 mol%) was used.
123

Magnetic nickel ferrite nanoparticles as an efficient…
r
A
O
O
t
OE
+
(Path 1)
(Path 2)
O
H2N
(Path 3)
+ NH4OAc
-
AcOH
+ ArCHO
-
H2O
-
H2O
O
Ar
O
O
O
OEt
OEt
N
H
O
O
Target Product
-
AcOH
-
H2O
(Path 3')
Ar
(Path 2')
+
c
+
ArCHO
NH4OA
-
H2O
(Path 1')
O
O
OEt
+
O
NH2
NiFe2O4 MNPs
=
Scheme 2 Proposed mechanistic paths for the synthesis of polyhydroqunoline derivatives
Table 4 Comparison of the catalytic efficiency of NiFe2O4 MNPs with known catalysts
Entry Catalyst
Solvent
–
Conditions Time
(min)
Yield
(%)a
References
1
2
Nanocrystalline copper(II)
oxide
140 °C
35
32
80
86
[32]
[24]
(ZnFe0.2Al1.8O4)
Water–
HCl
MW
3
4
5
6
Yb(OTf)3
EtOH
EtOH
–
rt
480
60
20
4
90
91
86
94
[34]
Scolecite
reflux
rt
[29]
ZnO Nps
[30]
NiFe2O4 MNPs
–
MW
This work
Reactions were carried out with 4-hydroxybenzaldehyde 1m (1 mmol), dimedone 2 (1 mmol), ammo-
nium acetate 3 (1.5 mmol), ethyl acetoacetate 4 (1 mmol), and 23.4 mg of NiFe2O4 MNPs (10 mol%)
a
Isolated yield
The effect of microwave power inputs from 400 to 600 W on the synthesis of
compound 5m (Table 3, entry 13) as a model reaction was evaluated (Table 2). The
reaction yield increased with the microwave power at 500 W in comparison to 400
and 450 W but decreased at 600 W. Also, we investigated this reaction in thermal
conditions without microwave irradiation in the absence of catalyst and with
123

H. Ahankar et al.
Table 5 Reusability and
recovery of the catalyst
Run
Yield (%)a
Recovery of NiFe2O4 MNPs (%)
Fresh
First
94
94
90
93
91
97
96
96
95
93
Second
Third
Forth
a
Isolated yield
catalyst in solvent-free conditions for the synthesis of compound 5m (Table 3, entry
13). Ultimately, solvent-free conditions under microwave irradiation were preferred
due to short reaction times and high yields.
Then, various aromatic aldehydes carrying electron-donating and electron-
withdrawing groups on the aromatic ring in the ortho, meta, and para positions and
heterocyclic aldehydes were evaluated. Yields of the all reactions were good to
excellent. It was found that the aldehydes with electron-donating groups reacted
longer than in comparison to aldehydes with electron-withdrawing groups
(Table 3).
A proposed mechanism for the synthesis of polyhydroqunoline derivatives is
shown in Scheme 2. A Knoevenagel reaction involves the evident coupling of
aldehydes with active methylene compounds (dimedone and ethyl acetoacetate) in
paths 2 and 20. Also, in paths 3 and 30 a Michael addition of intermediates gives the
target products.
In addition, we compared the efficiency of catalytic activity of the NiFe2O4
MNPs with some known catalysts from the prior methods (Table 4). The result
expresses that this work is superior to some of the previous methods in terms of
magnetic separation of catalyst, reaction time, and yield.
Finally, the recyclability, reusability, and catalytic activity of the reaction
catalyst were examined. After the magnetic separation of catalyst from the reaction
mixture, the catalyst was washed with ethanol and dried to remove any remaining
ethanol, and reused in the further reactions for several times. As shown in Table 5,
NiFe2O4 MNPs could be reused at least five times without any inordinate reduction
in of its activity.
Conclusions
To summarize, the reported method offers a new, simple, and efficient route for the
synthesis of polyhydroquinolines derivatives via a four-component Hantzsch
condensation without solvent under microwave irradiation using magnetic nickel
ferrite nanoparticles as catalyst. Some important superiorities of this method are
short reaction time, no use of hazardous solvents, easy work-up, high yields, and
high purity. Furthermore, the use of the recyclable, reusable, inexpensive, and
commercially available catalyst makes it a useful procedure in modern synthetic
methodologies.
123

Magnetic nickel ferrite nanoparticles as an efficient…
Acknowledgments This work was supported by the ‘‘Iran National Science Foundation: INSF’’.
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