Fe3O4 nanoparticles: As an efficient, green and magnetically reusable catalyst for the one-pot synthesis of 1,8-dioxo- decahydroacridine derivatives under solvent-free conditions

Article abstract of DOI:10.1016/j.crci.2012.08.010

An efficient and environmentally friendly method for the one-pot synthesis of 1,8-dioxo-decahydroacridines has been developed in the presence of Fe ₃O₄ nanoparticles. The multicomponent reactions of aldehydes, dimedone and amines wer

Full text of DOI:10.1016/j.crci.2012.08.010

C. R. Chimie 15 (2012) 969–974
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´
Full paper/Memoire
Fe3O4 nanoparticles: As an efficient, green and magnetically reusable
catalyst for the one-pot synthesis of 1,8-dioxo-decahydroacridine
derivatives under solvent-free conditions
*
Mohammad Ali Ghasemzadeh, Javad Safaei-Ghomi , Halimeh Molaei
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, 51167 Kashan, I.R. Iran
A R T I C L E I N F O
A B S T R A C T
Article history:
An efficient and environmentally friendly method for the one-pot synthesis of 1,8-dioxo-
decahydroacridines has been developed in the presence of Fe3O4 nanoparticles. The
multicomponent reactions of aldehydes, dimedone and amines were carried out under
solvent-free conditions to obtain some 1,8-dioxo-9-aryl-10-aryl-decahydroacridine
derivatives. The present approach provides several advantages including high yields,
short reaction times, little catalyst loading and facile catalyst separation.
Received 28 February 2012
Accepted after revision 22 August 2012
Available online 19 September 2012
Keywords:
Fe3O4
´
ß 2012 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
1,8-dioxo-decahydroacridine
Solvent-free
Multicomponent reactions
Nanoparticles
Catalysts
1. Introduction
used as an efficient catalyst in many organic transforma-
tions including regioselective synthesis of 3-[(2-chloro-
Nanoscience and nanotechnology is an amazing and
growing research area that includes the preparation,
characterization and application of nanostructures with
various shapes and sizes in many chemical transforma-
tions. Nanoparticle properties are significantly different in
their bulk analogues due to their high surface-to-volume
ratio and coordination sites which provide a larger number
of active sites per unit area [1]. Recently, magnetic Fe3O4
nanoparticles have gained extensive interests because of
their wide use in several areas, including drug delivery,
medicinal applications, remediation and industry [2]. In
comparison with other nanocatalysts, Fe3O4 nanoparticles
(nano-Fe3O4) in particular, are environmentally benign,
economic and comparatively anti-toxic [3]. An important
property of these nanoparticles is simple and convenient
separation from the reaction media by a simple magnetic
separation. In recent years, magnetic nanoparticles were
quinolin-3-yl)methyl]pyrimidin-4(3H)ones [4], synthesis
of propargylic amines [5], coupling of phenols with aryl
halides [6], synthesis of
a-aminonitriles [7], Suzuki
reaction [8], synthesis of quinoxalines [9], synthesis of
sulfonamides [10], Sonogashira–Hagihara reaction [11],
Paal-Knorr reaction, aza-Michael addition and pyrazole
synthesis [12].
Research in multicomponent reactions (MCRs) is an
encouraging and hot topic of organic chemistry, because of
their advantageous in preparation of small molecule
heterocyclic libraries and in drug discovery procedures
[13]. MCRs are efficient, environmentally friendly, fast,
atom economic and time saving. They supply an effective
tool for the preparation of various compounds with
pharmaceutical and biological properties [14], including
heterocyclic compounds [15].
MCRs of aldehydes, dimedone and amines have received
much attention in recent years. During the last decades,
great consideration has been paid to the preparation of
acridine derivatives due to their highly absolute biological
and physiological activities such as anti-cancer [16],
* Corresponding author.
E-mail address: safaei@kashanu.ac.ir (J. Safaei-Ghomi).
1631-0748/$ – see front matter ß 2012 Acade´mie des sciences. Published by Elsevier Masson SAS. All rights reserved.
http://dx.doi.org/10.1016/j.crci.2012.08.010

970
M.A. Ghasemzadeh et al. / C. R. Chimie 15 (2012) 969–974
O
O
Ar
O
nano-Fe3O4
ArCHO
Ar'NH2
+
2
+
Solvent-free
120OC
O
N
Ar'
Scheme 1. Three-component reaction of aldehydes, dimedone and amines catalyzed by Fe3O4 nanoparticles.
cytotoxic [17], anti-tumor [18], anti-multidrug-resistant
[19], antimicrobial [20] and anti-fungal properties [21].
There are several methods reported in the literature for
the synthesis of 1,8-dioxo-decahydroacridines via three-
component coupling of aldehydes, dimedone and amines
in the presence of diverse catalysts including ceric
ammonium nitrate (CAN) [22], fluorotailed acidic imida-
zolium salts [23], 1-butyl-3-methylimidazolium bromide
[bmim]Br [24], 1-methylimidazolium triflouroacetate
[Hmim]TFA [25], proline [26], amberlyst-15 [27], car-
bon-based solid acid (SBSA) [28], silica-bonded N-propyl
sulfamic acid (SBNPSA) [29] and 4-dodecylbenzenesulfo-
nic acid (DBSA) [30]. However, many of these methods
suffer from disadvantages such as toxic organic solvents,
unsatisfactory yields, long reaction times, expensive
catalysts, laborious work-up procedures, the requirement
of special apparatus and harsh reaction conditions. Thus,
the development of simple, efficient, high-yielding and
eco-friendly methods using new catalysts for the synthesis
of these compounds would be highly desirable.
2. Results and discussion
Fe3O4 nanoparticles were prepared according to the
procedure reported by Zhang et al. [9] from the reaction of
FeCl2.4H2O and FeCl3.6H2O with solutions of hydrochloric
acid and then sodium hydroxide.
The XRD pattern of the Fe3O4 nanoparticles is shown in
Fig. 1. All reflection peaks can be readily indexed to pure
cubic crystal phase of Fe3O4 with F-33 mspace group
(JCDPS No. 75-0449). Also no specific peak due to any
impurities was observed. The broad peaks indicate that the
particles are in nanoscale size. The crystallite size diameter
(D) of the magnetic nanoparticles has been calculated by
Debye–Scherrer equation (D = K
(full-width at half-maximum or half-width) is in radians
and is the position of the maximum of diffraction peak, K
l/bcosu), where b FWHM
u
is the so-called shape factor, which usually takes a value of
˚
l is the X-ray wavelength (l = 1.5406 A for
about 0.9, and
Cu Ka). Average crystallite size of the prepared nano-Fe3O4
has been found to be 40 nm.
In accordance with the above mentioned points related
to the important growth of nanotechnology and MCRs in
the synthesis of heterocyclic compounds and also in
continuation of our research on the application of
nanocatalysts in organic synthesis [31–34], herein we
wish to report an efficient and novel method for the
synthesis of 1,8-dioxo-decahydroacridines via one-pot
MCRs of aldehydes, dimedone and aromatic amines in
high yields and short reaction times by using nano-Fe3O4
with high specific surface area and average crystalline size
of 40 nm as a green, robust and easily recoverable catalyst
(Scheme 1).
The XRD patterns of magnetite and maghemite are very
similar and the lattice parameter must be precisely
determined. Magnetite is an inverse-spinel with the lattice
˚
parameter of 8.3941 A. Cations are arranged with one
Fe3+ per filled tetrahedral hole, and Fe2+ and the remaining
Fe3+ randomly distributed in the octahedral holes. This
places half of the smaller cations, Fe3+, in the smaller
tetrahedral sites (as compared to the larger Fe2+ cations
and the larger octahedral sites).
The lattice parameter of synthesized magnetite is
˚
8.3876 A, which is consistent with the expected lattice
parameter for Fe3O4 particles. This value is closer to that of
Fig. 1. The XRD pattern of Fe3O4 nanoparticles.

M.A. Ghasemzadeh et al. / C. R. Chimie 15 (2012) 969–974
971
Fig. 2. SEM image of Fe3O4 nanoparticles.
˚
stoichiometric magnetite (8.3941 A) than that of maghe-
magnetite is related to presence of vacancies within the OH
sites, and the absence of Fe2+ cations.
˚
mite (8.346 A) [35,36].
In addition, the specific surface area was measured by
nitrogen physisorption (the BET method), the specific
surface area was approximately 98 m2/g. Also, the
theoretical particle size was calculated from the surface
area and magnetite density (5.18 g/cm3) from the equation
was 11.8 nm.
In early studies, to optimize the reaction conditions, the
reaction of benzaldehyde, dimedone and aniline was
chosen as the model reaction for the one-pot synthesis
of the corresponding acridine derivative.
The reaction conditions were optimized on the basis of
the catalyst, solvent and different temperature for the
synthesis of 1,8-dioxo-decahydroacridines.
Our initial studies were carried out by using several
nanoparticles including Mn3O4, CuO, CaO, MgO and Fe3O4
under various reaction conditions. The optimized condi-
tions were obtained when the reactions carried out in the
presence of nano-Fe3O4 under solvent-free conditions at
120 8C (Table 1).
In continuation of our research, the model reaction was
carried out by using various amounts of Fe3O4 nanopar-
ticles. The optimum amount of nano-Fe3O4 was 10 mol% as
shown in Table 1. Increasing this amount did not show any
change in yield and time of the reaction (Table 1, Entry 10).
The influence of solvent was studied when the model
reaction was performed using Fe3O4 nanoparticles under
various solvents and solvent-free conditions (Table 1,
ꢀ
ꢁ
6000
ꢀ S
DBET
¼
r
In order to investigate the morphology and particle size
of Fe3O4 nanoparticles, SEM images of magnetic nanopar-
ticles are presented in Fig. 2. These results show that
spherical Fe3O4 nanoparticles were obtained with an
average diameter of 45 nm as confirmed by XRD analysis.
The IR spectra of prepared Fe3O4 nanoparticles is shown
in Fig. 3. The results in Fig. 3 show that the data are the
same as reported in literature. A strong peak at around
570 cmꢁ1 is related to Fe-O stretching frequency. Whereas
the IR spectra of Fe2O3 reported in literature is more
complicated in comparison with the IR spectra of magne-
tite [37–40]. Difference of IR spectra of maghemite from
Fig. 3. FT-IR spectrum of Fe3O4 nanoparticles.

972
M.A. Ghasemzadeh et al. / C. R. Chimie 15 (2012) 969–974
Table 1
Optimization of model reaction by using various catalysts, solvents and
amount of magnetic nanoparticles.a
Entry
Catalyst
Catalyst
(mol %)
Solvent
Time
Yields
(%)b
(min)
1
Mn3O4
CuO
20
20
20
20
20
20
20
20
15
10
5
EtOH
120
150
200
180
60
55
45
30
40
75
45
25
85
85
85
80
2
EtOH
3
CaO
EtOH
4
MgO
EtOH
5
Fe3O4
Fe3O4
Fe3O4
Fe3O4
Fe3O4
Fe3O4
Fe3O4
EtOH
6
DMF
140
300
25
7
Toluene
Solvent-free
Solvent-free
Solvent-free
Solvent-free
8
9
25
10
11
25
35
a
Reaction conditions: benzaldehyde (1 mmol), dimedone (2 mmol)
and aniline (1 mmol).
Fig. 4. Recoverability of Fe3O4 nanoparticles in the model reaction.
b
Isolated yields.
and Me (Table 2, Entries 11, 14) afforded the desired
products in short reaction times and high yields.
Entries 5–8). The best results were obtained under solvent-
free conditions (Table 1, Entry 8). As shown in Table 1, the
time of reaction was significantly decreased, but the yield
of product formation increased in comparison with solvent
conditions.
3. Catalyst recovery
After completion of the reaction, the reaction mixture
was dissolved in chloroform and then the catalyst was
separated magnetically. The magnetic Fe3O4 nanoparticles
were washed three to four times with chloroform and
methanol and dried at 100 8C for 5 h. The separated catalyst
was used several times with a slightly decreased activity as
shown in Fig. 4.
We next used several kinds of aldehydes and amines to
investigate their three-component reactions under the
optimal reaction conditions (Scheme 1, Table 2). As shown
in Table 2, aldehydes containing either electron-with-
drawing or electron- releasing groups gave the corre-
sponding 1,8-dioxo-decahydroacridines in high yields. In
addition, it was specifically considerable that aryl alde-
hydes bearing electron-withdrawing groups such as NO2
and Cl reacted very smoothly in short reaction times and
higher yields (Table 2, Entries 8,9) while electron-releasing
substitutions such as OMe and Me (Table 2, Entries 4, 5)
showed less reactivity in the cyclization reaction. As shown
in Table 2, these condensation reactions also proceed
suitably when different aromatic amines were used in the
synthesis of 1,8-dioxo-9-aryl-10-aryl-decahydroacridine
derivatives. In this case, we found that aromatic amines
containing electron-donating substituents such as OMe
4. Conclusions
In summary, an efficient, mild and green method for the
synthesis of 1,8-dioxo-decahydroacridine derivatives has
been developed in the presence of Fe3O4 nanoparticles
under solvent-free conditions. The products were obtained
in excellent yields and the reaction times were significant-
ly short. The present approach demonstrates a simple and
appropriate method for the three-component coupling of
aldehydes, dimedone and amines in order to synthesis of
Table 2
One-pot synthesis of 1,8-dioxo-decahydroacridines catalyzed by nano-Fe3O4.a
Entry
Ar
Ar0
Product
Time (min)
Yieldb
m.p (8C)
Lit. m.p (8C)
1
Ph
Ph
4a
4b
4c
4d
4e
4f
25
40
30
35
50
35
20
15
15
20
20
10
12
18
30
15
85
75
80
80
70
75
88
90
92
90
85
90
95
88
80
90
254–255
225–227
208–210
260–262
270–272
219–221
298–299
288–290
244–246
254–256
260–262
272–274
269–270
215–216
239–241
233–235
(254–256)[22]
–
2
o-MeC6H4
m-MeC6H4
p-MeC6H4
o-OMeC6H4
p-OMeC6H4
m-NO2C6H4
p-NO2C6H4
p-ClC6H4
p-BrC6H4
Ph
Ph
3
Ph
–
4
Ph
(260–263)[30]
(270–272)[22]
(220–222)[22]
(297–299)[22]
(289–290)[30]
(244–246)[22]
(255–257)[30]
(260–263)[28]
–
5
Ph
6
Ph
7
Ph
4g
4h
4i
8
Ph
9
Ph
10
11
12
13
14
15
16
Ph
4j
p-MeC6H4
p-MeC6H4
p-MeC6H4
p-OMeC6H4
p-OMeC6H4
p-OMeC6H4
4k
4l
p-NO2C6H4
p-ClC6H4
Ph
4m
4n
4o
4p
(270–271)[28]
(215–217)[23]
(238–240)[28]
–
p-MeC6H4
p-CNC6H4
a
All the reactions were carried out under solvent-free conditions.
Isolated yields.
b

M.A. Ghasemzadeh et al. / C. R. Chimie 15 (2012) 969–974
973
some heterocyclic compounds via magnetic nanoparticles
as novel, effective and simple reusable catalyst.
2H, 2 ꢀ CH), 2.05–2.09 (d, J = 16.5 Hz, 2H, 2 ꢀ CH), 2.12–2.16
(d, J = 16.5 Hz, 2H, 2 ꢀ CH), 2.18–2.22 (d, J = 16 Hz, 2H,
2 ꢀ CH), 2.32 (s, 3H, CH3), 5.25 (s, 1H, CH), 7.13–7.31 (m, 5H,
5. Experimental method
ArH), 7.55–7.57 (m, 4H, ArH); 13C NMR (100 MHz, CDCl3):
d
22.2, 26.9, 29.7, 32.3, 32.4, 41.5, 51.3, 112.1, 114.8, 127.4,
128.8, 129.4, 130.1, 131.6, 135.2, 139.1, 144.8, 150.1, 195.7.
Anal. Calcd. For C30H33NO2: C 81.97, H 7.57, N 3.19. Found C
81.82, H 7.65, N 3.28. MS (EI) (m/z): 439 (M+).
5.1. Materials and techniques
Chemicals were purchased from the Sigma-Aldrich and
Merckinhighpurity. Allofthematerialswereofcommercial
reagent grade and were used without further purification.
All melting points are uncorrected and were determined in
capillary tube on Boetius melting point microscope. 1H NMR
and 13C NMR spectra were obtained on Bruker 400 MHZ
spectrometer with CDCl3 as solvent using tetramethylsilane
(TMS) as an internal standard, the chemical shift values are
3,3,6,6-Tetramethyl-9-(3-methylphenyl)-10-phenyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
Yellow powder; IR (KBr) (
max/cmꢁ1): 2954, 2873, 1642,
1574, 1362, 1221, 842; 1H NMR (400 MHz, CDCl3):
0.79
(4c).
v
d
(s, 6H, 2 ꢀ CH3), 0.94 (s, 6H, 2 ꢀ CH3), 1.78–1.85 (d,
J = 16.2 Hz, 2H, 2 ꢀ CH), 2.05–2.08 (d, J = 16.6 Hz, 2H,
2 ꢀ CH), 2.13–2.17 (d, J = 16.6 Hz, 2H, 2 ꢀ CH), 2.20–2.46
(d, J = 16.2 Hz, 2H, 2 ꢀ CH), 2.31 (s, 3H, CH3), 5.24 (s, 1H,
CH), 6.91(s, 1H, ArH), 7.13–7.26 (m, 3H, ArH), 7.44–7.61
in d. FT-IR spectrum was recorded on Magna-IR, spectrom-
eter 550 Nicolet in KBr pellets in the range of 400–
4000 cmꢁ1. The elemental analyses (C, H, N) were obtained
from a Carlo ERBA Model EA 1108 analyzer. The N2
adsorption/desorption analysis (BET) was performed at
–196 8C using anautomatedgas adsorption analyzer (Tristar
3000, Micromeritics). Powder X-ray diffraction (XRD) was
(m, 5H, ArH); 13C NMR (100 MHz, CDCl3):
d 22.1, 26.8, 29.8,
32.3, 32.3, 41.5, 51.4, 112.1, 115.1, 127.4, 128.7, 129.8,
131.1, 132.1, 135.7, 138.9, 145.1, 150.1, 195.7. Anal. Calcd.
For C30H33NO2: C 81.97, H 7.57, N 3.19. Found C 82.08, H
7.48, N 3.11. MS (EI) (m/z): 439 (M+).
carried out on a Philips diffractometer of X’pert Company
˚
3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-10-(p-tolyl-
with monochromatized Ag K
a
radiation (
l
= 1.5406 A).
phenyl)-1,2,3,4,5,6,7,8,9,10
dione (4l). Yellow powder; IR (KBr) (
2873, 1639, 1576, 1514, 1359, 1222, 863; 1H NMR
(400 MHz, CDCl3):
decahydroacridine-1,8-
Microscopic morphology of products was visualized by SEM
(LEO 1455VP). The mass spectra were recorded on a Joel D-
30 instrument at an ionization potential of 70 eV.
v
max/cmꢁ1): 2956,
d
0.92 (s, 6H, 2 ꢀ CH3), 1.12 (s, 6H,
2 ꢀ CH3), 1.84–1.88 (d, J = 17.6 Hz, 2H, 2 ꢀ CH), 2.07–2.13
(m, 4H, 4 ꢀ CH), 2.23–2.28 (d, J = 17.6 Hz, 2H, 2 ꢀ CH), 2.50
(s, 3H, CH3), 5.34 (s, 1H, CH), 7.09-7.11 (d, J = 7.2 Hz, 2H,
ArH), 7.37–7.39 (d, J = 7.2 Hz, 2H, ArH), 7.59–7.61 (d,
J = 8.1 Hz, 2H, ArH), 8.12-8.14 (d, J = 8.1 Hz, 2H, ArH); 13C
5.2. Preparation of Fe3O4 nanoparticles
To a solution of FeCl2.4H2O (2.5 g) and FeCl3.6H2O (6 g)
in 30 mL deionized water was added dropwise 1.0 mL of
concentrated hydrochloric acid at room temperature. The
solution was added in to 300 mL of 1.5 mol Lꢁ1 NaOH and
then the solution was stirred vigorously at 70 8C until
precipitation. Afterwards, the prepared magnetic nano-
particles were separated magnetically, washed with
deionized water and then dried.
NMR (100 MHz, CDCl3):
d 23.4, 26.7, 29.7, 32.4, 32.9, 41.7,
50.1, 113.5, 116.5, 123.5, 128.8, 129.7, 138.2, 146.2, 148.1,
150.4, 152.9, 195.7. Anal. Calcd. For C30H32N2O4: C 74.36, H
6.66, N 5.78. Found C 74.22, H 6.78, N 5.89. MS (EI) (m/z):
484 (M+).
3,3,6,6-Tetramethyl-9-(4-cyanophenyl)-10-(4-meth-
oxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-
5.3. General procedure for the synthesis of 1,8-dioxo-
decahydroacridine (4a-p)
dione (4p). Yellow powder; IR (KBr) (
2875, 2224, 1640, 1574, 1510, 1364, 1221, 849; 1H NMR
(400 MHz, CDCl3):
v
max/cmꢁ1): 2957,
d
0.79 (s, 6H, 2 ꢀ CH3), 0.96 (s, 6H,
A mixture of aldehyde (1 mmol), dimedone (2 mmol),
aromatic amine (1 mmol) and Fe3O4 nanoparticles (0.02 g,
0.1 mmol, 10 mol%) in a round bottom flask was heated
with stirring in the oil bath at 120 8C for appropriate times.
During the procedure, the reaction was monitored by Thin
Layer Chromatography (TLC). Upon completion, the reac-
tion mixture was cooled to room temperature and the
reaction mixture was dissolved in chloroform. The catalyst
was insoluble in CHCl3 and separated magnetically. The
solvent was evaporated and the solid was obtained
recrystallized from ethanol to afford the pure acridines.
2 ꢀ CH3), 1.84–1.89 (d, J = 17.6 Hz, 2H, 2 ꢀ CH), 2.06–2.10
(d, J = 17.6 Hz, 2H, 2 ꢀ CH), 2.13–2.22 (m, 4H, 4 ꢀ CH), 3.93
(s, 3H, OCH3), 5.28 (s, 1H, CH), 7.06–7.08(d, J = 8.4 Hz, 2H,
ArH), 7.11–7.13 (d, J = 8.4 Hz, 2H, ArH), 7.54 (m, 4H, ArH);
13C NMR (100 MHz, CDCl3):
d 26.7, 29.7, 32.3, 33.7, 41.8,
50.1, 55.7, 109.5, 113.5, 115.1, 119.3, 128.8, 131.1, 132.0,
150.9, 151.6, 160.1, 195.7. Anal. Calcd. For C31H32N2O3: C
77.47, H 6.71, N 5.83. Found C 77.32, H 6.65, N 5.99. MS (EI)
(m/z): 480 (M+).
Acknowledgements
5.4. Spectral data of new compounds
The authors are grateful to University of Kashan for
supporting this work by Grant NO: 65384.
3,3,6,6-Tetramethyl-9-(2-methylphenyl)-10-phenyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
Yellow powder; IR (KBr) (
max/cmꢁ1): 2952, 2875, 1644,
1572, 1366, 1224, 845; 1H NMR (400 MHz, CDCl3):
0.81 (s,
6H, 2 ꢀ CH3), 0.95 (s, 6H, 2 ꢀ CH3), 1.79–1.84 (d, J = 16 Hz,
(4b).
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