One-Pot Synthesis of 1,4-Dihydropyridine Derivatives Catalyzed by Silica-Coated Magnetic NiFe2O4 Nanoparticles-Supported H14[NaP5W30O110]

Article abstract of DOI:10.1134/S1070363217120325

Silica-coated magnetic NiFe₂O₄ nanoparticles-supported H₁₄[NaP₅W₃₀O₁₁₀] (NiFe₂O₄@SiO₂-H₁₄[NaP₅W₃₀O₁₁₀]) was succ

Full text of DOI:10.1134/S1070363217120325

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 12, pp. 2922–2929. © Pleiades Publishing, Ltd., 2017.
One-Pot Synthesis of 1,4-Dihydropyridine Derivatives Catalyzed
by Silica-Coated Magnetic NiFe2O4 Nanoparticles-Supported
H14[NaP5W30O110]1
B. Malekia*, A. V. Mofrada, R. Tayebeea, A. Khojastehnezhadb,
H. Alinezhadc, and E. Rezaei Sereshtd
a Department of Chemistry, Hakim Sabzevari University, Sabzevar, 96179-76487 Iran
*e-mail: b.maleki@hsu.ac.ir
b Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, Iran
c Faculty of Chemistry, University of Mazandaran, Babolsar, 47416-95447 Iran
D Department of Chemistry, Hakim Sabzevari University, Sabzevar, 96179-76487 Iran
Received April 20, 2017
Abstract—Silica-coated magnetic NiFe2O4 nanoparticles-supported H14[NaP5W30O110] (NiFe2O4@SiO2-
H14[NaP5W30O110]) was successfully synthesized and shown to be a versatile and highly efficient heterogeneous
catalyst for one-pot multicomponent synthesis of 1,4-dihydropyridine derivatives under solvent-free condition.
The synthesized catalyst can be magnetically recovered and reused four times without significant loss in
catalytic efficiency.
Keywords: NiFe2O4@SiO2-H14[NaP5W30O110], 1,4-dihydropyridines, magnetically recyclable catalyst
DOI: 10.1134/S1070363217120325
Multicomponent reactions (MCRs) are widely used
in heterocyclic synthesis due to their advantages such
as atom economy and bond-forming efficiency both of
which belong to the green chemistry principles [1].
These reactions can also be used in the synthesis of 1,4-
dihydropyridines which have attracted significant
attention due to their biological activity, such as anti-
tumor, vasodilator, bronchodilator, antiatherosclerotic,
and geroprotective [2]. Furthermore, 1,4-dihydro-
pyridine derivatives are analogs of NADH coenzymes
[3] which can be used for the treatment of Alzheimer’s
disease and tumor therapy [4]. Some cardiovascular
agent such as nifepidine, nicardipine, and amlodipine
are dihydropyridine derivatives important for the
treatment of hypertension [5].
cellular space [8], as well as antimalarial [9], antitumor
[10], antibacterial [11], antitubercular [12], and
acetylcholinesterase inhibitory activities [13]. Acridine
derivatives were also used in the synthesis of con-
jugates with peptides, proteins, and nucleic acids,
which demonstrated DNA-binding properties [14].
Due to biological importance of 1,4-dihydropyri-
dine derivatives, many classical methods have been
reported for their synthesis [15]. Some other synthetic
procedures have recently been proposed for the
synthesis of polyhydroquinolines, 1,8-dioxohexahydro-
acridines, and 2,5-dioxo-1,2,3,4,5,6,7,8-octahydro-
quinolines in presence of various catalysts such as
Co3O4-CNTs [16], Fe3O4@chitosan [17], SBA-15/
SO3H [18], poly(AMPS-co-AA) [19], 1,3-di(bromo or
chloro)-5,5-dimethylhydantoin [20], urea [21], anilines
or ammonium acetate [22] in the presence of p-do-
decylbenzenesulfonic acid (DBSA) [23], Amberlyst-15
[24], ammonium chloride, Zn(OAc)2· H2O, or L-proline
[25], ZnO nanoparticles [26], nano-Fe3O4 [27], 1-methyl-
imidazolium trifluoroacetate ([Hmim]TFA) [28],
nanoporous silica-supported ionic liquid (SBA-IL)
[29], silica-based sulfonic acid [30] under microwave
irradiation [31], HClO4–SiO2 [32], and ceric ammo-
nium nitrate (CAN) [33].
Polyhydroquinolines, 1,8-dioxohexahydroacridines,
and 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines have
shown various biological activities. Polyhydroquino-
lines are used in the synthesis of valuable drugs,
includng those for the treatment of angina pectoris and
cardiovascular diseases [6, 7]. Acridine derivatives
containing a 1,4-showed a positive ionotropic effect
which improves the entry of calcium to the intra-
1 The text was submitted by the authors in English.
2922

ONE-POT SYNTHESIS OF 1,4-DIHYDROPYRIDINE DERIVATIVES
2923
Scheme 1.
SiO2
2
Tetraethyl orthosilicate (TEOS)
NH4OH
H2O
NiFe2O4
SiO2
NiCl2 + FeCl3
NiFe2O4
NiFe2O4@SiO2
H14[NaP5W30O110
]
SiO2
NiFe2O4
SiO2
H [NaP W O ]
30 110
=
14
5
NiFe2O4@SiO2-H14[NaP5W30O110] (NFS-PRS)
Despite obvious advantages, the above synthetic
methods also suffer from some limitations such as low
yields, difficult preparations of catalysts, and long
reaction time. In order to overcome these restrictions,
in continuation of our previous studies on organic
reactions [34] we have become interested in using a
nanocatalyst with a supported heteropolyacid for the
synthesis of polyhydroquinolines, 1,8-dioxohexahydro-
acridines, and 2,5-dioxo-1,2,3,4,5,6,7,8-octahydro-
quinolines.
Curie temperature, magnetization, and relatively high
permeability.
The catalyst NiFe2O4@SiO2-H14[NaP5W30O110
]
(NFS-PRS) was synthesized as shown in Scheme 1
and was characterized by FT-IR, scanning electron
microscopy, transmission electron microscopy, X-ray
diffraction, energy-dispersive X-ray spectroscopy, and
vibrating sample magnetometry (the data are available
from the authors as supporting information).
The obtained catalyst was used first in the synthesis
of hexahydroquinoline 4a as model reaction (Scheme 2,
Table 1). For this purpose, 0.02 g of the catalyst was
added to a mixture of benzaldehyde (1 mmol),
ammonium acetate (5 mmol), ethyl acetoacetate
(1 mmol), and dimedone (1 mmol), and the mixture
was heated at 100–130°C under solvent-free
conditions (Table 1, entry nos. 1–4). The best results
were obtained at 120°C (entry no. 3). We then tested
different amounts of the catalyst (entry nos. 5, 6) and
found that the optimum amount of the catalyst was
0.02 g (run no. 3). In addition, the reaction was carried
out in different solvents under reflux, but the results
were unsatisfactory (entry nos. 7, 8).
Nanocatalysts are the best alternatives to usual
catalysts because they have a large surface-to-volume
ratio which increases their catalytic activity. Also, their
selectivity and stability can be improved by changing
the size, shape, and composition. Nanocatalysts can be
recovered from the reaction mixture by filtration or
centrifugation, though these separation methods could
lead to loss of nanocatalyst [35]. The best solution for
this problem is the use of magnetic nanoparticles
which have attracted great attentions due to their wide
application in biological researches [36]. Magnetic
nanoparticles (MNPs) can act as supports to
immobilize the catalyst which can be easily separated
from the reaction mixture using an external magnet
[37]. Preyssler heteropolyacid H14NaP5W30O120 (HPA)
has remarkable properties like high thermal and
hydrolytic stability, acidic protons, high solubility in
polar solvents, low surface area, and safety. We
utilized NiFe2O4 as magnetic source because of its
remarkable properties including high saturation, high
The scope and generality of this four-component
one-pot Hantzsch synthesis of polyhydroquinoline
derivatives was demonstrated with different 1,3-
dicarbonyl compounds and aldehydes (Scheme 3,
Table 2). All reactions proceeded efficiently within
10–60 min at 120°C under solvent-free condition to
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

2924
MALEKI et al.
Table 1. Optimization of the synthesis of hexahydroquinoline 4a (Scheme 1)
O
O
CHO
O
O
O
Conditions
OEt
NH4OAc
+
+
+
OC2H5
Me
N
H
O
1
2
3
4a
Entry no.
Catalyst, g
Conditions
Reaction time, min
Yield,a %
1
2
3
4
5
6
7
8
NFS-PRS, 0.02 g
NFS-PRS, 0.02 g
NFS-PRS, 0.02 g
NFS-PRS, 0.02 g
NFS-PRS, 0.01 g
NFS-PRS, 0.03 g
NFS-PRS, 0.02 g
NFS-PRS, 0.02 g
Solvent-free/100°C
Solvent-free/110°C
Solvent-free/120°C
Solvent-free/130°C
Solvent-free/120°C
Solvent-free/120°C
Ethanol/reflux
10
10
10
10
20
10
60
60
72
80
94
92
82
94
68
65
Methanol/reflux
a
Isolated yield.
afford the corresponding polyhydroquinoline derivatives
in good yields (77–96%).
1,8-dioxodecahydroacridines in 75–92% yield, whereas
anilines with electron-withdrawing groups failed to
react.
We also used NFS-PRS to catalyze the synthesis of
1,8-dioxodecahydroacridines under analogous conditions.
The catalyst was added to a mixture of an aromatic
aldehyde (1 mmol), 5,5-dimethylcyclohexane-1,3-dione
or cyclohexane-1,3-dione (2 mmol), and ammonium
acetate (5 mmol). The progress of the reaction was
monitored by TLC; after reaction completion, the
catalyst was easily separated by an external magnet.
We then used different substituted anilines as a source
of nitrogen instead of ammonium acetate (Table 2).
Anilines containing electron-donating groups (R3 = H,
4-Me, 4-MeO) smoothly reacted under the given
conditions to afford the corresponding 10-substituted
Having obtained satisfactory results, we continued
to study the reaction using dimedone, Meldrum’s acid,
various aldehydes, and ammonium acetate for one-pot
synthesis of 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquino-
lines under solvent-free conditions at 120°C with
NiFe2O4@SiO2-H14[NaP5W30O110
]
(NFS-PRS) as
catalyst (0.02 g); the corresponding octahydroquino-
lines 9a–9g were thus obtained in good to high yields
(Scheme 3, Table 2).
The main advantage of the proposed protocol is
simple separation of the catalyst from the reaction
mixture. In all cases, the reaction procedure was clean,
Scheme 2.
O
O
CHO
O
O
O
Solvent-free
120°C
OEt
NH4OAc
+
+
+
OC2H5
Me
N
H
O
1
2
3
4a
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

ONE-POT SYNTHESIS OF 1,4-DIHYDROPYRIDINE DERIVATIVES
2925
Scheme 3.
R1
O
O
O
O
OEt
Me
3
OEt
Me
R2
R2
NH4OAc
O
N
H
4a−4o
R1
R2
R2
O
O
O
2
NH4OAc
R1
R1
R2
R2
N
H
O
CHO
5a−5f
NiFe2O4@SiO2@ H14[NaP5W30O110
Solvent-free, 120οC
O
]
R1
R2
R2
R1
+
O
2
1
O
O
R2
R2
O
R2
R2
R1
R1
2
N
NH2
R3
R3
7a−7g
6
R1
NH4OAc
O
O
O
O
O
N
H
O
8
9a−9g
For R1, R2, and R3, see Table 2.
safe, simple, and consistent with the green chemistry
principles. The reusability and recovery of NFS-PRS
was investigated in the synthesis of 4a and 5b. After
completion of the reaction, the catalyst was separated
from the reaction mixture using an external magnet,
dried at 100°C for 2 h, and reused in the same reaction.
In four successive runs, the yields of 4a and 5b were
94, 93, 90, and 90% and 95, 92, 92, and 90%, respectively.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

2926
MALEKI et al.
Table 2. One-pot synthesis of polyhydroquinolines, 1,8-dioxodecahydroacridines, and 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines
in the presence of NiFe2O4@SiO2-H14[NaP5W30O110
]
Compound no.
R1
R2
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
H
R3
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
Reaction time, min
Yield,a %
94
90
89
90
85
92
90
90
88
90
87
82
87
92
89
85
95
93
92
82
94
92
89
75
81
92
89
77
80
96
95
95
96
92
84
mp, °C (lit. data)
4a
H
10
30
35
40
25
30
20
40
30
10
20
10
10
10
5
200–202 (200–202) [19]
242–244 (245–247) [16]
207–209 (210–211) [16]
240–242 (245–246) [17]
190–192 (193–195) [17]
240–242 (242–244) [17]
249–251 (252–253) [32]
226–228 (224–226) [33]
171–173 (175–176) [17]
252–254 (257–259) [17]
201–203 (202–204) [20]
240–242 (240–241) [20]
200–202 (196–198) [17]
237–239 (236) [17]
4b
4-O2N
2-Cl
4c
4d
2,4-Cl2
2-MeO
4-Cl
4e
4f
4g
4-Br
4h
2-Thienyl
3-O2N
4-Me
3-MeO
H
4i
4j
4k
4l
4m
4-O2N
4-Cl
H
4n
H
4o
4-Me
H
H
241–243 (240–241) [20]
190–192 (190–192) [22]
244–245 (241–243) [25]
298–300 (299–301) [25]
284–286 (286–288) [25]
280–282 (279–281) [20]
264–266 (268–270) [20]
256–258 (260–262) [27]
210–212 (215–216) [27]
288–290 (293–294) [23]
281–283 (285–287) [23]
252–254 (254–255) [27]
212–214 (215–216) [27]
280–283 (285–287) [23]
213–215 (210–212) [30]
190–192 (192–194) [30]
180–182 (184–186) [30]
186–188 (188–190) [31]
189–191 (190–192) [30]
212–214 (213–215) [31]
236–238 (234–240) [30]
5a
Me
Me
Me
Me
H
30
25
20
60
10
15
35
20
25
15
20
20
25
20
10
15
5
5b
4-Br
5c
4-Cl
5d
4-O2N
H
5e
5f
4-Cl
H
7a
H
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
Me
4-Me
7b
H
4-MeO
7c
4-Me
4-MeO
H
4-Me
7d
4-Me
7e
H
7f
H
4-MeO
7g
3-O2N
H
4-Me
9a
–
–
–
–
–
–
–
9b
4-Br
9c
2,4-Cl
4-Cl
9d
9e
3-O2N
4-MeO
2,3-(MeO)2
10
15
25
9f
9g
a
Isolated yield.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

ONE-POT SYNTHESIS OF 1,4-DIHYDROPYRIDINE DERIVATIVES
2927
In summary, we have proposed a novel procedure
for the synthesis of 1,4-dihydropyridine derivatives in
the presence of a heterogeneous magnetic nanocatalyst
under solvent-free conditions. The proposed procedure
is advantageous due to its environmental and economical
efficiency, short reaction time, experimental simplicity,
generality, easy work-up, and reusability of the catalyst.
separated from the reaction mixture by means of an
external magnet. The crude product was poured into
crushed ice, and the solid product was filtered off and
recrystallized from ethanol (5 mL).
General procedure for the synthesis of 1,8-di-
oxodecahydroacridines 5a–5f and 7a–7g. A mixture
of aldehyde 1 (1 mmol), dimedone or cyclohexane-1,3-
dione (2, 2 mmol), ammonium acetate (5 mmol) or
aromatic aniline 6 (1.2 mmol), and NFS-PRS (0.02 g)
was heated on an oil bath at 120°C for a time indicated
in Table 2. The subsequent procedure was the same as
in the synthesis of 4a–4o.
EXPERIMENTAL
All reagents were purchased achieved from com-
mercial sources. The melting points were measured by
a Stuart BI Barnstead Electrothermal IA9200 apparatus
and are uncorrected. The IR spectra were recorded in
KBr on a Shimadzu 435-U-04 FT-IR spectrometer.
General procedure for the synthesis of 2,5-dioxo-
1,2,3,4,5,6,7,8-octahydroquinolines 9a–9g. A mixture
of aldehyde 1 (1 mmol), dimedone (2 mmol),
Meldrum’s acid (1 mmol), ammonium acetate
(5 mmol), and NFS-PRS (0.02 g) was heated on an oil
bath at 120°C for a time indicated in Table 2. The
mixture was then treated as described above for the
synthesis of 4a–4o.
1
The H NMR spectra were obtained using a Bruker
300 MHz spectrometer in DMSO-d6 or CDCl3 with
TMS as internal standard. The particle size and
morphology of the nanocatalyst were studied using
Philips CM-200 and Titan Krios transmission electron
microscopes and Philips XL 30 and S-4160 scanning
electron microscopes with gold coating; the particle
size distribution was determined using a CORDOUAN
Vasco3A laser particle size analyzer.
The products were identified by comparing their
melting points with those reported in the literature
(Table 2), as well as by spectral data. Spectroscopic
data for some representative compounds are given
below.
Silica-coated magnetic NiFe2O4 nanoparticles-
supported H14[NaP5W30O110] (NFS-PRS]. Magnetic
NiFe2O4 nanoparticles were prepared by reaction
between NiCl2 and FeCl3 in presence of H2O and
NH4OH under alkaline conditions and were coated
with silica by treatment with tetraethyl orthosilicate. In
the next step, the obtained NiFe2O4@SiO2 (NFS, 1 g)
was dispersed in water (50 mL) and sonicated at room
Ethyl 2,7,7-trimethyl-5-oxo-4-phenyl-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate (4a). IR spec-
trum, ν, cm–1: 3235, 3216, 3087, 1699, 1604, 1063,
1
697. H NMR spectrum (300 MHz, DMSO-d6), δ,
ppm: 0.94 s (3H), 1.09 s (3H), 1.14 t (3H, J = 7.3 Hz),
2.13–2.34 m (4H), 2.37 s (3H), 4.05 q (2H, J =
7.3 Hz), 5.02 s (1H), 5.74 s (1H), 7.03–7.34 m (5H).
13C NMR spectrum (75 MHz, DMSO-d6), δC, ppm:
14.5, 19.4, 21.7, 27.9, 36.8, 37.7, 59.9, 106.3, 113.8,
126.8, 127.10, 128.4, 143.7, 147.4, 149.5, 167.7, 194.11.
temperature for 15 min.
A
solution of
H14[NaP5W30O110] (0.75 g) in water (5 mL) was
prepared and added dropwise to the suspension of
NFS, and the mixture was stirred for 12 h at room
temperature. The solvent was evaporated under
reduced pressure, and the supported catalyst was
collected by an external magnet, dried in a vacuum
overnight, and calcined at 250°C for 2 h.
Ethyl
2,7,7-trimethyl-4-(3-nitrophenyl)-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (4i).
IR spectrum, ν, cm–1: 3307, 2965, 1693, 1615, 1169,
1
763. H NMR spectrum (300 MHz, DMSO-d6), δ,
General procedure for the synthesis of poly-
hydroquinolines 4a–4o. A mixture of aldehyde 1
(1 mmol), dimedone or cyclohexane-1,3-dione (2,
1 mmol), ethyl acetoacetate (3, 1.2 mmol), ammonium
acetate (5 mmol) and NFS-PRS (0.02 g) was heated on
an oil bath at 120°C for a time indicated in Table 2).
The progress of the reaction was monitored by TLC
(n-hexane–ethyl acetate, 2 : 1). When the reaction was
complete, 5 ml of hot ethanol (96%) was added, and
the mixture was stirred for 2 min. The catalyst was
ppm: 0.96 s (3H), 1.04 s (3H), 1.22 t (3H, J = 7.3 Hz),
2.10–2.34 m (4H), 2.38 s (3H), 4.01 q (2H, J =
7.3 Hz), 4.96 s (1H), 6.32 s (1H), 6.74–7.38 m (4H).
13C NMR spectrum (75 MHz, DMSO-d6), δC, ppm:
14.21, 19.35, 21.3, 27.6, 33.4, 33.93, 59.8, 105.7,
112.7, 121.5, 122.11, 128.9, 134.11, 144.9, 148.6,
149.8, 151.3, 166.12, 196.3.
3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (5d). IR spec-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

2928
MALEKI et al.
trum, ν, cm–1: 3390, 3075, 2959, 1650, 1519, 1484,
1347, 1221, 1170. H NMR spectrum (300 MHz,
Keirabadi, M., Khojastehbakht-Koopaei, B., and
Shahbazi-Alavi, H., Res. Chem. Intermed., 2016,
vol. 42, no. 2, p. 827. doi 10.1007/s11164-015-2057-7
1
DMSO-d6), δ, ppm 0.87 s (6H), 1.02 s (6H), 2.04 d
(2H, J = 16.3 Hz), 2.15 d (2H, J = 16.3 Hz), 2.26 d
(2H, J = 17.0 Hz), 2.34 d (2H, J = 17.0 Hz), 5.05 s
(1H), 7.44 d (2H, J = 8.5 Hz), 7.98 d (2H, J = 6.9 Hz),
8.49 s (1H). 13C NMR spectrum (75 MHz, DMSO-d6),
δC, ppm: 27.7, 29.12, 32.12, 34.11, 51.3, 112.9, 123.8,
129.7, 146.4, 149.11, 154.12, 195.9.
2. Sausins, A. and Duburs, G., Heterocycles, 1988, vol. 27,
no. 1, p. 269. doi 10.3987/REV-87-370
3. Visentin, S., Ronaldo, B., Stilo, D.A., Frrutero, R.,
Novara, M., Carbone, E., Roussel, C., Vanthuyne, N.,
and Gasco, A., J. Med. Chem., 2004, vol. 47, no. 10,
p. 2688. doi 10.1021/jm031109v
4. (a) Bretzel, R.G., Bollen, C.C., Maeser, E., Federlin, K.F.,
Drug Future, 1992, vol. 17, p. 456; (b) Boer, R. and
Gekeler, V., Drug Future, 1995, vol. 25, no. 5, p. 499.
3,3,6,6-Tetramethyl-9,10-diphenyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (7e). IR
spectrum, ν, cm–1: 3082, 3055, 2961, 2930, 2893,
2861, 1722, 1640, 1582, 1490, 1362, 1273, 1220,
1132, 1081, 1015, 917, 899, 842, 798, 738, 699, 680,
609, 587, 579, 532, 470. 1H NMR spectrum (300 MHz,
CDCl3), δ, ppm: 7.56 d (3H, J = 6.4 Hz), 7.44 d (2H,
J = 7.6 Hz), 7.25 d (4H, J = 7.2 Hz), 7.10 d.d (1H, J =
7.2, 6.8 Hz), 5.29 s (1H), 2.24–2.11 m (4H), 2.07 d
(2H, J = 17.2 Hz), 1.82 d (2H, J = 17.6 Hz), 0.94 s
(6H), 0.79 s (6H). 13C NMR spectrum (75 MHz,
CDCl3), δC, ppm: 195.77, 162.21, 159.80, 149.68,
141.97, 141.94, 138.74, 129.91, 129.33, 129.16, 129.08,
115.33, 114.68, 114.47, 114.30, 49.99, 41.63, 32.21,
31.98, 29.53, 26.51.
5. Buhler, F.R. and Kiowski, W., J. Hypertens., 1987,
vol. 5, p. S3. doi 10.1097/00004872-198708003-00002
6. Dekamine, M.G., Ilkhanizadeh, S., Latifidoost, Z.,
Daemi, H., Karimi, S. and Barikani, M., RSC Adv.,
2014, vol. 4, no. 100, p. 56658. doi 10.1039/C4RA11801D
7. Love, B. and Snader, K.M., J. Org. Chem., 1956,
vol. 21, p. 1914.
8. Janis, R.A. and Triggle, D.J., J. Med. Chem., 1983,
vol. 26, no. 6, p. 775. doi 10.1021/jm00360a001
9. Guetzoyan, L., Yu, X.M., Ramiandrasoa, F., Peth, S.,
Rogier, C., Pradines, B., Cresteil, M., Perree-Fauvet, T.,
and Mahy, J.P., Bioorg. Med. Chem., 2009, vol. 17,
no. 23, p. 8032. doi 10.1016/j.bmc.2009.10.005
10. Su, T.L., Lin, Y.W., Chou, T.C., Zhang, X., Bacheri-
kov, V.A., Chen, C.H., Liu, L.F., and Tsai, T.J., J. Med.
Chem., 2006, vol. 49, no. 12, p. 3710. doi 10.1021/
jm060197r
4-(2,3-Dimethoxyphenyl)-7,7-dimethyl-4,6,7,8-
tetrahydroquinoline-2,5(1H,3H)-dione (9g). IR
spectrum, ν, cm–1: 3220, 2939, 1616, 1485, 1385,
1
11. Wainwright, M.J., Antimicrob. Chemother., 2001,
1290, 1222, 1069, 793. H NMR spectrum (300 MHz,
vol. 47, no. 1, p. 1. doi 10.1093/jac/47.1.1
DMSO-d6), δ, ppm: 10.11 s (1H), 6.92 m (2H), 6.50
d.d (1H), 4.46 d (1H), 3.82 s (3H), 3.79 s (3H), 2.94
d.d (1H), 2.47 d (2H), 2.23 d (1H), 2.19 q (2H), 1.07 s
(3H), 1.04 s (3H).
12. (a) Aly, E.I. and Abadi, A.H., Arch. Pharmacol. Res.,
2004, vol. 27, no. 7, p. 713. doi 10.1007/bf02980137;
(b) Tripathi, R.P., Verma, S.S., Pandey, J., Agarwal, K.C.,
Chaturvedi, V., Manju, Y.K., Srivastva, A.K., Gaikwad, A.,
and Sinha, S., Bioorg. Med. Chem. Lett., 2006, vol. 16,
no. 19, p. 5144. doi 10.1016/j.bmcl.2006.07.025
ACKNOWLEDGMENTS
The authors thank Hakim Sabzevari University for
financial support to this research.
13. Dos Santos Pisoni, D., Sobieski da Costa, J., Gamba, D.,
Petzhold, C.L., de Amorim Borges, A.C., Ceschi, M.A.,
Lunardi, P., and Saraiva Gonçalves, C.A., Eur. J. Med.
Chem., 2010, vol. 45, no. 2, p. 526. doi 10.1016/
j.ejmech.2009.10.039
REFERENCES
14. (a) Delfourne, E., Roubin, C., and Bastide, J., J. Org.
Chem., 2000, vol. 65, no. 18, p. 5476. doi 10.1021/
jo000011a; (b) Antonini, J., Polucci, P., Magnano, A.,
and Martelli, S., J. Med. Chem., 2001, vol. 44, no. 20,
p. 3329. doi 10.1021/jm010917o; (c) Ferlin, M.G.,
Marzano, C., Chiarelotto, G., Baccichetti, F., and
Bordin, F., Eur. J. Med. Chem., 2000, vol. 35, no. 9,
p. 827. doi 10.1016/S0223-5234(00)00170-7
15. (a) Hantzsch, A., Justus Liebigs Ann. Chem., 1882,
vol. 215, no. 1, p. 1; (b) Ahluwalia, V.K., Goyal, B., and
Das, U., J. Chem. Res., Synop., 1997, no. 7, p. 266. doi
10.1039/A608002B
1. (a) Moeinpour, F., Dorostkar-Ahmai, N., Sardashti-
Birjandi, A., Khojastehnezhad, A., and Vafaei, M., Res.
Chem. Intermed., 2014, vol. 5, no. 9, p. 3145. doi
10.1007/s11164-013-1160-x; (b) Maleki, B. and Sheikh, S.,
RSC Adv., 2015, vol. 5, no. 54, p. 42 997. doi 10.1039/
C5RA04458H; (c) Maleki, B., Babaee, S., and Tayebee, R.,
Appl. Organomet. Chem., 2015, vol. 6, no. 29, p. 408.
doi 10.1002/aoc.3306; (d) Maleki, B., Sheikh, E.,
Rezaei Seresht, E., Eshghi, H., Sedigh Ashrafi, S.,
Khojastehnezhad, A., and Veisi, H., Org. Prep. Proced.
Int., 2016, vol. 48, no. 1, p. 37. doi 10.1080/
00304948.2016.1127098; (e) Safaei-Ghomi, J., Asgari-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017

ONE-POT SYNTHESIS OF 1,4-DIHYDROPYRIDINE DERIVATIVES
2929
16. Zarnegar, Z., Safari, J., and Mansouri-Kafroudi, Z.,
Catal. Commun., 2015, vol. 59, p. 216. doi 10.1016/
j.catcom.2014.10.023
17. Maleki, A., Kamalzare, M., and Aghaei, M., J. Nano-
struct. Chem., 2015, vol. 5, no. 1, p. 95. doi 10.1007/
s40097-014-0140-z
18. Rostamnia, S. and Pourhassan, F., Chin. Chem. Lett.,
2013, vol. 24, no. 5, p. 401. doi 10.1016/j.cclet.2013.03.020
19. Maleki, B., Tayebee, R., Sepehr, Z., and Kermanian, M.,
Acta Chim. Slov., 2012, vol. 59, no. 4, p. 814.
20. Maleki, B., Tayebee, R., Kermanian, M., and Sedigh
Ashrafi, S., J. Mex. Chem. Soc., 2013, vol. 57, no. 4,
p. 290.
21. Bakibaev, A.A., Fillimonov, V.D., and Nevgodova, E.S.,
Russ. J. Org. Chem., 1991, vol. 27, p. 1991.
22. Martin, N., Quinteiro, M., Seoane, C., Soto, J.L., Mora, A.,
Suarez, M., Ochoa, E., Morales, A., and Del Bosque, J.R.,
J. Heterocycl. Chem., 1995, vol. 32, no. 1, p. 235. doi
10.1002/jhet.5570320139
30. Mohammadi Ziarani, G., Asadi, S., Badiei, A.,
Mousavi, S., and Gholamzadeh, P., Res. Chem.
Intermed., 2015, vol. 41, no. 2, p. 637. doi 10.1007/
S11164-013-1217-X
31. Tu, S., Wei, Q., Ma, H., Shi, D., Gao, Y., and Cui, G.,
Synth. Commun., 2001, vol. 31, no. 17, p. 2657. doi
10.1081/SCC-100105393
32. Maheswara, M., Siddaiah, V., Lakishmi, G., Damu, V.,
and Rao, C. V., Arkivoc, 2006, part ii, p. 201.
33. Ko, S. and Yao, C.F., Tetrahedron, 2006, vol. 62,
no. 31, p. 7293. doi 10.1016/j.tet.2006.05.037
34. (a) Maleki, B., Barat Nam Chalaki, S., Sedigh Ashrafi, S.,
Rezaei Seresht, E., Moeinpour, F., Khojastehnezhad, A.,
and Tayebee, R., Appl. Organomet. Chem., 2015, vol. 5,
no. 29, p. 290. doi 10.1002/aoc.3288; (b) Maleki, B.,
Akbarzadeh, E., and Babaee, S., Dyes Pigm., 2015,
vol. 123, p. 222. doi 10.1016/j.dyepig.2015.08.009;
(c) Maleki, B., Org. Prep. Proced. Int., 2016, vol. 48,
no. 1, p. 81. doi 10.1080/00304948.2016.1127104
23. Jin, T.S., Zhang, J.S., Guo, T.T., Wang, A.Q., and
Li, T.S., Synthesis, 2004, vol. 2004, no. 12, p. 2001. doi
10.1055/s-2004-829151
24. Das, B., Thirupathi, P., Mahender, I., Reddy, V.S., and
Rao, Y.K., J. Mol. Catal., 2006, vol. 247, no. 1, p. 233.
doi 10.1016/j.molcata.2005.11.048
25. Balalaie, S., Chadegani, F., Darviche, F., and
Bijanzadeh, H.R., Chin. J. Chem., 2009, vol. 27, no. 10,
p. 1953. doi 10.1002/cjoc.200990328
26. Safaei-Ghomi, J., Ghasemzadeh, M.A., and Zahedi, S.,
J. Mex. Chem. Soc., 2013, vol. 57, no. 1, p. 1.
27. Ghasemzadeh, M.A., Safaei-Ghomi, J., and Molaei, H.,
C. R. Chim., 2012, vol. 15, no. 11, p. 969. doi 10.1016/
j.crci.2012.08.010
28. Dabiri, M., Baghbanzadeh, M., and Arzroomchilar, E.,
Catal. Commun., 2008, vol. 9, no. 5, p. 939. doi
10.1016/j.catcom.2007.09.023
29. Mohammadi Ziarani, G., Seyedakbari, L., Asadi, S., and
Yadavi, M., Res. Chem. Intermed., 2016, vol. 42, no. 2,
p. 499. doi 10.1007/s11164-015-2036-z
35. (a) Roduner, E., Chem. Soc. Rev., 2006, vol. 35, no. 7,
p. 583. doi 10.1039/B502142C; (b) Chng, L.L.,
Erathodiyil, N., and Ying, J.Y., Acc. Chem. Res., 2013,
vol. 46, no. 8, p. 1825. doi 10.1021/ar300197s
36. Sahoo, S.K. and Labhasetwar, V., Drug Discover
Today, 2003, vol. 8, no. 24, p. 1112. doi 10.1016/S1359-
6446(03)02903-9
37. (a) Polshettiwar, V., Luque, R., Fihri, A., Zhu, H.,
Bouhrara, M., and Basset, J.-M., Chem. Rev., 2011,
vol. 111, no. 5, p. 3036. doi 10.1021/cr100230z;
(b) Maleki, B., Nasiri, N., Tayebee, R., Khojastehne-
zhad, A., and Akhlaghi, H.A., RSC Adv., 2016, vol. 6,
no. 82, p. 79 128. doi 10.1039/C6RA15800E;
(c) Maleki, B., Eshghi, H., Barghamadi, M., Nasiri, N.,
Khojastehnezhad, A., Sedigh Ashrafi, S., and
Pourshiani, O., Res. Chem. Intermed., 2016, vol. 44,
p. 3071. p. 10. doi 1007/s11164-015-2198-8;
(d) Maleki, B., Baghayeri, M., Ayazi Jannat Abadi, S.,
Tayebee, R., and Khojastehnezhad, A., RSC Adv., 2016,
vol. 6, no. 99, p. 96 644. doi 10.1039/C6RA20895A
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 12 2017