Sulfonic acid-functionalized graphitic carbon nitride composite: a novel and reusable catalyst for the one-pot synthesis of polysubstituted pyridine in water under sonication

Article abstract of DOI:10.1007/s13738-019-01820-1

Graphitic carbon nitride as an interesting sustainable soft nanomaterial has drawn broad interdisciplinary attention because of unique electronic structure and chemical stability. An ultrasound-assisted preparation of a series of polysubstituted pyridines

Full text of DOI:10.1007/s13738-019-01820-1

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-019-01820-1
ORIGINAL PAPER
Sulfonic acid‑functionalized graphitic carbon nitride composite:
a novel and reusable catalyst for the one‑pot synthesis
of polysubstituted pyridine in water under sonication
Mahtab Edrisi1 · Najmedin Azizi1
Received: 2 February 2019 / Accepted: 3 December 2019
© Iranian Chemical Society 2019
Abstract
Graphitic carbon nitride as an interesting sustainable soft nanomaterial has drawn broad interdisciplinary attention because
of unique electronic structure and chemical stability. An ultrasound-assisted preparation of a series of polysubstituted pyri-
dines in the presence of a polar and strongly acidic sulfonated magnetic graphitic carbon nitride (Fe3O4@g-C3N4-SO3H)
under milder and faster reaction conditions in water as a green medium was reported. One-pot sequential multicomponent
reaction of aromatic aldehydes with acyclic and cyclic ketones, malononitrile and ammonium acetate was aforded the
pyridine derivatives in good-to-excellent yields. In view of eco-friendly and economic considerations, this approach ofers
a straightforward and convenient route to generate biologically active pyridine derivative in an environmentally friendly
manner. The Fe3O4@g-C3N4-SO3H showed high stability and reusability over several reaction sets without noteworthy loss
of activity, and thus, this method is a cheap and eco-friendly procedure.
Keywords Multicomponent reaction · Polysubstituted pyridines · Sonochemistry · Sulfonated magnetic graphitic carbon
nitride · Water chemistry
Introduction
size and surface morphology of the g-C3N4 nanostructure [3,
4]. In addition, doping g-C3N4 with metal and/or nonmetal
ions, copolymerization with organic molecules and modif-
cation with carbon materials appeared and showed signif-
cant improvement in their catalytic activity [5, 6]. However,
bare g-C3N4 sufers from active sites and less specifc sur-
face area and to expand the reactivity, the functionalization
of g-C3N4 with acidic, basic or ionic groups is an excellent
method to modify their electronic and optical properties
which improve the photocatalytic activity of g-C3N4 [2].
Metal doping as well as combining various semiconduc-
tors with proper energy levels to modify the photocatalytic
activity of g-C3N4 is well known, but efective modifers for
g-C3N4 catalysts for selective organic transformations have
not been reported yet [7–10]. Furthermore, immobilization
of homogeneous catalysts on heterogeneous nanomaterial
supports in catalysis science was reported recently [11–17].
The use of ultrasound to accelerate a chemical process
is named sonochemistry and was reported by Richards and
Loomis for the frst time [18]. Ultrasonic irradiation difers
from conventional energy sources in time and energy and
has much more advantages regarding reaction rates and the
yields of the process and may entirely alter the spreading of
Carbon-based nanomaterials, for instance, graphene, carbon
nanotubes (CNTs), graphite carbon nitride (g-C3N4), ordered
porous carbon and carbon aerogels, have concerned exces-
sive attention due to its wide potential applications in catal-
ysis, adsorption, gas separation, drug delivery and energy
storage [1]. Among the carbon-based nanomaterials, gra-
phitic carbon nitrides (g-C3N4) are inspiring great research
eforts because they exhibit several desirable performances,
such as resistant to acidic or basic media, low toxicity and
high stability as well as unique structure which gives it wor-
thy photocatalytic activity [2]. Recently, signifcant efort
has been placed on the design and fabrication of nanostruc-
ture to achieve high photocatalytic activity by adjusting the
* Mahtab Edrisi
lashkarizadehm@yahoo.com
Najmedin Azizi
azizi@ccerci.ac.ir
1
Chemistry and Chemical Engineering Research Center
of Iran, P.O. Box 14335-186, Tehran, Iran
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
products or even cause the creation of diverse substances
[19–23]. Ultrasound-enhanced organic transformations
allow the humble preparation of highly functionalized het-
erocyclic compounds via adiabatic collapse of the transient
cavitation bubbles. Furthermore, these strong collapses of
cavitation bubbles also rise the local temperature leading to
the blustery fow of the liquid and enhanced mass transfer
[24, 25].
employed to prepare 2-amino-3-cyanopyridine scafold via
assembling aldehydes, ketones, malononitrile and ammo-
nium acetate under diferent catalytic conditions [38–44].
Experimental section
General
Heterocyclic molecules play a signifcant role in bio-
chemical processes and pharmaceutical industry along with
material science [26, 27]. Among the widespread hetero-
cyclic compounds, nitrogen-containing heterocycles have
been utilized as important building blocks in biologically
active nature products, organic materials and pharmaceuti-
cals [28, 29]. Functionalized cyanopyridine derivatives are
an interesting class of pyridine family that have been found
in natural products and organic materials. The pyridine ring
system also fnds in cosmetics and biomimetics and reac-
tive pharmacophores and biodegradable agrochemicals [30].
Due to extensive industrial applications, the multicompo-
nent approach to the synthesis of new heterocycles in water
as green solvents has gained renewed interests [31–37]. In
recent years, several multicomponent reactions have been
All reagents are commercially accessible and were pur-
chased from Merck, Fluka and Aldrich chemical compa-
nies and used as received. Melting points were measured
on Buchi 535 melting point apparatus. Sonication was per-
formed in by Hielscher ultrasonic device (Vial Tweeter at
UIS250v) with Sonotrode LS24d5 and with a frequency of
24 kHz and a nominal power of 250 W, and the best results
were obtained when a continuously switched on irradiation
at 100% of the maximum power output (amplitude).
Preparation of Fe3O4@g‑C3N4‑SO3H catalyst
The g-C3N4 powder was synthesized by the reported method
[19]. To prepare g-C3N4, melamine (10.0 g) was put on a
NH2
H2N
N
N
N
N
N
N
N
N
N
NH2
N
N
N
N
N
N
N
N
N
H2N
N
N
NH2
H2N
N
NH2
550 oC, 4h
500 oC, 2h
N
N
N
N
N
N
N
N
N
N
NH2
Melamine
N
N
N
g-C3N4 nanosheets
Fe2+/Fe3+ in H2O
NH3, pH=10
80 oC
30 min
80 oC, 30 min
SO3H
HN
NH2
SO3H
NH
NH2
N
N
N
N
N
N
N
H2N
N
N
N
N
N
N
N
NH2
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
SO3H
SO3H
NH
HN
N
N
N
N
N
H2N
N
N
N
N
N
N
N
N
NH2
Cl.SO3H, r.t.
N
N
N
O3S
N
SO3
N
CH2Cl2, r.t. 10 h
N
N
N
N
N
N
N
N
N
N
O3S
SO3
Fe3O4@g-C3N4-SO3H
Fe3O4@g-C3N4
Scheme 1 Formation process of Fe3O4@g-C3N4-SO3H
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Journal of the Iranian Chemical Society
40 cm×120 cm ceramic boat without a cap and heated in a
mufe furnace at 550 °C for 4 h in static air at a ramp rate
of 2.5 °C min−1 and a light yellow powder was obtained.
The Fe3O4@g-C3N4 was prepared according to the previous
report [49]. In the next step, Fe3O4@g-C3N4 (1.0 g) and dry
CH2Cl2 (25 mL) were taken in a three-neck round-bottom
fask that was equipped with a constant pressure dropping
funnel. Subsequently, chlorosulfonic acid (2.0 mL) in dry
CH2Cl2 (25 mL) was added in an ice bath under vigorous
stirring within 20 min. After completion of the addition, the
reaction mixture was stirred for 5 h at room temperature. The
resultant solid was washed with ethyl acetate and methanol
and dried under vacuum at 60 °C (Scheme 1). The number of
acidic functional groups present at the surface of the catalyst
69
65
60
55
Fe3O4@g-C3N4-SO3H
3363.09cm-1
584.09cm-1
50
48
52
50
1028.67cm-1
1202.05cm-1
1653.37cm-1
45
40
35
Fe3O4
3428.96cm-1
577.80cm-1
31
74
72
70
68
66
g-C3N4
1637.44cm-1
64
63
4000
3500
3000
2500
2000
1500
1000
500450
cm-1
Fig. 1 FTIR spectrum of g-C3N4, Fe3O4 and Fe3O4@g-C3N4-SO3H
Fig. 2 EDS spectrum of the
Fe3O4@g-C3N4-SO3H
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Journal of the Iranian Chemical Society
Fig. 3 SEM image of Fe3O4@g-C3N4-SO3H
Fig. 4 XRD patterns of
Fe3O4@g-C3N4-SO3H
was evaluated by acid–base titration which determined to
about 0.48 mmol/g.
General procedure: synthesis
of 2‑amino‑3‑cyanopyridine derivatives (5a–5o)
To the solution of respective aldehyde derivatives
(1.0 mmol) in water (2 mL), cyclohexanone (1.0 mmol),
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Journal of the Iranian Chemical Society
Fig. 5 VSM analysis of Fe3O4
and Fe3O4@g-C3N4-SO3H
Fig. 6 TG analysis of
Fe3O4@g-C3N4-SO3H
malononitrile (1.0 mmol) and ammonium acetate (1.2 mmol)
were added at room temperature, respectively. Then, the
Fe3O4@g-C3N4-SO3H (20 mg, 0.96 mol%) was added and
the reaction mixture was sonicated by an ultrasonic probe
in continuous mode for 8–15 min. After reaction comple-
tion which was monitored by TLC, the reaction mixture
was permitted to stand for 10 min at room temperature and
the magnetic catalyst was recovered by the application of
an external permanent magnet to give the corresponding
2-amino-3-cyanopyridine derivatives. The crude products
were washed with water, ethanol or diethyl ether to give the
analytically pure pyridine compounds. Further purifcation
was done using fash column chromatography using EtOAc/
hexane as the eluent, if required.
Results and discussion
In continuation of our earlier research work, to develop envi-
ronmentally benign protocols in various organic transfor-
mations [45–48], herein, we reported a green and efcient
preparation of polysubstituted pyridines using ultrasound as
promoter and sulfonated magnetic graphitic carbon nitride
(Fe3O4@g-C3N4-SO3H) as a green nanocatalyst in pure
water. The use of graphitic surface not only heterogenized
the acidic SO3H catalyst, but also provided an ionic medium
by the in-built nitrogenous framework of g-C3N4 for the
multicomponent reaction. A sulfonated magnetic graphitic
carbon nitride (Fe3O4@g-C3N4-SO3H) has been prepared
more simply via sequential calcination of melamine and sul-
fonation at room temperature with chlorosulfuric acid, and
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at 1300 to 1637 cm−1 represent the carbon–nitrogen bond-
ing groups and in the Fe3O4 spectrum, an intense peak at
577 cm−1 showed the Fe–O bond (metal–oxygen absorption
band) in the crystalline lattice of Fe3O4 and the hydroxyl
groups attached by the hydrogen bonds in the iron oxide
surface appeared at 3428 cm−1. The Fe3O4@g-C3N4-SO3H
catalyst displays a framework band at 1202 and 1653 cm−1
which matches to the characteristic breathing mode of
the triazine units. The distinguishing bands at 1028 (S–O
stretching) and 1202 cm−1 (O=S=O stretching in SO3H)
in the FT-IR spectrum indicate that the g-C3N4 possesses
SO3H groups. The broad stretching absorption seen in the
region 2700–3400 cm−1 belongs to the presence of NH,
acidic SO3H and absorbed water. Furthermore, the 584 cm−1
absorption peaks correspond to the Fe–O bond vibration of
Fe3O4 nanoparticles in the composite.
Table 1 Solvent screening for the model reaction
CH3COONH4
Ph
N
Fe3O
N4-SO3H
4@g-C3
CN
CHO
4
CN
(20 mg)
+
Solvents
(2 mL)
O
CN
NH2
2
5a
8 min
1a
3
Entry
Solvent
Yields (%)
1
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
Water
88 (68, 72, 77, 89)a
2b
84
78
72
68
38
97
45
38
57
62
86
72
64
46
52
58
94
78
82
55
3c
4d
5e
6f
Spectrophotometer
7
8
9
CHCl3
Toluene
THF
DMF
MeOH
CH3CN
Ethyl acetate
Water
Water
Water
Water
The EDS spectroscopy which is one of the most imperative
techniques to determine the elemental composition of the
catalyst was used to characterize the elemental constituents
of Fe3O4@g-C3N4-SO3H (Fig. 2). The existence of Fe, C,
N, O and S elements was confrmed correctly in the EDS
spectra.
10
11
12
13
14
15g
16h
17i
18j
19k
20l
21m
The SEM of Fe3O4@g-C3N4-SO3H is shown in Fig. 3.
The SEM image of the Fe3O4@g-C3N4-SO3H confrms that
a layered, fat, sheet-like lamellar structure with accumulat-
ing layers has been preserved. Furthermore, deposition of
SO3H group on C3N4 nanosheets did not change the shape
and size of the g-C3N4.
Water
Water
Water
The XRD analysis reveals that the characteristic bend-
ing peaks at 13.2° and 27.1° were belonged to g-C3N4;
however, characteristic peaks of the magnetite Fe3O4 in the
Fe3O4@g-C3N4-SO3H were not appeared. In relationship
with pure g-C3N4, no ostensible change can be detected that
confrm the phase structure of the graphitic carbon nitride
as well as Fe3O4 does not change after the surface amend-
ment (Fig. 4).
aYields of 5, 10, 15 and 40 mg of catalyst, respectively
bWithout ultrasound at 60 °C for 400 min
c80% Power
d50% Power
eUltrasound bath
fWithout catalyst
The VSM (Vibrating-Sample Magnetometer) analysis
was conducted to evaluate the magnetic properties of Fe3O4
and the synthesized Fe3O4@g-C3N4-SO3H catalyst. Based
on the obtained reduction in Fe3O4 saturation magnetiza-
tion curve, it is confrmed that the Fe3O4 was coated on the
surface of the g-C3N4-SO3H catalyst (Fig. 5).
gFe3O4 as catalyst
hg-C3N4 as catalyst
iFe3O4@g-C3N4 as catalyst
jg-C3N4-SO3H as catalyst
kSBA-15-SO3H as catalyst
lFe3O4@C-SO3H as catalyst
mFe3O4, g-C3N4 and melamine as catalyst
In order to monitoring Fe3O4@g-C3N4-SO3H weight
changes, the thermogravimetric analysis (TG) was applied
with constant heating rate. Considering the obtained curve,
there is a slight diminish in weight near 80– 130 °C caused
by water or elimination of some organic compounds which
have been used during the synthesis procedure of the cata-
lyst. The next mild falling down until 480 °C is about the
elimination of SO3H groups which confirmed that the
its application has been established in the efective synthesis
of pyridine derivatives.
The FT-IR spectra of Fe3O4@g-C3N4-SO3H and the start-
ing materials such as g-C3N4 and Fe3O4 were recorded from
450 to 4000 cm−1 (Fig. 1). In the g-C3N4 spectrum, the peaks
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Journal of the Iranian Chemical Society
Table 2 Ultrasound-
promoted greener syntheses
of multisubstituted pyridine
derivatives in water under
optimum conditions
aIsolated yield
catalyst is relatively stable until this temperature, but by
increasing the heating rate to around 490 °C, a signifcant
loss in the weight occurred due to the thermal decomposition
of Fe3O4@g-C3N4-SO3H catalyst structure (Fig. 6).
The reactions of benzaldehyde 1a (1 mmol), malononi-
trile 2 (1 mmol), cyclohexanone 3 (1 mmol) and ammo-
nium acetate 4 (1.2 mmol) are depicted in Table 1. In the
model reaction, polysubstituted pyridines 5a was obtained
in 88% yield at room temperature under ultrasonic irra-
diation in the presence of Fe3O4@g-C3N4-SO3H (20 mg,
0.96 mol%) in ethanol (2 mL) and the results are shown
in Table 1. To clarify the ultrasonic efect, an experiment
was conducted without ultrasound under alternative ther-
mal reaction. Inspection of Table 1 showed that there was
a notable ultrasonic outcome on this reaction. The reaction
time in the ultrasonic system was 8 min (Table 1, entry 1),
whereas without ultrasound, it was needed 400 min to get
Fig. 7 Recyclability experiments of Fe3O4@g-C3N4-SO3H
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Journal of the Iranian Chemical Society
Scheme 2 Proposed mechanism
NH2
N
SO3H
NH
HO3S
SO3H
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
N
SO3H
NH
O
H
HN
N
N
N
S O
O
Cat
N
N
N
N
N
O3S
N
SO3
N
N
N
N
N
N
O3S
SO3
NH2
NH2
N
H
N
O
N
O
S O
H
O
S O
O
N
H
O
O
Cat
Cat
Cat
O S
O
H
O S O
O
NH4OAC
H
O
H
H
CN
NH2
CN
CN
(O)
-H2
H
N
N
H
NH2
N
NH2
the similar yield at 60 °C (Table 1, entry 2). Several con-
trol experiments were conducted to assess the efects of the
ultrasound irradiation. Obviously, the power of ultrasound
has a great efect on the rate of reactions. The one-pot reac-
tions were signifcantly accelerated by higher power (100%)
as indicated by the quantitate yields of 5a and short reac-
tion times. On the other hand, at the lower frequency, (80%
and 50%) the reaction rate decreased and long reaction was
needed to complete (Table 1, entries 3, 4). Furthermore,
same reaction in the sonication baths gives only 58% of
yield under the same reaction conditions (Table 1, entry 5).
The model reaction in the absence of Fe3O4@g-C3N4-SO3H
(20 mg, 0.96 mol%) gives only 54% yield (Table 1, entry 6).
Next, various solvents such as water, THF, DMF, CHCl3,
methanol and toluene (Table 1, entries 7–14) have been
screened to determine the efciency of this model reaction.
According to the obtained results, MeOH and EtOH gave
good yields, while the other organic solvents such as THF,
CH3CN, CHCl3, ethyl acetate and toluene were not satisfac-
tory. When the model one-pot condensation reaction was
carried out with water, to our surprise, the reaction proceeds
well to give expected 5a as a single product after simple
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Journal of the Iranian Chemical Society
fltration. Considering chemical yields, simple work-up
and environmentally friendly nature of water, we selected
as ideal reaction media for further investigations. Actually,
this procedure does not need any hazardous organic solvent
and polysubstituted pyridine 5a was separated in the analyti-
cally pure compound by simple buchner fltration of the fnal
aqueous mixture and did not require further purifcation in
most cases.
Conclusions
In summary, a highly efcient, mild and easily recyclable
Fe3O4@g-C3N4-SO3H as a powerful, easy-to-use catalyst
for the preparation of polysubstituted pyridines derivatives
under ultrasound irradiation has developed. One-pot, mul-
ticomponent reaction of various aldehydes with numerous
ketones, ammonium acetate and malononitrile gave the pyri-
dines in good-to-excellent yields and short reaction times.
The reusability, easy accessibility, low cost and unprece-
dented reactivity of Fe3O4@g-C3N4-SO3H in water mean it
has a countless potential for environmentally benign applica-
tions in industry.
Under the optimized reaction condition, to verify the
overview of the system, a series of polysubstituted pyri-
dines were synthesized via this sonication procedure and
the outcomes are summarized in Table 2. The obtained
data indicated that Fe3O4@g-C3N4-SO3H was an efcient
catalyst for one-pot multicomponent reaction of substituted
aldehydes with a variety of ketones, such as acetophenone,
cyclohexanone and cycloheptanone, in an aqueous medium
under ultrasonic irradiation. The reaction was success-
fully applied to various aromatic aldehydes bearing elec-
tron donating along with electron-withdrawing substituents
containing nitro, chloro, methoxy, methyl functionalities.
All the reactions proceeded smoothly and provided a quick
and eco-friendly approach to pyridine derivatives (5a–p) in
good-to-excellent yields (70–97%) in less than 15 min and
allowed the isolation of target compounds more simply.
The recovery and reusability of the catalyst were
exceedingly desirable regarding industrial application
and green chemistry. The possibility of recycling the
Fe3O4@g-C3N4-SO3H (20 mg, 0.96 mol%) was examined
using the reaction of benzaldehyde (1.0 mmol), cyclohex-
anone (1.0 mmol), malononitrile (1.0 mmol) and ammo-
nium acetate (1.2 mmol) in water (2.0 mL) under the
optimized condition in a model reaction, and the results
are plotted in Fig. 7. Upon reaction completion, the
Fe3O4@g-C3N4-SO3H was easily separated by external per-
manent magnet and washed with 4 M HCl and ethyl acetate,
respectively, and reused for the next run. Apparently, the
Fe3O4@g-C3N4-SO3H did not lose catalytic activity after
fve runs.
Acknowledgements We gratefully acknowledge the fnancial support
of the Iran National Science Foundation (INSF) and the Chemistry and
Chemical Engineering Research Center of Iran.
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