Sulfonic acid-functionalized magnetic carbon nitride as highly efficient ionic composite for sustainable assembly of 1,2,3-triazoles

Article abstract of DOI:10.1007/s13738-021-02164-5

Abstract: An efficient and straightforward method for constructing of biologically active 4-aryl-NH-1,2,3-triazoles by the 1,3-dipolar cycloaddition reaction of β-nitrostyrene?and sodium azide in the presence of acidic graphitic carbon nitride (Fe₃

Full text of DOI:10.1007/s13738-021-02164-5

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-021-02164-5
ORIGINAL PAPER
Sulfonic acid‑functionalized magnetic carbon nitride as highly
efcient ionic composite for sustainable assembly of 1,2,3‑triazoles
Mostafa Saadat1 · Najmedin Azizi2 · Mahnaz Qomi1
Received: 12 September 2020 / Accepted: 2 January 2021
© Iranian Chemical Society 2021
Abstract
An efcient and straightforward method for constructing of biologically active 4-aryl-NH-1,2,3-triazoles by the 1,3-dipolar
cycloaddition reaction of β-nitrostyrene and sodium azide in the presence of acidic graphitic carbon nitride (Fe3O4@g-C3N4–
SO3H) ionic nanocomposite has developed. Using a magnetically recoverable acidic ionic catalyst allows eco-friendly and
facile conversion and simplifes experimental setup and work-up procedure that enables the direct synthesis of triazole
derivatives under mild conditions. The designed catalytic system provides a broader scope under short reaction times in
good to excellent yields. Fe3O4@g-C3N4–SO3H could be simply recovered by magnetic separation using an external magnet,
maintaining stable activity up to fve cycles without appreciable loss of activity.
Graphic abstract
Keywords Fe3O4@g-C3N4–SO3H · Cycloaddition reaction · Green chemistry · Magnetically recoverable catalyst ·
β-nitrostyrene · 1,2,3-triazoles
* Najmedin Azizi
Introduction
azizi@ccerci.ac.ir
1
Privileged nitrogen-containing rings, 1,2,3-triazoles, and
their derivatives are a remarkable group of active hetero-
cyclic compounds and have a massive signifcance in biol-
ogy, medicine, nanotechnology, catalysis, and corrosion
Active Pharmaceutical Ingredients Research Center
(APIRC), Tehran Medical Sciences, Islamic Azad
University, Tehran, Iran
2
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
inhibitors [1, 2]. The 1,2,3-triazole core has engaged a
unique place in material science as versatile ligands in the
optical materials as well as light stabilizers and optical
brightening agents [3]. Many of the approved nitrogen-rich
fve-membered drugs such as celecoxib, pyrazofurin, HIV
protease inhibitors have a triazole moiety [4]. Furthermore,
conjugation of fuorophores such as coumarin and its deriva-
tives with sugar scafold provided as a fuorescent triazole
extensively used in analytical chemistry as chemosensors,
biosensing, bio labeling, and bioimaging (Fig. 1) [5]. The
widespread applications of triazole derivatives have led to
the extension of numerous procedures for their synthesis,
involving the cyclization of triazenes, Wolf’s cyclo con-
densation of α-diazo ketones, and α-diazoamides. [6–8]
Thermal 1,3-dipolar cycloaddition (Huisgen cycloaddition)
between an organic azide and alkyne was the classical pro-
cedure for 1,2,3-triazole synthesis [9]. Click chemistry is
a newer and greener approach to the synthesis 1,2,3-tria-
zole by the Cu catalyzed cycloaddition of azide and alkyne
or organocatalytic cycloaddition reactions of azides with
enolizable groups due to its simple work-up, purifcation
steps, and good to excellent yields [10–23].
drawbacks, such as a small specifc surface area and low cat-
alytic activity, limiting its practical application. As a result,
modifcation of its texture and surface functionalization is
required to improve its properties.
Experimental section
General
All substances and solvents are commercially accessible
and were obtained from commercial sources and used as
received. Melting points were recorded on a Buchi R-535
apparatus.
Fabrication of Fe3O4@g‑C3N4–SO3H nanocomposite
The Fe3O4@g-C3N4–SO3H catalyst was prepared according
to our previous paper (Scheme 1) and used directly after
characterizations. [39].
The g-C3N4 nanosheet was constructed by a simple hydro-
thermal method. Melamine (10.0 g) loaded in an alumina
crucible with a cover and heated to 550 °C for 4 h with a
ramp rate of 5 °C/min and then cooled to room temperature.
The obtained light yellow product was collected and ground
well into a powder. g-C3N4 nanosheets obtained by thermal
oxidation of bulk g-C3N4 in the semiclosed system. 2.0 g
bulk g-C3N4 powders were transferred into a 70 mL crucible
with a cover and were sustained for 2 h at 500 °C to obtain a
g-C3N4 nanosheet. The Fe3O4@g-C3N4 prepared by a one-
step solvent, thermal method, and the schematic exhibited
in Scheme 1. g-C3N4 nanosheets (1.0 g) dispersed in water
(100 mL) using ultrasonic for 2 h to form a uniform suspen-
sion. Then, FeCl3.6H2O (2.0 g in 15 mL water), FeCl2.4H2O
(0.8 g in 10 mL water), and 8 mL of ammonia (32% aqueous
solution) were added, and the mixture was stirred at 80 °C
for 30 min. After that, the resulting suspension heated for
another 30 min at 90 °C to provide the Fe3O4@g-C3N4 nano-
composite after washing with deionized water and absolute
alcohol and drying in a vacuum oven at 60 °C. Sulfonation
of Fe3O4@g-C3N4 also performed using our reported pro-
cedure. [33] Briefy, Fe3O4@g-C3N4 (1.0 g) was taken in
a round-bottomed fask equipped with a constant pressure
Graphene-based nanocomposite, one of the thinnest mate-
rials in the universe, has inspired huge interest in biosensors,
energy storage devices, materials science, condensed matter
physics, and biology [24, 25]. Due to its exceptional proper-
ties, such as excellent mechanical, electrical, and thermal
properties, graphene research has reached an unexpectedly
great height and has emerged as a champion in composite
materials [26–28]. Various synthesis routes have recently
been devised for producing diferent polymer and metal-
based nanocomposite and fabricating hybrid nanocomposite
to address the needs of the composite industry [29].
Graphitic carbon nitride (g-C3N4) is the new type of
sheet-like polymeric carbon-based material with broad
interdisciplinary attention. [30–32] It can be fabricated from
direct thermal condensation of economic nitrogen-rich com-
pounds such as urea, cyanamide, and melamine. [33–35] As
an analog of graphene, it has to contain two-dimensional
frameworks of tri-s-triazine connected via a nitrogen atom.
Along with high physicochemical stability, this unique struc-
ture has been the hotspot in the various research felds in
recent years. [36–38] However, g-C3N4 sufers from several
Scheme 1 Preparation of Fe3O4@g-C3N4–SO3H nanocomposite
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Journal of the Iranian Chemical Society
dropping funnel and a gas inlet tube for passing HCl gas and
dried dichloromethane (100 mL) added to it. Next, chloro-
sulfonic acid (1.2 mL) was added dropwise to the above
suspension for 40 min and further stirred for 12 h at room
temperature. Subsequently, Fe3O4@g-C3N4–SO3H nano-
composite was collected using an external magnet, washed
with dichloromethane, water and ethanol, and dried at 60 °C
in a vacuum oven for 8 h.
ArH), 8.24 (br s, 1H, triazole ring), 13.12 (br s, 1H, NH).
13C NMR (125.7 MHz, DMSO-d6): δ=128.4, 128.9, 129.3,
129.8, 130.1, 135.2.
1
Table 1, entry 6: H NMR (DMSO-d6, 500 MHz):
δ=7.35-7.37 (m, 1H, ArH), 7.49 (t, J=7.2 Hz, 1H, ArH),
7.76-7.59 (m, 2H, ArH), 8.40 (br s, 1H, triazole ring),
12.18 (br s, 1H, NH). 13C NMR (125.7 MHz, DMSO-d6):
δ=119.7, 126.1, 128.3, 129.5, 129.9, 131.6, 144.1.
1
Table 1, entry 7: H NMR (DMSO-d6, 500 MHz):
General procedure for synthesizing
4‑aryl‑NH‑1,2,3‑triazoles
δ=7.36 (s, 1H, ArH), 7.68 (d, J=7.1 Hz, 1H, ArH), 7.79 (d,
J=7.1 Hz, 1H, ArH), 8.12 (br s, 1H, triazole ring), 14.12 (br
s, 1H, NH). 13C NMR (125.7 MHz, DMSO-d6): δ=121.7,
126.8, 128.9, 129.9, 130.3, 134.6, 140.2.
In a 5 mL round-bottomed fask equipped with a magnetic
stirrer, a solution of the respective β-nitrostyrene deriva-
tives (0.5 mmol), NaN3 (0.8 mmol), DMF (4 mL), and
Fe3O4@g-C3N4–SO3H (20 mg) was added. The resulting
1
Table 1, entry 11: H NMR (DMSO-d6, 500 MHz):
δ=2.27 (s, 3H, Me), 7.25 (d, J=5.8 Hz, 2H, ArH), 7.78 (d,
J=5.7 Hz, 2H, ArH), 8.12 (s, 1H, triazole ring) 14.26 (br
s, 1H, NH).. 13C NMR (125.7 MHz, DMSO-d6): δ=24.2,
126.7, 130.4, 130.9, 138.6.
mixture was stirred vigorously at 70 C̊ for 60-240 min. After
completion of the reaction as monitored by TLC, the mixture
was allowed to cool down to room temperature. Next, water
(10 mL) was added under vigorous stirring. The nanocom-
posite was removed by an external magnetic and washed
with 5 M HCl and ethyl acetate, and reused for the next reac-
tions. The resulting crude products were washed with 5 M
sodium hydroxide solution and recrystallized from ethanol
or ethyl acetate to give the corresponding pure 1,2,3-tria-
zoles as identifed by melting points. In the cases of the
crude oil products, ethyl acetate (2×10 mL) was added, and
the contents were transferred to a separating funnel. The
combined organic layers were washed with water, dried
over Na2SO4, and fltered. The solvent’s evaporation gave
the crude product, which was purifed by silica gel column
chromatography (ethyl acetate: petroleum ether) to obtain
the desired products.
1
Table 1, entry 13: H NMR (DMSO-d6, 500 MHz):
δ=7.49 (d, J=7.2 Hz, 2H, ArH), 7.90 (d, J=7.4 Hz, 2H,
ArH), 8.24 (br s, 1H, triazole ring), 12.15 (br s, 1H, NH).
13C NMR (125.7 MHz, DMSO-d6): δ=125.3, 127.2, 128.6,
129.8, 130.2, 134.6.
1
Table 1, entry 15: H NMR (DMSO-d6, 500 MHz):
δ=6.47-7.42 (m, 3H), 7.92 (s, 1H, triazole ring). 13C NMR
(125.7 MHz, DMSO-d6): δ = 108.6, 112.3, 129.5, 140.3,
143.7, 147.1.
Results and discussion
In a continuation of our interest toward the synthetic applica-
tions of graphitic carbon nitride as a highly active catalyst
in organic synthesis, [40–42] we wish to report herein an
acidic graphitic carbon nitride (Fe3O4@g-C3N4–SO3H) as
a magnetic catalyst for the assembly of 1,2,3-triazoles from
the reaction between β-nitrostyrene derivatives and sodium
azide under mild conditions. We investigated our study by
optimizing the reaction conditions using β-nitrostyrene
(1a) and sodium azide as model substrates. Initial test-
ing of β-nitrostyrene (1a) (0.5 mmol) with sodium azide
(0.8 mmol) with Fe3O4@g-C3N4–SO3H (20 mg) as a cat-
alyst in the water at room temperature was not good and
provided low yields of the desired triazoles (2a). Various
solvents were examined in the model reaction (Table 1,
entries 2−14), and the solvent plays a signifcant role in this
cycloaddition reaction. The result of 1a with NaN3 in difer-
ent solvents (water, methanol, ethanol, THF, toluene, CHCl3,
and CH3CN) failed to produce the desired products in longer
reaction times. The reaction proceeds quickly in DMF with a
catalytic amount of Fe3O4@g-C3N4–SO3H (20 mg) to aford
1,2,3-triazole 2a in both good isolated yields and purity. We
then investigated the efect of reaction temperature and the
Selected data
Table 1, entry 1: 1H NMR (DMSO-d6, 500 MHz): δ=7.34
(s, 1H, triazole ring), 7.47-8.01 (m, 5H, ArH), 9.87 (s, 1H,
NH, triazole ring). 13C NMR (125.7 MHz, DMSO-d6):
δ=125.1, 128.2, 128. 9, 129.8, 131.1, 161.9.
1
Table 1, entry 2: H NMR (DMSO-d6, 500 MHz):
δ = 3.94 (s, 3H, OMe), 3.97 (s, 3H, OMe), 7.01 (d,
J = 7.8 Hz, 1H, ArH), 7.41–7.44 (m, 2H, ArH), 8.61 (br.
s, 1H, triazole ring). 13C NMR (125.7 MHz, DMSO-d6):
δ = 56.8, 57.9, 108.9, 111.9, 119.1, 129.2, 136.4, 149.3,
149.7, 150.7
1
Table 1, entry 3: H NMR (DMSO-d6, 500 MHz):
δ = 7.34-7.36 (m, 1H, ArH), 7.49 (s, 1H, ArH), 7.58-7.92
(m, 3H, ArH), 8.69 (br s, 1H, triazole ring), 9.25 (br s, 1H,
triazole ring). 13C NMR (125.7 MHz, DMSO-d6): δ=119.1,
126.2, 127.9, 129.2, 129.8, 131.0, 142.8.
1
Table 1, entry 4: H NMR (DMSO-d6, 500 MHz):
δ=7.55 (d, J=7.2 Hz, 2H, ArH), 7.88 (d, J=7.3 Hz, 2H,
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Journal of the Iranian Chemical Society
Scheme 2 Proposed mechanism
of the reaction in the presence
of Fe3O4@g-C3N4–SO3H nano-
composite
Fig. 1 Triazole-based drugs
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Journal of the Iranian Chemical Society
amount of catalyst and DMF under various conditions. The
best result was obtained at 70 °C with 20 mg of catalyst in
4 mL of DMF (Table 1, entry 6). The reaction underwent
completion in 60 min to obtain 1,2,3-triazoles in 97% yields
with simple work-up. Furthermore, a comparative fndings
of catalysts efciency of diferent elements of the compos-
ite such as Fe3O4, g-C3N4, Fe3O4@g-C3N4, g-C3N4–SO3H,
Fe3O4@SO3H (Table 1, entries 15-19) are outlined in
Table 1 which indicated that Fe3O4@g-C3N4–SO3H nano-
composite superior to all elements of the composite due to
self ionic properties and high surface area of the catalyst.
Following these optimized procedures, the scope
and limitations of the reaction were examined with
β-nitrostyrene derivatives (Table 2). As will be read-
ily seen from Table 2, this reaction is tolerant of a
wide range of functional groups and demonstrated
to be a straightforward system for the preparation of
100
80
60
40
20
0
1
2
3
Run
4
5
Fig. 2 Reusability experiments of magnetic nanocatalyst
Table 1 Solvent screening for the model reaction
Entry
Solvent (mL)
Catalyst (mg)
Temp.
Time (min)
Yields (%)a
1
2
3
4
5
6
7
8
DMF (1 mL)
DMF (2 mL)
DMF (3 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
CHCl3 (4 mL)
Toluene (4 mL)
THF (4 mL)
Water (4 mL)
EtOH (4 mL)
MeOH (4 mL)
CH3CN (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
DMF (4 mL)
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
5
rt
rt
rt
rt
600
600
600
600
600
60
60
60
60
60
60
60
60
60
60
60
60
60
40
58
64
68
74
97
97
45
60
42
25
30
32
56
42
35
48
90
81
45
60
76
97
97
50
70
100
70
70
70
70
70
70
70
70
70
70
70
70
70
70
70
70
70
9
10
11
12
13
14
15b
16c
17d
18e
19f
20
21
22
23
24
60
60
60
60
60
60
10
15
25
50
aIsolated yields. bFe3O4 as catalyst. cg-C3N4 as catalyst. dFe3O4@g-C3N4 as catalyst. e.g.-C3N4–SO3H as catalyst. fFe3O4@SO3H as catalyst
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Journal of the Iranian Chemical Society
Table 2 Magnetic
Entry
1
Ar-
Yield (%)[a]
97
Time (min)
60
M.P. (founded)
M.P. (reported)
149–151 [63]
nanocomposite-catalyzed
cycloaddition reaction of
nitroolefns with NaN3 under
optimized conditions
145–148
2
3
79
82
240
190
100–103
173–175
102–104 [47]
172–173 [46]
4
5
84
77
200
120
152–153
184–187
150–152 [47]
185–186 [64]
6
7
85
79
150
240
95–97
94–96 [47]
166–168
168–170 [64]
8
9
78
88
80
191–193
146–149
191–192 [44]
148–152 [63]
220
10
11
12
92
95
89
240
180
220
168–170
156–159
54–57
167–172 [63]
158–160 [63]
53–54 [64]
13
14
83
87
90
184–187
88–89
185–189 [63]
87–88 [64]
120
15
16
77
75
160
160
64–66
84–86
63–64 [64]
85–87 [64]
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Journal of the Iranian Chemical Society
Table 3 Comparison of the activity of magnetic acid carbon nitride nanocomposite with the reported methods
Entry catalyst
Reaction conditions
Starting materials
Azide source
Yield (%) Ref.
1
2
3
4
Pd‐MCM‐41
Sulfated tungstate
CXH–SO3H
–
DMF, 80 °C, .083 h;
DMF, 60 °C, 1 h
DMSO, 60 °C, 4 h
DMSO, 90, 12 h
β‐nitrostyrenes
β‐nitrostyrenes
β‐nitrostyrenes
TMSN3
NaN3
NaN3
99
95
92
78
45
49
47
48
Nitroalkenes or vicinal
NaN3
acetoxy
5
Al-MCM-41
Ethanol/water, 80 °C, 0.5 h, Benzaldehydes and
NaN3
24
49
MW
nitromethane
β‐nitrostyrenes
β‐nitrostyrenes
Nitroolefns/alkynes
6
7
8
9
Amino sulfonic acid
Amberlyst-15
Cu/ascorbate
DMF, 60 °C, 12 h
DMF, 50 °C, 4 h
H2O, 100, 1 h
NaN3
NaN3
NaN3
NaN3
94
95
99
98
50
51
52
53
Fe3O4@nSiO2‐SO3H@ Methanol/DMF 140 °C, 8 h, Benzaldehydes and
MS‐NHCOCH3
sealed tube;
nitromethane
10
NH4OAc
DMF, 80 °C, 12 h,
Enolizable ketones and
4-nitrophenyl azide
93
54
NH4OAc
11
12
p-TsOH
CuFe2O4
DMF, 60 °C, 6 h,
β‐nitrostyrenes
NaN3
NaN3
89
90
55
56
DMSO, 120 °C, 0.08333 h,
Benzaldehydes and
MW
nitromethane
13
14
15
16
17
18
19
20
21
GO-Fe3O4@CuO
Fe3O4@CD-CIT/CuSO4 H2O, 45 min. rt, US
l-phenylalanine/CuSO4 H2O, 80 min. 40 °C, US
Cu/ascorbate
H2O, 45 °C, 80 min. US
Coumarin alkyne
Sugar alkyne
Phenylacetylene
Glucose alkyne
Flavanones
Phenyl acetylene
Phenyl acetylene
Phenyl acetylene
β‐nitrostyrenes
Sugar-N3
97
96
97
97
89
92
57
58
59
60
61
62
63
Coumarinazide c
3-azidocoumain
Coumarin azide
Aryal azide
Phenyl azide
1-azido-4-nitro benzene 98
H2O, 55 min. 40 °C, US
H2O, 100 °C, 1 h
EtOH/water, 100 min., rt
Neat, rt, 2 h
H2O, rt, 12 h
DMF, 70 °C, 1 h
CuO/rGO
Cs/PVA-CuNp
Cu(PPh3)NO3
Cu@Fe NPs
Benzyl azide
NaN3
88
97
64
Fe3O4@g-C3N4–SO3H
This work
4-aryl-NH-1,2,3-triazoles in a simpler manner. A vari-
ety of β-nitrostyrene bearing substitutions with various
steric and electronic properties at the ortho-, meta-, and
para-positions with the electron-donating groups and the
electron-withdrawing group was converted to triazole
products in good to excellent yields. Furthermore, hetero-
cyclic substituted β-nitrostyrene derivatives also screened,
and the pure triazoles could directly obtain in good yields
(Table 2, entries 15,16).
groups to generate an activated intermediate that reacts with
the sodium azide via [3+2]-cycloaddition followed by the
elimination of HNO2 to aford the desired 1,2,3-triazole [65].
The catalytic activity of the Fe3O4@g-C3N4–SO3H nano-
composite for the formation of triazole derivatives compared
with the earlier reported procedure and the results shown in
Table 3. The data in Table 3 clearly showed that the present
method is more versatile and more straightforward, which
involves short reaction time, reusable catalyst, suitable to
high product yield, to furnish regioselective synthesis of
triazole derivatives.
The stability and reusability are signifcant advantages of
magnetic catalysts in industrial processes. The recycling use
of the Fe3O4@g-C3N4–SO3H was performed in the model
reaction (2a), and the results indicated that it was easy to
collect the nanocatalyst due to its magnetic properties. After
the reaction completion, water (10 mL) was added to the
reaction mixture, and the nanocomposite was recovered with
the aid of an external magnet. This recovered nanocatalyst
was washed with 5 M HCl solutions and reused up to 5
cycles, and the results are shown in Fig. 2. The XRD data
and FTIR spectra showed no changes in the structure and
morphology of the nanocatalyst.
Conclusions
In summary, we have disclosed a simple, efcient, and envi-
ronmentally benign heterogeneous acidic ionic system for
the regioselective synthesis of 4-Aryl-NH-1,2,3-triazoles by
1,3-dipolar cycloaddition reaction of nitroolefns with NaN3.
Fe3O4@g-C3N4–SO3H be quickly recovered by an external
magnet and reused without loss of its catalytic activity. The
promising aspect of the presented procedures is operational
simplicity, large-scale availability, short reaction time, and
good to excellent yields.
The tentative catalytic cycle is shown in Scheme 2. We
reasoned that a plausible catalytic cycle could be readily ini-
tiated via activation of the nitroolefn with the sulfonic acid
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Journal of the Iranian Chemical Society
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