The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19 magnetic nanoparticles as efficient catalyst and their application in complexation with Hg2+ ions

Article abstract of DOI:10.1007/s13738-018-1514-9

Abstract: In this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone derivatives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe₁₂O₁₉ magnetic nanoparticles. SrFe₁₂O₁₉ was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70?nm which can be recycled and readily and separated from the reaction mixture using an external magnet. Short reaction times and high yields of desired products are the main advantages of the presented procedure. Subsequently, the spectrophotometric method was used to investigation of the complexation process between 2-amino-4,6-diphenylnicotinonitrile as organo-ligand and several metal ions such as Ag⁺, Cd²⁺, Co²⁺, Cr³⁺, Cu²⁺, Fe³⁺, Hg²⁺, Mn²⁺, Ni²⁺, Pb²⁺, and Zn²⁺ in CH₃CN solution at 25?°C. According to the obtained results, the absorption spectra of organo-ligand in the CH₃CN solution only were changed by the addition of Hg²⁺ ions, which indicates the formation of one absorbing complex compound between organo-ligand and Hg²⁺ ions. The stoichiometry of the resulting complex was calculated from the computer fitting of the molar absorbance measurements in different mole ratios. Graphical abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s13738-018-1514-9

Journal of the Iranian Chemical Society
https://doi.org/10.1007/s13738-018-1514-9
ORIGINAL PAPER
The green synthesis of 2-amino-3-cyanopyridines using SrFe12O19
magnetic nanoparticles as efficient catalyst and their application
in complexation with Hg2+ ions
Zohreh kheilkordi1 · Ghodsi Mohammadi Ziarani1 · Shahriyar Bahar1 · Alireza Badiei2
Received: 23 April 2018 / Accepted: 8 October 2018
© Iranian Chemical Society 2018
Abstract
In this paper, a family of 2-amino-4,6-diphenylnicotinonitriles are prepared from aromatic aldehydes, acetophenone deriva-
tives, malononitrile, and ammonium acetate via one-pot reaction catalyzed by SrFe12O19 magnetic nanoparticles. SrFe12O19
was an efficient, green, and reusable nanomagnetic heterogeneous catalyst with the average particles’ size of 70 nm which
can be recycled and readily and separated from the reaction mixture using an external magnet. Short reaction times and
high yields of desired products are the main advantages of the presented procedure. Subsequently, the spectrophotometric
method was used to investigation of the complexation process between 2-amino-4,6-diphenylnicotinonitrile as organo-ligand
and several metal ions such as Ag+, Cd2+, Co2+, Cr3+, Cu2+, Fe3+, Hg2+, Mn2+, Ni2+, Pb2+, and Zn2+ in CH3CN solution at
25 °C. According to the obtained results, the absorption spectra of organo-ligand in the CH3CN solution only were changed
by the addition of Hg2+ ions, which indicates the formation of one absorbing complex compound between organo-ligand
and Hg2+ ions. The stoichiometry of the resulting complex was calculated from the computer fitting of the molar absorbance
measurements in different mole ratios.
Graphical abstract
Electronic supplementary material The online version of this
article (https://doi.org/10.1007/s13738-018-1514-9) contains
supplementary material, which is available to authorized users.
Extended author information available on the last page of the article
Vol.:(0123456789)
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Journal of the Iranian Chemical Society
Keyword SrFe12O19 · One-pot · Magnetic nanoparticles · 2-amino-4,6-diphenylnicotinonitriles · Solvent-free reaction ·
Complexation
using tetramethylsilane (TMS) as an internal standard in
DMSO-d6 solution. Mass spectrometry (MS) analysis was
carried out on a model 5973 mass-selective detector (Agi-
lent). UV–Vis spectra were recorded on an Analytik Jena
Specord S600 Spectrophotometer. The X-ray powder dif-
fraction (XRD) pattern of SrFe12O19 nanoparticles was pre-
pared by a Philips X’pert MPD diffractometer using Cu Kα
radiation (λ=0.15478 nm). The scanning electron micros-
copy (SEM) analysis was taken with SEM (MV2300). The
specific surface area and pore size distribution of the mag-
netic nanoparticles were measured by N2 adsorption–des-
orption at 77 K with Brunauer–Emmett–Teller (BET) and
Barret–Joyner–Halenda (BJH) methods using a BELSORP
analysis software. Magnetization measurements at room
temperature were performed using a vibrating-sample mag-
netometer (VSM) (Meghnatis Daghigh Kavir Co; Kashan
Kavir; Iran).
Introduction
2-amino-4,6-diphenylnicotinonitrile derivatives are a class
of heteroaromatic rings containing nitrogen atoms which
showed a wide range of biological activities including
A2A adenosine receptor antagonists, anti-microbial agents,
inhibitors of HIV-1 integrase, IKK-β inhibitors, and anti-
tumor, anti-inflammatory, and anti-parkinsonism [1–6].
Hexagonal strontium hexaferrite (SrFe12O19), known as
M-type strontium hexaferrite (SrM), was discovered in the
1950s by Philips’ laboratories [7]. Strontium hexaferrite is
usually used as magnetic recordings, microwave devices,
and permanent magnets [8–10]. The magnetic properties of
SrFe12O19 depend on the shape and size of the particles,
several methods have been used to prepare strontium fer-
rite, including sol–gel [11, 12], hydrothermal [13], salt melt
methods [14], ball milling [15], self-propagating high-tem-
perature synthesis [16], and the chemical co-precipitation
method [17]. The chemical co-precipitation methodology
due to its simplicity and good control of grain size is usually
used to synthesize of magnetic oxides [18]. In this work, the
SrFe12O19 magnetic nanoparticles was used as catalyst in the
synthesis of 2-amino-4,6-diphenylnicotinonitrile derivatives.
After that, the complexation ability of the 2-amino-4,6-di-
phenylnicotinonitrile as organo-ligand with some metal ions
was investigated. According to the literature [19–22]. The
kind, number, distance, and orientation of the donor atoms
of the organo-ligand that are structurally accessible to the
complexed metal ions can be affect the formation constant
and selectivity of the resulting complex. To examine the
possible reactions between organo-ligand and metal ions,
the spectrophotometric titration was used and complexation
procedures were analyzed using absorbance alteration that
occurs by the conversion of metal-to-organo-ligand ratio in
CH3CN solution.
Preparation of SrFe12O19 nanoparticles
The SrFe12O19 MNPs synthetic method was published before
[23–25]. At first, Fe(NO3)3.9H2O and Sr(NO3)3 powders
with molar ratio of 10:1 for Fe to Sr. were dissolved in
deionized water (100 ml for 0.1 mol of Fe3+) and stirred at
60 °C. Then, citric acid was slowly poured into solution and
stirred vigorously using a magnetic stirrer. Afterward, the
solution was cooled to room temperature and ammonium
hydroxide was added until of the solution was adjusted to 7.
Then, a cationic surfactant with ratio of 0:4 for surfactant to
strontium was added to it. After evaporation of the solvent, a
powder was obtained which then calcined at 900 °C for 1 h.
General procedure for the synthesis
of 2‑Amino‑4,6‑diphenylnicotinonitrile derivatives
A mixture of aromatic aldehydes (1 mmol), malononitrile
(1 mmol, 0.06 g), acetophenone derivatives (1 mmol),
ammonium acetate (1.5 mmol, 0.11 g), and SrFe12O19
(0.02 g) as a nanomagnetic heterogeneous catalyst was
heated under green conditions at 100 °C for the appropriate
time as mentioned in Table 2. The completion of the reaction
was monitored by TLC. After completion of the reaction,
the mixture was dissolved in hot EtOH, and then, SrFe12O19
nanoparticles were readily separated from the solution using
an external magnet. The solution was cooled.
Experimental
Materials
All chemical compounds were purchased from Merck
Company and used without further purification. Melting
points were measured by capillary tube method with an
Electrothermal 9200 apparatus. Infrared (IR) spectra were
recorded from KBr pellets using a Fourier transform (FT)-
IR Bruker Tensor 27 instrument. 1H NMR (500 MHz) and
13C NMR (125 MHz) spectra were run on a Bruker DPX
To obtain the pure crystalline product, the new compound
was characterized by IR and NMR spectroscopy techniques.
The melting points of the products were compared with
those reported in the literature.
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Journal of the Iranian Chemical Society
Table 1 Optimization of reaction conditions for the synthesis of
Results and discussion
2-amino-4,6-diphenylnicotinonitrile
Synthesis of 2‑amino‑4, 6‑diphenylnicotinonitrile
derivatives using SrFe12O19 MNPs
Entry
Solvent
Temp
Time (h)
Yielda (%)
1
2
3
4
H2O
EtOH
–
Reflux
Reflux
80 °C
5
4
1
20
30
50
90
Initially, we investigated the condensation of benzalde-
hyde (1 mmol, 0.10 ml), acetophenone (1 mmol, 0.11 ml),
ammonium acetate (1.5 mmol, 0.11 g), and malononitrile
(1 mmol, 0.06 g) as a model of reaction in the presence of
SrFe12O19 MNPs (0.02 g) in various conditions. As shown
in Table 1, we applied different solvents including water,
ethanol, and solvent-free systems in different temperature
that the best result was obtained in the solvent-free condi-
tion at 100 °C (Table 1, entry 3) (Schemes 1, 2).
–
100 °C
8 min
Reaction condition: benzaldehyde (1 mmol, 0.10 g), acetophenone
(1 mmol, 0.12 g), ammonium acetate (1.5 mmol, 0.11 g), malononi-
trile (1 mmol, 0.06 g), and SrFe12O19 MNPs (0.02 g)
aIsolated yields
2‑Amino‑4‑(2‑methoxyphenyl)‑6‑(4‑methylphenyl)
nicotinonitrile (5 l)
After optimization of the reaction conditions, 2-amino-
4,6-diphenylnicotinonitrile derivatives were prepared via
the one-pot green condensation of arylaldehydes, various
acetophenones, malononitrile, and ammonium acetate
using SrFe12O19 MNPs (0.02 g) as catalyst under solvent-
free condition at 100 °C (Table 2). The results were excel-
lent in terms of reaction times and yields. As shown in
Table 2, we investigated the effect of substituents on the
aromatic ring under these reaction conditions which both
categories including electron-withdrawing and electron-
donating substituents on their aromatic ring led to create
the products with excellent yields in short reaction time.
FT-IR (KBr) υmax(Cm− 1): 3467(NH2), 3378 (NH2), 2210
1
(CN), 1626 (C=N), 1577 (C=C). H NMR (500 MHz,
DMSO-d6): δ (ppm)=2.36 (s, 3H, Me), 3.80 (s, 3H, OMe),
6.88 (s, 2H, NH2), 7.07–7.11 (t, 2H, Ar), 7.14 (s, 1H, pyri-
dine ring), 7.19–7.20 (d, 1H, Ar), 7.28–7.30 (d, 2H, Ar),
7.33–7.35 (d.d, 1H, Ar), 7.47–750 (t.d, 2H, Ar). 13C NMR
(125 MHz, DMSO-d6): δ (ppm) = 21.35, 55.98, 89.30,
110.42, 112.25, 117.25, 121.10, 126.68, 127.52, 129.70,
130.46, 131.27, 135.35, 140.19, 153.21, 156.50, 158.73,
160.54. Ms (EI): m/z=315 (M+), 300, 256, 239, 205, 167,
149, 134, 113, 57.
Table 2 Synthesis of 2-amino-
4,6-diphenylnicotinonitrile
derivatives 5a–l in the presence
of SrFe12O19 MNPs
Entry
No.
R1
R2
Time (min)
Yield (%)
m.p.
m.p. [Refs.]
1
2
3
4
5
6
7
8
5a
5b
5c
5d
5e
5f
5 g
5 h
5i
H
H
H
H
H
H
H
H
4-Me
4-OMe
4-Me
4-OMe
4-Me
8
5
10
12
6
13
7
10
9
90
91
89
89
90
88
86
87
88
91
90
91
186–187
185–188
170–173
181–182
196–199
194–196
143–148
160–163
164–166
173–175
190–193
203–206
186–178 [26]
188–190 [26]
175–176 [26]
180–182 [26]
200–202 [27]
198–201 [27]
148–150 [27]
165–166 [28]
166–167 [28]
172–174 [29]
194–196 [29]
New
4-Cl
4-Me
4-OMe
3-NO2
2-OMe
4-F
H
H
4-Cl
4-Cl
2-OMe
9
10
11
12
5j
5 k
5 l
7
8
11
Scheme 1 Synthesis of
2-amino-4,6-diphenylnicotinon-
itrile using SrFe12O19 MNPs as
model reaction
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Journal of the Iranian Chemical Society
Scheme 2 Synthesis of
2-amino-4,6-diphenylnicoti-
nonitrile derivatives 5a–l in the
presence of SrFe12O19
Likewise, the reaction time of aromatic aldehydes with
electron-withdrawing groups was rather faster than that
of electron-donating groups. Moreover, recyclability and
reusability of the catalyst were considered. The new prod-
uct was characterized by FT-IR and NMR spectroscopy
data.
which led to the reduction of two water molecules and the
generation of intermediates 6 and 7, respectively. After-
wards, the reaction between intermediate 7 (enamine) with
intermediate 6 (alkylidene malononitrile) will produce the
intermediate 8, followed by cyclization, tautomerization,
and aromatization to afford 2-amino-4,6-diphenylnicoti-
nonitrile 11.
In a probable mechanism (Scheme 3), initially,
SrFe12O19 MNPs as catalyst can concurrently activate both
the aromatic aldehydes 1 and acetophenone derivative 2 as
electrophile species. Then, malononitrile 3 and ammonium
acetate 4 reacted with two activated electrophile groups
As shown in Table 3, we compared the presented method
for the synthesis of 2-amino-4,6-diphenylnicotinonitrile
derivatives with the other previously explored methods.
The present methodology has extraordinarily improved the
Scheme 3 Suggested mechanism for the preparation of 2-amino-4, 6-diphenylnicotinonitrile derivatives
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Journal of the Iranian Chemical Society
Table 3 Comparison of
different conditions in the
synthesis of compound 5a
Entry Catalyst
Solvent
H2O
H2O/EtOH Reflux
–
H2O
–
Condition Time (h) Yield (%) Refs.
1
GOa
80 °C
5
1
96
92
86
95
90
90
93
90
90
91
90
[30]
[31]
2
Nano-CuO2-MFRb
{Fe3O4@SiO2(CH2)3Im}C(CN)3
Cellulose-SO3H
Fe3O4@TiO2@O2PO2(CH2)NHSO3H
ClO4−/Al-MCM-41
FePO4
3
100 °C
60 °C
90 °C
40 min
2.5
20 min
[27]
[29]
[32]
4
5
6
–
80 °C
2
4
2
4
[33]
[34]
[35]
[36]
[28]
This work
7
EtOH
H2O
EtOH
MeCN
–
Reflux
Reflux
Reflux
Reflux
100 °C
8
Bu4N+Br−
9
Yb(PFO)3
10
11
Cu/Cc
6
SrFe12O19
8 min
aGraphene oxide
bNano-sized CuO2 on melamine–formaldehyde resin
cCopper nanoparticles on charcoal
Fig. 2 Room-temperature hysteresis loops of SrFe12O19 MNPs
Fig. 1 SEM image of SrFe12O19 nanoparticles
Table 4 Reuse of SrFe12O19
Entry Time (min) Yield (%)
MNPs for the synthesis of 1a
synthesis of compounds in different terms including reaction
time and yield.
1
2
8
8
90
85
Characterization of the SrFe12O19 MNPs
The SrFe12O19 MNPs were characterized by different methods
including FT-IR, XRD, SEM, and VSM techniques [37, 38].
The shape, size, and morphology of SrFe12O19 MNPs were
studied by X-ray diffraction (XRD). The SEM images Fig. 1
of SrFe12O19 MNPs show spherical nanoparticles with aver-
age size of 70 nm. As shown in Fig. 2, the magnetic behavior
of SrFe12O19 nanoparticles was investigated using vibrating-
sample magnetometry (VSM) at room temperature. The mag-
netic saturation of SrFe12O19 MNPs is about 79 emu/g. There-
fore, according to the hysteresis loops in the magnetization
curves, SrFe12O19 nanoparticles are ferromagnetic at room
temperature.
The reusability of the catalyst was determined under opti-
mized conditions for the model reaction. The recycled cata-
lyst was washed with hot EtOH and then reused. As shown in
Table 4, the catalyst can be recovered and reused for two times
and the significant reduction in its activity was not observed.
The yields for the two runs were found to be 90 and 85%,
respectively.
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Journal of the Iranian Chemical Society
and Hg2+ ions. For the evaluation of the stoichiometry of
the formed Hg2+–ligand complex, the mole ratio method was
used [39]. For this purpose, 2.5 mL of 5.0×10−5 mol L−1
of 2-amino-4,6-diphenylnicotinonitrile solution in CH3CN
was placed in the spectrophotometer cuvette and the elec-
tronic absorption spectra were measured. Then, a 10 µL of
0.01 mol L−1 of Hg2+ solution in CH3CN was added to the
solution in stepwise manner using a Hamilton syringe. After
each addition, the spectral change of the solution was meas-
ured. As can be seen in Fig. 4, the absorbance of the solution
at wavelength of 350 nm was decreased with the addition of
Hg2+ ions to the solution. The addition of the Hg2+ ion solu-
tion was continued until the desired cation-to-ligand mole
ratio was achieved. A typical absorbance–mole ratio plot is
represented in Fig. 5. According to the slope change of the
Spectrophotometric studies
of complexation reactions
between 2‑amino‑4,6‑diphenylnicotinonitrile
and metal ions
In the continuation of our studies, we have investigated
the possible complexation reactions between 2-amino-
4, 6-diphenylnicotinonitrile and various metal cations in
CH3CN solution at 25 °C. As shown in Fig. 3, while the vari-
ous cations have no considerable interaction with 2-amino-
4,6-diphenylnicotinonitrile, but the absorbance of the
CH3CN solution of organo-ligand at wavelength of 350 nm
was significantly decreased with the addition of Hg2+ ions.
The spectral change indicated the formation of one absorb-
ing complex between 2-amino-4,6-diphenylnicotinonitrile
Fig. 3 The UV–Vis spectra of
2-amino-4,6-diphenylnicotinon-
itriles (5×10−5 M) without and
in the presence of Ag2+, Cd2+
,
Co2+, Cr3+, Cu2+, Fe3+, Hg2+
,
Mn2+, Ni2+, Zn2+, and Pb2+ ions
in CH3CN solution
Fig. 4 The UV–Vis spectra of
2-amino-4,6-diphenylnicotinon-
itriles (5×10−5 M) and its Hg2+
complexes in CH3CN solution
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Journal of the Iranian Chemical Society
Fig. 5 Typical absorbance–mole
ratio plot as [Hg2+
350 nm
]/[Ligand] at
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resulting curve at 1:2 [M]/[L] mole ratio, the stoichiometry
of the formed complex is 1:2.
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Conclusions
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In conclusion, we have developed an efficient one-pot
four-component synthesis of 2-amino-4,6-diphenylnico-
tinonitrile derivatives using SrFe12O19 as catalyst under
green conditions. The present method offers notewor-
thy advantages, such as simple, high yield, short reaction
time, eco-friendly, recycle, and reusability of the SrFe12O19
catalyst. In the present methodology, we studied the com-
plexation ability of 2-amino-4, 6-diphenylnicotinonitrile
with some metal ions using the spectrophotometric meth-
ods. The results showed that, among different metal ions,
Hg2+ ion has a good selectivity for the complexation with
2-amino-4,6-diphenylnicotinonitrile.
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Affiliations
Zohreh kheilkordi1 · Ghodsi Mohammadi Ziarani1 · Shahriyar Bahar1 · Alireza Badiei2
2
* Ghodsi Mohammadi Ziarani
School of Chemistry, College of Science, University
of Tehran, Tehran, Iran
gmohammadi@alzahra.ac.ir; gmziarani@hotmail.com
1
Department of Chemistry, Alzahra University, Vanak
Square, Tehran, Iran
1 3