Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile promoted by amino-functionalized CoFe2O4@SiO2 nanoparticles under conventional heating, microwave and ultrasound irradiations

Article abstract of DOI:10.1515/znb-2017-0114

Amino-functionalized CoFe₂O₄@SiO₂ nanoparticles have been used as an efficient catalyst for the preparation of 2,4-diamino-6-arylpyrimidine-5-carbonitrile derivatives by the one-pot reaction of aromatic aldehydes, malononitrile, and guanidine hydrochloride under conventional heating, microwave, and ultrasound irradiations. This method provides several advantages including mild reaction conditions, the reusability of the catalyst and low catalyst loading, and the use of microwave and ultrasonic irradiation as a valuable and powerful tool.

Full text of DOI:10.1515/znb-2017-0114

Z. Naturforsch. 2017; aop
Samaneh Barkhordarion-Mohammadi and Javad Safaei-Ghomi*
Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile
promoted by amino-functionalized CoFe O4@SiO2 nanoparticles
under conventional heating, microwave 2and ultrasound
irradiations
https://doi.org/10.1515/znb-2017-0114
the application of microwave and ultrasound irradiations
has been proven to be very beneficial. Microwave and
ultrasound irradiations are used for a variety of organic
syntheses due to short reaction times, easy workup, and
excellent yields [15–18]. The practical rate acceleration
upon microwave irradiation is owing to material-wave
interactions leading to thermal and specific effects. The
reaction is heated from the inside because the micro-
wave energy is transferred immediately to the reagents.
The solid catalysts absorb the microwave energy; con-
sequently, they can serve as an internal heat source for
the reactions [19, 20]. Ultrasound irradiation has been
developed to hasten the chemical reactions proceeding
Received June 25, 2017; accepted October 15, 2017
Abstract: Amino-functionalized CoFe2O4@SiO2 nanoparti-
cles have been used as an efficient catalyst for the prep-
aration of 2,4-diamino-6-arylpyrimidine-5-carbonitrile
derivatives by the one-pot reaction of aromatic aldehydes,
malononitrile, and guanidine hydrochloride under con-
ventional heating, microwave, and ultrasound irradia-
tions. This method provides several advantages including
mild reaction conditions, the reusability of the catalyst
and low catalyst loading, and the use of microwave and
ultrasonic irradiation as a valuable and powerful tool.
Keywords: CoFe2O4@SiO2; heterogeneous catalyst; micro- through the formation, growth, and implosive collapse
wave; pyrimidine; ultrasound irradiation.
of bubbles in a liquid. Collapsing bubbles generate high
temperatures and pressures [21, 22]. Compared with con-
ventional heating, which creates thermal energy in the
macro system, ultrasound irradiation is able to activate
numerous reactions by the activation energy in micro-
1 Introduction
Pyrimidines are one of the biologically substantial scaf- environments [23, 24]. In this study, we report the use of
folds due to their wide range of biological and pharmaceu- amino-functionalized CoFe2O4@SiO2 nanoparticles as
tical properties such as antihypertensive [1], antimicrobial an efficient catalyst for the preparation of 2,4-diamino-
[2, 3], antitumor [4], antimalarial [5], antioxidant [6], 6-arylpyrimidine-5-carbonitrile derivatives by the one-pot
protein kinase inhibitors [7], and antagonists of GPR40 reaction of aromatic aldehydes, malononitrile, and guani-
[8]. Therefore, the development of efficient methods for dine hydrochloride under conventional heating, micro-
the synthesis of pyrimidines is of great interest. A number wave, and ultrasound irradiations (Scheme 1).
of methods have been developed for the synthesis of
pyrimidines in the presence of catalysts such as sodium
acetate [9], Bi(NO3)3⋅5H2O [10], NaOH [11, 12], CuO micro- 2 Results and discussion
spheres [13], and K2CO3 [14]. Despite the availability of
these methods, there remains enough scope for the use of Initially, we focused on the systematic evaluation of dif-
an efficient and reusable catalyst with high catalytic activ- ferent catalysts in the reaction of benzaldehyde, malo-
ity for the preparation of pyrimidines. The completion nonitrile, and guanidine hydrochloride as a model
of the reactions under conventional heating conditions reaction. Yields were determined in the presence of Et3N,
requires several hours and the yields are low. The main Na2CO3, nano-CuI, nano-Fe3O4, nano-CoFe2O4, nano-
concern for the improvement of high-throughput proce- CoFe2O4@SiO2, and amino-functionalized CoFe2O4@SiO2
dures is the rate of the applied reactions. In this regard, nanoparticles, and the results are shown in Table 1. When
the reaction was carried out using amino-functionalized
CoFe2O4@SiO2 nanoparticles as the catalyst, the products
*Corresponding author: Javad Safaei-Ghomi, Department of
were obtained in good to high yields. In this research,
Chemistry, Qom Branch, Islamic Azad University, Qom, Iran,
microwave and ultrasound irradiations are used as green
and complementary techniques for the preparation of
pyrimidines. When the catalysis was performed under
e-mail: safaei@kashanu.ac.ir
Samaneh Barkhordarion-Mohammadi: Department of Chemistry,
Qom Branch, Islamic Azad University, Qom, Iran
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ꢀS. Barkhordarion-Mohammadi and J. Safaei-Ghomi: Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile
Ar
under conventional heating and assistance of microwave
CoFe2O4@SiO2/PrNH2 NPs
CN
CN
NH
NH2
CN
+
+
ArCHO
⋅ HCl
N
and ultrasound irradiation improved the yields of the
reactions and shortened the reaction times. The amount
of used catalyst in the ultrasound method was lower than
that on microwave irradiation because, in the latter, the
catalyst acts as an internal heat source. The possible
explanation for the positive association of irradiation is
that the ultrasonic irradiation could increase the number
H2N
EtOH, H2O
H2N
N
))))
NH2
MWI /
reflux /
Scheme 1:ꢀThree-component reaction of aldehydes, malononitrile,
and guanidine hydrochloride under conventional heating, micro-
wave, and ultrasound irradiations.
microwave and ultrasound irradiations, the reaction rate of active cavitation bubbles and the size of the individual
increased considerably. The best results were obtained bubbles, both of which are predictable resulting in higher
under ultrasound irradiation (40 W) in ethanol–water maximum collapse temperature and accelerated respec-
(3:7) and it was found that the reaction gave satisfying tive reaction. With the optimal conditions in hand, we
results in the presence of amino-functionalized CoFe2O4@ turned to explore the efficacy of the catalyst using differ-
SiO2 nanoparticles at 8 mg, which gave excellent yields of ent aromatic aldehydes and the results are summarized in
products (Table 1). Longer reaction times were required Table 2. Aromatic aldehydes with electron-withdrawing
Table 1:ꢀOptimization of reaction conditions using different catalysts.a
Entry
Solvent
Conditions
Catalyst
Amount
Time (min)
Yield (%)b
1
H2O
Reflux
Et3N
10 mol%
10 mol%
5 mol%
25 mg
25 mg
25 mg
25 mg
20 mg
25 mg
30 mg
10 mg
15 mg
20 mg
20 mg
20 mg
6 mg
300
300
300
180
180
150
150
90
38
30
25
48
51
62
64
79
82
82
83
86
86
78
85
89
92
92
84
92
2
EtOH
Reflux
Et3N
3
EtOH
Reflux
Na2CO3
4
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
EtOH–H2O (3:7)
Reflux
Nano-CuI
5
Reflux
Nano-Fe3O4
6
Reflux
Nano-CoFe2O4
7
Reflux
Nano-CoFe2O4@SiO2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
Nano-CoFe2O4@SiO2/PrNH2
8
Reflux
9
Reflux
90
10
11
12
13
14
15
16
17
18
19
20
Reflux
90
MWI (400 W)
MWI (400 W)
MWI (400 W)
MWI (300 W)
MWI (500 W)
US (40 W)
US (40 W)
US (40 W)
US (30 W)
US (50 W)
15
15
15
15
15
10
8 mg
10
10 mg
10 mg
10 mg
10
10
10
aReaction conditions: benzaldehyde (1 mmol), malononitrile (1 mmol), and guanidine hydrochloride (1 mmol); bisolated yield.
Table 2:ꢀSynthesis of 5-pyrimidinecarbonitriles 4a–4h using nano-CoFe2O4@SiO2/PrNH2.
Entry
Product
Ar
Time (min) MWIa
Yield (%) MWI
Time (min) USb
Yield (%) USc
m. p. (°C)
m. p. (°C) [L]
1
2
3
4
5
6
7
8
4a
4b
4c
4d
4e
4f
C6H5
15
15
15
20
20
15
15
15
86
90
90
81
83
88
87
84
10
10
10
15
15
10
10
10
92
96
96
87
89
94
93
90
237–239
265–267
260–262
236–238
255–257
275–276
232–235
225–227
237–239 [25, 26]
4-Cl-C6H4
4-Br-C6H4
4-OMe-C6H4
4-Me-C6H4
2,6-Cl2-C6H3
2-Cl-C6H4
3-Me-C6H4
265–266 [25, 26]
260–262 [25, 26]
236–238 [25, 26]
255–257 [25, 26]
–
–
–
4g
4h
aMicrowave irradiations (400 W) and 15 mg of catalyst; bultrasound irradiations (40 W), and 8 mg of catalyst; cisolated yield.
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S. Barkhordarion-Mohammadi and J. Safaei-Ghomi: Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrileꢂ ꢂ3
groups reacted faster than those with electron-donat-
3 Conclusions
ing groups. It has been observed that better yields are
achieved with substrates having electron-withdrawing In conclusion, we have developed a simple and highly
groups. efficient procedure for the synthesis of 2,4-diamino-6-aryl-
A mechanism for the reaction is outlined in Scheme 2. 5-pyrimidinecarbonitriles using amino-functionalized
The reaction occurs through initial formation of the cyano CoFe2O4@SiO2 nanoparticles as efficient catalyst under
olefin A from the condensation of malononitrile and aryl microwave and ultrasound irradiations. The remarkable
aldehyde, which is itself activated by the catalyst through advantages of this methodology are its easy work-up,
hydrogen bonding. The second step is followed by Michael short reaction times, use of a magnetically recoverable
addition, cycloaddition, isomerization, and aromatization catalyst, high to excellent product yields, operational
to afford the 5-pyrimidinecarbonitriles. The amino groups simplicity, little catalyst loading, and use of microwave
distributed on the surface of CoFe2O4@SiO2 activate the irradiations and ultrasonic irradiation as a valuable and
C=O and C≡N groups for better reaction with nucleophiles powerful technology.
through hydrogen bonding [27, 28].
We also investigated the recycling of amino-function-
alized CoFe2O4@SiO2 nanoparticles as a nanomagnetic
catalyst; its reusability was achieved by the reaction of
4 Experimental section
benzaldehyde (1 mmol), malononitrile (1 mmol), guani-
All organic materials were purchased commercially from
dine hydrochloride (1 mmol), and 8 mg of nano-CoFe2O4@
Sigma-Aldrich and Merck, and were used without further
SiO2-PrNH2 under ultrasound irradiations (40 W). In the
purification. All melting points are uncorrected and were
recycling procedure for the catalyst, after completion
determined in capillary tube on Boetius melting point
of the reaction, 5 mL of ethanol was added and magnet
microscope. Fourier-transform infrared spectra were
was introduced into the mixture in the form of a magnetic
recorded with KBr pellets using a Magna-IR spectrometer
stirrer bar and the catalyst was separated magnetically.
550 from Nicolet. Nuclear magnetic resonance (NMR)
The catalyst was washed with water and acetone, dried in
spectra were recorded on a Bruker 400 MHz spectrometer
an oven at 70°C for 150 min, and used directly with new
with dimethyl sulfoxide (DMSO) as solvent and tetra-
substrates under the same conditions and without further
methylsilane as internal standard. Powder X-ray diffraction
purification. The results showed that the catalyst had
was carried out on a Philips diffractometer from the X’pert
been reused in model reactions for five reaction cycles.
Company. We used the Milestone microwave (Microwave
It was found that the product yields decreased to a small
Labstation, MLS GmbH, ATC-FO 300) for the syntheses.
extent on each reuse (run 1, 92%; run 2, 92%; run 3, 91%;
CoFe2O4@SiO2-PrNH2 nanoparticles were prepared accord-
run 4, 91%; run 5, 90%).
ing to the method reported in the literature with some mod-
ifications [24]. The microscopic morphology of the products
was visualized using scanning electron microscope (MIRA3
Ar
TESCAN). The magnetic measurements of the samples were
CN
CN
CN
CN
NH
NH2
+
⋅ HCl
+
O
carried out in a vibrating sample magnetometer (Meghnatis
Daghigh Kavir Co., Kashan Kavir, Iran) at room temperature
in an applied magnetic field sweeping between 10 kOe (1
kOeꢀ=ꢀ7.96ꢀ×ꢀ104 A m−1). The synthesis and characterization of
the CoFe2O4@SiO2-PrNH2 nanoparticles are described in the
Supporting Information, which is available online. Spectral
data were consistent with the literature values [25, 26].
H2N
H
− H2O
Ar
H
A
Ar
N
Ar
Ar
CN
CN
N
CN
N
N
HN
− H2
NH2
H2N
N
NH2
H2N
H2N
NH
B
4.1 General procedure for the synthesis
of 2,4-diamino-6-aryl-5-pyrimidine-
carbonitrile (4a–h)
= CoFe2O4@SiO2/PrNH2 NPs
A mixture of aldehydes (1 mmol), malononitrile (1 mmol),
guanidine hydrochloride (1 mmol), solvent EtOH–H2O
Scheme 2:ꢀProposed mechanism for the formation of
5-pyrimidinecarbonitriles.
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4ꢀ ꢀS. Barkhordarion-Mohammadi and J. Safaei-Ghomi: Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrile
(3:7), and amino-functionalized CoFe2O4@SiO2 nanopar- δ (ppm)ꢀ=ꢀ3.59 (3H, s, OCH3), 7.59–7.62 (4H, 2 NH2), 7.30 (2 H,
ticles nano-(CoFe2O4@SiO2-PrNH2) was subjected under m, ArH), 8.35 (2H, m, ArH). – 13C NMR (100 MHz, [D6]
conventional heating, microwave, and ultrasound irradia- DMSO): δ (ppm)ꢀ=ꢀ54.31, 79.18, 113.45, 117.92, 125.67, 128.12,
tions. The reaction was monitored using thin layer chro- 160.21, 164.91, 167.40, 169.33. – Analysis for C12H11N5O: calcd.
matography. After completion of the reaction, the catalyst C 59.74, H 4.60, N 29.03; found C 59.65, H 4.45, N 28.95.
was separated magnetically. The precipitate was filtered
and recrystallized with n-hexane-ethyl acetate to obtain
4.2.5 2,4-Diamino-6-p-tolylpyrimidine-5-carbonitrile (4e)
the pure products.
M. p. 255–257°C, IR (KBr): v̅ ꢀꢀ3=428, 3323, 3214 (NH2), 2192
(CN), 1639, 1601, 1510 cm−1. – 1H NMR (400 MHz, [D6]DMSO):
δ (ppm)ꢀ=ꢀ2.09 (3H, s, CH3), 7.51–7.62 (4H, 2 NH2), 7.94–7.98
(2H, m, ArH), 8.02–8.07 (2H, m, ArH). – 13C NMR (100 MHz,
[D6]DMSO): δ (ppm)ꢀ=ꢀ21.93, 80.73, 118.57, 128.59, 130.62,
134.80, 140.53, 163.45, 165.56, 169.67. – Analysis for C12H11N5:
calcd. C 63.99, H 4.92, N 31.09, found C 63.85, H 4.83, N 31.15.
4.2 Spectral data
4.2.1 2,4-Diamino-6-phenylpyrimidine-5-carbonitrile (4a)
M. p. 237–239°C. – IR (KBr): v
̅
ꢀ=ꢀ3400, 3359 (NH),
2
1
2223 (CN) cm−1. – H NMR (400 MHz, [D6]DMSO): δ
(ppm)ꢀ=ꢀ7.70–7.82 (4H, 2NH2), 7.93–7.98 (3H, m, ArH),
13
8.30–8.37 (2H, m, ArH). – C NMR (100 MHz, [D6]DMSO): 4.2.6 2,4-Diamino-6-(2,6-dichlorophenyl)pyrimidine-
δ (ppm)ꢀ=ꢀ79.09, 117.85, 128.03, 128.05, 130.13, 137.03, 162.87,
164.91, 169.33. – Analysis for C11H9N5: calcd. C 62.55, H 4.29,
N 33.16; found C 62.43, H 4.22, N 33.10.
5-carbonitrile (4f)
M. p. 275–276°C, IR (KBr): v
̅
ꢀ=ꢀ3408, 3349, 3307 (NH), 2188
2
1
(CN), 1643, 1619 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
13
(ppm)ꢀ=ꢀ6.85–6.90 (4H, 2 NH2), 7.05–7.09 (3H, m, ArH); C
4.2.2 2,4-Diamino-6-(4-chlorophenyl)pyrimidine-
5-carbonitrile (4b)
NMR(100 MHz, [D6]DMSO): δ (ppm)ꢀ=ꢀ77.02, 118.17, 127.32,
128.54, 130.21, 133.43, 163.39, 167.38, 168.55. – Analysis for
C11H7Cl2N5: calcd. C 47.17, H 2.52, N 25.00; found C 47.08, H
2.45, N 24.85.
M. p. 265–267°C. – IR (KBr): v
̅
ꢀ=ꢀ3436, 3163 (NH), 2196 (CN),
2
1627, 1697, 1521 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
1
(ppm)ꢀ=ꢀ7.65 (4H, 2 NH2), 7.98 (2H, m, ArH), 8.45 (2H, m,
ArH). – 13C NMR(100 MHz, [D6]DMSO): δ (ppm)ꢀ=ꢀ76.35, 4.2.7 2,4-Diamino-6-(2-chlorophenyl)pyrimidine-
118.23, 128.76, 130.47, 135.51, 136.32, 163.39, 165.49, 168.66.
– Analysis for C11H8ClN5: calcd. C 53.78, H 3.28, N 28.51;
found C 53.65, H 3.20, N 28.45.
5-carbonitrile (4g)
M. p. 232–235°C, IR (KBr): v
̅
ꢀ=ꢀ3477, 3314, 3234 (NH), 2192
2
(CN), 1692, 1580 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
(ppm)ꢀ=ꢀ6.38–6.42 (4H, 2 NH2), 7.51 (2H, m, ArH), 7.61 (2H,
m, ArH). – 13C NMR (100 MHz, [D6]DMSO): δ (ppm)ꢀ=ꢀ78.43,
117.83, 127.58, 128.47, 128.92, 129.92, 130.63, 133.20, 164.70,
166.74, 169.46. – Analysis for C11H8ClN5: calcd. C 53.78, H
3.28, N 28.51, found C 53.62, H 3.17, N 28.42.
1
4.2.3 2,4-Diamino-6-(4-bromophenyl)pyrimidine-
5-carbonitrile (4c)
M. p. 260–262°C. – IR (KBr): v̅ ꢀꢀ=3421, 3299 (NH2), 2188 (CN),
1637, 1601, 1489 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
1
(ppm)ꢀ=ꢀ6.85–6.92 (4H, 2 NH2), 7.02–7.04 (2 H, Jꢀ=ꢀ8 Hz,
ArH), 7.09–7.11 (2 H, Jꢀ=ꢀ8 Hz, ArH). – 13C NMR(100 MHz, 4.2.8 2,4-Diamino-6-(3-methylphenyl)pyrimidine-
[D6]DMSO): δ (ppm)ꢀ=ꢀ76.12, 118.39, 128.70, 130.40, 135.59,
136.22, 163.17, 165.32, 168.52. – Analysis for C11H8BrN5: calcd.
C 45.54, H 2.78, N 24.14; found: C 45.45, H 2.65, N 24.04.
5-carbonitrile (4h)
M. p. 225–227°C. – IR (KBr): v
̅
ꢀ=ꢀ3450, 3350 (NH), 2196
2
(CN), 1695, 1569 cm−1. – H NMR (400 MHz, [D6]DMSO): δ
(ppm)ꢀ=ꢀ2.37 (3H, s, CH3), 7.09–7.15 (4H, 2 NH2), 7.35–7.37
(2H, d, Jꢀ=ꢀ8 Hz), 7.78–7.80 (2H, d, Jꢀ=ꢀ8 Hz). – 13C NMR
(100 MHz, [D6]DMSO): δ (ppm)ꢀ=ꢀ23.84, 78.52, 117.85, 124.47,
129.20, 129.34, 131.22, 134.61, 137.53, 164.34, 166.75, 168.42.
1
4.2.4 2,4-Diamino-6-(4-methoxyphenyl)pyrimidine-
5-carbonitrile (4d)
M. p. 236–238°C. – IR (KBr): v
̅ ꢀꢀ3=388, 3323, 3285, 3206 (NH2), – Analysis for C12H11N5: calcd. C 63.99, H 4.92, N 31.09;
2200 (CN), 1645, 1480 cm−1. – 1H NMR (400 MHz, [D6]DMSO): found C 63.85, H 4.85, N 30.98.
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S. Barkhordarion-Mohammadi and J. Safaei-Ghomi: Synthesis of 2,4-diamino-6-aryl-5-pyrimidinecarbonitrileꢂ
[10] M. Zahedifar, H. Sheibani, Res. Chem. Intermed. 2015,
5 Supporting information
41, 105.
[11] Q. Zhuang, H. X. Han, S. Wang, S. Tu, L. Rong, Synth. Commun.
2009, 39, 516.
Synthesis and characterization of the CoFe2O4@SiO2-
PrNH2 nanoparticles and copies of the H NMR spectra of
the products are given in the Supporting Information,
which is available online (DOI: https://doi.org/10.1515/
znb-2017-0114).
[12] S. Tao, S. Xia, L. Rong, C. Cao, S. Tu, Res. Chem. Intermed.
2012, 38, 2065.
[13] S. J. Ahmadi, S. Sadjadi, M. Hosseinpour, Monatsh. Chem.
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D. R. Patil, S. M. Salunkhe, S. A. Sankpal, Indian J. Chem. B
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Acknowledgments: The authors are grateful to the Islamic
Azad University, Qom branch, for supporting this work.
The authors are also grateful to Dr. Hossein Shahbazi-
Alavi for his help.
[15] J. Safaei-Ghomi, E. Afkhami, H. Shahbazi-Alavi, A. Ziarati, Iran.
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Z. Naturforsch.ꢂ
ꢂ2017 | Volume x | Issue x(b)
Graphical abstract
Samaneh Barkhordarion-Mohammadi and
Javad Safaei-Ghomi
Synthesis of 2,4-diamino-6-aryl-5-pyrimi-
dinecarbonitrile promoted by amino-func-
tionalized CoFe2O4@SiO2 nanoparticles
under conventional heating, microwave
and ultrasound irradiations
https://doi.org/10.1515/znb-2017-0114
Z. Naturforsch. 2017; x(x)b: xxx–xxx
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