One-pot synthesis of pyrido[2,3-d:5,6-d′]dipyrimidines using CoFe2O4@SiO2-PA-CC-guanidine-SA magnetic nanoparticles in water

Article abstract of DOI:10.1002/aoc.6293

In this study, the synthesis of pyrido[2,3-d:5,6-d′]dipyrimidines using CoFe₂O₄@SiO₂-PA-CC-guanidine-SA magnetic nanoparticles with excellent yields has been reported. Pyrido[2,3-d:5,6-d′]dipyrimidines were synthesized fro

Full text of DOI:10.1002/aoc.6293

Received: 1 December 2020
DOI: 10.1002/aoc.6293
Revised: 19 April 2021
Accepted: 30 April 2021
F U L L P A P E R
One-pot synthesis of pyrido[2,3-d:5,6-d0]dipyrimidines using
CoFe2O4@SiO2-PA-CC-guanidine-SA magnetic nanoparticles
in water
Hedieh Rostami
| Lotfi Shiri
Department of Chemistry, Faculty of
In this study, the synthesis of pyrido[2,3-d:5,6-d0]dipyrimidines using
CoFe2O4@SiO2-PA-CC-guanidine-SA magnetic nanoparticles with excellent
yields has been reported. Pyrido[2,3-d:5,6-d0]dipyrimidines were synthesized
from the four-component reaction of barbituric acid derivatives, benzaldehyde
derivatives and ammonium acetate in water at room temperature. The
synthesized catalyst was identified using Fourier-transform infrared spectros-
copy (FT-IR), scanning electron microscopy (SEM), energy-dispersive X-ray
spectroscopy (EDX), X-ray powder diffraction (XRD), thermogravimetric
analysis (TGA) and vibrating sample magnetometer (VSM) techniques.
Basic Sciences, Ilam University, Ilam, Iran
Correspondence
Lotfi Shiri, Department of Chemistry,
Faculty of Basic Sciences, Ilam University,
P.O. Box 69315-516, Ilam, Iran.
Email: l.shiri@ilam.ac.ir;
lshiri47@gmail.com
Funding information
Ilam University
K E Y W O R D S
ammonium acetate, barbituric acid, benzaldehyde, magnetic nanoparticles, pyrido
[2,3-d:5,6-d0]dipyrimidines
1 | INTRODUCTION
high yield, low cost and low reaction time and eco-
friendly.[23] In the multicomponent reactions, separation
Heterocyclic compounds[1a,b] that contain pyrimidine
ring in their structure have important biological activi-
ties.[2] Pyrido[2,3-d:5,6-d0]dipyrimidines[3,4] are an impor-
tant class of the heterocyclic compounds that pyrimidine
ring is existing in their structure. Pyridodipyrimidine
derivatives because of their biological activities such as
antitumor agents,[5] inhibiting dihydrofolate reductases
or tyrosine kinases,[6] anti-inflammatory,[7] antifolate,[8]
of the intermediate is not necessary because which
reactants come together in a single reaction vessel to
form
a
product. During the past two decades,
nanocatalysts were noticed in organic synthesis because
of their high catalytic activity.[24] nanocatalysts have high
activity, but their separation from the reaction mixture is
tedious and needs hard procedures like filtration and
centrifuge. For this reason, chemists have introduced
magnetic nanocatalysts[25] that have a suitable activity
and can be easily separated from the reaction mixture
using an external magnet.
In this research, we report the synthesis of pyrido
[2,3-d:5,6-d0]dipyrimidines using CoFe2O4@SiO2-PA-CC-
guanidine-SA magnetic nanoparticles (MNPs) in water as
a green solvent at room temperature (Scheme 1).
antihypertensive,[9]
antibacterial,[10]
anti-HIV,[11]
anticonvulsants,[12] antimicrobial,[13] calcium channel
antagonists,[14] analgesic,[15] tuberculostatic[16] and
potassium-sparing[17] have attracted considerable atten-
tion. The synthesis of pyrido[2,3-d:5,6-d0]dipyrimidines
was reported in various conditions such as the use of
microwave (MW),[18] under catalyst-free conditions[19]
and various catalysts such as β-CD.[20]
Multicomponent reactions (MCRs)[21,22] are a suitable
strategy for the synthesis of heterocyclic compounds.
Multicomponent reactions in comparison with multistep
reactions have advantages such as high atom-economy,
2 | EXPERIMENTAL
All chemicals and solvents used in this study were pur-
chased from Merck and Fluka Chemical Companies and
Appl Organomet Chem. 2021;e6293.
wileyonlinelibrary.com/journal/aoc
© 2021 John Wiley & Sons, Ltd.
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https://doi.org/10.1002/aoc.6293

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ROSTAMI AND SHIRI
SCHEME 1 Synthesis of pyrido[2,3-d:5,6-d0]
dipyrimidines
were used without further purification. Fourier transform
infrared (FT-IR) was recorded as KBr pellets on a
VRTEX 70 model Bruker FT-IR spectrophotometer. H
3-aminopropyltrimethoxysilane (2 ml) was added to the
reaction mixture, and then the reaction mixture was
refluxed for 12 h. Then, the reaction mixture was cooled
at room temperature, and the product (CoFe2O4@SiO2-
PA MNPs) was extracted by an external magnet and
washed several times with ethanol and dried at room
temperature.
1
and 13C NMR spectra were recorded by Bruker DRX-250
Avance instrument using TMS as internal standard and
DMSO-d6 as solvent. Scanning electron microscopy
(SEM) and energy-dispersive X-ray spectroscopy (EDX)
were performed with a JEOL JEM-2010 instrument.
Thermogravimetric analysis (TGA) was provided using a
NETZSCH instrument. Magnetic properties of the cata-
lyst were performed using a vibrating sample magnetom-
eter (VSM) MDKFD.
2.4 | Synthesis of CoFe2O4@SiO2-PA-
CC MNPs
For the synthesis of CoFe2O4@SiO2-PA-CC MNPs,
cyanuric chloride (CC) (1.85 g, 10 mmol) and Et3N
(1.4 ml, 10 mmol) were added to the mixture of
CoFe2O4@SiO2-PA MNPs (2 g) and tetrahydrofuran
(THF) (10 ml). Then, the reaction mixture was stirred at
room temperature for 10 h. Subsequently, the product
(CoFe2O4@SiO2-PA-CC MNPs) was extracted by an
external magnet and washed five times by hot THF and
dried at room temperature.
2.1 | Synthesis of CoFe2O4 MNPs
For the synthesis of CoFe2O4 MNPs, a mixture of
CoCl2.6H2O (0.005 mol, 1.19 g) and FeCl3.6H2O
(0.01 mol, 2.705 g) was dissolved into 50-ml distilled
water. Then, 3 g of NaOH was dissolved in 25-ml
distilled water and was added to the mixture dropwise.
The prepared mixture was refluxed for 1 h. Finally,
the mixture was cooled at room temperature, and then
the black precipitate was extracted using an external
magnet. The prepared black precipitate was washed
several times with H2O and EtOH and dried at room
temperature.
2.5 | Synthesis of CoFe2O4@SiO2-PA-CC-
guanidine MNPs
The obtained CoFe2O4@SiO2-PA-CC nanoparticles (1 g),
guanidinium chloride (0.764 g, 8 mmol) and Et3N
(1.1 ml, 8 mmol) were added to the DMF (12 ml) and
stirred at 60ꢀC for 12 h. After completion of the reaction,
the product (CoFe2O4@SiO2-PA-CC-guanidine MNPs)
was extracted with an external magnet and washed five
times with hot ethanol and dried at room temperature.
2.2 | Synthesis of CoFe2O4@SiO2 MNPs
The obtained CoFe2O4 nanoparticles (1 g) were dispersed
in distilled water (10 ml) and ethanol (25 ml) by sonica-
tion for 30 min. Next, PEG (2.68 g), H2O (10 ml), ammo-
nium solution (5 ml) and tetraethylorthosilicate (TEOS)
(1 ml) were added into the mixture, and the mixture was
stirred at room temperature for 38 h. After, the product
was extracted by an external magnet and washed several
times with EtOH and dried at room temperature.
2.6 | Synthesis of CoFe2O4@SiO2-PA-CC-
guanidine-SA MNPs
CoFe2O4@SiO2-PA-CC-guanidine (0.5 g) was dispersed
in CH2Cl2 (10 ml) by sonication for 20 min.
Next, chlorosulfonic acid (1.5 ml) was added dropwise
to the reaction mixture and the reaction mixture was
stirred for 3 h at room temperature. Then, the product
(CoFe2O4@SiO2-PA-CC-guanidine-SA) was extracted by
an external magnet and washed several times with
CH2Cl2, EtOH, respectively, and dried at room
temperature.
2.3 | Synthesis of CoFe2O4@SiO2-PA
MNPs
The obtained CoFe2O4@SiO2 nanoparticles (1.5 g) was
dispersed in 50-ml EtOH by sonication for 30 min. Next,

ROSTAMI AND SHIRI
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2.7 | General procedure for the synthesis
of pyrido[2,3-d:5,6-d0]dipyrimidine
derivatives
guanidine-SA (0.06 g) were stirred at room temperature
in H2O (2 ml) as the solvent, and the progress of the
reaction was monitored by TLC. After completion of the
reaction, the catalyst was separated using an external
magnet and the solid product was collected by filtration
and for the more purification of the product, was used of
recrystallization procedure with ethanol.
A mixture of benzaldehyde derivative (0.5 mmol),
barbituric or thiobarbituric acid (1 mmol), ammonium
acetate (0.6 mmol) and CoFe2O4@SiO2-PA-CC-
SCHEME 2 The general route for the synthesis of
CoFe2O4@SiO2-PA-CC-guanidine-SA MNPs
FIGURE 1 FT-IR spectra of CoFe2O4@SiO2
(A), CoFe2O4@SiO2-PA (B), CoFe2O4@SiO2-PA-
CC (C), CoFe2O4@SiO2-PA-CC-guanidine
(D) and CoFe2O4@SiO2-PA-CC-guanidine-SA
(E) MNPs

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ROSTAMI AND SHIRI
3 | RESULTS AND DISCUSSION
3.1 | Characterization of CoFe2O4@SiO2-
PA-CC-guanidine-SA MNPs
The general route for the synthesis of CoFe2O4@SiO2-
PA-CC-guanidine-SA
MNPs
is
illustrated
in
Scheme 2.[24,26–28] The synthesized catalyst was charac-
terized using FT-IR spectroscopy, SEM, EDX, XRD, TGA
and VSM analysis.
3.2 | FT-IR studies
The FT-IR spectra of CoFe2O4@SiO2 (A), CoFe2O4@
SiO2-PA (B), CoFe2O4@SiO2-PA-CC (C), CoFe2O4@SiO2-
PA-CC-guanidine
(D)
and
CoFe2O4@SiO2-
PA-CC-guanidine-SA (E) are shown in Figure 1. The
stretching vibration at 1089 cmꢁ1 is related to the Si–O
bond that approved the presence of SiO2 at the surface of
CoFe2O4 MNPs (Figure 1A). The characteristic peaks at
2897–2949 cmꢁ1 are related to the stretching vibration of
methylene groups (CH2) and also the broadening band at
3435 cmꢁ1 for the NH2 group that confirmed the linkage
of 3-aminopropyltrimethoxysilane on the surface
of CoFe2O4@SiO2 (Figure 1B). Two peaks in the region
1406 and 1712 cmꢁ1 belong to the C═N stretching vibra-
tions that these peaks, is a strong reason for the existence
of cyanuric chloride on the surface of CoFe2O4
(Figure 1C). Also, the peak observed at 3300 cmꢁ1 is a
good reason for the existence of guanidine on the surface
of CoFe2O4 (Figure 1D). The absorption bands at 3000–
3500 cmꢁ1 are related to the OH stretching vibration of
the SO3H group. Also, the absorption band observed at
1085 cmꢁ1 is related to the O═S═O group (Figure 1E).
FIGURE 2 SEM images of CoFe2O4@SiO2-PA-CC-guanidine
3.3 | SEM studies
(a) and CoFe2O4@SiO2-PA-CC-guanidine-SA (b) MNPs
The
surface
morphology
of
CoFe2O4@SiO2-
PA-CC-guanidine-SA MNPs was characterized using
SEM analysis. SEM images of CoFe2O4@SiO2-
PA-CC-guanidine (a) and CoFe2O4@SiO2-PA-CC-guani-
dine-SA MNPs (b), are shown in Figure 2. According to
the SEM images, nanoparticles are spherical and the par-
ticles size is in the range of nanomaterial.
synthesized. It must be noted that the nitrogen peak is
not observed because of the overlap with the peaks of
other elements.
3.5 | XRD analysis
The XRD patterns for the CoFe2O4 (orange colour)
and CoFe2O4@SiO2-PA-CC-guanidine-SA (blue colour)
MNPs were shown in Figure 4. The XRD pattern of
CoFe2O4@SiO2-PA-CC-guanidine-SA shows six peaks at
2Ɵ = 30.21ꢀ, 35.76ꢀ, 43.36ꢀ, 54.06ꢀ, 57.61ꢀ and 63.16ꢀ that
the peaks of CoFe2O4@SiO2-PA-CC-guanidine-SA are
3.4 | EDX analysis
The EDX analysis of CoFe2O4@SiO2-PA-CC-guanidine-
SA MNPs is shown in Figure 3, which approves the
presence of Fe, Co, O, Si, C and S elements in the catalyst
and proves that the nanoparticles have been successfully

ROSTAMI AND SHIRI
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FIGURE 5 TGA curve of CoFe2O4@SiO2-PA-CC-guanidine-
SA MNPs
FIGURE 3 EDX spectrum of CoFe2O4@SiO2-PA-CC-
guanidine-SA MNPs
FIGURE 6 VSM curves of CoFe2O4 (a) and CoFe2O4@SiO2-
PA-CC-guanidine-SA (b)
FIGURE 4 XRD patterns of CoFe2O4 (orange colour) and
CoFe2O4@SiO2-PA-CC-guanidine-SA (blue colour) MNPs
to the decomposition of the organic moieties on
CoFe2O4@SiO2-PA-CC-guanidine-SA.
consistent with the peaks of CoFe2O4. Also, the XRD
pattern of CoFe2O4@SiO2-PA-CC-guanidine-SA proves
that the crystal structure of CoFe2O4 has not changed
with the placement of groups on its surface.
3.7 | VSM analysis
The magnetic properties of CoFe2O4 (a) and
CoFe2O4@SiO2-PA-CC-guanidine-SA (b) were investi-
gated using VSM at room temperature (Figure 6). VSM
value for CoFe2O4 nanoparticles (40 emu/g) is higher
than CoFe2O4@SiO2-PA-CC-guanidine-SA (24 emu/g). A
decrease in the magnetic property of CoFe2O4@SiO2-PA-
CC-guanidine-SA is due to the existence of the silica shell
and the successful grafting of organic layers on CoFe2O4
nanoparticles.
3.6 | TGA analysis
The TGA curve of CoFe2O4@SiO2-PA-CC-guanidine-SA
MNPs is shown in Figure 5. The TGA of the synthesized
CoFe2O4@SiO2-PA-CC-guanidine-SA MNPs showed a 6%
weight loss in one step at a temperature below 200ꢀC
owing to the removal of physically adsorbed water and
solvent. The other weight loss was in the region of 200ꢀC
to 800ꢀC approximately (11%), which was mainly related
For the estimate the amount of acidic groups on the
surface of nanocatalyst, was used of back titration
procedure using KOH solution (0.01 mol/L) and result

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ROSTAMI AND SHIRI
shown that the amount of acidic groups on the surface of
the catalyst, is 1.2 mmol/g.
A plausible mechanism for the synthesis of pyrido
[2,3-d:5,6-d0]dipyrimidines based on previously reported
reactions is shown in Scheme 3.[31] Initially, the reaction
of (thio)barbituric acid with ammonium acetate leads to
produce the intermediate (I). On the other hand, in the
presence of acidic nanocatalyst, Knoevenagel condensa-
tion takes place between benzaldehyde and (thio)
barbituric acid and the intermediate (II) is produced.
Next, intermediate (I) reacts with intermediate (II) and
intermediate (III) is formed. In the following, intermedi-
ate (III) performs an intramolecular reaction to form the
intermediate (IV). Finally, with the elimination of H2O
from intermediate (IV), compound 3 is produced.
3.8 | Catalytic studies
After the synthesis and characterization of CoFe2O4@SiO2-
PA-CC-guanidine-SA MNPs, the catalytic activity of it,
was investigated in the synthesis of pyrido[2,3-d:5,6-d0]
dipyrimidines. To optimize the reaction conditions, the
reaction between benzaldehyde, thiobarbituric acid and
ammonium acetate was selected as a model reaction. In
this aim, the model reaction was studied in various
conditions including the type of solvent and amount of
catalyst (Table 1). The best reaction conditions were
obtained in H2O as solvent in the presence of 0.06 g of
catalyst (Table 1, entry 3).
The activity of the CoFe2O4@SiO2-PA-CC-guanidine-
SA MNPs for the synthesis of pyrido[2,3-d:5,6-d0]
dipyrimidine (3b) was compared with previous work that
results are shown in Table 3.
After obtaining optimum conditions, some of the
pyrido[2,3-d:5,6-d0]dipyrimidine derivatives were synthe-
sized and the obtained results are shown in Table 2.
It should be noted that the electron-withdrawing and
electron-releasing groups effected on the time and yield
of the synthesis of pyrido[2,3-d:5,6-d0]dipyrimidine deriv-
atives. The pyrido[2,3-d:5,6-d0]dipyrimidine derivatives
with benzaldehydes with electron-withdrawing groups
are synthesized in the lower time and higher yield in
comparison with benzaldehydes with electron-donating
groups.
The most important advantage of the magnetic cata-
lyst is recoverability and reusability. In this regard, we
have studied the recoverability and reusability of the
CoFe2O4@SiO2-PA-CC-guanidine-SA MNPs in the syn-
thesis of compound 3a. For this purpose, the reusability
of the nanostructure catalysts for subsequent catalytic
cycles was examined in the selected synthesis. After the
completion of the reaction, the nanocatalyst was sepa-
rated by applying an external magnetic field and washed
with EtOAc several times and then dried. This catalyst
without loss of its catalytic activity can be reused for four
TABLE 1 Effect of different
amounts of catalyst and solvent on the
model reactiona
Entry
Solvent
H2O
Temp (ꢀC)
Catalyst (g)
0.04
Time (min)
Yield (%)
1
2
3b
4
5
6
7
8
9
r.t
r.t
r.t
r.t
r.t
r.t
r.t
r.t
r.t
20
20
20
20
20
20
20
20
20
70
85
95
80
85
10
50
50
40
H2O
0.05
H2O
0.06
EtOH
0.06
H2O/EtOH
PEG-400
CH3CN
DMF
0.06
0.06
0.06
0.06
Toluene
0.06
aReaction conditions: benzaldehyde (0.5 mmol), thiobarbituric acid (1 mmol), ammonium acetate
(0.6 mmol), r.t, 2 ml solvent.
bOptimum conditions

ROSTAMI AND SHIRI
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TABLE 2 Synthesis of pyrido[2,3-d:5,6-d/]dipyrimidine derivatives using CoFe2O4@SiO2-PA-CC-guanidine-SAa
Entry
Ar
R
X
Product
Yield (%)b
95
MP (oC)(Ref.)
1
C6H5
H
S
238-239[29]
259 (dec)[29]
240-241[29]
>300[29]
2
3
4
4-ClC6H4
H
H
H
S
S
S
90
88
91
3-OMeC6H4
4-NO2C6H4
5
6
4-OMeC6H4
H
H
S
S
94
94
>300[29]
4-N (Me)2C6H4
>300[29]
7
8
C6H5
H
H
O
O
94
89
>300[30]
4-ClC6H4
>300[30]
(Continues)

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ROSTAMI AND SHIRI
TABLE 2 (Continued)
Entry
Ar
R
X
Product
Yield (%)b
89
MP (oC)(Ref.)
9
4-MeC6H4
H
O
>300[30]
10
11
12
4-NO2C6H4
4-OMeC6H4
2,4-Cl2C6H3
H
H
H
O
O
O
89
88
86
293[30]
>300[30]
>300[29]
aReaction conditions: aldehyde (0.5 mmol), barbituric acid derivative (1 mmol), ammonium acetate (0.6 mmol), cat (0.06 g), r.t, 2 ml solvent, 15–50 min.
bIsolated yield.
SCHEME 3 Proposed mechanism for the synthesis of
compound 3

ROSTAMI AND SHIRI
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TABLE 3 Comparison of activity the synthesized catalyst with other reported catalysts in the synthesis of compound 3b
Entry
Catalyst
Conditions
H2O, ultrasonic
H2O, ultrasonic
H2O, r.t
Time (min)
Yield (%)
Ref.
1
2
3
4
CuFe2O4 NPs
[H-NMP]+[HSO4]ꢁ
4
98
98
91
90
Naeimi and Didar[31]
Naeimi et al.[29]
Naeimi et al.[32]
This work
5
Fe-MCM-41-IL
34
20
CoFe2O4@SiO2-PA-CC-guanidine-SA
H2O, r.t
FIGURE 7 Reusability of CoFe2O4@SiO2-
PA-CC-guanidine-SA MNPs in the synthesis of
compound 3a
runs. These reactions were performed under optimum
conditions. The obtained results are illustrated in
Figure 7.
DATA AVAILABILITY STATEMENT
Data are available in the article's Supporting
Information.
ORCID
4 | CONCLUSIONS
Hedieh Rostami https://orcid.org/0000-0002-3513-0417
Lotfi Shiri https://orcid.org/0000-0002-9474-0602
In this study, an efficient and reusable heterogeneous
magnetic catalyst (CoFe2O4@SiO2-PA-CC-guanidine-SA)
was synthesized and characterized by FT-IR, SEM, XRD,
EDS, TGA and VSM techniques. This catalyst is efficient
for the synthesis of a wide range of pyrido[2,3-d:5,6-d0]
dipyrimidine derivatives in water at room temperature
with good yields. This catalyst (CoFe2O4@SiO2-PA-CC-
guanidine-SA) has advantages such as high activity and
easy separation from the reaction mixture using an exter-
nal magnet and also can be recovered and reused five
times without any significant loss of its activity.
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ACKNOWLEDGMENT
We are grateful of Ilam University for the financial
support of this work.
AUTHOR CONTRIBUTIONS
Hedieh Rostami: Conceptualization; formal analysis;
resources; software. Lotfi Shiri: Conceptualization;
formal analysis; resources; software; supervision.

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How to cite this article: H. Rostami, L. Shiri,
Appl Organomet Chem 2021, e6293. https://doi.org/
10.1002/aoc.6293
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