Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles

Article abstract of DOI:10.1134/S1070363217040326

The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes and ammonium acetate using Fe₃O₄ nanoparticles as efficient and magnetically recyclable catalysts. Aromatic aldehydes substituted with electron-withdrawing groups or none, reacted successfully with 1,3-dimethylbarbituric acid and ammonium acetate to give new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives (can be also named as pyrido[2,3-d:6,5-d′]dipyrimidines) in high yields over relatively short reaction time. The Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron-donating substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity. The new products were characterized on the basis of FT-IR, ¹H NMR and ¹³C NMR spectral data.

Full text of DOI:10.1134/S1070363217040326

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 4, pp. 863–867. © Pleiades Publishing, Ltd., 2017.
Efficient One-Pot Synthesis
of Some New Pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines
Catalyzed by Magnetically Recyclable Fe3O4 Nanoparticles1
M. Fattahi, A. Davoodnia*, and M. Pordel
Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, 91756-87119 Iran
*e-mail: adavoodnia@mshdiau.ac.ir; adavoodnia@yahoo.com
Received February 25, 2017
Abstract—The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes
and ammonium acetate using Fe3O4 nanoparticles as efficient and magnetically recyclable catalysts. Aromatic
aldehydes substituted with electron‐withdrawing groups or none, reacted successfully with 1,3-dimethyl-
barbituric acid and ammonium acetate to give new pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine derivatives (can
be also named as pyrido[2,3-d:6,5-d']dipyrimidines) in high yields over relatively short reaction time. The
Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron‐donating
substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity.
The new products were characterized on the basis of FT-IR, 1H NMR and 13C NMR spectral data.
Keywords: pyrimidopyridopyrimidines, pyridodipyrimidines, Fe3O4 nanoparticles, magnetically recyclable
DOI: 10.1134/S1070363217040326
INTRODUCTION
Several methods have been reported for the syn-
thesis of pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines
such as reaction of 1,3-diarylbarbituric acid with pyr-
role-2-carbaldehyde and liquor ammonia [11], reaction
of 6-amino-1,3-dimethyluracil with aromatic al-
dehydes followed by oxidation by the air and catalyzed
by p-TSA in [bmim]Br media [15], SBA-15-SO3H
catalyzed reaction of 6-aminouracil with different
aldehydes under solvent-free conditions [16], micro-
wave irradiation of 6-amino-1-methyluracil and
aromatic aldehyde in the presence of acetic acid [17],
reaction of 2,6-diaminopyrimidin-4(3H)-one with
isatins in the presence of p-TSA [18], reaction of 6-
amino-2-butylthiopyrimidin-4(3H)-one with aryl al-
Over recent years pyrimidine-fused pyridines,
especially pyrido[2,3-d]pyrimidines, have been studied
intensively due to their important biological activities
including antitumor [1, 2], anticonvulsant and
antidepressant [3], antibacterial [4], antiviral [5],
antiinflammatory [6], antitubercular [7], antifungal [8],
cytotoxic [9, 10], and some others.
There are various tricyclic pyrimidopyridopyrimi-
dines including pyrimido[5',4':5,6]pyrido[2,3-d]pyrimi-
dines (1), pyrimido[4',5':5,6]pyrido[3,2-d]pyrimidines
(2), and pyrimido[4',5':5,6]pyrido[2,3-d]pyrimidines
(3) (see figure), that are constructed from two fused
pyridopyrimidine and pyrimidine rings. Among them,
pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidines 1, which
can be named as pyrido[2,3-d:6,5-d']dipyrimidines, are
of most interest. Derivatives of 1 demonstrated anti-
bacterial [11], antiviral [5] and NAD-type redox
catalytic [12] activities. Some of them act as inhibitors
of α-glucosidase and α-amylase [13]. Solid-state ribbons
have also been described from the self-assembly of an
amine derivative of 1, which demonstrates the
potential of these heterocyclic compounds in supra-
molecular synthesis applications [14].
N
N
N
N
N
1
N
N
N
N
N
N
N
N
N
N
2
3
1 The text was submitted by the authors in English.
Structures of various pyrimidopyridopyrimidines.
863

864
FATTAHI et al.
Scheme 1.
No reaction
O
N
Ar
O
NH4OAc
Me
3
N
1
O
nano Fe3O4
EtOH/H2O
reflux
Me
4
O
i
2
−
a
2
r
o
Me
O
f
O
N
nano Fe3O4
O
Ar
O
+
Ar
H
EtOH/H2O
reflux
N
O
Me
Me
N
N
Me
for 5a−5f
O
N
N
H
N
O
1
2a−2i
Me
Me
5a−5f
Ar = C6H5 (a), Ar = 4-ClC6H4 (b), Ar = 2-ClC6H4 (c), Ar = 4-FC6H4 (d), Ar = 4-O2NC6H4 (e), Ar = 4-pyridyl (f), Ar =
4-MeC6H4 (g), Ar = 4-MeOC6H4 (h), Ar = 4-HOC6H4 (i).
dehydes using sulfonic acid supported on hydroxy-
apatite-encapsulated-γ-Fe2O3 [19], and by multistep
syntheses [20].
of the catalyst of choice, a blank reaction was carried
out in the absence of Fe3O4 nanoparticles. Refluxing in
EtOH, H2O, or EtOH–H2O lasted for 180 min and led
to moderate yields of 5b (Table 1).
Considering the above facts and due to our interest
in the synthesis of new heterocyclic compounds with
potential biological activities [21–28], we report here
efficient synthetic approach to some new pyrimido
[5',4':5,6]pyrido[2,3-d]pyrimidine derivatives by one-
pot cyclocondensation reaction of 1,3-dimethylbarbi-
turic acid with aromatic aldehydes and ammonium acetate
using nano Fe3O4 as a catalyst (Scheme 1).
The scope of the reaction was further studied with
different aromatic aldehydes under the optimized
reaction conditions (Table 2). Aromatic aldehydes
substituted with electron-withdrawing group or none
2a–2f gave pyrimido[5',4':5,6]pyrido[2,3-d]-
pyrimidines 5a–5f in high yields within short reaction
time. The reaction with electron-rich aldehydes did not
give the expected tricyclic products even upon
prolonged reaction time, instead, the Knoevenagel
condensation reaction occurred and the products 4g–4i
were isolated in high yields (Table 2). Formation of the
products 5a–5f probably proceed via Knoevenagel
intermediates 4a–4f that reacted with second equi-
valent of 1,3-dimethylbarbituric acid 1 and ammonium
acetate 3. Under these conditions, attempts to isolate
the intermediates 4a–4f failed. To prove this hypo-
thesis, 1,3-dimethylbarbituric acid 1 (1 mmol) was
allowed to interact with aromatic aldehydes 2a–2i in
the absence of ammonium acetate 3 under the same
reaction conditions. In that case Knoevenagel products
4a–4i were isolated. Finally, the reaction of 4a–4f with
1,3-dimethylbarbituric acid 1 and ammonium acetate
3, conducted under similar conditions, gave 5a–5f in
high yields.
RESULTS AND DISCUSSIONS
Treatment of 1,3-dimethylbarbituric acid 1 (2 mmol)
and 4-chlorobenzaldehyde 2b (1 mmol) with
ammonium acetate 3 (1.2 mmol) in the presence of
Fe3O4 nanoparticles in aqueous ethanol, followed by
refluxing of the mixture gave the corresponding
pyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine 5b in high
yield (Table 1). A mixture EtOH–H2O (50 : 50) proved
to be much better media than the others tested
including EtOH, H2O, CHCl3, and solvent-free
conditions. The latter solvents supported formation of
the target product in moderate yield within long
reaction time. The optimal amount of the catalyst was
determined to be 0.75 g (Table 1, entry 11). The higher
amount of the catalyst had no significant effect on the
yield and reaction time. To demonstrate the efficiency
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 4 2017

EFFICIENT ONE-POT SYNTHESIS
865
Table 1. Optimization of conditions for synthesis of 5b catalyzed
Table 2. Synthesis of pyrimido[5',4':5,6]pyrido[2,3-d]pyri-
midines 5a–5f and Knoevenagel products 4g–4i using Fe3O4
nanoparticles as the catalysta
by Fe3O4 nanoparticlesa
Entry Catalyst,
Time, Yieldb,
Solvent
T, °C
no.
g
–
–
–
min
180
180
180
180
120
120
90
%
45
47
52
70
76
73
78
68
78
80
89
72
68
mp, ºC
Time, Yieldb,
Ar
1
EtOH
H2O
EtOH–H2O Reflux
Reflux
min
%
found
calculated
2
Reflux
3
4g 4-MeC6H4
30
93
95
91
144–146 142–142.5
[29]
4
0.050 EtOH
0.075 EtOH
0.050 H2O
0.075 H2O
0.075 CHCl3
Reflux
Reflux
Reflux
Reflux
Reflux
5
4h 4-MeOC6H4 25
151–153 149–151
[30]
6
7
4i 4-HOC6H4
20
291–293 293–295
[30]
8
240
105
40
9
0.025 EtOH–H2O Reflux
0.050 EtOH–H2O Reflux
0.075 EtOH–H2O Reflux
0.075 EtOH–H2O 50
5a C6H5
35
30
35
20
20
25
80
89
80
85
91
82
186–188
187–189
226–228
159–161
210–212
245–246
New
New
New
New
New
New
10
11
12
13
5b 4-ClC6H4
5c 2-ClC6H4
5d 4-FC6H4
5e 4-O2NC6H4
5f 4-Pyridyl
30
70
0.075 EtOH–H2O Room
120
temperature
14
15
16
0.100 EtOH–H2O Reflux
30
50
40
87
78
80
0.075
0.075
–
–
100
120
a
Reaction conditions: 1,3-dimethylbarbituric acid 1 (2 mmol), an
aromatic aldehyde 2a–2i (1 mmol), ammonium acetate 3
(1.2 mmol), Fe3O4 nanoparticles (0.075 g), EtOH/H2O (5 mL,
50 : 50), reflux.
a
Reaction conditions: 1,3-dimethylbarbituric acid 1 (2 mmol), 4-
chlorobenzaldehyde 2b (1 mmol) and ammonium acetate 3
(1.2 mmol).
Isolated yields.
b
b
Isolated yields.
Structures of new products 5a–5f were elucidated
of the catalyst was confirmed by comparing FT‐IR
spectra of the recovered catalyst after the fourth run
with that of the fresh catalyst used in the model
reaction. The spectra were almost identical.
1
on the basis of spectral data. For example, H NMR
spectrum of 5e in DMSO-d6 and D2O demonstrated a
singlet at 3.15 ppm assigned to four methyl groups. A
singlet at 6.25 ppm (methine group), as well as two
doublets in the aromatic region assigned to para-
substituted aromatic ring indicated formation of the
compound 5e. IR spectrum of 5e demonstrated a band
at 3425 cm–1 (NH) and a strong band at 1693 cm–1
(C=O). The 13C NMR spectrum was consistent with
the assigned structure.
EXPERIMENTAL
Nanosize Fe3O4 was purchased from Tecnan
Spanish company. All other chemicals were purchased
from Merck and Aldrich and used without purification.
Melting points were measured on a Stuart SMP3
melting point apparatus. IR spectra were recorded on a
1
Tensor 27 Bruker spectrophotometer in KBr disks. H
Recyclability and reusability of Fe3O4 nanoparticles
were studied in the synthesis of compound 5b under
optimized conditions. Fe3O4 Nanoparticles were
readily recovered from the reaction mixture using the
procedure outlined in the experimental section. The
catalyst could be used at least four times with only a
slight reduction in activity. Retention of the structure
and 13C NMR spectra were measured on a Bruker 300
spectrometer at 300 and 75 MHz.
General procedure for the synthesis of pyrimido-
[5',4':5,6]pyrido[2,3-d]pyrimidine 5a–5f and
Knoevenagel products 4g–4i catalyzed by Fe3O4
nanoparticles. A mixture of 1,3-dimethylbarbituric
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 4 2017

866
FATTAHI et al.
acid 1 (2 mmol) with an aromatic aldehyde 2a–2i
(1 mmol), ammonium acetate 3 (1.2 mmol) and Fe3O4
nanoparticles (0.075 g) in EtOH–H2O (2.5 : 2.5 mL)
was refluxed for 20–35 min. The reaction was
monitored by TLC. Upon completion of the process,
the catalyst was separated using an external magnet.
The reaction mixture was cooled down to room
temperature. The crude product was filtered off and
crystallized from ethanol to give compounds 5a–5f and
4g–4i in high yields. The isolated catalyst was washed
with hot ethanol, dried at 60°C under vacuum for 1 h
and reused in the following similar experiments. The
synthesized earlier products 4g–4i were characterized
D2O), δ, ppm: 28.5, 34.4, 91.5, 125.1, 127.1, 128.0,
144.2, 152.0, 163.5.
5-(2-Chlorophenyl)-1,3,7,9-tetramethyl-5,10-
dihydropyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-
2,4,6,8(1H,3H,7H,9H)-tetraone (5c). IR spectrum, ν,
1
cm–1: 3434 (NH), 1680 (C=O). H NMR spectrum
(DMSO-d6–D2O), δ, ppm: 3.12 s (12H, 4NCH3), 5.96 s
(1H, CH), 7.06–7.35 m (4H, Harom). 13C NMR spec-
trum (DMSO-d6–D2O), δ, ppm: 28.3, 34.2, 89.6, 126.2,
127.1, 129.6, 130.9, 133.1, 142.5, 151.9, 162.8.
5-(4-Fluorophenyl)-1,3,7,9-tetramethyl-5,10-
dihydropyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-
2,4,6,8(1H,3H,7H,9H)-tetraone (5d). IR spectrum, ν,
1
by IR and H NMR spectra and their melting points
were close to those of authentic samples [29, 30].
1
cm–1: 3489 (NH), 1670 (C=O). H NMR spectrum
(DMSO-d6–D2O), δ, ppm: 3.14 s (12H, 4NCH3), 6.07 s
(1H, CH), 6.89–7.08 m (4H, Harom). 13C NMR spec-
trum (DMSO-d6–D2O), δ, ppm: 28.4, 33.4, 91.4, 114.6,
128.8, 140.4, 151.8, 158.9, 162.1, 166.4.
1,3-Dimethyl-5-(4-methylbenzylidene)pyrimi-
dine-2,4,6(1H,3H,5H)-trione (4g). IR spectrum, ν, cm–1:
1664 (C=O). 1H NMR spectrum (CDCl3), δ, ppm: 2.36
s (3H, CH3), 3.30 s (3H, NCH3), 3.34 s (3H, NCH3),
7.20 d (J = 7.8 Hz, 2H, Harom), 7.98 d (J = 7.8 Hz, 2H,
Harom), 8.47 s (1H, =CH).
1,3,7,9-Tetramethyl-5-(4-nitrophenyl)-5,10-
dihydropyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-
2,4,6,8(1H,3H,7H,9H)-tetraone (5e). IR spectrum, ν,
1
cm–1: 3425 (NH), 1693 (C=O). H NMR spectrum
5-(4-Methoxybenzylidene)-1,3-dimethylpyri-
midine-2,4,6(1H,3H,5H)-trione (4h). IR spectrum,
(DMSO-d6–D2O), δ, ppm: 3.15 s (12H, 4NCH3), 6.25 s
(1H, CH), 7.30 d (J = 7.8 Hz, 2H, Harom), 8.03 d (J =
7.8 Hz, 2H, Harom). 13C NMR spectrum (DMSO-d6–D2O),
δ, ppm: 28.5, 34.6, 91.0, 123.4, 128.4, 145.5, 151.8, 154.2,
163.1.
1
ν
max, cm–1: 1665 (C=O). H NMR spectrum (CDCl3),
δ, ppm: 3.39 s (3H, NCH3), 3.41 s (3H, NCH3), 3.91 s
(3H, OCH3), 6.98 d (J = 8.7 Hz, 2H, Harom), 8.33 d (J =
8.7 Hz, 2H, Harom), 8.50 s (1H, =CH).
1,3-Dimethyl-5-(4-hydroxybenzylidene)pyrimi-
1,3,7,9-Tetramethyl-5-(4-pyridyl)-5,10-dihyd-
ropyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6,8-
(1H,3H,7H,9H)-tetraone (5f). IR spectrum, ν, cm–1:
dine-2,4,6(1H,3H,5H)-trione (4i). IR spectrum, ν, cm–1:
1
3199 (OH), 1642 (C=O). H NMR spectrum (DMSO-
1
d6), δ, ppm: 3.20 s (3H, NCH3), 3.22 s (3H, NCH3),
6.89 d (J = 8.7 Hz, 2H, Harom), 8.28 d (J = 8.7 Hz, 2H,
Harom), 8.32 s (1H, =CH), 10.85 s (1H, OH).
3481 (NH), 1690 (C=O). H NMR spectrum (DMSO-
d6–D2O), δ, ppm: 3.15 s (12H, 4NCH3), 6.38 s (1H,
CH), 7.77 d (J = 6.6 Hz, 2H, Harom), 8.63 d (J = 6.6 Hz,
2H, Harom). 13C NMR spectrum (DMSO-d6–D2O), δ,
ppm: 28.5, 35.9, 89.6, 125.7, 141.0, 151.8, 163.0,
167.9.
1,3,7,9-Tetramethyl-5-phenyl-5,10-dihydropyri-
mido[5',4':5,6]pyrido[2,3-d]pyrimidine-2,4,6,8-
(1H,3H,7H,9H)-tetraone (5a). IR spectrum, ν, cm–1:
1
3545 (NH), 1663 (C=O). H NMR spectrum (DMSO-
CONCLUSIONS
d6–D2O), δ, ppm: 3.15 s (12H, 4NCH3), 6.14 s (1H,
CH), 7.01–7.17 m (5H, Harom). 13C NMR spectrum
(DMSO-d6–D2O), δ, ppm: 28.4, 33.8, 91.5, 124.9,
127.2, 128.0, 144.6, 151.9, 163.2.
Fe3O4 nanoparticles were used as the efficient
catalyst in the synthesis of new pyrimido[5',4':5,6]-
pyrido[2,3-d]pyrimidine derivatives by one-pot
reaction of 1,3-dimethylbarbituric acid, aromatic
aldehydes substituted with electron‐withdrawing group
or none, and ammonium acetate under refluxing in
EtOH–H2O leading to high yields within short reaction
time. Under the same conditions the use of an aromatic
aldehyde substituted with electron‐donating group
gave the corresponding Knoevenagel products. Fe3O4
Nanoparticles can be magnetically separated from the
5-(4-Chlorophenyl)-1,3,7,9-tetramethyl-5,10-
dihydropyrimido[5',4':5,6]pyrido[2,3-d]pyrimidine-
2,4,6,8(1H,3H,7H,9H)-tetraone (5b). IR spectrum, ν,
1
cm–1: 3541 (NH), 1630 (C=O). H NMR spectrum
(DMSO-d6–D2O), δ, ppm: 3.16 s (12H, 4NCH3), 6.18 s
(1H, CH), 7.05 d (J = 7.2 Hz, 2H, Harom), 7.14 d (J =
7.2 Hz, 2H, Harom). 13C NMR spectrum (DMSO-d6–
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 4 2017

EFFICIENT ONE-POT SYNTHESIS
867
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ACKNOWLEDGMENTS
The authors express their gratitude to the Islamic
Azad University, Mashhad Branch, Iran for its financial
support.
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