ZnO-CeO2 nanocomposite: Efficient catalyst for the preparation of thieno[2,3-d]pyrimidin-4(3H)-one derivatives

Article abstract of DOI:10.1515/mgmc-2017-0038

The Zinc oxide-cerium oxide (ZnO-CeO₂) nanocomposite was prepared by a coprecipitation method and characterized by X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), and particle size distribution analysis. The XRD p

Full text of DOI:10.1515/mgmc-2017-0038

Main Group Met. Chem. 2018; aop
Farzaneh Ghayour, Mohammad Reza Mohammad Shafiee* and Majid Ghashang
ZnO-CeO2 nanocomposite: efficient catalyst for
the preparation of thieno[2,3-d]pyrimidin-4(3H)-
one derivatives
https://doi.org/10.1515/mgmc-2017-0038
with Gewald reagents, which like various organic trans-
formations need an acid catalyst for their progression.
Remarkably, hazardous liquid acid catalysts such as HCl,
H2SO4, and so on have been considered to upgrade the
reaction yields (Zhang et al., 2004; Dzhavakhishvili et al.,
2008, 2009; Abbas et al., 2013; Kjaer et al., 2013; Sánchez
et al., 2014). However, no examples were reported on the
use of heterogeneous catalytic systems under solvent-
free conditions. Thus, the provision of new and efficient
methods for the synthesis of thienopyrimidines is of great
importance.
Nanocomposites especially when composed of
metal oxide mixtures are attractive for catalysis because
of easy availability, simple usability, affordability, and
large surface area, which allow wide application of
these materials as a catalyst. During the past decades,
Received August 6, 2017; accepted March 5, 2018
Abstract: The Zinc oxide-cerium oxide (ZnO-CeO2) nano-
composite was prepared by a coprecipitation method and
characterized by X-ray diffraction (XRD), field emission
scanning electron microscopy (FE-SEM), and particle size
distribution analysis. The XRD pattern shows the cubic
phase of cerium oxide as the dominant phase. The FE-
SEM images show the homogeneity distribution of zinc
and cerium oxides in the sample. The mean particle size
of the nanocomposite determined by dynamic light scat-
tering technique was 58 nm. The catalytic activity of ZnO-
CeO2 nanocomposite was examined on the synthesis of
thieno[2,3-d]pyrimidin-4(3H)-one derivatives. In all cases,
the products were obtained in good to excellent yields.
Keywords: 2-amino-thiophenes; thieno[2,3-d]pyrimidin- metal oxide nanocomposites have been extensively
4(3H)-one; ZnO-CeO2 nanocomposite.
investigated in multicomponent reactions due to the
facility of recovery and reusability. Zinc oxide (ZnO)
based composites are low cost and nontoxic materials
that shows thermal and chemical stability as well as
good catalytic activity. Enjamuri et al. (2016) reported
that ZnO-cerium oxide (CeO2) mixed oxide could be an
efficient catalyst for the transformation of alcohol to
aldehyde. The same composite system of CeO2-ZnO was
reported by Mishra and Rao (2006) for the cyclohexanol
dehydrogenation reaction. Similarly, ZnO-based com-
posites have been used for the catalytic aromatization
of methylbromide to aromatics (Chen et al., 2018), syn-
thesis of diethyl carbonate (An et al., 2012), synthesis
of 2-methylpyrazine (Park et al., 2003), condensation
reaction of Claisen-Schmidt (Li et al., 2017), synthesis
of 3-substituted indoles (Rajesh et al., 2015), synthesis
of 2-aminothiophenes via Gewald reaction (Javadi and
Tayebee, 2016), and etc.
Introduction
Thienopyrimidines, a class of heterocyclic compounds
composed of pyrimidine and thiophene nucleus, are
useful subcores present in the structure of a large number
of essential medications and known as antimalarial,
antiallergic, biological, anti-inflammatory, antitumor,
antimalarial, and antimicrobial agents. Moreover, thien-
opyrimidines act as tyrosine kinases and exhibit high
biological activity against human pathogenic bacteria
(Nasr et al., 2002; Aly et al., 2010; Wang et al., 2010;
Kotaiah et al., 2012; Abbas et al., 2013; Elrazaz et al., 2015;
Wilding et al., 2015). The useful strategy for thienopyrimi-
dine synthesis is the condensation reaction of aldehydes
In continuation of our catalytic investigations
(Shafiee et al., 2013, 2014, 2017; Ghashang et al., 2014,
2015, 2016a,b; Behmaneshfar et al., 2015; Baziar and
Ghashang, 2016; Ghashang, 2016; Taghrir et al., 2016;
Sheikhan-Shamsabadi and Ghashang, 2017), the present
study investigates the synthesis of ZnO-CeO2 nanocom-
posite using a simple coprecipitation method. To con-
tinue, we report a novel and convenient synthesis of
*Corresponding author: Mohammad Reza Mohammad Shafiee,
Department of Chemistry, Faculty of Sciences, Islamic Azad
University, Najafabad Branch, P.O. Box 517, Najafabad, Iran,
e-mail: mohammadreza.mohammadshafiee@gmail.com
Farzaneh Ghayour and Majid Ghashang: Department of Chemistry,
Faculty of Sciences, Islamic Azad University, Najafabad Branch, P.O.
Box 517, Najafabad, Iran. http://orcid.org/0000-0002-7959-6438
(M. Ghashang)
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ꢀꢀꢀꢁ
2ꢀ ꢀF. Ghayour et al.: Preparation of thieno[2,3-d]pyrimidin-4(3H)-one
thieno[2,3-d]pyrimidin-4(3H)-one derivatives involving
the condensation of 2-amino-4,5,6,7-tetrahydrobenzo[b]
thiophene-3-carboxamide with various aldehydes using
ZnO-CeO2 nanocomposite as an efficient catalyst.
Results and discussion
The ZnO-CeO2 nanocomposite was prepared by a copre-
cipitation method in the natural atmosphere. The syn-
thesized nanoparticles were characterized by X-ray
fluorescence (XRF), X-ray diffraction (XRD), field emis-
sion scanning electron microscopy (FE-SEM), and particle
size distribution analysis. The XRF test was used to deter-
mine the chemical composition of the synthetic nano-
composite sample. Despite the fact that primary metal
salts with similar molar ratio have been used, the results
show that the dominant phase is CeO2 [ZnO (30.1%) and
CeO2 (69.9%)]. One of the reasons is the difference solu-
bility product constant (Ksp of Zn(OH)2ꢀ=ꢀ3.0ꢀ×ꢀ10−17 and
Ce(OH)4ꢀ=ꢀ2ꢀ×ꢀ10−48). Figure 1 shows the XRD pattern of the
ZnO-CeO2 nanocomposite. The XRD pattern states that
nanocomposites consist of two phases: ZnO and CeO2.
ZnO is well crystallized in hexagonal phase with charac-
teristic peaks at 31.7, 34.4, 36.2, 47.5, 56.5, 62.8, 67.9, and
69.0 [2θ°] and CeO2 crystallized in cubic phase with char-
acteristic peaks at 28.5, 33.1, 47.5, 56.3, 76.7, and 88.4 [2θ°].
The FE-SEM analysis investigated the surface morphology
of ZnO-CeO2 nanocomposite, and the result is shown in
Figure 2. The FE-SEM images indicate that the nanocom-
posite consists of uniform particles, and zinc and cerium
oxides are homogeneously distributed in the sample. The
results also demonstrate that the nanocomposite has an
average particle size of less than 100 nm. The particle size
distribution curve of the nanocomposite performed by
dynamic light scattering technique is shown in Figure 3.
Before analysis, the sample was dispersed in ethanol (1 g
Figure 2:ꢀFE-SEM photographs of ZnO-CeO2 nanocomposite.
900
GHAUOR~1.CAF
Figure 3:ꢀParticle size distribution analysis of ZnO-CeO2
400
100
0
nanocomposite.
in 25 mL) and sonicated for 30 min. The mean particle
size of the nanocomposite determined by this method is
approximately 58 nm.
The catalytic activity of the ZnO-CeO2 nanocom-
posite was examined by the reaction of 2-amino-4,5,6,7-
tetrahydrobenzo[b]thiophene-3-carboxamide with various
20
30
40
50
60
70
80
90
Position (°2θ)
Figure 1:ꢀXRD pattern of ZnO-CeO2 nanocomposite.
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F. Ghayour et al.: Preparation of thieno[2,3-d]pyrimidin-4(3H)-oneꢂ ꢂ3
Table 1:ꢀOptimization of the reaction condition for the synthesis of
thieno[2,3-d]pyrimidin-4(3H)-ones.
was selected as the model. This reaction was studied
under solvent-free conditions and in a solvent medium
at different temperatures (Table 1). The obtained results
show that the reaction at room temperature does not lead
to the product and states that the heat is necessary for
the product formation. Based on the results, the follow-
ing condition was selected as optimal conditions: catalyst
amount (0.05 g), temperature (140°C), and solvent-free.
The results show that the conditions at which the reac-
tion temperature is less than 100°C will not be productive.
For this reason, the use of solvents whose boiling point
is less than 100°C such as ethanol, ethyl acetate, hexane,
dichloromethane, diethyl ether, and acetonitrile was not
effective. As shown in Table 1, a systematic reduction of
catalyst will result in a regular reduction in reaction time
and yield. The further increase in catalyst content will not
have a significant effect on the product yield.
Entry
Catalyst (g)
T (°C)
Solvent (5 mL)
Yield (%)a
1
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
0.05
—
0.025
0.075
0.1
0.05
0.05
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
Reflux
140
n-Hexane
CH2Cl2
Et2O
EtOAc
Toluene
MeOH
EtOH
H2O
—
—
—
2
3
—
4
—
5
—
6
—
7
—
8
—
9
90
—
10
11
12
13
14
15
140
—
140
—
85
86
50
60
—
140
—
140
—
100
—
80
—
aIsolated yields; time: 1.5 h.
The efficacy and generality of this catalytic system
were investigated by the use of various derivatives of aro-
matic aldehydes containing electron-donating and elec-
aldehydes leading to the formation of thieno[2,3-d]pyrimi- tron-withdrawing groups. The results are summarized in
din-4(3H)-one derivatives.
Table 2. As can be seen from the table, aromatic aldehydes
To find the optimal conditions for the synthesis of containing electron-withdrawing groups are more reac-
thieno[2,3-d]pyrimidin-4(3H)-one derivatives, the reac- tive in the reaction to their electron-donating groups. The
tion between benzaldehyde (1 mmol) and 2-amino-4,5,6,7- reactivity of aromatic aldehydes substituted with moder-
tetrahydrobenzo[b]thiophene-3-carboxamide (1 mmol) ate electron-donating groups (such as methyl, methoxy,
Table 2:ꢀPreparation of thieno[2,3-d]pyrimidin-4(3H)-one derivatives using ZnO-CeO2 nanocomposite.
Ar
NH2
HN
N
S
C
NH2
O
CeO2-MgO
nano-composite
O
+
ArCHO
S
140°C
Solvent-free
Entry
Product
Aldehyde
Time (h)
Yield (%)a
M.p. [lit. m.p. (°C)] (ref.)
1
1C
2C
Benzaldehyde
1.5
1.5
1.5
1
90
87
80
89
92
95
86
73
71
74
69
65
73
62
264–266 [266–268] (Dzhavakhishvili et al., 2008)
272–274 [272–274] (Dzhavakhishvili et al., 2008)
268–270 [265–267] (Dzhavakhishvili et al., 2008)
266–268 [268–270] (Dzhavakhishvili et al., 2009)
>300 [>300] (Dzhavakhishvili et al., 2008)
>300 [>300] (Dzhavakhishvili et al., 2008)
291–293 [new compound]
>300 [>300] (Dzhavakhishvili et al., 2008)
235–237 [229–231] (Dzhavakhishvili et al., 2008)
285–287 [288–290] (Dzhavakhishvili et al., 2009)
288–290 [–] (Abbas et al., 2013)
2
4-Methylbenzaldehyde
4-Methoxybenzaldehyde
4-Chlorobenzaldehyde
4-Nitrobenzaldehyde
3
3C
4
4C
5
5C
1
6
6C
4-Bromobenzaldehyde
4-tert-Butylbenzaldehyde
4-Hydroxybenzaldehyde
4-(N,N-Dimethyl amino)benzaldehyde
4-Fluorobenzaldehyde
Cinnamaldehyde
4-Pyridinecarboxaldehyde
2-Phenylacetaldehyde
Pentanal
1
1.5
2
2
1
1.5
2.5
1.5
1.5
7
7C
8
8C
9
9C
10
11
12
13
14
10C
11C
12C
13C
14C
>300[–] (Kjaer et al., 2013)
264–266 [265–268] (Zhang et al., 2004)
207–209 [205–208] (Sánchez et al., 2014)
aIsolated yield.
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4ꢀ ꢀF. Ghayour et al.: Preparation of thieno[2,3-d]pyrimidin-4(3H)-one
100
90
80
70
60
50
40
30
20
10
0
and 4-tert-butyl), cinnamaldehyde, and aliphatic alde-
hydes is similar to that of the unsubstituted benzaldehyde.
However, 4-hydroxybenzaldehyde and 4-(N,N-dimethyl
amino)benzaldehyde that have stronger electron-donat-
ing ability compared with that of 4-methylbenzaldehyde
or 4-methoxybenzaldehyde show less reactivity. While
pentanal as an aliphatic aldehyde has moderate yield
(62%) under the treatment with ZnO-CeO2 nanocompos-
ite, 2-phenylacetaldehyde produced the corresponding
product in good yield (73%). The heteroaromatic alde-
hydes, e.g. 4-pyridinecarboxaldehyde, are more inactive
than those of electron-withdrawing substituted benzalde-
hydes such as 4-nitrobenzaldehyde.
1
2
3
4
5
6
7
8
9
10
Run no.
Figure 4:ꢀCatalyst recovery.
At the reaction pathway, first, the activation of car-
bonyl functional group by an acid-base interaction with
Noticeably, the catalyst could be recovered from the
the Lewis site of metal oxide catalyst is established. The reaction medium and reused for several times. The results
activated aldehyde is prone to accept a nucleophilic of catalyst recovery are shown in Figure 4. The catalyst
attack of an amino group to form an imine intermediate was recovered, washed with acetone, and reused for the
(1). The cyclization of intermediate (1) was followed by synthesis of compound 1C.
air oxidation rebound on the targeted product formation
(Scheme 1).
The structure of the products were characterized by Conclusion
13
1
1H- and C-NMR spectra. The H-NMR spectrum of com-
pound 7C shows two peaks as singlet one at δ 1.32 ppm The catalytic synthesis of some novel thieno[2,3-d]pyrimi-
corresponding to the tert-butyl group and another at δ din-4(3H)-one derivatives over ZnO-CeO2 nanocomposite
12.25 ppm corresponding to the amide (N-H) proton. Eight as an efficient catalyst was reported. The catalyst was
protons that appeared as multiplets are aliphatic protons characterized by XRF, XRD, FE-SEM, and particle size
located in a ring. The ortho protons from the tert-butyl distribution analysis. The procedure is efficient as the
group appeared at δ 7.32 ppm while meta position protons products were obtained in good to excellent yields and
appeared at δ 8.01 ppm both as doublets.
the catalyst could be recovered and reused several times.
The corresponding signals for the tert-butyl group and
other sp3 carbon atoms were observed at δꢀ=ꢀ22.4, 23.2, 24.1,
13
26.2, 31.2, and 34.7 ppm in the C-NMR spectrum, while Experimental
δꢀ=ꢀ165.7 ppm is related to the carbonyl group. The other
All reagents were purchased from Merck and Aldrich (Tehran, Iran)
signals located at δꢀ=ꢀ114.7, 124.7, 126.8, 127.1, 128.3, 130.9,
145.8, 153.4, and 159.3 ppm are assigned to be sp2 carbon
atoms.
and used without further purification. All yields refer to isolated
products after purification. The powder XRD patterns were measured
with D8 Advance Bruker AXS diffractometer (Karlsruhe, Germany)
using Cu-Kα irradiation. FE-SEM was taken by a Hitachi S-4160
(Japan) photograph to examine the shape of the sample. The NMR
spectra were recorded on a Bruker Avance DPX 400 MHz instrument
(Bruker BioSpin, Fallanden, Switzerland). The spectra were meas-
ured in DMSO-d6 relative to tetramethylsilane (0.00 ppm). Elemental
analyses (C, H, N) were carried out on a Perkin-Elmer 2400 analyzer
(Perkin Elmer, Norwalk, CT, USA). DLS measurement was done using
a Zetasizer Nano ZS instrument (Zetasizer Nano ZS, Model ZEN3600,
Malvern Instruments, Malvern, UK). TLC was performed on silica gel
Polygram SIL G/UV 254 plates (Merck, Darmstadt, Germany).
O
NH2
NH2
O
NH2
Cat.
H
Ar
S
O
Cat.
N
(1)
ArCHO
–H2O
S
Ar
Cyclization
Ar
O
O
Oxidation
NH
NH
NH
Ar
N
Preparation of ZnO-CeO2 nanocomposite
S
S
Scheme 1:ꢀProposed mechanism for the synthesis of thieno[2,3-d]
pyrimidin-4(3H)-one derivatives.
In a 250 mL beaker, cerium ammonium nitrate (10 mmol) and zinc
chloride (10 mmol) were dissolved in 100 mL of water (solution A).
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F. Ghayour et al.: Preparation of thieno[2,3-d]pyrimidin-4(3H)-oneꢂ ꢂ5
In a separate beaker, 2-aminoethanol (60 mmol) and glycerol (10 mL) 2-(4-(tert-Butyl)phenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-
were dissolved in water (100 mL; solution B). Solution B was slowly d]pyrimidin-4(3H)-one (Table 2, 7C):ꢁ1H-NMR (400 MHz, DMSO-
added dropwise to solution A under vigorous magnetic stirring. d6): δꢀ=ꢀ1.32 (s, 9H), 1.61–2.96 (m, 8H), 7.32 (d, Jꢀ=ꢀ7.8 Hz, 2H), 8.01
The mixture was continuously stirred for another 60 min. The result- (d, Jꢀ=ꢀ7.8 Hz, 2H), 12.25 (s, 1H, NH); 13C-NMR (100 MHz, DMSO-d6):
ing precipitate was filtered, washed with water several times, dried at δꢀ=ꢀ22.4, 23.2, 24.1, 26.2, 31.2, 34.7, 114.7, 124.7, 126.8, 127.1, 128.3, 130.9,
ambient temperature, and finally calcined at 500°C for 2 h.
145.8, 153.4, 159.3, 165.7 ppm. Elemental Analysis Found: C, 71.09; H,
6.67; N, 8.22; S, 9.39% C20H22N2OS; requires: C, 70.97; H, 6.55; N, 8.28;
S, 9.47%.
Synthesis of 2-amino-4,5,6,7-tetrahydrobenzo[b]
2-(Pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimi-
din-4(3H)-one (Table 2, 12C):ꢁ1H-NMR (400 MHz, DMSO-d6): δꢀ=ꢀ1.62–
2.96 (m, 8H), 8.09 (d, Jꢀ=ꢀ8.0 Hz, 2H), 8.58 (d, Jꢀ=ꢀ8.0 Hz, 2H), 12.49 (s,
1H, NH); 13C-NMR (100 MHz, DMSO-d6): δꢀ=ꢀ22.5, 23.3, 24.3, 26.4, 115.3,
121.7, 122.4, 126.8, 128.5, 131.2, 146.4, 149.6, 160.3, 166.4 ppm.
thiophene-3-carboxamide
To a mixture of cyclohexanone (1 mmol), cyanoacetamide (1 mmol),
and sulfur (1 mmol) in 5 mL of ethanol, the ZnO-CeO2 nanocomposite
(0.05 g) was added as a catalyst. The resulting mixture was refluxed
for 10 h (thin-layer chromatography monitoring). In the end, the
mixture was filtered, washed with hot ethanol, and cooled, and the
resultant crystals were purified in ethanol. 1H-NMR (400 MHz, DMSO-
d6): δꢀ=ꢀ5.12 (s, 2H, NH2), 6.09 (s, 1H, C5), 6.29 (s, 2H, NH2), 7.31–7.44 (m,
5H); 13C-NMR (100 MHz, DMSO-d6): δꢀ=ꢀ164.7, 161.1, 138.6, 136.8, 129.2,
128.4, 128.1, 108.3, 105.4 ppm.
Acknowledgment: We are thankful to the Najafabad
Branch, Islamic Azad University Research Council, for
partial support of our research.
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Synthesis of 2-phenyl-5,6,7,8-tetrahydrobenzo[4,5]
thieno[2,3-d]pyrimidin-4(3H)-one
To a mixture of benzaldehyde (1 mmol) and 2-amino-4,5,6,7-
tetrahydrobenzo[b]thiophene-3-carboxamide (1 mmol), 0.05 g of ZnO-
CeO2 nanocomposite was added, and the reaction mixture was heated
at 140°C until the reaction was complete (the reaction was followed by
thin-layer chromatography, n-hexane:EtOAc 9:1). After completion, the
reaction mixture is cooled to ambient temperature and combined with
boiling ethanol. The insoluble catalyst is separated off by filter paper,
and the pure product is obtained by recrystallization in ethanol.
2-Phenyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-
4(3H)-one (Table 2, 1C):ꢁ1H-NMR (400 MHz, DMSO-d6): δꢀ=ꢀ1.72–1.80
(m, 4H), 2.71–2.90 (m, 4H), 7.39 (t, Jꢀ=ꢀ8.0 Hz, 2H), 7.69 (t, Jꢀ=ꢀ8.1 Hz,
1H), 7.98 (d, Jꢀ=ꢀ8.0 Hz, 2H), 12.26 (s, 1H, NH) ppm.
Behmaneshfar, A.; Ghashang, M.; Mohammad Shafiee, M. R.; Saffar-
Teluri, A.; Fazlinia, A.; Esfandiari, H. Optimization of the prepa-
ration condition of 2,4,5-triphenyl-1H-imidazole over BaSO4
nanoparticles as catalyst using a response surface methodology
(RSM). Curr. Nanosci. 2015, 11, 56–63.
2-(p-Tolyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-
4(3H)-one (Table 2, 2C):ꢁ1H-NMR (400 MHz, DMSO-d6): δꢀ=ꢀ1.61–2.77
(m, 11H), 7.30 (d, Jꢀ=ꢀ7.9 Hz, 2H), 7.98 (d, Jꢀ=ꢀ7.9 Hz, 2H), 11.89 (s, 1H, NH)
ppm.
Chen, H.; Chen, T.; Chen, K.; Fu, J.; Ouyang, P. Catalytic aromatiza-
tion of methyl bromide to aromatics over bimetallic CuO-ZnO/
HZSM-5. Catal. Commun. 2018, 103, 38–41.
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Dzhavakhishvili, S. G.; Gorobets, N. Y.; Shishkina, S. V.; Shishkin, O.
V.; Desenko, S. M.; Groth, U. M. Diversification of a thieno[2,3-d]
pyrimidin-4-one scaffold via regioselective alkylation reactions.
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2-(4-Methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]
pyrimidin-4(3H)-one (Table 2, 3C):ꢁ1H-NMR (400 MHz, DMSO-d6):
δꢀ=ꢀ1.72–1.81 (m, 4H), 2.75–2.92 (m, 4H), 3.85 (s, 3H), 7.18 (d, Jꢀ=ꢀ8.0 Hz,
2H), 7.95 (d, Jꢀ=ꢀ8.1 Hz, 1H), 11.99 (s, 1H, NH) ppm.
2-(4-Chlorophenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]
pyrimidin-4(3H)-one (Table 2, 4C):ꢁ1H-NMR (400 MHz, DMSO-d6):
δꢀ=ꢀ1.76–1.82 (m, 4H), 2.71–2.92 (m, 4H), 7.56 (t, Jꢀ=ꢀ8.0 Hz, 2H), 8.11 (d,
Jꢀ=ꢀ7.9 Hz, 2H), 12.33 (s, 1H, NH) ppm.
2-(4-Nitrophenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d] Elrazaz, E. Z.; Serya, R. A. T.; Ismail, N. S. M.; Abou El Ella, D. A.;
pyrimidin-4(3H)-one (Table 2, 5C):ꢁ1H-NMR (400 MHz, DMSO-d6):
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