A three-component process for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using nanosized nickel aluminate spinel crystals as highly efficient catalysts

Article abstract of DOI:10.1002/jccs.201800450

NiAl₂O₄ spinel nanocrystals were synthesized as mesoporous catalysts and were fully characterized using Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy-dispersive X-ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives via a one-pot, three-component condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium acetate or primary aromatic amine under microwave irradiation. By far, the most obvious advantages of the offered process are efficiency and recyclability of the catalyst as well as a significantly shorter reaction time.

Full text of DOI:10.1002/jccs.201800450

Received: 25 November 2018
DOI: 10.1002/jccs.201800450
Revised: 28 March 2019
Accepted: 5 April 2019
A R T I C L E
A three-component process for the synthesis of
2,3-dihydroquinazolin-4(1H)-one derivatives using nanosized
nickel aluminate spinel crystals as highly efficient catalysts
Javad Safaei-Ghomi | Raheleh Teymuri
Department of Organic Chemistry, Faculty
of Chemistry, University of Kashan,
Kashan, I. R. Iran
NiAl2O4 spinel nanocrystals were synthesized as mesoporous catalysts and were
fully characterized using Fourier-transform infrared spectroscopy (FT-IR), X-ray
diffraction patterns (XRD), scanning electron microscopy (SEM), and Energy-
dispersive X-ray spectroscopy (EDS). These nanocrystals catalyzed the synthesis
of 2,3-dihydroquinazolin-4(1H)-one derivatives via a one-pot, three-component
condensation reaction of aromatic aldehydes, isatoic anhydride, and ammonium
acetate or primary aromatic amine under microwave irradiation. By far, the most
obvious advantages of the offered process are efficiency and recyclability of the
catalyst as well as a significantly shorter reaction time.
Correspondence
Javad Safaei-Ghomi, Department of Organic
Chemistry, Faculty of Chemistry, University
of Kashan, 51167 Kashan, I. R. Iran.
Email: safaei@kashanu.ac.ir
Funding information
the University of Kashan, Grant/Award
Number: 159196/XXII
K E Y W O R D S
dihydroquinazolinone, microwave, NiAl2O4 spinel nanocrystals, one-pot
significantly short reaction times.[13–15] Several reasons have
been proposed to account for the effect of microwaves on
1 | INTRODUCTION
Multicomponent reactions (MCRs) have emerged as a most
popular synthetic tool for the prompt and favorable access of
diverse heterocycles.[1–3] In contrast, divergent syntheses of
MCRs offer an efficient and easy methodology for the genera-
tion of complex scaffolds avoiding for instance protecting
group strategies or time-consuming purification processes.[4]
Nitrogen-containing fused-heterocycles are an integral part of
biological and small molecule drugs or synthetic molecules
and physiologically active natural products.[5–8] Noteworthily,
one of this fused heterocycle is 2,3-dihydroquinazolinone
(DHQZ-1) that has wide pharmacological properties including
anti-inflammatory, antibacterial, antitumor, and anticonvulsant
(Figure 1).[9–12]
During the last two decades, there has been interest in
exploring the potential of microwave energy as a means of
rate enhancement in the synthesis. Actually, microwave irra-
diation can be considered as a highly powerful tool owing to
versatility, which enables the use of a wide variety of experi-
mental conditions and very often leads to enhanced yields in
chemical reactions and catalytic systems such as rapid
heating, superheating, selective heating, hot spots, and
simultaneous cooling.[16]
Having looked at this importance, many methods for
the synthesis of the 2,3-dihydroquinazolinone moiety have
been reported such as solvent-free and refluxing pro-
cesses.[17,18] In addition, various catalysts were employed
including, KAl(SO4)2Á12H2O,[17] silica sulfuric acid
(SSA),[18]
aluminum
methanesulfonate,[19]
ZnO
nanoparticles,[20] and Al(H2PO4)3.[21] Whereas the major-
ity of these procedures have noticeable negative aspects
such as long reaction times, low yields, harsh reaction
conditions, and use of expensive and toxic catalysts.
Therefore, to abstain these limitations, the exploration of
an efficient, easily available catalyst with high catalytic
activity and short reaction times for the preparation of
dihydroquinazolines is still favored. Nickel aluminate
(NiAl2O4) is a ternary oxide including an AB2O4 spinel
structure that is important in many application fields
© 2019 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2019;1–9.
http://www.jccs.wiley-vch.de
1

2
SAFAEI-GHOMI AND TEYMURI
FIGURE 3 Powder X-ray diffraction patterns of NiAl2O4 spinel
nanocrystals
O, Al–O, and Ni–O–Al bonds. These peaks indicate the for-
mation of metal oxide, confirmed by X-ray diffraction
(XRD) as the single-phase NiAl2O4 spinel. The above
results of the FT-IR spectra suggest that the NiAl2O4 spinel
nanocrystals were synthesized successfully.
The XRD patterns of NiAl2O4 spinel nanocrystals are
depicted in Figure 3. This figure reveals high phase purity of
the nanocatalyst and has a perfect agreement with the
reported XRD pattern for nano-NiAl2O4 (JCPDS
No. 82–2,250). Average crystalline size of the NiAl2O4 spi-
nel nanocrystals was calculated to be 25–35 nm that was
obtained from FWHM Scherrer's formula.
Using the scanning electron microscopy (SEM) image,
the morphology and particle size of NiAl2O4 spinel nano-
crystals are confirmed (Figure 4). As indicated in Figure 2,
the size of particle diameters is in the range of nanometers.
The average diameters of the NiAl2O4 spinel nanocrystals
are obtained to be about 25–35 nm.
FIGURE 1 Reported biologically active quinazolinone and
quinazolinone-based molecules
because of its high surface area, high mechanical resis-
tance, and high thermal and chemical stabilities as well as
catalytic features.[22,23] We have used metal aluminates with
a spinel structure as a particularly effective catalyst in dif-
ferent chemical reactions.[24,25] Consequently, we have
developed a favorable microwave-assisted approach for the
preparation of 2,3-dihydroquinazolin-4(1H)-ones via the
condensation reaction of isatoic anhydride, aldehydes, and
primary amine or ammonium acetate using NiAl2O4 spinel
nanocrystals as reusable and mesoporous catalysts.
The elemental composition of NiAl2O4 spinel nano-
crystals was shown using the EDS spectrum (Figure 5). Ele-
mental analysis results showed that the content of nickel,
aluminum, and oxygen in the NiAl2O4 spinel nanocrystals
was 48.56, 15.13, 36.31 (wt%), respectively.
2 | RESULTS AND DISCUSSION
The Fourier-transform infrared spectroscopy (FT-IR) spec-
trum of NiAl2O4 is illustrated in Figure 2. The weak absorp-
tion bond observed at 1,630 cm−1 is attributed to the
bending vibration of absorbed water, and the absorption
bond at 3,428 cm−1 is attributed to the O–H stretching
mode. Nickel-oxygen stretching frequencies appeared in the
range 493–716 cm−1, associated with the vibrations of Ni–
FIGURE 2 The FT-IR spectrum of NiAl2O4 spinel nanocrystals
FIGURE 4 SEM image of NiAl2O4 spinel nanocrystals

SAFAEI-GHOMI AND TEYMURI
3
TABLE 2 Investigation of the power effect of microwave
irradiation on the preparation of 2,3-dihydroquinazolin-4(1H)-one
derivativesa
Entry
Powerc (W)
300
Time (min)
Yieldb (%)
1
2
4
20
15
15
84
94
94
400
500
aReactions conditions:: isatoic anhydride (1 mmol), aniline (1.2 mmol),
benzaldehyde (1.0 mmol), and nano-NiAl2O4 (8%).
bIsolated yields.
cMicrowave irradiation (400 W).
2,3-dihydroquinazolin-4(1H)-one derivatives through a three-
component one-pot condensation of isatoic anhydride, aro-
matic aldehyde, and primary amines/ or ammonium acetate
using NiAl2O4 spinel nanocrystals as catalysts under micro-
wave irradiation (Scheme 1).
FIGURE 5 EDS of NiAl2O4 spinel nanocrystals
Beforehand, the reaction of isatoic anhydride, benzalde-
hyde, and aniline was picked out as a model reaction. And
now, the effect of experimental factors comprising the type
and amount of catalyst and solvent was investigated to find
the best condition for this reaction and the results are listed in
Table 1. To begin with solvent examination, it was demon-
strated that EtOH is the most effective condition for this con-
densation of isatoic anhydride, aromatic aldehyde, and
primary amines/ or ammonium acetate (Table 1, entry 7).
According to the table, comparison of this entry with the
entries 8–12 of Table 1 (various catalysts containing
KAl(SO4)2Á12H2O, Al(H2PO4)3, aluminum methanesulfonate,
SCHEME 1 Condensation of isatoic anhydride, benzaldehyde,
and aniline under microwave irradiation
As a result of our great interest in preparation of heterocy-
clic compounds by applying heterogeneous catalysts,[26,27]
herein we wish to report an efficient procedure to synthesize
TABLE 1 The effect of reaction conditions on the synthesis of 2,3-diphenyl-2,3-dihydroquinazolin-4(1H)-one under various conditionsa
Time (min)
Isolated yieldb (%)
Entry
Solvent
Catalytic system (mol%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (8%)
Nano-NiAl2O4 (12%)
KAl(SO4)2.12H2O
MWc
20
25
20
20
20
15
15
15
—
—
—
—
Δ
MWc
50
55
35
40
45
80
94
93
—
—
—
—
Δ
1
Solvent-free
Water
120
180
180
180
180
150
120
—
40
45
Trace
25
30
60
75
—
88
80
80
88
2
3
DCM
4
Acetone
5
Acetonitrile
Methanol
Ethanol
6
7
8
Ethanol
9
Ethanol
240
300
35
10
11
12
Solvent-free
Solvent-free
Solvent-free
Silica sulfuric acid (20%)
Al(H2PO4)3 (16%)
Nano ZnO (20%)
180
aReactions conditions: isatoic anhydride (1 mmol), aniline (1.2 mmol), and benzaldehyde (1.0 mmol). Conditions: under ultrasonic irradiation (MW) with a power
intensity of 40%; under high stirring condition (Δ).
bIsolated yield.
cMicrowave irradiation (400 W).

4
SAFAEI-GHOMI AND TEYMURI
TABLE 3 Synthesis of monosubstituted 2,3-dihydroquinazoline-4(1H)-ones using nano-NiAl2O4 (8%)a
Time (min)
Yieldd (%)
Entry
Name
Productb
MWc
Δ
MWc
Δ
Mp (ꢀC)[ref]
1
4a
10
100
96
78
219–221[18]
2
3
4
4b
4c
4d
10
12
15
100
110
120
97
97
95
78
78
77
214–215[21]
199–201[18]
233–235[18]
5
6
4e
4f
12
12
110
110
95
94
77
76
192–193[28]
203–205[19]
7
8
4g
4h
15
12
120
110
93
96
76
78
225–226[29]
204–206[21]
9
4i
4j
15
15
120
120
92
89
75
72
177–179[18]
10
209–211[19]
aReactions conditions: isatoic anhydride (1 mmol), ammonium acetate (1.2 mmol), aldehyde (1.0 mmol), and nano-NiAl2O4 (8%).
bAll products were characterized using IR, 1H NMR, and 13CNMR spectroscopy methods.
cMicrowave irradiation (400 W).
dIsolated yield.

SAFAEI-GHOMI AND TEYMURI
5
TABLE 4 Synthesis of disubstituted 2,3-dihydroquinazoline-4(1H)-ones using nano-NiAl2O4 (8%)a
Time (min)
Yieldd (%)
Entry
Name
Productb
MWc
Δ
MWc
Δ
Mp (ꢀC)[ref]
1
4k
15
120
94
73
205–207[18]
2
4l
15
120
96
70
193–195[18]
3
4
4m
4n
15
17
120
150
95
93
73
70
217–219[18]
212–214[30]
5
6
4o
4p
17
15
150
120
92
95
70
73
184–185[19]
216–218[21]
7
8
9
4q
4r
4s
17
20
15
150
170
120
92
90
94
70
68
72
211–213[29]
237–239
191–192

6
SAFAEI-GHOMI AND TEYMURI
TABLE 4 (Continued)
Time (min)
Yieldd (%)
Entry
Name
Productb
MWc
Δ
MWc
Δ
Mp (ꢀC)[ref]
10
4t
15
120
95
78
156–157[18]
11
4u
15
110
95
75
134–135[31]
12
13
4v
25
22
210
220
88
89
82
81
161–163[32]
146–147[32]
4w
14
15
4x
4y
40
40
300
300
Trace
Trace
Trace
Trace
—
aReactions conditions: isatoic anhydride (1 mmol), primery amine (1.2 mmol), aldehyde (1.0 mmol), and nano-NiAl2O4 (8%), temperature = 45ꢀC.
bAll products were characterized using IR, 1H NMR, and 13CNMR spectroscopy methods.
cMicrowave irradiation (400 W).
dIsolated yield.
and nano-ZnO) reveals that the NiAl2O4 spinel nanocrystals
are the most efficient catalysts for the microwave synthesis of
2,3-dihydroquinazolin-4(1H)-one derivatives. The optimized
quantity of nano-NiAl2O4 for this synthesis is 8 mol%
(Table 1, entry 7).
In continuation, the current reaction was carried out
under different powers of microwave irradiation to detect the
proper power of microwave irradiation as represented in
Table 2. As can be seen, this reaction effectively proceeds
with 8 mol% of NiAl2O4 as a nanocatalyst with 400 power
of microwave irradiation.
that the microwave approach is very effective for this syn-
thesis as presented in Tables 3 and 4. From the table, when
the 2,3-dihydroquinazolin-4(1H)-one derivatives were syn-
thesized using a heating method, they were produced in
lower yields at higher reaction times, but performing these
reactions under microwave conditions produced excellent
yields of 2,3-dihydroquinazolin-4(1H)-ones at significantly
short times. Therefore, the microwave method is more envi-
ronmentally friendly because of its basic green chemistry
concept.
It should be noted that the effect of electronic nature and
position of substituents on the phenyl rings did not show a
strong influence on the reaction, therefore, the products were
obtained in high yields in relatively short reaction times. In
our continued study, this reaction was carried out with
Various monosubstituted and disubstituted 2,3-
dihydroquinazolin-4(1H)-ones were prepared using NiAl2O4
spinel nanocrystals under the obtained optimized conditions.
Comparison of heating and microwave methods demonstrates

SAFAEI-GHOMI AND TEYMURI
7
t-butyl amine, isatoic anhydride, and benzaldehyde, but the
yield was very low; because t-butyl amine as a bulky amine
is considerably less nucleophilic than other aliphatic amines
such as ethyl amine (Table 4, entry 14).
When pivaldehyde was used for the preparation of
2,3-quinazoline derivatives, the reaction efficiency was
reported to be trace. Indeed, the steric bulk of the t-butyl
group can severely deactivate the electrophilicity of the
aldehyde functionality, resulting in drastically reduced
yields.
On the basis of the point mentioned above, a reasonable
mechanism for the preparation of 2,3-dihydroquinazolin-4
(1H)-one derivatives using the NiAl2O4 spinel nanocrystals
is suggested in Scheme 2. The first point is interaction of
NiAl2O4 spinel nanocrystals as catalysts with isatoic anhy-
dride to produce a reactive intermediate (I). And now, the
N-nucleophilic primary amine attacks on the carbonyl unit
of I to produce a reactive intermediate II, which in turn
affords III through the decarboxylation reaction. Subse-
quently, the proton transfer of III affords 2-amino-N-
substituted-amide IV. Besides that the reaction of an acti-
vated aldehyde with IV proceeds to produce the imine
intermediate V. The part of the amide functional group in
intermediate IV could be formed using the tautomerism
phenomenon in the presence of the NiAl2O4 spinel nano-
crystals. Accordingly, intermediate VI could be prepared
by an intermolecular nucleophilic attack of the amide nitro-
gen on activated imine carbon, followed by a 1,5-proton
transfer to yield the final 2,3-dihydroquin-azoline-4-(1H)-
ones as the concluding product. These steps are efficiently
carried out on the high surface area of NiAl2O4 spinel
nanocrystals under microwave irradiation. For the afore-
mentioned mechanism, the significant roles of NiAl2O4
spinel nanocrystals are activation of carbonyl groups and
efficient development of the reaction on their high surface
area. We assumed that the nano-NiAl2O4 initiated both
activation of carbonyl groups and nucleophilic attack of
primary amine as it possesses Lewis acidic Ni2+ and Al3+
sites.
Another distinguishing feature of NiAl2O4 spinel nano-
crystals is recoverability without considerable loss of catalytic
activity. To prove this feature, after the accomplishment of
the reaction, 5 mL ethanol was added to the reaction mixture
and the nanocatalyst was recycled via filtration and washed
with acetone to remove the residual product. The NiAl2O4
spinel nanocrystal was reused for the new condensation reac-
tion of isatoic anhydride, aldehyde, and primary amine under
similar reaction conditions up to six cycles. There is an insig-
nificant loss of catalytic activity providing the products in
high yield (Figure 6).
3 | EXPERIMENTAL
All reagent-grade chemicals and solvents were purchased
commercially from Sigma-Aldrich and Merck. All of the
reagents were used without further purification. The
microwave irradiation was applied in reactions using the
Milestone microwave (Microwave Labstation, MLS
GmbH- ATC-FO 300). Melting points of products were
determined by Electro thermal 9,200. All IR spectra were
recorded by means of a FT-IR Magna spectrometer
550 Nicolet using KBr plates. NMR spectra were recorded
using DMSO-d6 as a solvent and are reported as parts per
million (ppm) downfield from TMS as an internal stan-
dard. The NMR spectra were obtained on a Bruker
Avance-400 MHz spectrometer. The elemental analyses
(C, H, and N) were carried out using a Carlo ERBA
Model EA 1108 analyzer. Powder XRD of NiAl2O4 spinel
nanocrystals was obtained using a Philips diffractometer
of X'pert Company. Microscopic morphology of the
SCHEME 2 Proposed reaction mechanism for the formation of
substituted 2,3-dihydroquinazoline-4(1H)-ones using nano-NiAl2O4
(8%) under microwave irradiation
FIGURE 6 Recovery of NiAl2O4 spinel nanocrystals for
synthesis of 4k

8
SAFAEI-GHOMI AND TEYMURI
nanoparticles was visualized using a SEM (MIRA 3 TES-
CAN). Energy-dispersive X-ray spectroscopy (EDS)
images of the nanoparticles were obtained using a Sigma
ZEISS, Oxford Instruments Field Emission.
3.3.2 | 3-benzyl-2-(4-nitrophenyl)-
2,3-dihydroquinazolin-4(1H)-one (4s)
M.p. 191–192ꢀC. FT-IR (KBr): 3,412, 3,017, 2,332, 1,592,
1
1,512, 1,425, and 774 cm−1. H NMR (400 MHz, DMSO-
d6): δ (ppm) 8.18(d, J = 8, 1H), 7.69(d, J = 8, 1H), 7.55 (d,
2H, J = 8), 7.31–7.20 (m, 8H), 6.72–6.63 (m, 2H), 5.95 (d,
1H, J = 4 Hz), 5.29 (d, 1H, J = 12 Hz), and 3.96 (d,
J = 12 Hz, 1H). 13C NMR (100 MHz, DMSO-d6) δ
ppm = 163.1, 148.4, 141.1, 133.0, 132.4, 128.5, 125.2(2C),
123.8, 123.2, 121.3, 117.5, 113.9, 114.8, 114.2, 68.1, and
52.7. Anal. calcd. For C20H14N3O3Br: C, 56.66; H, 3.30;
and N, 9.90, Found: C, 56.72; H, 3.43; and N, 9.81.
3.1 | Preparation of NiAl2O4 spinel
nanocrystals
Precursor sols of NiAl2O4 were prepared by a sol–gel tech-
nique using citric acid as a chelating agent. To begin with, a
substantial amount of nickel (II) nitrate hexahydrate (Ni
[NO3]2Á6H2O) and aluminum nitrate (Al[NO3]3Á9H2O) was
dissolved in deionized water. Prior to that, a proper amount
of citric acid was added to the above solution with stirring.
The molar ratio of metal ions to citric acid was 1:2. Subse-
quently, the mixed solution was stirred for 1 h and then
heated in an 80ꢀC water bath until a highly viscous gel was
formed. The green gels were dried in an oven at 110ꢀC and
then fired to the desired temperatures (600ꢀC) for 5 h.
4 | CONCLUSIONS
To recapitulate briefly, we have reported a prompt and effi-
cient method for the synthesis of 2,3-dihydroquinazolin-4
(1H)-one derivatives via three-component one-pot condensa-
tion of isatoic anhydride, aromatic aldehyde, and primary
amines/ or ammonium acetate using NiAl2O4 spinel nano-
crystals as catalysts under microwave irradiation. The cur-
rent method provides obvious advantages such as
environmental friendliness, a significantly shorter reaction
time, markedly excellent yields, and a simple workup proce-
dure. In our opinion, we expect this method will find exten-
sive applications in the field of combinatorial chemistry and
diversity-oriented synthesis.
3.2 | General procedure for the preparation of
2,3-dihydroquinazolin-4(1H)-ones
NiAl2O4 spinel nanocrystals as an efficient catalyst were
added to an ethanol solution of isatoic anhydride (1 mmol),
ammonium acetate (1.2 mmol) or primary aromatic amine
(1.1 mmol) and aldehyde (1.0 mmol) was irradiated by
microwave irradiation (400 W) for the desired times.
The progress of the reaction was monitored by TLC (7:3 n-
hexane:ethyl acetate) when the starting material had
completely disappearance, the catalyst was removed by filtra-
tion. A volume of 10 mL ice water was added and the precipi-
tated product was filtered. At the end of the process, the residue
was recrystallized from ethanol to obtain the crude product.
ACKNOWLEDGMENTS
The authors are grateful to the University of Kashan for
supporting this work by grant no: 159196/XXII.
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How to cite this article: Safaei-Ghomi J,
Teymuri R. A three-component process for the
synthesis of 2,3-dihydroquinazolin-4(1H)-one
derivatives using nanosized nickel aluminate spinel
crystals as highly efficient catalysts. J Chin Chem
Soc. 2019;1–9. https://doi.org/10.1002/jccs.
201800450